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Chemical Compound Review

Tocris-0607     octadec-17-ynoic acid

Synonyms: CHEMBL182310, AG-J-98399, BSPBio_001367, KBioGR_000087, KBioSS_000087, ...
 
 
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Disease relevance of octadec-17-ynoic acid

  • However, after partial blockade of cytochrome P-450 4A enzymes with 17-octadecynoic acid (17-ODYA), hypoxia increased the diameter by 65 +/- 6 micrometer (P < 0.05) [1].
 

High impact information on octadec-17-ynoic acid

  • Microiontophoresis of ACh evoked vasodilation that conducted along arterioles; the local (direct) response was inhibited by N(omega)-nitro-L-arginine (LNA), and both local and conducted responses were inhibited by 17-octadecynoic acid (17-ODYA) [2].
  • High sensitivity toward the specific P450 inhibitor 17-octadecynoic acid suggested that omega-hydroxylation of VLCFAs is catalyzed by P450 enzymes belonging to the CYP4A/F subfamilies [3].
  • In contrast, we observed that CYP450 inhibitors such as SKF-525A, 17-octadecynoic acid, 1-aminobenzotriazole, and 6-(2-propargyloxyphenyl)hexanoic acid reduced 12(S)-HETE levels, 3T6 fibroblast growth, and DNA synthesis induced by FBS [4].
  • The high sensitivity toward the more specific cytochrome P450 inhibitors ketoconazole and 17-octadecynoic acid suggests that hydroxylation of C22:0 and omega-hydroxy-C22:0 may be catalyzed by one or more cytochrome P450 hydroxylases belonging to the CYP4A and/or CYP4F subfamily [5].
  • Carbenoxolone, a gap junction inhibitor, significantly attenuated the SLIGRL-amide-evoked, EDHF-dependent relaxation, although neither 17-octadecynoic acid, a P450 epoxygenase inhibitor, nor catalase, a hydrogen peroxide scavenger, revealed inhibitory effects [6].
 

Biological context of octadec-17-ynoic acid

  • Enzyme inactivation by 17-octadecynoic acid and 16-hydroxy-17-octadecynoic acid is due to alkylation of the prosthetic heme group to given an adduct tentatively identified as N-(2-oxo-3-hydroxy-17-carboxyheptadecyl)protoporphyrin IX by its chromatographic and spectroscopic properties [7].
  • This study examined whether cortical or papillary blood flow is altered after removal of the clip from the renal artery of 1-K,1C hypertensive rats, and the effects of blockade of the renal metabolism of arachidonic acid by P-450 with 17-octadecynoic acid (17-ODYA) on the fall in blood pressure [8].
 

Anatomical context of octadec-17-ynoic acid

 

Associations of octadec-17-ynoic acid with other chemical compounds

  • Miconazole (10 microM) or 17-octadecynoic acid (17-ODYA; 10 microM) diminished local vasodilation by 15-20% and conducted responses by 50-70% (P < 0.05), suggesting a role for cytochrome P-450 (CYP) metabolites in arteriolar responses to ACh [12].
  • This ACh-induced relaxation was inhibited and converted to constriction by catalase (-53 +/- 10%, n = 6) or KCl (-30 +/- 3%, n = 7), whereas 17-octadecynoic acid and 6-(2-propargylloxyphenyl) hexanoic acid, two inhibitors of cytochrome P450 monooxygenase, had no significant effect (3 +/- 1% and 20 +/- 8%, n = 5, respectively) [13].
  • The cytochrome P-450 monooxygenase inhibitor 17-octadecynoic acid (17-ODYA) and the protein kinase C inhibitor staurosporine both significantly attenuated the effects of fenoldopam by 67% [14].
  • In contrast, 17-octadecynoic acid (17-ODYA; 10(-5) M), a suicide-substrate inhibitor of renal cytochrome P450 omega-hydroxylase, completely blocked the transport response to bradykinin, while the cyclooxygenase inhibitor sodium meclofenamate (10(-5) M) had no effect [15].
  • The endothelium removal but not the inhibition of prostanoid synthesis with either 10 microM indomethacin or 10 microM 17-octadecynoic acid potentiated the contractions to noradrenaline and to KCl both under control conditions as well as after the chronic in vivo administration of L-NAME [16].
 

Gene context of octadec-17-ynoic acid

 

Analytical, diagnostic and therapeutic context of octadec-17-ynoic acid

  • Administration of 17-octadecynoic acid (17-ODYA), which is a P450 4A inhibitor, attenuated the constriction of third-order cremasteric arterioles in response to elevation of superfusion solution PO2 from approximately equal to 3 to 5 mm Hg to approximately equal to 35 mm Hg [20].

