Compounds based on a seven-membered ring fused to a five-membered ring. Heat can rearrange them to NAPHTHALENES which have two fused six-membered rings. They are similar to guaiazulenes which are SESQUITERPENES with a six-membered ring fused to a five-membered ring.

Sex-related differences in urinary excretion of egualen sodium in rats. (1/33)

Egualen sodium (sodium 3-ethyl-7-isopropyl-1-azulenesulfonate 1/3 hydrate) is a new antiulcer drug. There has been no difference observed in absorption between male and female rats, the relative amount of metabolites in male plasma has been higher than that in females, and the excretion ratios of metabolites in males have been significantly higher than those in females. However, the plasma concentration profile of total radioactivity in males has been higher than that in females. To clarify this discrepancy, the renal clearances and plasma concentrations of the unchanged drug and its metabolites were determined. The renal clearance of the unchanged drug in males was 21 times lower than that in females, and the urinary excretions in males and females were 2.1 and 39.5% of dose, respectively. This indicates that the major factor in the sex-related difference observed in the plasma concentration of total radioactivity is due to the difference in the renal clearance of the unchanged drug between the sexes. The results of treatments with probenecid in normal and gonadectomized rats revealed that egualen sodium was mainly excreted into urine by secretion through the renal tubule. Furthermore, the results of treatments with testosterone in rats revealed that the excretion of egualen sodium was highly affected by androgens. These facts indicated that the sex-related difference observed in the plasma concentration of total radioactivity can be attributed to the inhibition of renal tubular secretion of the unchanged drug by androgens. This is the first example of sex-related differences in both metabolism and excretion.  (+info)

Bicarbonate enhances peroxidase activity of Cu,Zn-superoxide dismutase. Role of carbonate anion radical and scavenging of carbonate anion radical by metalloporphyrin antioxidant enzyme mimetics. (2/33)

Much evidence exists for the increased peroxidase activity of copper, zinc superoxide dismutase (SOD1) in oxidant-induced diseases. In this study, we measured the peroxidase activity of SOD1 by monitoring the oxidation of dichlorodihydrofluorescein (DCFH) to dichlorofluorescein (DCF). Bicarbonate dramatically enhanced DCFH oxidation to DCF in a SOD1/H(2)O(2)/DCFH system. Peroxidase activity could be measured at a lower H(2)O(2) concentration ( approximately 1 microm). We propose that DCFH oxidation to DCF is a sensitive index for measuring the peroxidase activity of SOD1 and familial amyotrophic lateral sclerosis SOD1 mutants and that the carbonate radical anion (CO(3)) is responsible for oxidation of DCFH to DCF in the SOD1/H(2)O(2)/bicarbonate system. Bicarbonate enhanced H(2)O(2)-dependent oxidation of DCFH to DCF by spinal cord extracts of transgenic mice expressing SOD1(G93A). The SOD1/H(2)O(2)/HCO(3)(-)-dependent oxidation was mimicked by photolysis of an inorganic cobalt carbonato complex that generates CO(3). Metalloporphyrin antioxidants that are usually considered as SOD1 mimetic or peroxynitrite dismutase effectively scavenged the CO(3) radical. Implications of this reaction as a plausible protective mechanism in inflammatory cellular damage induced by peroxynitrite are discussed.  (+info)

Synthesis of new azulene derivatives and study of their effect on lipid peroxidation and lipoxygenase activity. (3/33)

The relationship between free radicals and acute or chronic inflammation has been well established. We have previously reported the significant antioxidant activity of the natural azulene derivatives chamazulene and guaiazulene. Furthermore, some synthetic azulene analogues have been found to possess anti-inflammatory activity. In this investigation we report the synthesis of five 3-alkyl or 3-(hydroxy)alkylazulene-1-carboxylic acids and esters, from tropolone, via the corresponding furanone. The synthesised compounds were tested for their effect on the peroxidation of rat hepatic microsomal membrane lipids, applying the 2-thiobarbituric acid test. Their anti-inflammatory activity was evaluated in vitro by the offered inhibition of soybean lipoxygenase. All the tested molecules were found to inhibit lipid peroxidation by 100% at 1 mM. They were also found to considerably inhibit lipoxygenase activity. The above results are discussed in relation to the structure and physicochemical properties of the examined azulene derivatives.  (+info)

