Hydroxyeicosatetraenoic acids. Medical search

Eicosatetraenoic acids substituted in any position by one or more hydroxy groups. They are important intermediates in a series of biosynthetic processes leading from arachidonic acid to a number of biologically active compounds such as prostaglandins, thromboxanes, and leukotrienes.

A lipoxygenase metabolite of ARACHIDONIC ACID. It is a highly selective ligand used to label mu-opioid receptors in both membranes and tissue sections. The 12-S-HETE analog has been reported to augment tumor cell metastatic potential through activation of protein kinase C. (J Pharmacol Exp Ther 1995; 274(3):1545-51; J Natl Cancer Inst 1994; 86(15):1145-51)

A P450 oxidoreductase that catalyzes the hydroxylation of the terminal carbon of linear hydrocarbons such as octane and FATTY ACIDS in the omega position. The enzyme may also play a role in the oxidation of a variety of structurally unrelated compounds such as XENOBIOTICS, and STEROIDS.

An enzyme that catalyzes the oxidation of arachidonic acid to yield 12-hydroperoxyarachidonate (12-HPETE) which is itself rapidly converted by a peroxidase to 12-hydroxy-5,8,10,14-eicosatetraenoate (12-HETE). The 12-hydroperoxides are preferentially formed in PLATELETS.

An enzyme that catalyzes the oxidation of arachidonic acid to yield 15-hydroperoxyarachidonate (15-HPETE) which is rapidly converted to 15-hydroxy-5,8,11,13-eicosatetraenoate (15-HETE). The 15-hydroperoxides are preferentially formed in NEUTROPHILS and LYMPHOCYTES.

An unsaturated, essential fatty acid. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is formed by the synthesis from dietary linoleic acid and is a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes.

An enzyme of the oxidoreductase class primarily found in PLANTS. It catalyzes reactions between linoleate and other fatty acids and oxygen to form hydroperoxy-fatty acid derivatives.

A class of compounds named after and generally derived from C20 fatty acids (EICOSANOIC ACIDS) that includes PROSTAGLANDINS; LEUKOTRIENES; THROMBOXANES, and HYDROXYEICOSATETRAENOIC ACIDS. They have hormone-like effects mediated by specialized receptors (RECEPTORS, EICOSANOID).

Enzymes catalyzing the oxidation of arachidonic acid to hydroperoxyarachidonates. These products are then rapidly converted by a peroxidase to hydroxyeicosatetraenoic acids. The positional specificity of the enzyme reaction varies from tissue to tissue. The final lipoxygenase pathway leads to the leukotrienes. EC 1.13.11.- .

Compounds that bind to and inhibit that enzymatic activity of LIPOXYGENASES. Included under this category are inhibitors that are specific for lipoxygenase subtypes and act to reduce the production of LEUKOTRIENES.

A family of biologically active compounds derived from arachidonic acid by oxidative metabolism through the 5-lipoxygenase pathway. They participate in host defense reactions and pathophysiological conditions such as immediate hypersensitivity and inflammation. They have potent actions on many essential organs and systems, including the cardiovascular, pulmonary, and central nervous system as well as the gastrointestinal tract and the immune system.

A 20-carbon-chain fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid, 5,8,11,14-eicosatetraenoic acid, only at position 5.

An enzyme that catalyzes the oxidation of arachidonic acid to yield 5-hydroperoxyarachidonate (5-HPETE) which is rapidly converted by a peroxidase to 5-hydroxy-6,8,11,14-eicosatetraenoate (5-HETE). The 5-hydroperoxides are preferentially formed in leukocytes.

A superfamily of hundreds of closely related HEMEPROTEINS found throughout the phylogenetic spectrum, from animals, plants, fungi, to bacteria. They include numerous complex monooxygenases (MIXED FUNCTION OXYGENASES). In animals, these P-450 enzymes serve two major functions: (1) biosynthesis of steroids, fatty acids, and bile acids; (2) metabolism of endogenous and a wide variety of exogenous substrates, such as toxins and drugs (BIOTRANSFORMATION). They are classified, according to their sequence similarities rather than functions, into CYP gene families (>40% homology) and subfamilies (>59% homology). For example, enzymes from the CYP1, CYP2, and CYP3 gene families are responsible for most drug metabolism.

The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990)

A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils.

Cell surface proteins that bind eicosanoids with high affinity and trigger intracellular changes influencing the behavior of cells. Among the eicosanoid receptors are receptors for the prostaglandins, thromboxanes, and leukotrienes.

A group of amides with the general formula of R-CONH2.

An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.

Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed.

A group of FLAVONOIDS characterized with a 4-ketone.

Enzyme complexes that catalyze the formation of PROSTAGLANDINS from the appropriate unsaturated FATTY ACIDS, molecular OXYGEN, and a reduced acceptor.

20-carbon saturated monocarboxylic acids.

A microanalytical technique combining mass spectrometry and gas chromatography for the qualitative as well as quantitative determinations of compounds.

Eighteen-carbon essential fatty acids that contain two double bonds.

7-Hydroxycoumarins. Substances present in many plants, especially umbelliferae. Umbelliferones are used in sunscreen preparations and may be mutagenic. Their derivatives are used in liver therapy, as reagents, plant growth factors, sunscreens, insecticides, parasiticides, choleretics, spasmolytics, etc.

Scaffolding proteins that play an important role in the localization and activation of 5-LIPOXYGENASE.

Trihydroxy derivatives of eicosanoic acids. They are primarily derived from arachidonic acid, however eicosapentaenoic acid derivatives also exist. Many of them are naturally occurring mediators of immune regulation.

A 20-carbon unsaturated fatty acid containing 4 alkyne bonds. It inhibits the enzymatic conversion of arachidonic acid to prostaglandins E(2) and F(2a).

A group of LEUKOTRIENES; (LTC4; LTD4; and LTE4) that is the major mediator of BRONCHOCONSTRICTION; HYPERSENSITIVITY; and other allergic reactions. Earlier studies described a "slow-reacting substance of ANAPHYLAXIS" released from lung by cobra venom or after anaphylactic shock. The relationship between SRS-A leukotrienes was established by UV which showed the presence of the conjugated triene. (From Merck Index, 11th ed)

(2S-(2 alpha,3 beta(1E,3E,5Z,8Z)))-3-(1,3,5,8-Tetradecatetraenyl)oxiranebutanoic acid. An unstable allylic epoxide, formed from the immediate precursor 5-HPETE via the stereospecific removal of a proton at C-10 and dehydration. Its biological actions are determined primarily by its metabolites, i.e., LEUKOTRIENE B4 and cysteinyl-leukotrienes. Alternatively, leukotriene A4 is converted into LEUKOTRIENE C4 by glutathione-S-transferase or into 5,6-di-HETE by the epoxide-hydrolase. (From Dictionary of Prostaglandins and Related Compounds, 1990)

Artifactual vesicles formed from the endoplasmic reticulum when cells are disrupted. They are isolated by differential centrifugation and are composed of three structural features: rough vesicles, smooth vesicles, and ribosomes. Numerous enzyme activities are associated with the microsomal fraction. (Glick, Glossary of Biochemistry and Molecular Biology, 1990; from Rieger et al., Glossary of Genetics: Classical and Molecular, 5th ed)

Widely distributed enzymes that carry out oxidation-reduction reactions in which one atom of the oxygen molecule is incorporated into the organic substrate; the other oxygen atom is reduced and combined with hydrogen ions to form water. They are also known as monooxygenases or hydroxylases. These reactions require two substrates as reductants for each of the two oxygen atoms. There are different classes of monooxygenases depending on the type of hydrogen-providing cosubstrate (COENZYMES) required in the mixed-function oxidation.

Organic compounds containing the -CO-NH2 radical. Amides are derived from acids by replacement of -OH by -NH2 or from ammonia by the replacement of H by an acyl group. (From Grant & Hackh's Chemical Dictionary, 5th ed)

Peroxides produced in the presence of a free radical by the oxidation of unsaturated fatty acids in the cell in the presence of molecular oxygen. The formation of lipid peroxides results in the destruction of the original lipid leading to the loss of integrity of the membranes. They therefore cause a variety of toxic effects in vivo and their formation is considered a pathological process in biological systems. Their formation can be inhibited by antioxidants, such as vitamin E, structural separation or low oxygen tension.

Chemical agents that increase the permeability of CELL MEMBRANES to CALCIUM ions.

12-Carbon saturated monocarboxylic acids.

A strain of albino rat used widely for experimental purposes because of its calmness and ease of handling. It was developed by the Sprague-Dawley Animal Company.

Drugs used to cause constriction of the blood vessels.

Non-nucleated disk-shaped cells formed in the megakaryocyte and found in the blood of all mammals. They are mainly involved in blood coagulation.

A non-steroidal anti-inflammatory agent (NSAID) that inhibits the enzyme cyclooxygenase necessary for the formation of prostaglandins and other autacoids. It also inhibits the motility of polymorphonuclear leukocytes.

A class of phenolic acids related to chlorogenic acid, p-coumaric acid, vanillic acid, etc., which are found in plant tissues. It is involved in plant growth regulation.

Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes.

Granular leukocytes having a nucleus with three to five lobes connected by slender threads of chromatin, and cytoplasm containing fine inconspicuous granules and stainable by neutral dyes.

A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed)

Enzymes that catalyze reversibly the formation of an epoxide or arene oxide from a glycol or aromatic diol, respectively.

Cells propagated in vitro in special media conducive to their growth. Cultured cells are used to study developmental, morphologic, metabolic, physiologic, and genetic processes, among others.

The outer zone of the KIDNEY, beneath the capsule, consisting of KIDNEY GLOMERULUS; KIDNEY TUBULES, DISTAL; and KIDNEY TUBULES, PROXIMAL.

Phospholipases that hydrolyze the acyl group attached to the 2-position of PHOSPHOGLYCERIDES.

FATTY ACIDS in which the carbon chain contains one or more double or triple carbon-carbon bonds.

A branch of the abdominal aorta which supplies the kidneys, adrenal glands and ureters.

A stable, physiologically active compound formed in vivo from the prostaglandin endoperoxides. It is important in the platelet-release reaction (release of ADP and serotonin).

The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)

A group of compounds derived from unsaturated 20-carbon fatty acids, primarily arachidonic acid, via the cyclooxygenase pathway. They are extremely potent mediators of a diverse group of physiological processes.

A constitutively-expressed subtype of prostaglandin-endoperoxide synthase. It plays an important role in many cellular processes.

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Chemical agents that increase the permeability of biological or artificial lipid membranes to specific ions. Most ionophores are relatively small organic molecules that act as mobile carriers within membranes or coalesce to form ion permeable channels across membranes. Many are antibiotics, and many act as uncoupling agents by short-circuiting the proton gradient across mitochondrial membranes.

Organic compounds that include a cyclic ether with three ring atoms in their structure. They are commonly used as precursors for POLYMERS such as EPOXY RESINS.

Body organ that filters blood for the secretion of URINE and that regulates ion concentrations.

Phospholipases that hydrolyze one of the acyl groups of phosphoglycerides or glycerophosphatidates.

The nonstriated involuntary muscle tissue of blood vessels.

The species Oryctolagus cuniculus, in the family Leporidae, order LAGOMORPHA. Rabbits are born in burrows, furless, and with eyes and ears closed. In contrast with HARES, rabbits have 22 chromosome pairs.

Single pavement layer of cells which line the luminal surface of the entire vascular system and regulate the transport of macromolecules and blood components.

The most common and most biologically active of the mammalian prostaglandins. It exhibits most biological activities characteristic of prostaglandins and has been used extensively as an oxytocic agent. The compound also displays a protective effect on the intestinal mucosa.

Important polyunsaturated fatty acid found in fish oils. It serves as the precursor for the prostaglandin-3 and thromboxane-3 families. A diet rich in eicosapentaenoic acid lowers serum lipid concentration, reduces incidence of cardiovascular disorders, prevents platelet aggregation, and inhibits arachidonic acid conversion into the thromboxane-2 and prostaglandin-2 families.

