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Chemical Compound Review:

CHEBI:34306 (5Z,8Z,11Z,14Z)-20- hydroxyicosa-5,8,11,14...

Synonyms: H3023_SIGMA, HMDB02344, HMDB05998, LS-63795, LMFA03060009, ...

Basora, N. et al., Luria, A. et al., Collins, X.H. et al., McGiff, J.C. et al., Roman, R.J. et al., et al.

Basora, Boulay, Bilodeau, Rousseau, Payet, Gross, Falck, Gross, Isbell, Moore, Nithipatikom, Kroetz, Huse, Thuresson, Grillo, McGiff, Quilley, Roman, Renic, Dunn, Takeuchi, Hacein-Bey, Evans, Day, Roman, Hopp, Anderson, Ward, Puddey, Hodgson, Beilin, Croft, Seubert, Zeldin, Nithipatikom, Gross, Fang, Faraci, Kaduce, Harmon, Modrick, Hu, Moore, Falck, Weintraub, Spector, Guo, Roman, Falck, Edwards, Scicli,

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Disease relevance of LMFA03060009

Recent studies have indicated that a deficiency in the production of 20-hydroxyeicosatetraenoic acid (20-HETE) in the outer medulla of the kidney may contribute to the abnormalities in the renal handling of sodium and the development of hypertension in Dahl salt-sensitive rats [1].
Several lines of data support the possibility that certain CYP metabolites resulting from the hydroxylation of AA such as 20-hydroxyeicosatetraenoic acid (20-HETE) are potent vasoconstrictors and may produce detrimental effects in the heart during ischemia and pro-inflammatory effects during reperfusion [2].
This study examined the effects of blocking the formation of 20-hydroxyeicosatetraenoic acid (20-HETE) on the acute fall in cerebral blood flow after subarachnoid hemorrhage (SAH) in the rat [3].
We have previously reported that HET0016 [N-hydroxy-N'-(4-butyl-2 methylphenyl)formamidine], a selective inhibitor of CYP4A and thus 20-HETE (20-hydroxyeicosatetraenoic acid) synthesis, inhibits endothelial cell proliferation and decreases angiogenesis induced by human glioma cell U251 [4].
We previously reported that the levels of epoxyeicosatrienoic acids (EETs) and 20-hydroxyeicosatetraenoic acid (20-HETE) are depressed in microsomes prepared from lungs of rats with acute Pseudomonas pneumonia [5].

High impact information on LMFA03060009

The omega-hydroxylation of arachidonic acid generates significant levels of 20-hydroxyeicosatetraenoic acid (20-HETE) in numerous tissues, particularly the vasculature and kidney tubules [6].
20-Hydroxyeicosatetraenoic acid mediates calcium/calmodulin-dependent protein kinase II-induced mitogen-activated protein kinase activation in vascular smooth muscle cells [7].
Microsomes (1 mg/ml) prepared from small renal arteries (200-500 microns) and incubated with [1-14C]arachidonic acid (0.5 mu Ci, 50 microM) produced a metabolite that coeluted with 20-hydroxyeicosatetraenoic acid (20-HETE) during reversed-phase high-performance liquid chromatography [8].
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 [9].
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 [9].

Chemical compound and disease context of LMFA03060009

INTRODUCTION: The present study evaluated the contribution of 20-hydroxyeicosatetraenoic acid (20-HETE) and its interaction with nitric oxide (NO) in cyclosporin A-induced nephrotoxicity and hypertension [10].
Induction of renal 20-hydroxyeicosatetraenoic acid by clofibrate attenuates high-fat diet-induced hypertension in rats [11].
CONCLUSIONS: These results support the hypothesis that cytochrome P-450 4A may act as an O2 sensor in the skeletal muscle microcirculation and suggest that 20-hydroxyeicosatetraenoic acid plays an important role in the enhanced response to elevated PO2 in the SHR with established hypertension [12].
Recent studies have indicated that arachidonic acid (AA) is metabolized by the cytochrome P450 4A (CYP4A) enzymes in cerebral arteries to produce 20-hydroxyeicosatetraenoic acid (20-HETE) and that this compound has effects on cerebral vascular tone that mimic those seen following subarachnoid hemorrhage (SAH) [13].
For example, CYP mediated hydroxylation of AA produces 20-hydroxyeicosatetraenoic acid (20-HETE) which has detrimental effects in the heart during ischemia, pro-inflammatory effects during reperfusion and potent vasoconstrictor effects in the coronary circulation [14].