Cardiovascular effects of orally administered HNS-32, an originally synthesized azulene-1-carboxamidine derivative, assessed in the in vivo rat model. (4/33)

HNS-32, an azulene-1-carboxamidine derivative, is an originally synthesized antiarrhythmic compound. Its cardiovascular effects after oral administration (1-10 mg/kg) were assessed using the pentobarbital-anesthetized in vivo rat model in comparison with those of verapamil (3 mg/kg, p.o.). Verapamil decreased the heart rate and mean blood pressure and prolonged the PR interval without changing the QRS width (n = 6). Similar results were observed for HNS-32 except that the QRS width was prolonged by the highest dose and the effects occurred slowly and lasted longer. These results suggest that HNS-32 is an orally active slowly-acting calcium plus sodium channel blocker.  (+info)

Radiosensitization and DNA repair inhibition by the combined use of novel inhibitors of DNA-dependent protein kinase and poly(ADP-ribose) polymerase-1. (5/33)

The DNA repair enzymes, DNA-dependent protein kinase (DNA-PK) and poly(ADP-ribose) polymerase-1 (PARP-1), are key determinants of radio- and chemo-resistance. We have developed and evaluated novel specific inhibitors of DNA-PK (NU7026) and PARP-1 (AG14361) for use in anticancer therapy. PARP-1- and DNA-PK-deficient cell lines were 4-fold more sensitive to ionizing radiation (IR) alone, and showed reduced potentially lethal damage recovery (PLDR) in G(0) cells, compared with their proficient counterparts. NU7026 (10 micro M) potentiated IR cytotoxicity [potentiation factor at 90% cell kill (PF(90)) = 1.51 +/- 0.04] in exponentially growing DNA-PK proficient but not deficient cells. Similarly, AG14361 (0.4 micro M) potentiated IR in PARP-1(+/+) (PF(90) = 1.37 +/- 0.03) but not PARP-1(-/-) cells. When NU7026 and AG14361 were used in combination, their potentiating effects were additive (e.g., PF(90) = 2.81 +/- 0.19 in PARP-1(+/+) cells). Both inhibitors alone reduced PLDR approximately 3-fold in the proficient cell lines. Furthermore, the inhibitor combination completely abolished PLDR. IR-induced DNA double strand break (DNA DSB) repair was inhibited by both NU7026 and AG14361, and use of the inhibitor combination prevented 90% of DNA DSB rejoining, even 24-h postirradiation. Thus, there was a correlation between the ability of the inhibitors to prevent IR-induced DNA DSB repair and their ability to potentiate cytotoxicity. Thus, individually, or in combination, the DNA-PK and PARP-1 inhibitors act as potent radiosensitizers and show potential as tools for anticancer therapeutic intervention.  (+info)

Photomutagenicity of cosmetic ingredient chemicals azulene and guaiazulene. (6/33)

The photomutagenicity of the popular skin conditioning agents azulene and guaiazulene were tested in Salmonella typhimurium TA98, TA100 and TA102. Following irradiation with UVA and/or visible light, both azulene and guaiazulene exhibited mutagenicity 4-5-fold higher than the spontaneous background mutation. In contrary, naphthalene, a structural isomer of azulene, was not photomutagenic under the same conditions. Azulene was photomutagenic when irradiated with UVA light alone, visible light alone, or a combination of UVA and visible light. Azulene and guaiazulene are not mutagenic when the experiment is conducted with the exclusion of light. Therefore, extreme care must be taken when using cosmetic products with azulene/guaiazulene as ingredients since after applying these products on the skin, exposure to sunlight is inevitable.  (+info)

Anticancer chemosensitization and radiosensitization by the novel poly(ADP-ribose) polymerase-1 inhibitor AG14361. (7/33)