The physiological narrowing of BLOOD VESSELS by contraction of the VASCULAR SMOOTH MUSCLE.

The physiological widening of BLOOD VESSELS by relaxing the underlying VASCULAR SMOOTH MUSCLE.

The circulation of the BLOOD through the vessels of the KIDNEY.

Placing of a hydroxyl group on a compound in a position where one did not exist before. (Stedman, 26th ed)

The relationship between the dose of an administered drug and the response of the organism to the drug.

The internal portion of the kidney, consisting of striated conical masses, the renal pyramids, whose bases are adjacent to the cortex and whose apices form prominent papillae projecting into the lumen of the minor calyces.

A cytoplasmic serine threonine kinase involved in regulating CELL DIFFERENTIATION and CELLULAR PROLIFERATION. Overexpression of this enzyme has been shown to promote PHOSPHORYLATION of BCL-2 PROTO-ONCOGENE PROTEINS and chemoresistance in human acute leukemia cells.

An analytical method used in determining the identity of a chemical based on its mass using mass analyzers/mass spectrometers.

The phenomenon whereby certain chemical compounds have structures that are different although the compounds possess the same elemental composition. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)

An octapeptide that is a potent but labile vasoconstrictor. It is produced from angiotensin I after the removal of two amino acids at the C-terminal by ANGIOTENSIN CONVERTING ENZYME. The amino acid in position 5 varies in different species. To block VASOCONSTRICTION and HYPERTENSION effect of angiotensin II, patients are often treated with ACE INHIBITORS or with ANGIOTENSIN II TYPE 1 RECEPTOR BLOCKERS.

Structurally related forms of an enzyme. Each isoenzyme has the same mechanism and classification, but differs in its chemical, physical, or immunological characteristics.

Chromatography on thin layers of adsorbents rather than in columns. The adsorbent can be alumina, silica gel, silicates, charcoals, or cellulose. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)

PRESSURE of the BLOOD on the ARTERIES and other BLOOD VESSELS.

The intracellular transfer of information (biological activation/inhibition) through a signal pathway. In each signal transduction system, an activation/inhibition signal from a biologically active molecule (hormone, neurotransmitter) is mediated via the coupling of a receptor/enzyme to a second messenger system or to an ion channel. Signal transduction plays an important role in activating cellular functions, cell differentiation, and cell proliferation. Examples of signal transduction systems are the GAMMA-AMINOBUTYRIC ACID-postsynaptic receptor-calcium ion channel system, the receptor-mediated T-cell activation pathway, and the receptor-mediated activation of phospholipases. Those coupled to membrane depolarization or intracellular release of calcium include the receptor-mediated activation of cytotoxic functions in granulocytes and the synaptic potentiation of protein kinase activation. Some signal transduction pathways may be part of larger signal transduction pathways; for example, protein kinase activation is part of the platelet activation signal pathway.

Any of the processes by which nuclear, cytoplasmic, or intercellular factors influence the differential control of gene action in enzyme synthesis.

Lipids containing one or more phosphate groups, particularly those derived from either glycerol (phosphoglycerides see GLYCEROPHOSPHOLIPIDS) or sphingosine (SPHINGOLIPIDS). They are polar lipids that are of great importance for the structure and function of cell membranes and are the most abundant of membrane lipids, although not stored in large amounts in the system.

The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5)

Highly reactive compounds produced when oxygen is reduced by a single electron. In biological systems, they may be generated during the normal catalytic function of a number of enzymes and during the oxidation of hemoglobin to METHEMOGLOBIN. In living organisms, SUPEROXIDE DISMUTASE protects the cell from the deleterious effects of superoxides.

An inducibly-expressed subtype of prostaglandin-endoperoxide synthase. It plays an important role in many cellular processes and INFLAMMATION. It is the target of COX2 INHIBITORS.

A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471).

Endothelin-1 and CYP450 arachidonate metabolites interact to promote tissue injury in DOCA-salt hypertension. (1/901)

Inhibition of cytochrome P-450 (CYP450) enzymes with cobalt chloride (CoCl2) prevented hypertension, organ hypertrophy, and renal injury induced by DOCA and salt (1% NaCl) in uninephrectomized (UNx) rats. Systolic blood pressure (SBP) rose to 193 +/- 6 mmHg by day 21 from control levels of 150 +/- 7 mmHg in response to DOCA-salt treatment, a rise that was prevented by CoCl2 (24 mg. kg-1. 24 h-1). The effects of DOCA-salt treatment, which increased protein excretion to 88.3 +/- 6.9 mg/24 h on day 21 from 9.0 +/- 1.1 mg/24 h on day 3, were prevented by CoCl2. CoCl2 also attenuated the renal and left ventricular hypertrophy and the increase in media-to-lumen ratio in hypertensive rats. DOCA-salt treatment increased excretion of endothelin (ET)-1 from 81 +/- 17 to 277 +/- 104 pg. 100 g body wt-1. 24 h-1 associated with a fourfold increase in 20-hydroxyeicosatetraenoic acid (20-HETE) excretion from 3.0 +/- 1.1 to 12.2 +/- 1.9 ng. 100 g body wt-1. 24 h-1 (days 3 vs. 21). CoCl2 blunted these increases by 58 and 72%, respectively. In aortic rings pulsed with [3H]thymidine, ET-1 increased its incorporation. Dibromododec-11-enoic acid, an inhibitor of 20-HETE synthesis, attenuated ET-1-induced increases in [3H]thymidine incorporation. We distinguished effects of CoCl2 acting via CO generation vs. suppression of CYP450-arachidonic acid metabolism by treating UNx-salt-DOCA rats with 1-aminobenzotriazole (ABT), which suppresses CYP450 enzyme activity, and compared these results to those produced by CoCl2. ABT reduced hypertension, as did CoCl2. Unlike CoCl2, ABT did not prevent organ hypertrophy and proteinuria, suggesting that these effects were partially related to CO formation. Blockade of the ETA receptor with BMS-182874 reduced SBP, organ hypertrophy, and proteinuria, indicating the importance of ET-initiated abnormalities to the progression of lesions in UNx-salt-DOCA. (+info)

Regulation of human airway mucins by acrolein and inflammatory mediators. (2/901)

Bronchitis, asthma, and cystic fibrosis, marked by inflammation and mucus hypersecretion, can be caused or exacerbated by airway pathogens or irritants including acrolein, an aldehyde present in tobacco smoke. To determine whether acrolein and inflammatory mediators alter mucin gene expression, steady-state mRNA levels of two airway mucins, MUC5AC and MUC5B, were measured (by RT-PCR) in human lung carcinoma cells (NCI-H292). MUC5AC mRNA levels increased after >/=0.01 nM acrolein, 10 microM prostaglandin E2 or 15-hydroxyeicosatetraenoic acid, 1.0 nM tumor necrosis factor-alpha (TNF-alpha), or 10 nM phorbol 12-myristate 13-acetate (a protein kinase C activator). In contrast, MUC5B mRNA levels, although easily detected, were unaffected by these agonists, suggesting that irritants and associated inflammatory mediators increase mucin biosynthesis by inducing MUC5AC message levels, whereas MUC5B is constitutively expressed. When transcription was inhibited, TNF-alpha exposure increased MUC5AC message half-life compared with control level, suggesting that transcript stabilization is a major mechanism controlling increased MUC5AC message levels. Together, these findings imply that irritants like acrolein can directly and indirectly (via inflammatory mediators) increase airway mucin transcripts in epithelial cells. (+info)

LXA4, aspirin-triggered 15-epi-LXA4, and their analogs selectively downregulate PMN azurophilic degranulation. (3/901)

The eicosanoid lipoxin A4 (LXA4) is biosynthesized in vivo by cells present at inflammatory sites and appears to be an endogenous anti-inflammatory mediator. Further, in the presence of aspirin, the 15-epimer of LXA4 (15-epi-LXA4) is biosynthesized and may mediate some of aspirin's desirable bioactions. LXA4, 15-epi-LXA4, and their stable analogs inhibit inflammation in established animal models, indicating that these compounds may be useful for treating inflammatory disease states. To investigate the cellular mechanisms by which these lipid mediators downregulate inflammation, we investigated whether these eicosanoids could influence receptor-mediated degranulation of human neutrophils, an event thought to play a major causative role in several inflammatory disease states. LXA4, 15-epi-LXA4, and their stable analogs potently (IC50 < 1 nM) and selectively downregulated neutrophil release of azurophilic granule contents but did not affect other neutrophil secretory functions. Thus the cellular basis of action of these natural off-switches to inflammation appears to involve downregulation of neutrophil azurophilic granule release. (+info)

Albumin modifies the metabolism of hydroxyeicosatetraenoic acids via 12-lipoxygenase in human platelets. (4/901)

12-Lipoxygenase and cyclooxygenase 1 are the dominating enzymes that metabolize arachidonic acid in human platelets. In addition to the conversion of arachidonic acid to 12(S)-hydroxyeicosatetraenoic acid, 12-lipoxygenase can also utilize 5(S)-hydroxyeicosatetraenoic acid and 15(S)-hydroxyeicosatetraenoic acid to form 5(S), 12(S)-dihydroxyeicosatetraenoic acid and 14(R), 15(S)-dihydroxyeicosatetraenoic acid, respectively. Furthermore, 15(S)-hydroxyeicosatetraenoic acid works as an inhibitor for 12-lipoxygenase. In the present paper we have studied the influence of albumin on the in vitro metabolism of 5 - and 15 -hydroxyeicosatetraenoic acids, and 5,15 -dihydroxyeicosatetraenoic acid by the platelet 12-lipoxygenase. The presence of albumin reduced the formation of 5(S),12(S)- dihydroxyeicosatetraenoic acid from 5(S)-hydroxyeicosatetraenoic acid, however, it had no effect on the 12(S)-hydroxyeicosatetraenoic acid production from endogenous arachidonic acid. In contrast, when 15(S)-hydroxyeicosatetraenoic acid was incubated with activated platelets, the formation of 14(R), 15(S)- dihydroxyeicosatetraenoic acid was stimulated by the presence of albumin. Furthermore, albumin reduced the inhibitory action 15(S)-hydroxyeicosatetraenoic acid had on 12(S)-hydroxyeicosatetraenoic acid formation from endogenous arachidonic acid. However, addition of exogenous arachidonic acid (20 microm) to the incubations inverted the effects of albumin on the conversion of 15(S)-hydroxyeicosatetraenoic acid to 14(R),15(S)- dihydroxyeicosatetraenoic acid and the production of 12(S)-hydroxyeicosatetraenoic acid in these incubations. Based on the Scatchard equation, the estimates of the binding constants to albumin were 1.8 x 10(5) for 15 -HETE, 1.4 x 10(5) for 12-HETE, and 0.9 x 10(5) for 5 -HETE respectively. These results suggest an important role of albumin for the regulation of the availability of substrates for platelet 12-lipoxygenase. (+info)

Polyisoprenyl phosphate (PIPP) signaling regulates phospholipase D activity: a 'stop' signaling switch for aspirin-triggered lipoxin A4. (5/901)

It is of wide interest to understand how opposing extracellular signals (positive or negative) are translated into intracellular signaling events. Receptor-ligand interactions initiate the generation of bioactive lipids by human neutrophils (PMN), which serve as signals to orchestrate cellular responses important in host defense and inflammation. We recently identified a novel polyisoprenyl phosphate (PIPP) signaling pathway and found that one of its components, presqualene diphosphate (PSDP), is a potent negative intracellular signal in PMN that regulates superoxide anion generation by several stimuli, including phosphatidic acid. We determined intracellular PIPP signaling by autocoids with opposing actions on PMN: leukotriene B4 (LTB4), a potent chemoattractant, and lipoxin A4 (LXA4), a 'stop signal' for recruitment. LTB4 receptor activation initiated a rapid decrease in PSDP levels concurrent with activation of PLD and cellular responses. In sharp contrast, activation of the LXA4 receptor reversed LTB4-initiated PSDP remodeling, leading to an accumulation of PSDP and potent inhibition of both PLD and superoxide anion generation. Thus, an inverse relationship was established for PSDP levels and PLD activity with two PMN ligands that evoke opposing responses. In addition, PSDP directly inhibited both isolated human recombinant (Ki = 6 nM) and plant (Ki = 20 nM) PLD. Together, these findings link PIPP remodeling to intracellular regulation of PMN function and suggest a role for PIPPs as lipid repressors in signal transduction, a novel mechanism that may also explain aspirin's suppressive actions in vivo in cell signaling. (+info)