Biological context of LMFA03060009

20-Carboxyeicosatetraenoic acid (20-COOH-AA) is a bioactive metabolite of 20-hydroxyeicosatetraenoic acid (20-HETE), an eicosanoid that produces vasoconstriction in the cerebral circulation [15].
The CYP4A enzymes catalyze the formation of 20-hydroxyeicosatetraenoic acid (20-HETE), which has potent effects on the renal vasculature and tubular ion transport [16].
Urinary 20-hydroxyeicosatetraenoic acid excretion is associated with oxidative stress in hypertensive subjects [17].
Renal microsomes from AT2 receptor knockout mice had less activity in hydroxylating arachidonic acid to 20-hydroxyeicosatetraenoic acid (20-meter) than controls, whereas renal AT1 receptor gene expression was increased in AT2 receptor knockout mice [18].
Arachidonic acid is omega-hydroxylated to 20-hydroxyeicosatetraenoic acid (20-HETE), which has effects on vasoactivity and renal tubular transport and has been implicated in the regulation of blood pressure [19].

Anatomical context of LMFA03060009

20-hydroxyeicosatetraenoic acid (20-HETE) metabolism in coronary endothelial cells [20].
In the present study, we show that the eicosanoid compound, 20-hydroxyeicosatetraenoic acid (20-HETE), an important arachidonic acid metabolite, activates mouse TRPC6 in a stable, overexpressing HEK293 cell line, Hek-t6.11 [21].
Cytochrome P450 enzymes of the 4A family (CYP4A) convert arachidonic acid to 20-hydroxyeicosatetraenoic acid (20-HETE) in blood vessels of several vascular beds [22].
Omega-oxidation of 20-hydroxyeicosatetraenoic acid (20-HETE) in cerebral microvascular smooth muscle and endothelium by alcohol dehydrogenase 4 [15].
This study examined the role of endogenous 20 hydroxyeicosatetraenoic acid (20-HETE) in elevating Cl- transport in the medullary thick ascending loop of Henle (MTAL) of 9-week-old male Dahl salt-sensitive (SS/Jr) and salt-resistant (SR/Jr) rats perfused in vitro [23].

Associations of LMFA03060009 with other chemical compounds

The administration of 14,15-epoxyeicosatrienoic acid or 20-hydroxyeicosatetraenoic acid did not change the latency of the rapid depolarization and did not allow the membrane potential to recover after the ischemic exposure [24].
The aim of this study was to investigate regulation of NFAT in human and rat intralobar pulmonary artery by two constrictors: phenylephrine (PE) and 20-hydroxyeicosatetraenoic acid (20-HETE), a cytochrome P-450 metabolite formed endogenously in lungs [25].
Furthermore, the participation of a variety of intracellular second messenger systems in the myogenic response, i.e. inositol trisphosphate, diacylglycerol, phospholipase A2, protein kinase C or 20-hydroxyeicosatetraenoic acid, is still unclear [26].
The properties of 20-hydroxyeicosatetraenoic acid and epoxyeicosatrienoic acids, vasoactivity and modulation of ion transport and mediation/modulation of the effects of vasoactive hormones, such as angiotensin II and endothelin, underscore their importance to renal vascular mechanisms and electrolyte excretion [27].
17-Octadecynoic acid (17-ODYA, 10(-5) M) significantly inhibited ANP secretion stimulated by ET-1 (10(-8) M) in the isolated perfused rat atria and inhibited pro-ANP-(1-30) secretion stimulated by ET-1 (10(-8) M) or 20-hydroxyeicosatetraenoic acid in cultured neonatal rat ventricular myocytes (NRVM) [28].