BACKGROUND: Poly(ADP-ribose) polymerase-1 (PARP-1) facilitates the repair of DNA strand breaks. Inhibiting PARP-1 increases the cytotoxicity of DNA-damaging chemotherapy and radiation therapy in vitro. Because classical PARP-1 inhibitors have limited clinical utility, we investigated whether AG14361, a novel potent PARP-1 inhibitor (inhibition constant <5 nM), enhances the effects of chemotherapy and radiation therapy in human cancer cell cultures and xenografts. METHODS: The effect of AG14361 on the antitumor activity of the DNA alkylating agent temozolomide, topoisomerase I poisons topotecan or irinotecan, or x-irradiation or gamma-radiation was investigated in human cancer cell lines A549, LoVo, and SW620 by proliferation and survival assays and in xenografts in mice by tumor volume determination. The specificity of AG14361 for PARP-1 was investigated by microarray analysis and by antiproliferation and acute toxicity assays in PARP-1-/- and PARP-1+/+ cells and mice. After intraperitoneal administration, the concentration of AG14361 was determined in mouse plasma and tissues, and its effect on PARP-1 activity was determined in tumor homogenates. All statistical tests were two-sided. RESULTS: AG14361 at 0.4 micro M did not affect cancer cell gene expression or growth, but it did increase the antiproliferative activity of temozolomide (e.g., in LoVo cells by 5.5-fold, 95% confidence interval [CI] = 4.9-fold to 5.9-fold; P =.004) and topotecan (e.g., in LoVo cells by 1.6-fold, 95% CI = 1.3-fold to 1.9-fold; P =.002) and inhibited recovery from potentially lethal gamma-radiation damage in LoVo cells by 73% (95% CI = 48% to 98%). In vivo, nontoxic doses of AG14361 increased the delay of LoVo xenograft growth induced by irinotecan, x-irradiation, or temozolomide by two- to threefold. The combination of AG14361 and temozolomide caused complete regression of SW620 xenograft tumors. AG14361 was retained in xenografts in which PARP-1 activity was inhibited by more than 75% for at least 4 hours. CONCLUSION: AG14361 is, to our knowledge, the first high-potency PARP-1 inhibitor with the specificity and in vivo activity to enhance chemotherapy and radiation therapy of human cancer.  (+info)

Novel poly(ADP-ribose) polymerase-1 inhibitor, AG14361, restores sensitivity to temozolomide in mismatch repair-deficient cells. (8/33)

PURPOSE: Mismatch repair (MMR) deficiency confers resistance to temozolomide, a clinically active DNA-methylating agent. The purpose of the current study was to investigate the reversal mechanism of temozolomide resistance by the potent novel poly(ADP-ribose) polymerase (PARP)-1 inhibitor, AG14361, in MMR-proficient and -deficient cells. EXPERIMENTAL DESIGN: The effects of AG14361, in comparison with the methylguanine DNA methyltransferase inhibitor, benzylguanine, on temozolomide-induced growth inhibition were investigated in matched pairs of MMR-proficient (HCT-Ch3, A2780, and CP70-ch3) and -deficient (HCT116, CP70, and CP70-ch2) cells. RESULTS: AG14361 enhanced temozolomide activity in all MMR-proficient cells (1.5-3.3-fold) but was more effective in MMR-deficient cells (3.7-5.2-fold potentiation), overcoming temozolomide resistance. In contrast, benzylguanine only increased the efficacy of temozolomide in MMR-proficient cells but was ineffective in MMR-deficient cells. The differential effect of AG14361 in MMR-deficient cells was not attributable to differences in PARP-1 activity or differences in its inhibition by AG14361, nor was it attributable to differences in DNA strand breaks induced by temozolomide plus AG14361. MMR-deficient cells are resistant to cisplatin, but AG14361 did not sensitize any cells to cisplatin. PARP-1 inhibitors potentiate topotecan-induced growth inhibition, but AG14361 did not potentiate topotecan in MMR-deficient cells more than in MMR-proficient cells. CONCLUSIONS: MMR defects are relatively common in sporadic tumors and cancer syndromes. PARP-1 inhibition represents a novel way of selectively targeting such tumors. The underlying mechanism is probably a shift of the cytotoxic locus of temozolomide to N(7)-methylguanine and N(3)-methyladenine, which are repaired by the base excision repair pathway in which PARP-1 actively participates.  (+info)