Angiotensin II inhibits HCO-3 absorption via a cytochrome P-450-dependent pathway in MTAL. (6/901)

The role of ANG II in the regulation of ion reabsorption by the renal thick ascending limb is poorly understood. Here, we demonstrate that ANG II (10(-8) M in the bath) inhibits HCO-3 absorption by 40% in the isolated, perfused medullary thick ascending limb (MTAL) of the rat. The inhibition by ANG II was abolished by pretreatment with eicosatetraynoic acid (10 microM), a general inhibitor of arachidonic acid metabolism, or 17-octadecynoic acid (10 microM), a highly selective inhibitor of cytochrome P-450 pathways. Bath addition of 20-hydroxyeicosatetraenoic acid (20-HETE; 10(-8) M), the major P-450 metabolite in the MTAL, inhibited HCO-3 absorption, whereas pretreatment with 20-HETE prevented the inhibition by ANG II. The addition of 15-HETE (10(-8) M) to the bath had no effect on HCO-3 absorption. The inhibition of HCO-3 absorption by ANG II was reduced by >50% in the presence of the tyrosine kinase inhibitors genistein (7 microM) or herbimycin A (1 microM). We found no role for cAMP, protein kinase C, or NO in the inhibition by ANG II. However, addition of the exogenous NO donor S-nitroso-N-acetylpenicillamine (SNAP; 10 microM) or the NO synthase (NOS) substrate L-arginine (1 mM) to the bath stimulated HCO-3 absorption by 35%, suggesting that NO directly regulates MTAL HCO-3 absorption. Addition of 10(-11) to 10(-10) M ANG II to the bath did not affect HCO-3 absorption. We conclude that ANG II inhibits HCO-3 absorption in the MTAL via a cytochrome P-450-dependent signaling pathway, most likely involving the production of 20-HETE. Tyrosine kinase pathways also appear to play a role in the ANG II-induced transport inhibition. The inhibition of HCO-3 absorption by ANG II in the MTAL may play a key role in the ability of the kidney to regulate sodium balance and extracellular fluid volume independently of acid-base balance. (+info)

Kinetic profile of the rat CYP4A isoforms: arachidonic acid metabolism and isoform-specific inhibitors. (7/901)

20-Hydroxyeicosatetraenoic acid (HETE), the cytochrome P-450 (CYP) 4A omega-hydroxylation product of arachidonic acid, has potent biological effects on renal tubular and vascular functions and on the control of arterial pressure. We have expressed high levels of the rat CYP4A1, -4A2, -4A3, and -4A8 cDNAs, using baculovirus and Sf 9 insect cells. Arachidonic acid omega- and omega-1-hydroxylations were catalyzed by three of the CYP4A isoforms; the highest catalytic efficiency of 947 nM-1. min-1 for CYP4A1 was followed by 72 and 22 nM-1. min-1 for CYP4A2 and CYP4A3, respectively. CYP4A2 and CYP4A3 exhibited an additional arachidonate 11,12-epoxidation activity, whereas CYP4A1 operated solely as an omega-hydroxylase. CYP4A8 did not catalyze arachidonic or linoleic acid but did have a detectable lauric acid omega-hydroxylation activity. The inhibitory activity of various acetylenic and olefinic fatty acid analogs revealed differences and indicated isoform-specific inhibition. These studies suggest that CYP4A1, despite its low expression in extrahepatic tissues, may constitute the major source of 20-HETE synthesis. Moreover, the ability of CYP4A2 and -4A3 to catalyze the formation of two opposing biologically active metabolites, 20-HETE and 11, 12-epoxyeicosatrienoic acid, may be of great significance to the regulation of vascular tone. (+info)

Regulation of P-450 4A activity in the glomerulus of the rat. (8/901)

We recently reported that an enzyme of the cytochrome P-450 4A family is expressed in the glomerulus, but there is no evidence that 20-hydroxyeicosatetraenoic acid (20-HETE) can be produced by this tissue. The purpose of present study was to determine whether glomeruli isolated from the kidney of rats can produce 20-HETE and whether the production of this metabolite is regulated by nitric oxide (NO) and dietary salt intake. Isolated glomeruli produced 20-HETE, dihydroxyeicosatrienoic acids, and 12-hydroxyeicosatetraenoic acid (4.13 +/- 0.38, 4.20 +/- 0.38, and 2. 10 +/- 0.20 pmol. min-1. mg protein-1, respectively) when incubated with arachidonic acid (10 microM). The formation of 20-HETE was dependent on the availability of NADPH and the PO2 of the incubation medium. The formation of 20-HETE was inhibited by NO donors in a concentration-dependent manner. The production of 20-HETE was greater in glomeruli isolated from the kidneys of rats fed a low-salt diet than in kidneys of rats fed a high-salt diet (5.67 +/- 0.32 vs. 2.83 +/- 0.32 pmol. min-1. mg protein-1). Immunoblot experiments indicated that the expression of P-450 4A protein in glomeruli from the kidneys of rats fed a low-salt diet was sixfold higher than in kidneys of rats fed a high-salt diet. These results indicate that arachidonic acid is primarily metabolized to 20-HETE and dihydroxyeicosatrienoic acids in glomeruli and that glomerular P-450 activity is modulated by NO and dietary salt intake. (+info)

... may refer to: 5-Hydroxyeicosatetraenoic acid 12-Hydroxyeicosatetraenoic acid (12-HETE) 15- ... Hydroxyeicosatetraenoic acid 20-Hydroxyeicosatetraenoic acid (20-HETE) 19-Hydroxyeicosatetraenoic acid (see 20- ... Hydroxyeicosatetraenoic acid) This set index page lists chemical compounds articles associated with the same name. If an ...

https://en.wikipedia.org/wiki/Hydroxyeicosatetraenoic_acid

... (5-HETE, 5(S)-HETE, or 5S-HETE) is an eicosanoid, i.e. a metabolite of arachidonic acid. It is ... 5-Hydroxyeicosatetraenoic acid is more properly termed 5(S)-hydroxyicosatetraenoic acid or 5(S)-HETE) to signify the (S) ... dihydroxyeicosatetraenoic acid (5(S),15(S)-diHETE), or 5-oxo-15-hydroxyeicosatetraenoic acid (5-oxo-15(S)-HETE). 5(S)-HETE, 5- ... arachidonic acid 5-hydroperoxide i.e. 5S-hydroperoxy-6E,8Z,11Z,14Z-eicosatetraenoic acid (5(S)-HpETE). 5-(S)-HpETE may then be ...

https://en.wikipedia.org/wiki/5-Hydroxyeicosatetraenoic_acid

15S-dihydroxy-eicosatetraenoic acid (5(S),15(S)-diHETE), 5-oxo-15(S)-hydroxyeicosatetraenoic acid (5-oxo-15(S)-HETE, a subset ... 15Z-eicosatetraenoic acid (12(S)-hydroxyeicosatetraenoic acid), (i.e. 12(S)-HETE), respectively, or further metabolized through ... hydroperoxyeicosatetraenoic acid and (15S)-hydroxyeicosatetraenoic acid on the acute- lymphoblastic-leukaemia cell line Jurkat ... 13E-eicosatetraenoic acid (15(R)-HpETE). Human cells release arachidonic acid (i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid) from ...

https://en.wikipedia.org/wiki/15-Hydroxyeicosatetraenoic_acid

... (12-HETE) is a derivative of the 20 carbon polyunsaturated fatty acid, arachidonic acid, ... 5-Hydroxyeicosatetraenoic acid 15-Hydroxyeicosatetraenoic acid Hamberg, M; Samuelsson, B (1974). "Prostaglandin endoperoxides. ... and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid ... Herbertsson H, Kühme T, Hammarström S (Jul 1999). "The 650-kDa 12(S)-hydroxyeicosatetraenoic acid binding complex: occurrence ...

https://en.wikipedia.org/wiki/12-Hydroxyeicosatetraenoic_acid

... , also known as 20-HETE or 20-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid, is an eicosanoid ... lauric acid) and/or longer chain (e.g. docosahexaenoic acid) fatty acids. They can also ω-hydroxylate and thereby reduce the ... 14Z-eicosatetraenoic acid, then to 18-carboxy-5Z,8Z,10Z,14Z-octadecatetraenoic acid, and then to the further chain-shortened ... 14Z-eicosatetraenoic acid which is rapidly reduced to 11,20-dihydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid; they also metabolize ...

https://en.wikipedia.org/wiki/20-Hydroxyeicosatetraenoic_acid

12-Hydroxyeicosatetraenoic acid (S isomer)= 12-hydroperoxyeicosatetraenoic acid (S isomer)>15-Hydroxyeicosatetraenoic acid (S ... 5S-hydroperoxy-eicosatetraenoic acid>5-Hydroxyeicosatetraenoic acid; the 5-oxo-eicosatrienoic and 5-oxo-octadecadienoic acid ... and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid ... see 5-Hydroxyeicosatetraenoic acid); relative potencies of the latter metabolites in binding to and activating OXER1 are: 5- ...

https://en.wikipedia.org/wiki/Eicosanoid_receptor

McGiff, John C.; Quilley, John (March 2001). "20-Hydroxyeicosatetraenoic acid and epoxyeicosatrienoic acids and blood pressure ... Imig, John D. (1 July 2013). "Epoxyeicosatrienoic acids, 20-hydroxyeicosatetraenoic acid, and renal microvascular function". ... 15-epoxyeicosatrienoic acids (EETs) and of 19- and 20-hydroxyeicosatetraenoic acids (19- and 20-HETEs), and characterized them ... epoxyeicosatrienoic acid (EET) and hydration products 5(R),6(R)- and 14(R),15(R)-dihydroxyeicosatrienoic acid (DHET)". Journal ...

https://en.wikipedia.org/wiki/John_R._Falck

... hydroxyeicosatetraenoic acids (HETEs), e.g. 5-HETE and 12-HETE; and oxoeicosanoids (oxo-ETE), e.g. 5-oxo-eicosatetraenoic acid ... Lipoxins are derived enzymatically from arachidonic acid, an ω-6 fatty acid. Structurally, they are defined as arachidonic acid ... which are metabolites of the omega 3 fatty acids, eicosapentaenoic acid or docosahexaenoic acid, as well as a range of ... 13E-eicosatetraenoic acid 15-epi-LxB4: 5S,14R,15R-trihydroxy-6E,8Z,10E,12E-eicosatrienoic acid Note that the two LXs have their ...

https://en.wikipedia.org/wiki/Lipoxin

This enzyme participates in arachidonic acid metabolism. Sok DE, Kang JB, Shin HD (1988). "15-Hydroxyeicosatetraenoic acid ... H+ The 3 substrates of this enzyme are 15-Hydroxyicosatetraenoic acid (i.e. 15(S)-15-hydroxy-5,8,11-cis-13-trans- ...

https://en.wikipedia.org/wiki/15-hydroxyicosatetraenoate_dehydrogenase

... is also a precursor to anandamide. Some arachidonic acid is converted into hydroxyeicosatetraenoic acids ( ... and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid ... β-hydroxy β-methylbutyric acid (HMB), and phosphatidic acids. Arachidonic acid is one of the most abundant fatty acids in the ... 5-oxo-eicosatetraenoic acid (5-oxo-ETE) (also see 5-Hydroxyeicosatetraenoic acid. The enzymes 15-lipoxygenase-1 (ALOX15 and 15- ...

