• HETEs
  • Figure 2) While metabolizing arachidonic acid primarily to PGG2, COX-2 also converts this fatty acid to small amounts of a racemic mixture of 15-Hydroxyicosatetraenoic acids (i.e., 15-HETEs) composed of ~22% 15(R)-HETE and ~78% 15(S)-HETE stereoisomers as well as a small amount of 11(R)-HETE. (wikipedia.org)
  • enzyme
  • These nonclassic eicosanoids are generally short-lived, being rapidly converted from epoxides to less active or inactive dihydroxy-eicosatrienoic acids (diHETrEs) by a widely distributed cellular enzyme, Soluble epoxide hydrolase (sEH), also termed Epoxide hydrolase 2. (wikipedia.org)
  • ALOX15 and ALOX15B, respectively 15(S)-HPETE → EXA4 via 15-LOX-1 EXA4 → EXC4 via LTC4 synthase aka "glutathione S-transferase II" EXC4 → EXD4 via unidentified gamma-glutamyltransferase class enzyme EXD4 → EXE4 via unidentified dipeptidase class enzyme The Arachidonic acid + O2 → 15(S)-HpETE → EXA4 → EXC4 → EXD4 → EXE4) metabolic pathway is analogous to the leukotriene-forming pathway (i.e. (wikipedia.org)
  • However this enzyme has a preference for metabolizing linoleic acid rather than arachidonic acid. (wikipedia.org)
  • fatty acids
  • only a relatively few of the active CYP genes code for EET-forming epoxygenases, i.e. protein enzymes with the capacity to attach atomic oxygen (see Allotropes of oxygen#Atomic oxygen) to the carbon-carbon double bonds of unsaturated long chain fatty acids such as arachidonic acid. (wikipedia.org)
  • Naturally occurring ligands for OXER1 are long chain polyunsaturated fatty acids containing either an hydroxyl (i.e. (wikipedia.org)
  • epoxide
  • Cytochrome P450 epoxygenases attack these double bonds to form their respective eicosatrienoic acid epoxide regioisomers (see Structural isomer, section on position isomerism (regioisomerism)) viz. (wikipedia.org)
  • HETE
  • The OXER1 G protein-coupled receptor resembles the hydroxy carboxilic acid subfamily of G protein-coupled receptors, which besides GPR109A, niacin receptor 1, and niacin receptor 2 may include the recently defined receptor for 12-HETE, GPR31, not only in its amino acid sequence but also in the hydroxy-carboxylic acid nature of its cognate ligands. (wikipedia.org)
  • 5-oxo-ETE>5-oxo-15-hydroxy-ETE>5-hydroperoxyicosatetraenoic acid (5-HpETE)>5-HETE>5,20-diHETE. (wikipedia.org)
  • It therefore forms linoleic acid metabolites (e.g. 13-hydoxyperoxy/hydroxy-octadecadienoic and 9-hydroperoxy/hydroxyl-octadecadienoic acids) in greater amounts than 15(S)-HpETE and 15(S)-HETE. (wikipedia.org)
  • receptor
  • We report here that the apparent inability of isolated human polymorphonuclear leukocytes (PMNs) to efficiently transform arachidonic acid (AA) is the consequence of A 2a receptor engagement by endogenous adenosine accumulating in incubation media. (aspetjournals.org)
  • LTBR1 and LTBR2 encode for proteins with 45% amino acid identity that belong to the G protein-coupled receptor superfamily. (wikipedia.org)
  • Recently, A G protein-couple receptor of the hydroxy carboxilic acid subfamily, Niacin receptor 1, has been proposed to mediate the responses of mouse tissues to 5-oxo-ETE. (wikipedia.org)
  • The human gene is located on chromosome 6q27 and encodes a G-protein coupled receptor protein composed of 319 amino acids. (wikipedia.org)
  • The GPR31 receptor is most closely related in amino acid sequence to the oxoeicosanoid receptor 1, a G-protein coupled receptor encoded by the GPR170 gene. (wikipedia.org)
  • epoxidation
  • We characterized the inhibitory activity of several acetylenic and olefinic compounds on cytochrome P450 (CYP)-derived arachidonic acid ω-hydroxylation and epoxidation using rat renal cortical microsomes and recombinant CYP proteins. (aspetjournals.org)
  • Among the acetylenic compounds, 6-(2-propargyloxyphenyl)hexanoic acid (PPOH) and N-methylsulfonyl-6-(2-propargyloxyphenyl)hexanamide were found to be potent and selective inhibitors of microsomal epoxidation with IC 50 values of 9 and 13 μM, respectively. (aspetjournals.org)
  • On the other hand, 17-octadecynoic acid inhibited both ω-hydroxylation and epoxidation of arachidonic acid with IC 50 values of 7 and 5 μM, respectively. (aspetjournals.org)
  • The olefinic compounds N-methylsulfonyl-12,12-dibromododec-11-enamide (DDMS) and 12,12-dibromododec-11-enoic acid (DBDD) exhibited a high degree of selectivity inhibiting microsomal ω-hydroxylation with an IC 50 value of 2 μM, whereas the IC 50 values for epoxidation were 60 and 51 μM for DDMS and DBDD, respectively. (aspetjournals.org)
  • These compounds are formed by epoxidation of any one of four double bonds of the arachidonic acid carbon backbone by cytochrome P450 epoxygenase enzymes. (wikipedia.org)
  • cells
  • The presence of a second inducible form of COX was first suggested by experiments, which showed a transient increase in the formation of PGE 2 from arachidonic acid by canine kidney cells upon stimulation with tumor promoters and carcinogens [ 5 , 6 ]. (mdpi.com)
  • These eoxin-like metabolites, termed eoxamides, are also formed by L1235 Reed-Sternberg cells and proposed to play a role in Hodgkins disease. (wikipedia.org)
  • The relative amounts of these metabolites made by specific cells and tissues depends in large part on the relative content of the appropriate enzymes. (wikipedia.org)
  • monolayer
  • the membrane-binding domain consists of a series of amphipathic α helices with several hydrophobic amino acids exposed to a membrane monolayer. (wikipedia.org)
  • responses
  • Animal studies and a limited set of human studies suggest that this family of metabolites serve as hormone-like autocrine and paracrine signalling agents that contribute to the up-regulation of acute inflammatory and allergic responses. (wikipedia.org)
  • respectively
  • Two BLT2-like receptors, Blt2a and Blt2b, with 49% amino acid identity to each other and 34% and 29%, respectively, amino acid identities to human BLT2 have been cloned from Zebrafish embryos. (wikipedia.org)