Illustrative complexes are (azulene)Mo2(CO)6 and (azulene)Fe2(CO)5. 1-Hydroxyazulene is an unstable green oil and it does not ... In naphth[a]azulene, a naphthalene ring is condensed at the 1,2-positions of azulene. In one such system deviation from ... Azulene is an organic compound and an isomer of naphthalene. Naphthalene is colourless, whereas azulene is dark blue. Two ... azulenes by Intramolecular Tropylium Ion-Mediated Furan Ring-Opening Reaction and X-ray Investigation of a Naphth[1,2-a]azulene ...
... is an azulene derivate obtained from vetiver oil. It is a bicyclic sesquiterpene and an isomer of guaiazulene. ... Gordon, Maxwell (1 February 1952). "The Azulenes". Chemical Reviews. 50 (1): 127-200. doi:10.1021/cr60155a004. v t e (Articles ... Azulenes, Sesquiterpenes, All stub articles, Hydrocarbon stubs). ...
Hafner, Klaus; Meinhardt, Klaus-Peter (1984). "Azulene". Organic Syntheses. 62: 134. doi:10.15227/orgsyn.062.0134. E. F. ...
Homolysis of the weakest bond in azulene occurs, followed by a hydrogen shift and ring closure so as to retain the aromaticity ... This is currently the preferred mechanism and is as follows: The isomerization of unsubstituted azulene to naphthalene was the ... The four described mechanisms would all result in the isomerization from azulene to naphthalene. Kinetic data and 13C-labeling ... At the time, they noticed the automerization of a substituted azulene shown below, but no further structural or mechanistic ...
Azulene Borepin "tropylium , ChemSpider". www.chemspider.com. p. Names. Retrieved 30 December 2018. tropylium "Tropylium". ...
D. M. Lemal; G. D. Goldman (1988). "Synthesis of azulene, a blue hydrocarbon". Journal of Chemical Education. 65 (10): 923. ...
A derivative of azulene, guaiazulene is a bicyclic sesquiterpene that is a constituent of some essential oils, mainly oil of ... Its low melting point makes guaiazulene difficult to handle, in contrast to the crystalline nature of the parent azulene. The ... Harmon AD, Weisgraber KH, Weiss U.; Weisgraber; Weiss (1979). "Preformed azulene pigments of Lactarius indigo (Schw.) Fries ( ... "The anti-inflammatory activity of azulene". Journal of the European Academy of Dermatology and Venereology. 15 (5): 486. doi: ...
Harmon, A. D.; Weisgraber, K. H.; Weiss, U. (1980). "Preformed azulene pigments of Lactarius indigo (Schw.) Fries (Russulaceae ...
Harmon AD, Weisgraber KH, Weiss U (1979). "Preformed azulene pigments of Lactarius indigo (Schw.) Fries (Russulaceae, ...
The blue color of L. indigo is due to (7-isopropenyl-4-methylazulen-1-yl)methyl stearate, an organic analogous to azulene, ... Harmon AD, Weisgraber KH, Weiss U (1979). "Preformed azulene pigments of Lactarius indigo (Schw.) Fries (Russulaceae, ...
Harmon AD, Weisgraber KH, Weiss U (1979). "Preformed azulene pigments of Lactarius indigo (Schw.) Fries (Russulaceae, ...
Buenker, R. J.; Peyerimhoff, S. D. (1969). "Ab initio SCF calculations for azulene and naphthalene". Chemical Physics Letters. ... the largest molecules included were naphthalene and azulene. Abstracts of many earlier developments in ab initio theory have ...
Azulene - composed of fused cyclopentadiene and cycloheptatriene rings. Sesquifulvalene - composed of linked cyclopentadiene ...
Notable counterexamples are cyclooctadecanonaene, azulene and trans-bicalicene. Quinoid Aromatic compound Tomlinson, Muriel ( ...
He also studied chemical characteristics of tropones, tropolones, other troponoids, and azulenes. Tetsuo Nozoe was married to ...
Thermal rearrangement of azulene to naphthalene has been observed.[citation needed] Aldose-ketose isomerism, aka Lobry de Bruyn ...
utilized intramolecular carbenoid generation to produce substituted azulenes through a Buchner type ring expansion. The anti- ... Annulation Strategy for the Synthesis of Substituted Azulenes. Preparation and Suzuki Coupling Reactions of 1-Azulenyl ... "Ring Expansion-Annulation Strategy for the Synthesis of Substituted Azulenes and Oligoazulenes. 2. Synthesis of Azulenyl ...