https://en.wikipedia.org/wiki/Arachidonic_acid

... as active in metabolizing arachidonic acid to 20-hydroxyeicosatetraenoic acid (20-HETE) by an omega oxidation reaction with the ... and therapeutic modulation of 20-hydroxyeicosatetraenoic acid (20-HETE) synthase and fatty acid ω-hydroxylase activities". ... "Functional variant of CYP4A11 20-hydroxyeicosatetraenoic acid synthase is associated with essential hypertension". Circulation ... "Functional variant of CYP4A11 20-hydroxyeicosatetraenoic acid synthase is associated with essential hypertension". Circulation ...

https://en.wikipedia.org/wiki/CYP4A22

... see 20-Hydroxyeicosatetraenoic acid, Epoxyeicosatetraenoic acid, and Epoxydocosapentaenoic acid sections on activities and ... CYP4A11 along with CYP4A22, CYP4F2, and CYP4F3 metabolize arachidonic acid to 20-Hydroxyeicosatetraenoic acid (20-HETE) by an ... see 20-Hydroxyeicosatetraenoic acid). In its capacity to form hydroxyl fatty acid, CYP4A11 is classified as a CYP monooxygease ... 20-epoxy-eicosapentaenoic acid isomers [i.e. 19,20-EDPs]) and eicosapentaenoic acid to epoxyeicosatetraenoic acids (EEQs, ...

https://en.wikipedia.org/wiki/CYP4A11

February 2010). "15-hydroxyeicosatetraenoic acid is a preferential peroxisome proliferator-activated receptor beta/delta ... These agents include various polyunsaturated fatty acids like arachidonic acid and arachidonic acid metabolites such as certain ... PPARG regulates fatty acid storage and glucose metabolism. The genes activated by PPARG stimulate lipid uptake and adipogenesis ... PPARG increases insulin sensitivity by enhancing storage of fatty acids in fat cells (reducing lipotoxicity), by enhancing ...

https://en.wikipedia.org/wiki/Peroxisome_proliferator-activated_receptor_gamma

... along with CYP4A22, CYP4A11, CYP4F3 and CYP2U1 also metabolize arachidonic acid to 20-Hydroxyeicosatetraenoic acid (20- ... and saturated fatty acids, such as lauric acid and stearic acid, induce CYP4F2. Besides that, there were findings that ... Lasker JM, Chen WB, Wolf I, Bloswick BP, Wilson PD, Powell PK (February 2000). "Formation of 20-hydroxyeicosatetraenoic acid, a ... It is α-, β-, and ω-oxidation of fatty acid carbon chains that degrades the acids, with the preferred pathway being the β- ...

https://en.wikipedia.org/wiki/CYP4F2

The enzyme also hydroxylates arachidonic acid (i.e. eicosatetraenoic acid to 20-Hydroxyeicosatetraenoic acid) (20-HETE) ... 12-hydroxyeicosatetraenoic acid (12-HETE) to 12,20-diHETE, lipoxins and possibly 5-oxo-eicosatetraenoic acid (5-oxo-ETE) to ... see 20-Hydroxyeicosatetraenoic acid). In spite of its relative impotency and/or importance in accomplishing these omega- ... "Functional variant of CYP4A11 20-hydroxyeicosatetraenoic acid synthase is associated with essential hypertension". Circulation ...

https://en.wikipedia.org/wiki/CYP4F11

"Oxidation of 15-hydroxyeicosatetraenoic acid and other hydroxy fatty acids by lung prostaglandin dehydrogenase". Archives of ... 10E-trienoic acid, or 12(S)-HHTrE) is a 17 carbon metabolite of the 20 carbon polyunsaturated fatty acid, arachidonic acid. It ... 8E-heptadecadienoic acid (12-oxo-5Z,8E-heptadecadienoic acid) and 12-hydroxy-heptadecadienoic acid. Acidic conditions (pH~1.1- ... Leukotriene B4 receptor 2 Leukotriene B4 receptor 1 Leukotriene B4 12-Hydroxyeicosatetraenoic acid 15-hydroxyicosatetraenoic ...

https://en.wikipedia.org/wiki/12-Hydroxyheptadecatrienoic_acid

... and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid ... Phospholipid-bound arachidonic acid → free arachidonic acid b) Free arachidonic acid + O2 → 5(S)-HpETE c) 5(S)-HpETE → 5(S)- ... 5-HETE and 5-hydroxy-15(S)-hydroxyeicosatetraenoic acid are examples of such analogs. 5-Oxo-ETE and many of its analogs are ... 5-Oxo-eicosatetraenoic acid (i.e. 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid; also termed 5-oxo-ETE and 5-oxoETE) is a ...

https://en.wikipedia.org/wiki/5-Oxo-eicosatetraenoic_acid

12-Hydroxyeicosatetraenoic acid, 15-Hydroxyeicosatetraenoic acid, and 20-Hydroxyeicosatetraenoic acid show numerous activities ... metabolize arachidonic acid to 20-Hydroxyeicosatetraenoic acid (20-HETE) and 19-hydroxyeicosatetraenoic acid by an omega ... 15-Hydroxyeicosatetraenoic acid (i.e. 15-HETE), 20-Hydroxyeicosatetraenoic acid (i.e. 20-HETE), and 19-HETE (see 20- ... and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid ...

https://en.wikipedia.org/wiki/Eicosanoid

... to 19-hydroxyeicosatetraenoic acid (i.e. 19-HETE; see 20-hydroxyeicosatetraenoic acid); eicosapentaenoic acid (i.e. EPA) to ... 5-hydroxyeicosatetraenoic acid (5-HETE) to 5,20-diHETE, 5-oxo-eicosatetraenoic acid (5-oxo-ETE) to 5-oxo,20-hydroxy-ETE, 12- ... They also metabolize AA to 18-hydroxyeicosatetraenoic acid (18-HETE) and 19-HETE. CYP4F11 inactivates or reduces the activity ... CYP4F22 ω-hydroxylates extremely long "very long chain fatty acids", i.e. fatty acids that are 28 or more carbons long. The ω- ...

https://en.wikipedia.org/wiki/Cytochrome_P450

Tandem cyclopropanation/fragmentation is a key step in the synthesis of 12-hydroxyeicosatetraenoic acid. (12) Simmons-Smith ...

https://en.wikipedia.org/wiki/Intermolecular_metal-catalyzed_carbenoid_cyclopropanations

If arachidonate is acted upon by a lipoxygenase instead of cyclooxygenase, Hydroxyeicosatetraenoic acids and leukotrienes are ... cancer cells can display irregular fatty acid metabolism with regard to both fatty acid synthesis and mitochondrial fatty acid ... The fatty acids in the fats obtained from land animals tend to be saturated, whereas the fatty acids in the triglycerides of ... Fatty acids are broken down to acetyl-CoA by means of beta oxidation inside the mitochondria, whereas fatty acids are ...

https://en.wikipedia.org/wiki/Fatty_acid_metabolism

14Z-eicosatetraenoic acid (see 20-Hydroxyeicosatetraenoic acid) and 12(S)-hydroperoxy-5Z,8Z,10E,12S,14Z-eicosatetraenoic acid ( ... are metabolites of the omega 3 fatty acids, eicosapentaenoic acid (for RvE1) or docosahexaenoic acid (for RvD2, NPD1, and Mar1 ... Wen H, Östman J, Bubb KJ, Panayiotou C, Priestley JV, Baker MD, Ahluwalia A (April 2012). "20-Hydroxyeicosatetraenoic acid (20- ... The metabolites of linoleic acid, including 13(S)-hydroxy-9Z,11E-octadecadienoic acid (13(S)-HODE), 13(R)-hydroxy-9Z,11E- ...

https://en.wikipedia.org/wiki/TRPV1

... and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid ... CYP4F3A and/or CYP43FB also omega oxidize arachidonic acid to 20-Hydroxyeicosatetraenoic acid (20-HETE) as well as ... 5-oxo-eicosatetraenoic acid, and 12-hydroxyeicosatetraenoic acid by an omega oxidation reaction, i.e. by adding a hydroxyl ... see 20-Hydroxyeicosatetraenoic acid#Cancer). EETS have a similar set of regulatory functions but often act in a manner opposite ...

https://en.wikipedia.org/wiki/CYP4F3

5-oxo-15-hydroxy-eicosatetraenoic acid, and 5-Hydroxyeicosatetraenoic acid. This family of agonists stimulates chemotactic ... and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid ... 5-hydroxyeicosatrieonic acid and 5-oxoeicosatrienoic acid are metabolites of Mead acid (5Z,8Z,11Z-eicosatrirenoid acid); they ... 12-Hydroxyeicosatetraenoic acid is an eicosanoid metabolite of arachidonic acid made by ALOX12 which stimulates leukocyte ...

https://en.wikipedia.org/wiki/Chemotaxis

... and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid ... ALOX5 products, particularly 5-hydroxyeicosatetraenoic acid and 5-oxo-eicosatetraenoic acid, promote the proliferation of these ... ALOX5 metabolizes the omega-3 fatty acid, Eicosapentaenoic acid (EPA, i.e. 4Z,8Z,11Z,14Z,17Z-eiosapentaenoic acid), to 5- ... ALOX5 metabolizes the omega-6 fatty acid, Arachidonic acid (AA, i.e. 5Z,8Z,11Z,15Z-eicosatrienoic acid), to 5- ...

https://en.wikipedia.org/wiki/Arachidonate_5-lipoxygenase

... and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid ... and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid ... 8Z-octadecadienoic acid (5-LO metabolites of sebaleic acid, i.e. 5Z,8Z-octadecadienoic acid); and 5(S)-hydroxy-6E,8Z,11Z,14Z, ... 11Z-eicosatrienoic acid (a 5-LO metabolite of mead acid); 5(S)-hydroxy-6E,8Z-octadecadienoic acid and 5(S)-oxo-6E, ...

https://en.wikipedia.org/wiki/Oxoeicosanoid_receptor_1

... and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid ... Omega hydroxy acids (also known as ω-hydroxy acids) are a class of naturally occurring straight-chain aliphatic organic acids n ... This metabolism of arachidonic acid produces 20-hydroxyarachidonic acid (i.e. 20-hydroxyeicosatetraeonic acid or 20-HETE), a ... The C16 and C18 omega hydroxy acids 16-hydroxy palmitic acid and 18-hydroxy stearic acid are key monomers of cutin in the plant ...

https://en.wikipedia.org/wiki/Omega_hydroxy_acid

2022). "20-hydroxyeicosatetraenoic acid (20-HETE) is a pivotal endogenous ligand for TRPV1-mediated neurogenic inflammation in ... They include vanillyl alcohol, vanillin, vanillic acid, acetovanillon, vanillylmandelic acid, homovanillic acid, capsaicin, etc ... 20-Hydroxyeicosatetraenoic_acid(20-HETE),N-Arachidonoyl_dopamine (NADA) and N-oleoyl-dopamineCID 5282106 from PubChem. Outside ...

https://en.wikipedia.org/wiki/Vanilloids

... increased production of 20-Hydroxyeicosatetraenoic acid (20-HETE); it is hypothesized that CYP4Z1 metabolizes arachidonic acid ... "Human CYP4Z1 catalyzes the in-chain hydroxylation of lauric acid and myristic acid". Biological Chemistry. 390 (4): 313-7. doi: ...

https://en.wikipedia.org/wiki/CYP4Z1

20-hydroxyeicosatetraenoic acid. A study has shown that humans bearing this variant in one or both of their CYP4A11 genes have ... Asp312Asn and Lys751Gln are the two common polymorphisms of XPD that result in a change in a single amino acid. This variation ... This variant protein has reduced enzyme activity in metabolizing arachidonic acid to the blood pressure-regulating eicosanoid, ... nucleotide 8590 position encodes a CYP4A11 protein that substitutes phenylalanine with serine at the protein's amino acid ...