Gene context of LMFA03060009

20-Hydroxyeicosatetraenoic acid is a potent dilator of mouse basilar artery: role of cyclooxygenase [29].
Functional variant of CYP4A11 20-hydroxyeicosatetraenoic acid synthase is associated with essential hypertension [30].
Renal arterial 20-hydroxyeicosatetraenoic acid levels: regulation by cyclooxygenase [31].
COX-2 supplanted the dominant oxygenase, the cytochrome P450 (CYP) enzyme, omega-hydroxylase, that synthesized 20-hydroxyeicosatetraenoic acid (20-HETE) [32].
Compared with nontransduced rats, human HO-1 gene overexpression in transduced rats was associated with a 35% decrease in urinary 20-hydroxyeicosatetraenoic acid, a potent vasoconstrictor and an inhibitor of tubular Na(+) transport, which may be related to the decrease in blood pressure [33].

Analytical, diagnostic and therapeutic context of LMFA03060009

We used in vitro albumin permeability (P(alb)) as a measure of injury and puromycin aminonucleoside (PAN) as an injurious agent to test the hypothesis that 20-hydroxyeicosatetraenoic acid (20-HETE) protects the glomerular filtration barrier from increased P(alb) [34].
The present study examined the role of 20-hydroxyeicosatetraenoic acid (20-HETE) on the angiogenesis induced by electrical stimulation in skeletal muscle [35].
This study describes a fluorescent HPLC assay for measuring 20-hydroxyeicosatetraenoic acid (20-HETE) and other cytochrome P-450 metabolites of arachidonic acid in urine, tissue, and interstitial fluid [36].
Intrarenal infusion of 17-ODYA reduced the metabolism of arachidonic acid to 20-hydroxyeicosatetraenoic acid by 41%, but it did not significantly influence the responses to increased renal perfusion pressure [37].
We measured tail-cuff and intra-arterial BP, weight change, sodium balance, 20-hydroxyeicosatetraenoic acid (20-HETE) excretion (by high-performance liquid chromatography), and renal expression of CYP 4A and CYP 2C (by real-time reverse transcriptase-polymerase chain reaction) [38].