... (2a,8b-dihydro-cyclopent[cd]azulene) is a polycyclic hydrocarbon with chemical formula C12H10, composed of one ... List of chemical compounds with unusual names Azulene Homoaromaticity Nickon, Alex; Silversmith, Ernest F. (2013). Organic ...
... is a tricyclic sesquiterpene alcohol which has a basic skeleton similar to the azulenes. It occurs in oregano among ...
"Incoherent broad-band cavity-enhanced absorption spectroscopy of azulene in a supersonic jet". Chemical Physics Letters. ...
The blue colouring of the fruit body is due to three azulene pigments.[citation needed] Whether Entoloma hochstetteri is ...
Existence of the Doubly Excited State that Mediates the Photoionization of Azulene". J. Chem. Phys. 138 (20): 201102-1-201102-4 ...
It is a blue-violet derivative of azulene which is biosynthesized from the sesquiterpene matricin. Chamazulene has anti- ... Azulenes, Hydrocarbons, All stub articles, Aromatic compound stubs). ...
... is an unstable isomer of the more common benzenoid aromatic compounds naphthalene and azulene. Fulvalene consists of ...
Bicyclo[6.2.0]decapentaene is a bicyclic organic compound and an isomer of naphthalene and azulene. Whether this substance is ...
The chromophore of azulene was discovered in yarrow and wormwood and named in 1863 by Septimus Piesse. Yarrow contains ...
... azulene (8.01%), toluene (4.36%), palmitic acid (4.01%) and linoleic acid (4.01%). In 2017, a case report documented E. ...
The valence isomers of naphthalene Naphthalene Azulene IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") ( ... no pair of valence isomers differ more strongly in appearance than colourless naphthalene and the intensely violet azulene. ...
This is in contrast to non-alternant hydrocarbons, such as azulene and fulvene that have large dipole moments. The Hückel ...
The red-coloured azulene compounds, ingested with the mushroom food, are more or less excreted with the urine. The milk cap's ...
The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database ...
Azulene. Azulene. Azulene is derived from German Chamomile, known for reducing skin inflammation. It soothes irritated skin and ... Formulated with Azulene that soothes the skin and Mango seed butter rich in essential fatty acids needed by dry skin. It ...
3-dienyl-azulene - C14H12, synthesis, structure, density, melting point, boiling point ... 3-dienyl-azulene , density of 4-buta-2,3-dienyl-azulene , refractive index of 4-buta-2,3-dienyl-azulene ... Tags: melting point of 4-buta-2,3-dienyl-azulene , boiling point of 4-buta-2, ...
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Antioxidants and multi-vitamins reduce signs of aging and improve collagen and elastin production. Carrot Oil, Mango Butter, and Plant Extracts prevent aging and provide moisture and nourishment to skin. Used for: Normal to Dry, Dehydrated, and Undernourished.
Chamazulene is a sesquiterpene, derived from azulene, and found in German chamomile, giving it a blue color. It is also found ...
THE POTIONS Azulene Ampoule is a soothing ampoule with azulene, also known as cyclopentacycloheptene. It helps soothe sensitive ... Azulene. Azulene is a natural ingredient derived from chamomile oil and is known for its bright blue color. Azulene is an oft- ... THE POTIONS Azulene Ampoule - 20 ml. THE POTIONS Azulene Ampoule is a soothing ampoule with azulene, also known as ... THE POTIONS Azulene Ampoule is a soothing ampoule with azulene, also known as cyclopentacycloheptene. It helps soothe sensitive ...
Hypoallergenic night mask with 85% snail mucin, instead of the usual water, and azulene, perfectly moisturizes and nourishes, ... instead of the usual water, and azulene, perfectly moisturizes and nourishes, softens the skin and evens out the overall skin ... ":"Snail \u0026 Azulene Sleeping Mask 80ml, Tiam","public_title":null,"options":["Default Title"],"price":2290,"weight":0," ...