https://en.wikipedia.org/wiki/Gene_polymorphism

... mead acid can form various hydroxyeicosatetraenoic acid (HETE) and hydroperoxy (HpETE) products. Two fatty acids, linoleic acid ... Mead acid, also referred to as eicosatrienoic acid, is chemically a carboxylic acid with a 20-carbon chain and three methylene- ... Both are 18 carbon fatty acids unlike mead acid, which has 20 carbons. Linoleic is an ω-6 fatty acid whereas linolenic is ω-3 ... Under severe conditions of essential fatty acid deprivation, mammals will elongate and desaturate oleic acid to make mead acid ...

https://en.wikipedia.org/wiki/Mead_acid

... see 20-Hydroxyeicosatetraenoic acid), i.e. 19-hydroxyhydroxyeicosatetraenoic acid and/or 20-hydroxyeicosatetranoic acid, take ... 13-epoxides isomers termed coronaric acids or isoleukotoxins. They metabolize the omega-3 fatty acid, docosahexaenoic acid, ... They metabolize the omega-6 fatty acids arachidonic acid, which possess four double bonds, to 8 different epoxide isomers which ... 17Z-eicosatetraenoic acid), 8,9-EEQ (i.e. 8,9-epoxy-5Z,11Z,14Z,17Z-eicosatetraenoic acid), 11,12-EEQ (i.e. 11,12-epoxy-5Z,8Z, ...

https://en.wikipedia.org/wiki/Epoxyeicosatetraenoic_acid

... see 15-Hydroxyeicosatetraenoic acid) and 12(S)-HETE (see 12-Hydroxyeicosatetraenoic acid). 15(S)-HpETE and 15(S)-HETE bind to ... gamma-linolenic acid, arachidonic acid, eicosapentaenoic acid, and docosahexaenoic acid when presented not only as free acids ... 15-Hydroxyicosatetraenoic acid 12-Hydroxyeicosatetraenoic acid GRCh38: Ensembl release 89: ENSG00000161905 - Ensembl, May 2017 ... By metabolizing the ω-3 polyunsaturated fatty acids, eicosapentaenoic acid and docosahexaenoic acid, into 17-HpDHA, 17-HDHA, ...

https://en.wikipedia.org/wiki/ALOX15

... fatty acids and various fatty acid-derived compounds such as certain members of the 15-hydroxyeicosatetraenoic acid family of ... fatty acid binding and activation, and peroxisomal and mitochondrial fatty acid β-oxidation. Activation of fatty acid oxidation ... arachidonic acid metabolites, e.g. 15(S)-HETE, 15(R)-HETE, and 15(S)-HpETE and 13-hydroxyoctadecadienoic acid, a linoleic acid ... Endogenous ligands include fatty acids such as arachidonic acid as well as other polyunsaturated ...

https://en.wikipedia.org/wiki/Peroxisome_proliferator-activated_receptor_alpha

... see 20-Hydroxyeicosatetraenoic acid). The EDP (see Epoxydocosapentaenoic acid) and EEQ (see epoxyeicosatetraenoic acid) ... activity for certain of these fatty acids in that it metabolizes arachidonic acid to 19-hydroxyeicosatetraenoic acid (19-HETE ... see 20-Hydroxyeicosatetraenoic acid) but also has epoxygenase activity in that it metabolizes docosahexaenoic acid to epoxides ... as products of the omega-3 fatty acids, docosahexaenoic acid and eicosapentaenoic acid, the EDP and EEQ metabolites contribute ...

https://en.wikipedia.org/wiki/CYP1A2

... metabolize arachidonic acid (also known as eicosatetraenoic acid) to 20-hydroxyeicosatetraenoic acid (20-HETE). 20-HETE ... The final products after successive oxidations include succinic acid, which can enter the citric acid cycle, and adipic acid. ... and therapeutic modulation of 20-hydroxyeicosatetraenoic acid (20-HETE) synthase and fatty acid ω-hydroxylase activities". ... see 20-Hydroxyeicosatetraenoic acid). Among the CYP450 superfamily, members of the CYP4A and CYP4F subfamilies viz., CYP4A11, ...

https://en.wikipedia.org/wiki/Omega_oxidation

15-Hydroxyeicosatetraenoic acid, 18-hydroxyeicosapentaenoic acid, 17-hydroxydocosahexaenoic acid, and 14-hydroxydocosahexaenoic ... 16Z-docosapentaenoic acid or osbond acid) is an isomer of n-3 DPA (clupanodonic acid) differing form the latter fatty acid only ... SPM are metabolites of arachidonic acid (AA), eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), or n-3 DPA (i.e. 7,10Z, ... hydroxyeicosatetraenoic acids (e.g., 5-HETE, 12-HETE), the hydroxylated heptadecatrieneoic acid, 12-HHT, and oxoeicosanoids (e. ...

https://en.wikipedia.org/wiki/Specialized_pro-resolving_mediators

... see 12-Hydroxyeicosatetraenoic acid) and the hepoxilins (Hx), HxA3 (i.e. 8R/S-hydroxy-11,12-oxido-5Z,9E,14Z-eicosatrienoic acid ... The epoxide, 5,6-epoxy-8Z,11Z,14Z-eicosatrienoic acid (5,6-EET) made by the metabolism of arachidonic acid by any one of ... Resolvin D1 (RvD1) and RvD2 (see resolvins) and maresin 1 are metabolites of the omega 3 fatty acid, docosahexaenoic acid. They ... acid Cannabidivarin Cannabigerol Cannabigerolic acid Cannabigerovarin Tetrahydrocannabivarin Tetrahydrocannabivarin acid WaTx ...

https://en.wikipedia.org/wiki/TRPA1

... see 20-Hydroxyeicosatetraenoic acid). The EDPs (see Epoxydocosapentaenoic acid) and EEQs (see epoxyeicosatetraenoic acid) have ... docosahexaenoic acid (DHA) and eicosapentaenoic acid, (EPA) to their corresponding epoxides, the epoxydocosapentaenoic acids ( ... capable of oxidizing arachidonic acid by adding a hydroxyl residue to carbons 18 or 19 to form 18-hydroxyeicosatetraenoic acid ... The enzyme metabolizes DHA primarily to 19R,20S-epoxyeicosapentaenoic acid and 19S,20R-epoxyeicosapentaenoic acid isomers ( ...

https://en.wikipedia.org/wiki/CYP4F12

5-oxo-eicosatetraenoic acid to 5-oxo-20-hydroxyeicosatetraenoic acid, 12-hydroxyeicosatetraenoic acid to 12,20- ... eicosatetraenoic acid) to the cell signaling molecules, 20-hydroxyeicosatetraenoic acid or to reduce or totally inactivate the ... dihydroxyeicosatetraenoic acid, and epoxyeicosatrienoic acids to 20-hydroxy-epoxyeicosatrienoic acids. They are classified as ... is used by cells to metabolize arachidonic acid (i.e. ...

https://en.wikipedia.org/wiki/Monooxygenase

12-hydroxyicosatetraenoate dehydrogenase which metabolizes 12-Hydroxyeicosatetraenoic acid (12-HETE) and LTB4 to their ... hydroxy-eicosamonoenoic acid, 5(S)-hydroxy-octadecadienoic acid, 5(S),15(S)-dihydroxyeicosatetraenoic acid, and the 6-trans ... hydroxy-eicosapentaenoic acid, 5(S)-hydroxy-eicosatrienoic acid, 5(S)-hydroxy-eicosadeinoic acid, 5(S)- ... The reaction (where R indicates a long chain [14 or more carbons] fatty acid) is: NADP+ + 5(S)-hydroxy fatty acid (i.e. 5(S)-OH ...

https://en.wikipedia.org/wiki/5-Hydroxyeicosanoid_dehydrogenase

It results in an increase of 13-hydroxyoctadecadienoic acid and decrease of 12-hydroxyeicosatetraenoic acid in the ... Acetylsalicylic acid/dipyridamole Cilostazol Nielsen-Kudsk, F; Pedersen, AK (May 1979). "Pharmacokinetics of Dipyridamole". ... A combination of dipyridamole and aspirin (acetylsalicylic acid/dipyridamole) is FDA-approved for the secondary prevention of ... Dipyridamole absorption is pH-dependent and concomitant treatment with gastric acid suppressors (such as a proton pump ...

https://en.wikipedia.org/wiki/Dipyridamole

... of 15-Hydroperoxyicosatetraenoic acid which is commonly reduced to the S stereoisomer 15-Hydroxyeicosatetraenoic acid by ... 15-LOX-2 has 38-39% amino acid sequence identity to human 15-LOX-1 and 12-lipoxygenase and 44% amino acid sequence identity to ... hydroxyeicosatetraenoic acid through a negative feedback mechanism that involves peroxisome proliferator-activated receptor ... converting this fatty acid to the S stereoisomer of 13-hydroperoxyoctadecadienoic acid which is likewise rapidly reduced to the ...

https://en.wikipedia.org/wiki/ALOX15B

5-hydroxyeicosatetraenoic acid, 5-oxo-eicosatetraenoic acid, and specialized pro-resolving mediators of the lipoxin and ... FLAP functions as a membrane anchor for 5-lipooxygenase and as an amine acid-bind protein. How FLAP activates 5-lipooxygenase ... Peters-Golden M, Brock TG (2003). "5-lipoxygenase and FLAP". Prostaglandins, Leukotrienes, and Essential Fatty Acids. 69 (2-3 ... and Essential Fatty Acids. 81 (1): 9-15. doi:10.1016/j.plefa.2009.05.022. PMID 19524426. Zintzaras E, Rodopoulou P, ...

https://en.wikipedia.org/wiki/5-lipoxygenase-activating_protein

... is also reported to have fatty acid monooxgenase activity for metabolizing arachidonic acid to 20-Hydroxyeicosatetraenoic acid ... see 12-hydroxyeicosatetraenoic acid). The CYP3A4 gene exhibits a much more complicated upstream regulatory region in comparison ... CYP3A4 also possesses epoxygenase activity in that it metabolizes arachidonic acid to epoxyeicosatrienoic acids (EETs), i.e ... Wen X, Wang JS, Kivistö KT, Neuvonen PJ, Backman JT (2001). "In vitro evaluation of valproic acid as an inhibitor of human ...

https://en.wikipedia.org/wiki/CYP3A4

... see 20-Hydroxyeicosatetraenoic acid), i.e. 19-hydroxyeicosatetraenoic acid and/or 20-hydroxyeicosatetranoic acid, take on ... Epoxide docosapentaenoic acids (epoxydocosapentaenoic acids, EDPs, or EpDPEs) are metabolites of the 22-carbon straight-chain ... arachidonic acid, to epoxyeicosatrienoic acids (EETs); another CYP epoxygenase pathway metabolizes the 20-carbon omega-3 fatty ... acid, eicosapentaenoic acid (EPA), to epoxyeicosatetraenoic acids (EEQs). CYP epoxygenases similarly convert various other ...

https://en.wikipedia.org/wiki/Epoxydocosapentaenoic_acid

... and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid ... and CYP4F11 ω-hydroxylate leukotriene B4 and very probably 5-hydroxyeicosatetraenoic acid and 5-oxo-eicosatetraenoic acid. This ... and possibly CYP4Z1 metabolize arachidonic acid to 20-Hydroxyeicosatetraenoic acid (20-HETE). Animal and human tissue studies ... One or more of these CYPs also omega hydroxylate 12-hydroxyeicosatetraenoic acid, lipoxins, hepoxilins, and acylceramides and ...

https://en.wikipedia.org/wiki/Cytochrome_P450_omega_hydroxylase

Lipoperoxidation products, as hydroxyeicosatetraenoic acids (HETEs) and 4-hydroxynonenal (4-HNE), are functionally involved in ...