References

Inhibition of renal outer medullary 20-HETE production produces hypertension in Lewis rats. Stec, D.E., Mattson, D.L., Roman, R.J. Hypertension (1997) [Pubmed]
Cytochrome P450 and arachidonic acid metabolites: role in myocardial ischemia/reperfusion injury revisited. Gross, G.J., Falck, J.R., Gross, E.R., Isbell, M., Moore, J., Nithipatikom, K. Cardiovasc. Res. (2005) [Pubmed]
20-HETE contributes to the acute fall in cerebral blood flow after subarachnoid hemorrhage in the rat. Kehl, F., Cambj-Sapunar, L., Maier, K.G., Miyata, N., Kametani, S., Okamoto, H., Hudetz, A.G., Schulte, M.L., Zagorac, D., Harder, D.R., Roman, R.J. Am. J. Physiol. Heart Circ. Physiol. (2002) [Pubmed]
Human U251 glioma cell proliferation is suppressed by HET0016 [N-hydroxy-N'-(4-butyl-2-methylphenyl)formamidine], a selective inhibitor of CYP4A. Guo, M., Roman, R.J., Falck, J.R., Edwards, P.A., Scicli, A.G. J. Pharmacol. Exp. Ther. (2005) [Pubmed]
Pulmonary cytochrome P-450 2J4 is reduced in a rat model of acute Pseudomonas pneumonia. Yaghi, A., Bradbury, J.A., Zeldin, D.C., Mehta, S., Bend, J.R., McCormack, D.G. Am. J. Physiol. Lung Cell Mol. Physiol. (2003) [Pubmed]
Regulation and inhibition of arachidonic acid omega-hydroxylases and 20-HETE formation. Kroetz, D.L., Xu, F. Annu. Rev. Pharmacol. Toxicol. (2005) [Pubmed]
20-Hydroxyeicosatetraenoic acid mediates calcium/calmodulin-dependent protein kinase II-induced mitogen-activated protein kinase activation in vascular smooth muscle cells. Muthalif, M.M., Benter, I.F., Karzoun, N., Fatima, S., Harper, J., Uddin, M.R., Malik, K.U. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
Inhibitors of cytochrome P-450 attenuate the myogenic response of dog renal arcuate arteries. Kauser, K., Clark, J.E., Masters, B.S., Ortiz de Montellano, P.R., Ma, Y.H., Harder, D.R., Roman, R.J. Circ. Res. (1991) [Pubmed]
Compensatory Mechanism for Homeostatic Blood Pressure Regulation in Ephx2 Gene-disrupted Mice. Luria, A., Weldon, S.M., Kabcenell, A.K., Ingraham, R.H., Matera, D., Jiang, H., Gill, R., Morisseau, C., Newman, J.W., Hammock, B.D. J. Biol. Chem. (2007) [Pubmed]
Nitric oxide/cytochrome P450 interactions in cyclosporin A-induced effects in the rat. Blanton, A., Nsaif, R., Hercule, H., Oyekan, A. J. Hypertens. (2006) [Pubmed]
Induction of renal 20-hydroxyeicosatetraenoic acid by clofibrate attenuates high-fat diet-induced hypertension in rats. Zhou, Y., Huang, H., Chang, H.H., Du, J., Wu, J.F., Wang, C.Y., Wang, M.H. J. Pharmacol. Exp. Ther. (2006) [Pubmed]
Differential effect of cytochrome P-450 omega-hydroxylase inhibition on O2-induced constriction of arterioles in SHR with early and established hypertension. Kunert, M.P., Roman, R.J., Falck, J.R., Lombard, J.H. Microcirculation (New York, N.Y. : 1994) (2001) [Pubmed]
Evidence that 20-HETE contributes to the development of acute and delayed cerebral vasospasm. Roman, R.J., Renic, M., Dunn, K.M., Takeuchi, K., Hacein-Bey, L. Neurol. Res. (2006) [Pubmed]
Role of epoxyeicosatrienoic acids in protecting the myocardium following ischemia/reperfusion injury. Seubert, J.M., Zeldin, D.C., Nithipatikom, K., Gross, G.J. Prostaglandins Other Lipid Mediat. (2007) [Pubmed]
Omega-oxidation of 20-hydroxyeicosatetraenoic acid (20-HETE) in cerebral microvascular smooth muscle and endothelium by alcohol dehydrogenase 4. Collins, X.H., Harmon, S.D., Kaduce, T.L., Berst, K.B., Fang, X., Moore, S.A., Raju, T.V., Falck, J.R., Weintraub, N.L., Duester, G., Plapp, B.V., Spector, A.A. J. Biol. Chem. (2005) [Pubmed]
Developmentally regulated expression of the CYP4A genes in the spontaneously hypertensive rat kidney. Kroetz, D.L., Huse, L.M., Thuresson, A., Grillo, M.P. Mol. Pharmacol. (1997) [Pubmed]
Urinary 20-hydroxyeicosatetraenoic acid excretion is associated with oxidative stress in hypertensive subjects. Ward, N.C., Puddey, I.B., Hodgson, J.M., Beilin, L.J., Croft, K.D. Free Radic. Biol. Med. (2005) [Pubmed]
Inhibition of pressure natriuresis in mice lacking the AT2 receptor. Gross, V., Schunck, W.H., Honeck, H., Milia, A.F., Kärgel, E., Walther, T., Bader, M., Inagami, T., Schneider, W., Luft, F.C. Kidney Int. (2000) [Pubmed]
