ChemicalBook Product Catalog Biochemical Engineering Biochemical Reagents (±)16-HETE

(±)16-HETE

Product Name(±)16-HETE
CAS128914-46-5
MFC20H32O3
MW320.47
EINECS
MOL File128914-46-5.mol

Chemical Properties

Boiling point	477.276±45.00 °C(Press: 760.00 Torr)(predicted)
Density	0.984±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
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
pka	4.752±0.10(predicted)

Usage And Synthesis

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.

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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