| Identification | Back Directory | [Name]
(±)16-HETE | [CAS]
128914-46-5 | [Synonyms]
(±)16-HETE
JEKNPVYFNMZRJG-UFINWASNSA-N
16-hydroxy-5(Z),8(Z),11(Z),14(Z)-eicosatetraenoic acid
5,8,11,14-Eicosatetraenoic acid, 16-hydroxy-, (5Z,8Z,11Z,14Z)- | [Molecular Formula]
C20H32O3 | [MOL File]
128914-46-5.mol | [Molecular Weight]
320.47 |
| Chemical Properties | Back Directory | [storage temp. ]
Store at -20°C | [solubility ]
0.1 M Na2CO3: 2 mg/ml; DMF: Miscible; DMSO: Miscible; Ethanol: Miscible; PBS (pH 7.2): 0.8 mg/ml |
| Hazard Information | Back Directory | [Description]
Electrolyte and fluid transport in the kidney are regulated in part by arachidonic acid and its metabolites. (±)16-HETE is the racemic version of a minor CYP450 metabolite of arachidonic acid released by the kidney upon angiotensin II stimulation. The biological activity of 16-HETE is stereospecific. 16(R)-HETE dose-dependently stimulates vasodilation of the rabbit kidney, however 16(S)-HETE does not affect perfusion pressure. At a concentration of 2 μM the (S)-enantiomer of 16-HETE inhibits proximal tubule ATPase activity by as much as 60%, whereas the (R)-isomer has negligible effects on ATPase activity. | [Uses]
16-HETE is arachidonic acid metabolite through subterminal hydroxylation by cytochrome P-450. 16-HETE exhibits vasodilatory and PMN inhibitory effects and serves as biomarker for early stages of non-alcoholic fatty liver disease[1][2][3]. | [Definition]
ChEBI: A HETE that consists of arachidonic acid bearing an additional hydroxy substituent at position 16. | [in vivo]
16-HETE (1-20 μg, i.a.) is stereospecificially involved in vasodilation, regulation of renal perfusion and in mechanisms of tubular transport with S- enantiomer in New Zealand white rabbit[2].
16-HETE (1 μg/kg/min) suppresses the increase of intracranial pressure (ICP) in a rabbit model of thromboembolic stroke[1]. | Animal Model: | New Zealand White rabbit[2] | | Dosage: | 1-20 μg | | Administration: | injection into artery | | Result: | 16S inhibited 60% ATPase activity at the concentration of 2 μM, while 16R enantiomer remained inactive. |
| Animal Model: | New Zealand White rabbit[1] | | Dosage: | 1 μg/kg/min | | Administration: | 6 hours constant infusion from Hours 1 to 2 after autologous clot embolization | | Result: | Reduced infarction area and less increased ICP. |
| [storage]
Store at -20°C | [References]
[1] Bednar MM, et al., 16(R)-hydroxyeicosatetraenoic acid, a novel cytochrome P450 product of arachidonic acid, suppresses activation of human polymorphonuclear leukocyte and reduces intracranial pressure in a rabbit model of thromboembolic stroke. Neurosurgery. 2000 Dec;47(6):1410-8; discussion 1418-9. PMID:11126912
[2] Carroll MA, e al., Cytochrome P-450-dependent HETEs: profile of biological activity and stimulation by vasoactive peptides. Am J Physiol. 1996 Oct;271(4 Pt 2):R863-9. DOI:10.1152/ajpregu.1996.271.4.R863
[3] Maciejewska D, et al., Metabolites of arachidonic acid and linoleic acid in early stages of non-alcoholic fatty liver disease--A pilot study. Prostaglandins Other Lipid Mediat. 2015 Sep;121(Pt B):184-9. DOI:10.1016/j.prostaglandins.2015.09.003 |
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