https://en.wikipedia.org/wiki/Hemozoin

Eicosanoid Hydroxyeicosatetraenoic acid Leukotriene Prostaglandin Thromboxane Specialized proresolving mediators Essential ... ω-3 fatty acid: α-linolenic acid or ALA (18:3n-3) ω-6 fatty acid: linoleic acid or LA (18:2n-6) These two fatty acids cannot be ... Only two fatty acids are known to be essential for humans: alpha-linolenic acid (an omega-3 fatty acid) and linoleic acid (an ... ω-6 fatty acids: gamma-linolenic acid or GLA (18:3n-6) dihomo-gamma-linolenic acid or DGLA (20:3n-6) arachidonic acid or AA (20 ...

https://en.wikipedia.org/wiki/Essential_fatty_acid

The GPR31 receptor is a receptor for very different arachidonic acid metabolite, 12-hydroxyeicosatetraenoic acid (12-HETE), ... 5-Hydroxyicosatetraenoic acid (5-HETE), 5-oxoicosanoic acid (5-oxo-ETE) and other members of this family of broadly bioactive ... The human gene is located on chromosome 6q27 and encodes a G-protein coupled receptor protein composed of 319 amino acids. The ... Oxoeicosanoid receptor 1 is the receptor for a family of arachidonic acid metabolites made by 5-lipoxygenase viz., ...

https://en.wikipedia.org/wiki/GPR31

Plasma 15-Hydroxyeicosatetraenoic Acid Predicts Treatment Outcomes in Aspirin-Exacerbated Respiratory Disease Elina Jerschow 1 ... Plasma 15-Hydroxyeicosatetraenoic Acid Predicts Treatment Outcomes in Aspirin-Exacerbated Respiratory Disease Elina Jerschow et ... Keywords: 15-hydroxyeicosatetraenoic acid; Aspirin desensitization; Aspirin-exacerbated respiratory disease; Eicosanoids; ... Patients with symptom improvement had higher baseline plasma 15-hydroxyeicosatetraenoic acid (15-HETE) levels than did patients ...

https://www.ncbi.nlm.nih.gov/pubmed/28159558

Keywords: 12-hydroxyeicosatetraenoic acid; 12-lipoxygenase; ALOX12 gene polymorphism; inflammaion; sickle; vaso-occlusion. ... Plasma Concentration of 12-Hydroxyeicosatetraenoic Acid, Single Nucleotide Polymorphisms of 12-Lipooxygenase Gene and Vaso- ... Plasma Concentration of 12-Hydroxyeicosatetraenoic Acid, Single Nucleotide Polymorphisms of 12-Lipooxygenase Gene and Vaso- ... hydroxyeicosatetraenoic acid. Setkowicz M, Mastalerz L, Gielicz A, Wojas-Pelc A, Sanak M. Setkowicz M, et al. Br J Dermatol. ...

https://pubmed.ncbi.nlm.nih.gov/34713264

20-Hydroxyeicosatetraenoic acid (20-HETE) has crucial roles in modulating the vascular response in the kidney and the ... Renoprotective Effect of TP0472993, a Novel and Selective 20-Hydroxyeicosatetraenoic Acid Renoprotective Effect of TP0472993, a ... SIGNIFICANCE STATEMENT In this study, we demonstrate that the pharmacological blockade of 20-hydroxyeicosatetraenoic acid (20- ... Novel and Selective 20-Hydroxyeicosatetraenoic Acid Synthesis Inhibitor, in Mouse Models of Renal Fibrosis. ...

https://pesquisa.bvsalud.org/portal/resource/pt/mdl-37142440

General 12-HETE(12-Hydroxyeicosatetraenoic Acid) ELISA Kit General 12-HETE(12-Hydroxyeicosatetraenoic Acid) ELISA Kit. To Order ... Description: A competitive Inhibition ELISA kit for detection of 12-Hydroxyeicosatetraenoic Acid from General in samples from ... Description: A competitive ELISA kit for quantitative measurement of 12-HETE (12-Hydroxyeicosatetraenoic Acid) in samples from ... Description: A competitive ELISA for quantitative measurement of Human 12 Hydroxyeicosatetraenoic acid in samples from blood, ...

https://www.gkts.net/general-12-hete12-hydroxyeicosatetraenoic-acid-elisa-kit/

Plasma 15-Hydroxyeicosatetraenoic Acid Predicts Treatment Outcomes in Aspirin-Exacerbated Respiratory Disease. The Journal of ... Plasma 15-Hydroxyeicosatetraenoic Acid Predicts Treatment Outcomes in Aspirin-Exacerbated Respiratory Disease. The Journal of ... Plasma 15-Hydroxyeicosatetraenoic Acid Predicts Treatment Outcomes in Aspirin-Exacerbated Respiratory Disease. The Journal of ...

https://www.niehs.nih.gov/research/atniehs/facilities/knockout/publications/index.cfm

Fatty Acids, Unsaturated/blood; Hydroxyeicosatetraenoic Acids/blood; Inflammation; Linoleic Acid/metabolism*; ... and AA-derived fatty acid diols. AA and LA hydroxy intermediates (hydroxyeicosatetraenoic and hydroxyoctadecadienoic acids) ... Here, we investigated the role of MPO in modulating biologically active arachidonic acid (AA) and linoleic acid (LA) ... In vitro experiments revealed significantly lower amounts of AA and LA epoxides, LA- and AA-derived fatty acid diols, and AA ...

https://tools.niehs.nih.gov/portfolio/index.cfm?do=portfolio.publicationDetail&id=1620630

Leukotrienes, lipoxins, and hydroxyeicosatetraenoic acids.. Spokas EG; Rokach J; Wong PY. Methods Mol Biol; 1999; 120():213-47 ... 8. Omega-3 fatty acids and their lipid mediators: towards an understanding of resolvin and protectin formation.. Weylandt KH; ... 9. [Anti-inflammatory pro-resolving derivatives of omega-3 and omega-6 polyunsaturated fatty acids].. Nowak JZ. Postepy Hig Med ... Mechanism of formation of leukotrienes and lipoxins from arachidonic acid catalyzed by homogenous lipoxygenase from potato ...

https://pubmedhh.nlm.nih.gov/biomarkers/search.php?id=20441482&mod=related&page=1&outid=&proj=

20-Hydroxyeicosatetraenoic acid is a potential therapeutic target in cardiovascular diseases. Elshenawy OH, Anwar-Mohamed A, El ... Acute doxorubicin cardiotoxicity alters cardiac cytochrome P450 expression and arachidonic acid metabolism in rats. Zordoky BN ...

https://pubmed.ncbi.nlm.nih.gov/?cmd=search&term=Anwar-Mohamed+A%5Bau%5D&dispmax=50

The role of 20-hydroxyeicosatetraenoic acid in adrenocorticotrophic hormone and dexamethasone-induced hypertension. J. ... "Amino Acid, Peptide, or Protein" semantic type). ... Nucleic Acids Res. 44, D20-6 (2016).. Article CAS Google ...

https://www.nature.com/articles/s41598-019-42806-6?error=cookies_not_supported&code=243d5009-aa0f-4ff4-a996-c87456d9fa94

Enhanced PI3K activity through hydroxyeicosatetraenoic acid (HETE) and prostaglandin E2 formation may relate to this elongated ... and Akt account for the effect of dietary fatty acids on prostate tumor growth promotion? 3) Are Bax and Bcl2 responsible for ... of survival has been observed following linoleic and arachidonic acid treatment of cells in culture. ...

http://grants1.nih.gov/grants/guide/rfa-files/RFA-CA-04-004.html

https://grants.nih.gov/grants/guide/rfa-files/RFA-CA-03-003.html

Prostaglandin-E2, 5-, 8-, and 11- hydroxyeicosatetraenoic acids, 9- and 13-hydroxyoctadecadienoic acids were considerably ... Moreover, a decrease in certain fecal amino acids was noted in both alcohol-fed groups. These data support an important role of ... Mice expressing a short hairpin ribonucleic acid targeting Alk in the VTA drank less ethanol compared with controls. ALK is ...

https://www.niaaa.nih.gov/about-niaaa/our-work/advisory-council/directors-reports-council/niaaa-directors-report-institute-12

Arachidonic Acids [D10.251.355.255.100] * Arachidonic Acid [D10.251.355.255.100.100] * Hydroxyeicosatetraenoic Acids [D10.251. ... Arachidonic Acids [D10.251.355.310.166] * Arachidonic Acid [D10.251.355.310.166.100] * Hydroxyeicosatetraenoic Acids [D10.251. ... Hydroxyeicosatetraenoic Acids Preferred Concept UI. M0010759. Registry Number. 0. Scope Note. Eicosatetraenoic acids ... Fatty Acids [D10.251] * Fatty Acids, Unsaturated [D10.251.355] * Fatty Acids, Essential [D10.251.355.310] * ...

https://meshb.nlm.nih.gov/record/ui?name=Hydroxyeicosatetraenoic+Acids

This hemeprotein, with potent vasoconstriction properties, and its metabolite 20-Hydroxyeicosatetraenoic acid (20-HETE) are ... Oxalic acid, as a metal ion chelator, promotes the formation of nephroliths, and therefore, is considered as a health concern ... Additionally, the oxalic acid constitution of beetroot is relatively abundant [13]; average content in raw beetroot and ... One of such efforts is a study on Lactic acid bacteria fermentation, where three phylus of Lactobacillus plantarum, ...

https://nutritionandmetabolism.biomedcentral.com/articles/10.1186/s12986-019-0421-0

Another example of these cooperative effects mediated by ROS is represented by hydroxyeicosatetraenoic acid (20-HETE) which ... The pre-treatment of rats with zinc and acetylsalicylic acid complex is more efficacious than acetylsalicylic acid alone in ... CaM is constituted by 148 amino acids composed of N- and C-terminal lobes, each of these contains two Ca2+-binding EF hands. So ... On the other hand, Zn2+ is an efficient Lewis acid able to form coordination bonds often integrated with four bonds into a ...

https://www.hindawi.com/journals/omcl/2022/7714542/

... there is a resultant enhancement in the formation of arachidonic acid ̶ derived 20-hydroxyeicosatetraenoic acid (20-HETE), ... The acid-base hypothesis: diet and bone in the Framingham Osteoporosis Study. Eur J Nutr. 2001 Oct. 40(5):231-7. [QxMD MEDLINE ... Acid-base status determines the renal expression of Ca2+ and Mg2+ transport proteins. J Am Soc Nephrol. 2006 Mar. 17(3):617-26 ... Loop diuretics (including furosemide, bumetanide, and ethacrynic acid), produce large increases in magnesium excretion through ...

https://emedicine.medscape.com/article/2038394-overview

Acetylation of COX-2 results in isoform modification that yields 15R-hydroxyeicosatetraenoic acid (15R-HETE) instead of PGG2. [ ... Omega-6 fatty acids, the essential substrates of dihomo-g-linolenic acid and arachidonic acid, are derivatives of linoleic acid ... Omega-3 fatty acids, the essential substrates of eicosapentaenoic acid, are derivatives of a-linolenic acid. As a result, ... As previously noted, COX metabolizes arachidonic acid (5,8,11,14-eicosatetraenoic acid) into PGH2 intermediates. Subsequently, ...

https://emedicine.medscape.com/article/126919-overview

... and hydroxyeicosatetraenoic acids (HETEs) is increased in patients with ulcerative colitis, and it is possible that mesalamine ... also known as 5-aminosalicylic acid (5-ASA). Chemically, mesalamine is 5-amino-2-hydroxybenzoic acid. ... Mucosal production of arachidonic acid (AA) metabolites, both through the cyclooxygenase pathways, i.e., prostanoids, and ... N-acetyl-5-aminosalicylic acid (N-Ac-5-ASA). Consider an alternative, selective assay for normetanephrine. ...

https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b2a5b110-7537-4ffc-bf0a-f0fe13379c9d&audience=professional

... and hydroxyeicosatetraenoic acids (HETEs) is increased in patients with ulcerative colitis, and it is possible that mesalamine ... also known as 5-aminosalicylic acid (5-ASA). Chemically, mesalamine is 5-amino-2-hydroxybenzoic acid. ... Mucosal production of arachidonic acid (AA) metabolites, both through the cyclooxygenase pathways, i.e., prostanoids, and ... Mesalamine (5-aminosalicylic acid)……..….4.0 grams. in suspension containing carbomer 934P, edetate disodium, potassium acetate ...