References

  1. Role of cytochrome P-450 4A in oxygen sensing and NO production in rat cremaster resistance arteries. Kerkhof, C.J., Bakker, E.N., Sipkema, P. Am. J. Physiol. (1999) [Pubmed]
  2. Vasomotor control in arterioles of the mouse cremaster muscle. Hungerford, J.E., Sessa, W.C., Segal, S.S. FASEB J. (2000) [Pubmed]
  3. {omega}-Oxidation of Very Long-chain Fatty Acids in Human Liver Microsomes: IMPLICATIONS FOR X-LINKED ADRENOLEUKODYSTROPHY. Sanders, R.J., Ofman, R., Duran, M., Kemp, S., Wanders, R.J. J. Biol. Chem. (2006) [Pubmed]
  4. Hydroxyeicosatetraenoic acids released through the cytochrome P-450 pathway regulate 3T6 fibroblast growth. Nieves, D., Moreno, J.J. J. Lipid Res. (2006) [Pubmed]
  5. Evidence for two enzymatic pathways for omega-oxidation of docosanoic acid in rat liver microsomes. Sanders, R.J., Ofman, R., Valianpour, F., Kemp, S., Wanders, R.J. J. Lipid Res. (2005) [Pubmed]
  6. Distinct roles for protease-activated receptors 1 and 2 in vasomotor modulation in rat superior mesenteric artery. Kawabata, A., Kubo, S., Nakaya, Y., Ishiki, T., Kuroda, R., Sekiguchi, F., Kawao, N., Nishikawa, H. Cardiovasc. Res. (2004) [Pubmed]
  7. Cytochrome P450BM-3 (CYP102): regiospecificity of oxidation of omega-unsaturated fatty acids and mechanism-based inactivation. Shirane, N., Sui, Z., Peterson, J.A., Ortiz de Montellano, P.R. Biochemistry (1993) [Pubmed]
  8. Role of changes in renal hemodynamics and P-450 metabolites of arachidonic acid in the reversal of one-kidney, one clip hypertension. Zou, A.P., Muirhead, E.E., Cowley, A.W., Mattson, D.L., Falck, J.R., Jiang, J., Roman, R.J. J. Hypertens. (1995) [Pubmed]
  9. EDHF contributes to strain-related differences in pulmonary arterial relaxation in rats. Karamsetty, M.R., Nakashima, J.M., Ou, L., Klinger, J.R., Hill, N.S. Am. J. Physiol. Lung Cell Mol. Physiol. (2001) [Pubmed]
  10. Characterization of endothelium-dependent relaxation independent of NO and prostaglandins in guinea pig coronary artery. Yamanaka, A., Ishikawa, T., Goto, K. J. Pharmacol. Exp. Ther. (1998) [Pubmed]
  11. Role of prostanoids and 20-HETE in mediating oxygen-induced constriction of skeletal muscle resistance arteries. Frisbee, J.C., Krishna, U.M., Falck, J.R., Lombard, J.H. Microvasc. Res. (2001) [Pubmed]
  12. Role of EDHF in conduction of vasodilation along hamster cheek pouch arterioles in vivo. Welsh, D.G., Segal, S.S. Am. J. Physiol. Heart Circ. Physiol. (2000) [Pubmed]
  13. Role of hydrogen peroxide in ACh-induced dilation of human submucosal intestinal microvessels. Hatoum, O.A., Binion, D.G., Miura, H., Telford, G., Otterson, M.F., Gutterman, D.D. Am. J. Physiol. Heart Circ. Physiol. (2005) [Pubmed]
  14. Dopamine D1 receptor-dependent inhibition of NaCl transport in the rat thick ascending limb: mechanism of action. Grider, J.S., Ott, C.E., Jackson, B.A. Eur. J. Pharmacol. (2003) [Pubmed]
  15. P450 arachidonate metabolites mediate bradykinin-dependent inhibition of NaCl transport in the rat thick ascending limb. Grider, J.S., Falcone, J.C., Kilpatrick, E.L., Ott, C.E., Jackson, B.A. Can. J. Physiol. Pharmacol. (1997) [Pubmed]
  16. Effects of the chronic in vivo administration of L-NAME on the contractile responses of the rat perfused mesenteric bed. Mendizabal, V.E., Feleder, E.C., Adler-Graschinsky, E. Journal of autonomic pharmacology. (1999) [Pubmed]
  17. Cytochrome P-450 metabolites but not NO, PGI2, and H2O2 contribute to ACh-induced hyperpolarization of pressurized canine coronary microvessels. Tanaka, M., Kanatsuka, H., Ong, B.H., Tanikawa, T., Uruno, A., Komaru, T., Koshida, R., Shirato, K. Am. J. Physiol. Heart Circ. Physiol. (2003) [Pubmed]
  18. 20-Hydroxyeicosatetraenoic acid is formed in response to EGF and is a mitogen in rat proximal tubule. Lin, F., Rios, A., Falck, J.R., Belosludtsev, Y., Schwartzman, M.L. Am. J. Physiol. (1995) [Pubmed]
  19. Bidirectional regulation of renal cortical Na+,K+-ATPase by protein kinase C. Bełtowski, J., Marciniak, A., Jamroz-Wiśniewska, A., Borkowska, E., Wójcicka, G. Acta Biochim. Pol. (2004) [Pubmed]
  20. Identification of a putative microvascular oxygen sensor. Harder, D.R., Narayanan, J., Birks, E.K., Liard, J.F., Imig, J.D., Lombard, J.H., Lange, A.R., Roman, R.J. Circ. Res. (1996) [Pubmed]
 
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