Catalytic activity and isoform-specific inhibition of rat cytochrome p450 4F enzymes. Xu, F., Falck, J.R., Ortiz de Montellano, P.R., Kroetz, D.L. J. Pharmacol. Exp. Ther. (2004) [Pubmed]
20-hydroxyeicosatetraenoic acid (20-HETE) metabolism in coronary endothelial cells. Kaduce, T.L., Fang, X., Harmon, S.D., Oltman, C.L., Dellsperger, K.C., Teesch, L.M., Gopal, V.R., Falck, J.R., Campbell, W.B., Weintraub, N.L., Spector, A.A. J. Biol. Chem. (2004) [Pubmed]
20-hydroxyeicosatetraenoic acid (20-HETE) activates mouse TRPC6 channels expressed in HEK293 cells. Basora, N., Boulay, G., Bilodeau, L., Rousseau, E., Payet, M.D. J. Biol. Chem. (2003) [Pubmed]
Inhibitors of cytochrome P450 4A suppress angiogenic responses. Chen, P., Guo, M., Wygle, D., Edwards, P.A., Falck, J.R., Roman, R.J., Scicli, A.G. Am. J. Pathol. (2005) [Pubmed]
Role of 20-HETE in elevating chloride transport in the thick ascending limb of Dahl SS/Jr rats. Ito, O., Roman, R.J. Hypertension (1999) [Pubmed]
Arachidonic acid metabolites contribute to the irreversible depolarization induced by in vitro ischemia. Tanaka, E., Niiyama, S., Sato, S., Yamada, A., Higashi, H. J. Neurophysiol. (2003) [Pubmed]
Constrictor-induced translocation of NFAT3 in human and rat pulmonary artery smooth muscle. Yaghi, A., Sims, S.M. Am. J. Physiol. Lung Cell Mol. Physiol. (2005) [Pubmed]
The myogenic response: established facts and attractive hypotheses. Schubert, R., Mulvany, M.J. Clin. Sci. (1999) [Pubmed]
20-hydroxyeicosatetraenoic acid and epoxyeicosatrienoic acids and blood pressure. McGiff, J.C., Quilley, J. Curr. Opin. Nephrol. Hypertens. (2001) [Pubmed]
Cytochrome P-450 metabolites in endothelin-stimulated cardiac hormone secretion. Lee, S.J., Landon, C.S., Nazian, S.J., Dietz, J.R. Am. J. Physiol. Regul. Integr. Comp. Physiol. (2004) [Pubmed]
20-Hydroxyeicosatetraenoic acid is a potent dilator of mouse basilar artery: role of cyclooxygenase. Fang, X., Faraci, F.M., Kaduce, T.L., Harmon, S., Modrick, M.L., Hu, S., Moore, S.A., Falck, J.R., Weintraub, N.L., Spector, A.A. Am. J. Physiol. Heart Circ. Physiol. (2006) [Pubmed]
Functional variant of CYP4A11 20-hydroxyeicosatetraenoic acid synthase is associated with essential hypertension. Gainer, J.V., Bellamine, A., Dawson, E.P., Womble, K.E., Grant, S.W., Wang, Y., Cupples, L.A., Guo, C.Y., Demissie, S., O'Donnell, C.J., Brown, N.J., Waterman, M.R., Capdevila, J.H. Circulation (2005) [Pubmed]
Renal arterial 20-hydroxyeicosatetraenoic acid levels: regulation by cyclooxygenase. Cheng, M.K., McGiff, J.C., Carroll, M.A. Am. J. Physiol. Renal Physiol. (2003) [Pubmed]
Renal COX-2, cytokines and 20-HETE: tubular and vascular mechanisms. Ferreri, N.R., McGiff, J.C., Carroll, M.A., Quilley, J. Curr. Pharm. Des. (2004) [Pubmed]
Functional expression of human heme oxygenase-1 gene in renal structure of spontaneously hypertensive rats. Goodman, A.I., Quan, S., Yang, L., Synghal, A., Abraham, N.G. Exp. Biol. Med. (Maywood) (2003) [Pubmed]
Protective effect of 20-hydroxyeicosatetraenoic acid (20-HETE) on glomerular protein permeability barrier. McCarthy, E.T., Sharma, R., Sharma, M. Kidney Int. (2005) [Pubmed]
CYP4A metabolites of arachidonic acid and VEGF are mediators of skeletal muscle angiogenesis. Amaral, S.L., Maier, K.G., Schippers, D.N., Roman, R.J., Greene, A.S. Am. J. Physiol. Heart Circ. Physiol. (2003) [Pubmed]
Fluorescent HPLC assay for 20-HETE and other P-450 metabolites of arachidonic acid. Maier, K.G., Henderson, L., Narayanan, J., Alonso-Galicia, M., Falck, J.R., Roman, R.J. Am. J. Physiol. Heart Circ. Physiol. (2000) [Pubmed]
Effects of intrarenal infusion of 17-octadecynoic acid on renal antihypertensive mechanisms in anesthetized rabbits. Evans, R.G., Day, K.H., Roman, R.J., Hopp, K.H., Anderson, W.P. Am. J. Hypertens. (1998) [Pubmed]
Inability to Upregulate Cytochrome P450 4A and 2C Causes Salt Sensitivity in Young Sprague-Dawley Rats. Sankaralingam, S., Desai, K.M., Glaeser, H., Kim, R.B., Wilson, T.W. Am. J. Hypertens. (2006) [Pubmed]

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