https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=e505ab99-1943-4216-a178-4d5dbe64e3b2&type=display

... and hydroxyeicosatetraenoic acids (HETEs) are synthesized via COX and lipoxygenase (LOX) activity and can have multiple ... oleic acid and linoleic acid diets have been reported to elevate the development of autoimmunity and intestinal inflammation in ... ω-3 polyunsaturated fatty acids ameliorate type 1 diabetes and autoimmunity. Xinyun Bi,1,2 Fanghong Li,1 Shanshan Liu,3 Yan Jin ... elegans) cDNA, mfat-1 (referred to herein as lenti-mfat-1), that encodes an ω-3 fatty acid desaturase (42). By adding a double ...

https://www.jci.org/articles/view/87388?key=bbb2df2018c8c18d1e0b

... such as arachidonic and 5-hydroxyeicosatetraenoic (5-HETE) acids, through phospholipase A2 (PLA2) and 5-lipoxygenase (5-LOX) ... This amino acid is a factor determining a proteins quaternary structure, and is very useful during collagen synthesis and its ... As a structural analog of indole-3-acetic acid (IAA), a common auxin also derived from tryptophan, melatonin, is involved in ... With concerns to melatonin biosynthesis in humans, the exogenous amino acid tryptophan through the action of tryptophan ...

https://www.mdpi.com/2073-4409/8/7/681

Hydroxyeicosatetraenoic Acids D10.251.355.96.450 D10.251.355.310.166.550 Hydroxyethylrutoside D3.830.219.266.450.284.888.500 ... Arachidonic Acid D10.251.355.96.100 Arachidonic Acids D10.251.355.96 Arachis hypogaea J2.500.850.500.77 (Replaced for 2015 by ... Fusidic Acid D10.570.938.515 Fuzzy Logic L1.224.65.250 L1.224.50.375.250 G-Quadruplexes G2.111.570.790.486.550 G2.111.570.820. ... 13-dienoic Acid D2.737.637.650.500.500 D1.248.497.158.685.750.744.650.500.500 D10.251.355.255.100.637.25.650.500.500 D1.339. ...

https://decs.bvs.br/P/mnchg2016.txt

Hydroxyeicosatetraenoic Acids - Preferred Concept UI. M0010759. Scope note. Eicosatetraenoic acids substituted in any position ... Eicosatetraenoic acids substituted in any position by one or more hydroxy groups. They are important intermediates in a series ... They are important intermediates in a series of biosynthetic processes leading from arachidonic acid to a number of ... of biosynthetic processes leading from arachidonic acid to a number of biologically active compounds such as prostaglandins, ...

https://decs.bvsalud.org/en/ths/resource/?id=28098&filter=ths_exact_term&q=%C3%81CIDOS+HIDROXIEICOSATETRAENOICOS

https://meshb-prev.nlm.nih.gov/record/ui?ui=D006893

Human 12-HETE12-Hydroxyeicosatetraenoic Acid ELISA Kit. 12-Hydroxyeicosatetraenoic Acid (12-HETE) ELISA Kit is an ELISA Kit for ... Human 12-HETE12-Hydroxyeicosatetraenoic Acid ELISA Kit * Pharmacopoeia roles and responses: A systemic resilience approach to ... the in vitro quantitative measurement of 12-Hydroxyeicosatetraenoic Acid (12-HETE) concentrations in serum, plasma… ...

http://www.lifchem.com/author/hefeilifang/

Sheep 5-hydroxyeicosatetraenoic acid,5-HETE ELISA kit. Add to Quote Already Added ...

https://bro-gen.com/urun-etiketi/bt-lab/

Further in vitro studies suggested that 15-hydroxyeicosatetraenoic acid (15-HETE) converted fibroblasts into CAFs by the ...

https://www.oncotarget.com/article/20312/text/

20-Hydroxyeicosatetraenoic Acid (20-HETE) Metabolism in Coronary Endothelial Cells. Kaduce, T. L., Fang, X., Harmon, S. D., ... 20-Hydroxyeicosatetraenoic acid is a potent dilator of mouse basilar artery: Role of cyclooxygenase. Fang, X., Faraci, F. M., ... 20-Hydroxyeicosatetraenoic acid contributes to the inhibition of K+ channel activity and vasoconstrictor response to ... 20-hydroxyeicosatetraenoic acid inhibition attenuates balloon injury-induced neointima formation and vascular remodeling in rat ...

https://augusta.elsevierpure.com/en/publications/?showAdvanced=false&allConcepts=true&inferConcepts=true&publicationYear=2011&publicationYear=2012&publicationYear=2014&publicationYear=2015&publicationYear=2017&publicationYear=2019&publicationYear=2020&format=&nofollow=true&ordering=type&descending=true&page=234

20-Hydroxyeicosatetraenoic Acid (20-HETE) Metabolism in Coronary Endothelial Cells. Kaduce, T. L., Fang, X., Harmon, S. D., ... 20-Hydroxyeicosatetraenoic acid is a potent dilator of mouse basilar artery: Role of cyclooxygenase. Fang, X., Faraci, F. M., ... 20-Carboxy-arachidonic acid is a dual activator of peroxisome proliferator-activated receptors α and γ. Fang, X., Dillon, J. S. ... 2-Chloroethylstearate: An in vivo fatty acid conjugate of 2-chloroethanol. Kaphalia, B. S. & Ansari, G. A. S., Nov 1987, In: ...

https://researchexperts.utmb.edu/en/publications/?page=2&ordering=type&descending=false&showAdvanced=false&allConcepts=true&inferConcepts=true&originalSearch=&improvedLayoutOrganisationUuid=

... whereas the level of 15S-hydroxy-eicosatetraenoic acid was significantly (P , 0.05) lower in the skin areas treated with 15-epi ... These lipids are eicosanoids of the arachidonic acid and linoleic acid pathway, as well as lysophophatidic acids (LPAs). ... docosahexaenoic acid derivatives were biologically more stable than SPM derived from arachidonic acid or eicosapentaenoic acid. ... leukotriene B4 and various hydroxyeicosatetraenoic acids and SPM, in an oxazolone (OXA)-induced hypersensitivity model for ...

https://publikationen.ub.uni-frankfurt.de/solrsearch/index/search/searchtype/authorsearch/author/Nerea+Ferreiros

Acute doxorubicin cardiotoxicity alters cardiac cytochrome P450 expression and arachidonic acid metabolism in rats. (nih.gov)
Modulation of arachidonic and linoleic acid metabolites in myeloperoxidase-deficient mice during acute inflammation. (nih.gov)
Here, we investigated the role of MPO in modulating biologically active arachidonic acid (AA) and linoleic acid (LA) metabolites during acute inflammation. (nih.gov)
20. Mechanism of formation of leukotrienes and lipoxins from arachidonic acid catalyzed by homogenous lipoxygenase from potato tubers. (nih.gov)
More specifically, increased prostate cancer cell proliferation and prolongation of survival has been observed following linoleic and arachidonic acid treatment of cells in culture. (nih.gov)
They are important intermediates in a series of biosynthetic processes leading from arachidonic acid to a number of biologically active compounds such as prostaglandins, thromboxanes, and leukotrienes. (nih.gov)
By 1964, after recognition of this basic structure, Bergstrom and colleagues successfully synthesized series 2 prostaglandins from arachidonic acid using sheep seminal fluid. (medscape.com)
Further investigations by Smith concluded that aspirin and indomethacin inhibited synthesis by specifically blocking oxygenation of arachidonic acid. (medscape.com)
Their distinct biosynthetic activity includes an endoperoxidase synthase reaction that oxygenates and cyclizes polyunsaturated fatty acid precursors (eg, arachidonic acid) to form prostaglandin G 2 (PGG2), and a peroxidase reaction that converts PGG2 to prostaglandin H 2 (PGH2), as shown below. (medscape.com)
Cyclooxygenase conversion of arachidonic acid into prostaglandin H2 (PGH2). (medscape.com)
Mucosal production of arachidonic acid (AA) metabolites, both through the cyclooxygenase pathways, i.e., prostanoids, and through the lipoxygenase pathways, i.e., leukotrienes (LTs) and hydroxyeicosatetraenoic acids (HETEs) is increased in patients with ulcerative colitis, and it is possible that mesalamine diminishes inflammation by blocking cyclooxygenase and inhibiting prostaglandin (PG) production in the colon. (nih.gov)
These lipids are eicosanoids of the arachidonic acid and linoleic acid pathway, as well as lysophophatidic acids (LPAs). (uni-frankfurt.de)
Curcumin and its potent antioxidant activity derived from arachidonic acid. (who.int)
20-Hydroxyeicosatetraenoic acid, also known as 20-HETE or 20-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid, is an eicosanoid metabolite of arachidonic acid that has a wide range of effects on the vascular system including the regulation of vascular tone, blood flow to specific organs, sodium and fluid transport in the kidney, and vascular pathway remodeling. (csnpharm.cn)
These data suggest that the bradykinin-dependent inhibition of Cl - transport in the mTAL of the rat is mediated by cytochrome P450 dependent metabolite(s) of arachidonic acid. (uky.edu)
Novel liquid chromatography-mass spectrometry method shows that vitamin E deficiency depletes arachidonic and docosahexaenoic acids in zebrafish (Danio rerio) embryos. (oregonstate.edu)
We also determined if α-tocopherol status alters embryonic lipid peroxidation products by analyzing 24 different oxidized products of arachidonic or docosahexaenoic (DHA) acids in embryos using LC with hybrid quadrupole-time of flight MS. Adult zebrafish were fed E- or E+ diets for 4 months, and then were spawned to obtain E- and E+ embryos. (oregonstate.edu)
Vitamin E deficiency during embryogenesis depleted DHA and arachidonic acid, and increased hydroxy-fatty acids derived from these PUFA, suggesting that α-tocopherol is necessary to protect these critical fatty acids. (oregonstate.edu)

20-Hydroxyeicosatetraenoic acid (20- HETE ) has crucial roles in modulating the vascular response in the kidney and the progression of albuminuria . (bvsalud.org)
To verify our hypothesis, this study investigated the effect of a novel and selective 20- HETE synthesis inhibitor, TP0472993, on the development of kidney fibrosis after folic acid - and obstructive-induced nephropathy in mice . (bvsalud.org)
SIGNIFICANCE STATEMENT In this study, we demonstrate that the pharmacological blockade of 20-hydroxyeicosatetraenoic acid (20- HETE ) synthesis using TP0472993 suppresses the progression of kidney fibrosis after folic acid - and obstructive-induced nephropathy in mice , indicating that 20- HETE might have key roles in the pathogenesis of kidney fibrosis . (bvsalud.org)
Description: Quantitative sandwich ELISA for measuring Human 12-hydroxyeicosatetraenoic acid (12-HETE) in samples from cell culture supernatants, serum, whole blood, plasma and other biological fluids. (gkts.net)
20-Hydroxyeicosatetraenoic acid (20-HETE) was recently identified as a novel contributor of ischemia-induced neovascularization based on the key observation that pharmacological interferences of CYP4A/20-HETE decrease ischemic neovascularization. (touro.edu)
NEW & NOTEWORTHY CYP4A/20-hydroxyeicosatetraenoic acid (20-HETE) was recently discovered as a novel contributor of ischemia-induced neovascularization. (touro.edu)
8-HETE, also known as 8S-HETE, belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. (bovinedb.ca)