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The embedded azulene unit in 2 possesses a record-high twisting degree (16.1°) as a result of the contiguous steric repulsion ... Helical Nanographenes Containing an Azulene Unit: Synthesis, Crystal Structures, and Properties.. Ma, Ji; Fu, Yubin; Dmitrieva ... Our study provides a novel synthetic strategy for helical nanographenes containing azulene units as well as their associated ... Three unprecedented helical nanographenes (1, 2, and 3) containing an azulene unit are synthesized. The resultant helical ...
... dc.contributor. ... Isolation and Antifouling Activity of Azulene Derivatives from the Antarctic Gorgonian Acanthogorgia laxa. es_ES. ...
Neues Paper online: "Annulated Azuleno[2,1,8-ija]azulenes: Synthesis and Properties" *09.01.2023. Neues Paper online: "High- ... Neues Paper online: "Annulated Azuleno[2,1,8-ija]azulenes: Synthesis and Properties". × Unsere Arbeit von L. Renn ist in ...
AzuFluorTM 483-Bpin: Azulene-Based Fluorescent Probe for ROS/RNS small molecule (tool compound) Invented by Lloyd Murfin , Tony ... AzuFluorTM 483-Bpin, Diethyl 2-amino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)azulene-1,3- dicarboxylate ... AzuFluorTM 483-Bpin: Azulene-Based Fluorescent Probe for ROS/RNS small molecule (tool compound) ...
Azulene. 1. - View Price Disclaimer : Medindia updates the prices regularly, however, there may be slight discrepancies in the ...
... and azulene) were identified in the exudate of Cistus ladanifer L. We studied the effect of each o … ... and azulene) were identified in the exudate of Cistus ladanifer L. We studied the effect of each on germination, cotyledon ... and azulene), with intermediate activity (cinnamic acid and hydroxycinnamic acid), and with high activity (methyl propionate ...
Azulene-based fluorescent chemosensor for adenosine diphosphate. López-Alled, C. M., Park, S. J., Lee, D. J., Murfin, L. C., ... Persistent azulene α-carbocations: synthesis from aldehydes, spectroscopic and crystallographic properties. Harabajiu, C., Hann ...
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Mąkosza, Mieczysław; Kędziorek, Mariusz; Ostrowski, Stanisław: Synthesis of Polycyano-Substituted Azulenes via Direct Oxidative ...
All rights reserved. Maharishi AyurVeda, TM, Transcendental Meditation, Maharishi Amrit Kalash, Vata, Pitta and Kapha are registered or common law trademarks licensed to Maharishi Foundation USA, Inc. and used under sublicense.. ...
Anti-UV activity of newly-synthesized water-soluble azulenes.. Ueki J; Sakagami H; Wakabayashi H. In Vivo; 2013; 27(1):119-26. ... Relationship between electronic structure and cytotoxic activity of azulenes.. Kurihara T; Noguchi M; Noguchi T; Wakabayashi H ...
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  • Azulene is a natural ingredient derived from chamomile oil and is known for its bright blue color. (meliorabeautyshop.ee)
  • Blue chamomile essential oil has a high content of azulene which bears a blue color. (selfgrowth.com)
  • Azulene packed blue chamomile soothes your lips for some true beauty z's! (hurrawbalm.com)
  • The mechanism(s) of thermal rearrangement of azulenes have been enigmatic for several decades. (bvsalud.org)
  • Of the two mechanisms proposed for naphthalene automerization, it is found that the benzofulvene (BF) route is favored over the naphthvalene mechanism by â ¼6 kcal/mol and is energetically lower than the norcaradiene-vinylidene mechanism (NVM) for the azulene-naphthalene rearrangement (Ea â ¼ 76.5 (74.6) kcal/mol). (bvsalud.org)
  • Accordingly, all proposed pathways were investigated with the optimal method, M06-2X/6-311+G(d,p), which confirms the norcaradiene-vinylidene mechanism (A) as the dominant unimolecular route (Ea ≈ 76 kcal/mol) able to account for the major products of pyrolyses using 13C- or substituent-labeled azulenes. (bvsalud.org)
  • The thermal rearrangement of azulene to naphthalene has been the subject of several experimental and computational studies. (bvsalud.org)