AA and LA hydroxy intermediates (hydroxyeicosatetraenoic and hydroxyoctadecadienoic acids) were also significantly lower in MPO-KO mice. (nih.gov)
In vitro experiments revealed significantly lower amounts of AA and LA epoxides, LA- and AA-derived fatty acid diols, and AA and LA hydroxy intermediates in stimulated polymorphonuclear neutrophils isolated from MPO-KO mice. (nih.gov)
Eicosatetraenoic acids substituted in any position by one or more hydroxy groups. (nih.gov)
At 36 hpf, E- embryos contained double the 5-hydroxy-eicosatetraenoic acids and 7-hydroxy-DHA concentrations, while other hydroxy-lipids remained unchanged. (oregonstate.edu)

17. Leukotrienes, lipoxins, and hydroxyeicosatetraenoic acids. (nih.gov)

Renoprotective Effect of TP0472993, a Novel and Selective 20-Hydroxyeicosatetraenoic Acid Synthesis Inhibitor, in Mouse Models of Renal Fibrosis. (bvsalud.org)
TS-011 is a selective inhibitor of 20-Hydroxyeicosatetraenoic acid synthesis. (csnpharm.cn)

Compared to wild-type mice, MPO-KO mice had significantly lower plasma levels of LA epoxides and corresponding LA- and AA-derived fatty acid diols. (nih.gov)
Therefore, COX - also known as prostaglandin-endoperoxide synthase (PTGS), fatty acid COX, prostaglandin H (PGH) synthase, and EC 1.14.99.1 - is implicated in the production of fever, inflammation, and pain. (medscape.com)
Twenty-carbon polyunsaturated fatty acid with cyclopentane ring. (medscape.com)

8. Omega-3 fatty acids and their lipid mediators: towards an understanding of resolvin and protectin formation. (nih.gov)
He localized the biologic activity to a fraction of lipid soluble acids that he termed "prostaglandin," hypothesizing that these substances originate in the prostate gland. (medscape.com)
To test the hypothesis that embryogenesis depends upon α-tocopherol (E) to protect embryo polyunsaturated fatty acids (PUFAs) from lipid peroxidation, new methodologies were applied to measure α-tocopherol and fatty acids in extracts from saponified zebrafish embryos. (oregonstate.edu)

Description: A competitive Inhibition ELISA kit for detection of 12-Hydroxyeicosatetraenoic Acid from General in samples from blood, serum, plasma, cell culture fluid and other biological fluids. (gkts.net)
A novel biological role of dehydroascorbic acid: Inhibition of Na+-dependent transport of ascorbic acid. (uniurb.it)

Functional variant of CYP4A11 20-hydroxyeicosatetraenoic acid synthase is associated with essential hypertension. (cdc.gov)

Description: Enzyme-linked immunosorbent assay kit for quantification of General 12-Hydroxyeicosatetraenoic acid in samples from serum, plasma, tissue homogenates and other biological fluids. (gkts.net)

Two decades later, the prostaglandins were deduced to be a family of related compounds that contain 20-carbon polyunsaturated fatty acids with a cyclopentane ring, as depicted below. (medscape.com)

The T8590C polymorphism of CYP4A11 and 20-hydroxyeicosatetraenoic acid in essential hypertension. (cdc.gov)

Furthermore, using sequence analysis of human genomic DNA, researchers concluded that the amino acids important for catalysis by COX-1 are conserved and are equally important for catalysis by COX-2. (medscape.com)

Chronic treatment with TP0472993 at doses of 0.3 and 3 mg/kg twice a day attenuated the degree of kidney fibrosis in the folic acid nephropathy and the unilateral ureteral obstruction (UUO) mice , as demonstrated by reductions in Masson's trichrome staining and the renal collagen content. (bvsalud.org)

One hallmark of acute inflammation is the peroxidation of polyunsaturated fatty acids forming bioactive products that regulate inflammation. (nih.gov)

These are eicosanoic acids with an attached hydroxyl group and four CC double bonds. (bovinedb.ca)

Funk and co-investigators localized COX-1 to 9q32-q33.3 via somatic hybrid deoxyribonucleic acid (DNA) analysis. (medscape.com)

9. Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid. (nih.gov)

Phytanic acid replaces other fatty acids, including such essential ones as linoleic and arachidonic acids, in lipid moieties of various tissues. (medscape.com)

2. CYP4F2-Catalyzed Metabolism of Arachidonic Acid Promotes Stromal Cell-Mediated Immunosuppression in Non-Small Cell Lung Cancer. (nih.gov)

Therefore, COX - also known as prostaglandin-endoperoxide synthase (PTGS), fatty acid COX, prostaglandin H (PGH) synthase, and EC 1.14.99.1 - is implicated in the production of fever, inflammation, and pain. (medscape.com)
He localized the biologic activity to a fraction of lipid soluble acids that he termed "prostaglandin," hypothesizing that these substances originate in the prostate gland. (medscape.com)
Their distinct biosynthetic activity includes an endoperoxidase synthase reaction that oxygenates and cyclizes polyunsaturated fatty acid precursors (eg, arachidonic acid) to form prostaglandin G2 (PGG2), and a peroxidase reaction that converts PGG2 to prostaglandin H2 (PGH2), as shown below. (medscape.com)
Cyclooxygenase conversion of arachidonic acid into prostaglandin H2 (PGH2). (medscape.com)
7. Rapid simultaneous analysis of prostaglandin E2, 12-hydroxyeicosatetraenoic acid and arachidonic acid using high performance liquid chromatography/electrospray ionization mass spectrometry. (nih.gov)

[ 13 ] The most abundant dietary PUFAs are the short-chain omega-3 alpha linolenic acid (ALA) and the omega-6 linoleic acid (LA), most often ingested as plant oils. (medscape.com)
More specifically, increased prostate cancer cell proliferation and prolongation of survival has been observed following linoleic and arachidonic acid treatment of cells in culture. (nih.gov)

For the dietary alteration of colonic arachidonic acid: eicosapentaenoic ratios resulted in large shifts in formation of COX and lipoxygenase metabolites. (nih.gov)

Omega-3 and omega-6 fatty acids are a group of essential polyunsaturated fatty acids (PUFAs) that play important roles in cell membrane structure, fluidity, and cell signaling. (medscape.com)

3. Interleukin-1 increases 15-hydroxyeicosatetraenoic acid production in human dermal fibroblasts. (nih.gov)

A single peroxisomal enzyme defect that causes deficiency of alpha-oxidation leads to accumulation of phytanic acid in blood and tissues of patients with Refsum disease. (medscape.com)

However, in whole kidney homogenate a 4-fold increase in the formation of 20-hydroxyeicosatetraenoic acid was measured along with a 3-fold increase in lipoxygenase-derived hydroxylation and prostanoid production. (cdc.gov)

They are important intermediates in a series of biosynthetic processes leading from arachidonic acid to a number of biologically active compounds such as prostaglandins, thromboxanes, and leukotrienes. (bvsalud.org)

Metabolic pathways for omega-6 and omega-3 fatty acids that result in a variety of inflammation mediators and cell function effectors. (medscape.com)
The omega-3 fatty acids EPA and DHA and their derivatives are important for retina and brain development, cognitive function, and in the production of minimally inflammatory eicosanoids as well inflammation resolving mediators termed resolvins and various tissue protectins. (medscape.com)
Arachidonic acid-derived epoxides, epoxyeicosatrienoic acids, are important regulators of vascular homeostasis and inflammation, and therefore manipulation of their levels is a potentially useful pharmacological strategy. (cdc.gov)

Two decades later, the prostaglandins were deduced to be a family of related compounds that contain 20-carbon polyunsaturated fatty acids with a cyclopentane ring, as depicted below. (medscape.com)

Dietary ω3 fatty acids can modulate substrate availability for cyclooxygenases (COXs) and lipoxygenases, thus modulating downstream eicosanoid formation. (nih.gov)

Furthermore, using sequence analysis of human genomic DNA, researchers concluded that the amino acids important for catalysis by COX-1 are conserved and are equally important for catalysis by COX-2. (medscape.com)

The data suggest that blood pressure homeostasis may be achieved by increasing production of the vasoconstrictor, 20-hydroxyeicosatetraenoic acid in the kidney of the Ephx2-null mice. (cdc.gov)

Funk and co-investigators localized COX-1 to 9q32-q33.3 via somatic hybrid deoxyribonucleic acid (DNA) analysis. (medscape.com)

A wettable micropores array was initially designed with high density by using polyacrylic acid (PAA) and hexadecyltrimethoxysilane (HDS), followed by the NaOH etching route. (bvsalud.org)

Patients with Refsum disease are unable to degrade phytanic acid because of a deficient activity of phytanoyl-CoA hydroxylase (PhyH), a peroxisomal enzyme catalyzing the first step of phytanic acid alpha-oxidation. (medscape.com)

By 1964, after recognition of this basic structure, Bergstrom and colleagues successfully synthesized series 2 prostaglandins from arachidonic acid using sheep seminal fluid. (medscape.com)

Blood levels of phytanic acid are increased in patients with Refsum disease. (medscape.com)

Anatomy10

Organisms2

Chemicals and Drugs64

Analytical, Diagnostic and Therapeutic Techniques and Equipment5

Phenomena and Processes11

Endothelin-1 and CYP450 arachidonate metabolites interact to promote tissue injury in DOCA-salt hypertension. (1/901)

Regulation of human airway mucins by acrolein and inflammatory mediators. (2/901)

LXA4, aspirin-triggered 15-epi-LXA4, and their analogs selectively downregulate PMN azurophilic degranulation. (3/901)

Albumin modifies the metabolism of hydroxyeicosatetraenoic acids via 12-lipoxygenase in human platelets. (4/901)

Polyisoprenyl phosphate (PIPP) signaling regulates phospholipase D activity: a 'stop' signaling switch for aspirin-triggered lipoxin A4. (5/901)

Angiotensin II inhibits HCO-3 absorption via a cytochrome P-450-dependent pathway in MTAL. (6/901)

Kinetic profile of the rat CYP4A isoforms: arachidonic acid metabolism and isoform-specific inhibitors. (7/901)

Regulation of P-450 4A activity in the glomerulus of the rat. (8/901)

Hydroxyeicosatetraenoic Acids

12-Hydroxy-5,8,10,14-eicosatetraenoic Acid

Alkane 1-Monooxygenase

Arachidonate 12-Lipoxygenase

Arachidonate 15-Lipoxygenase

Arachidonic Acid

Lipoxygenase

Eicosanoids

Arachidonic Acids

Amidines

Arachidonate Lipoxygenases

Lipoxygenase Inhibitors

Leukotrienes

8,11,14-Eicosatrienoic Acid

Arachidonate 5-Lipoxygenase

Cytochrome P-450 Enzyme System

Leukotriene B4

Masoprocol

Receptors, Eicosanoid

Formamides

Calcimycin

Chromatography, High Pressure Liquid

Flavanones

Prostaglandin-Endoperoxide Synthases

Eicosanoic Acids

Gas Chromatography-Mass Spectrometry

Linoleic Acids

Umbelliferones

5-Lipoxygenase-Activating Proteins

Lipoxins

5,8,11,14-Eicosatetraynoic Acid

SRS-A

Leukotriene A4

Microsomes

Mixed Function Oxygenases

Amides

Lipid Peroxides

Calcium Ionophores

Lauric Acids

Rats, Sprague-Dawley

Vasoconstrictor Agents

Sulfones

Blood Platelets

Hydrazines

Indomethacin

Caffeic Acids

Cyclooxygenase Inhibitors

Neutrophils

Linoleic Acid

Epoxide Hydrolases

Cells, Cultured

Kidney Cortex

Phospholipases A2

Fatty Acids, Unsaturated

Renal Artery

Thromboxane B2

Stereoisomerism

Prostaglandins

Cyclooxygenase 1

Enzyme Inhibitors

Ionophores

Epoxy Compounds

Kidney

Phospholipases A

Muscle, Smooth, Vascular

Rabbits

Endothelium, Vascular

Dinoprostone

Eicosapentaenoic Acid

Vasoconstriction

Vasodilation

Renal Circulation

Hydroxylation

Dose-Response Relationship, Drug

Kidney Medulla

Protein Kinase C-alpha

Mass Spectrometry

Isomerism

Angiotensin II

Isoenzymes