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17-ODYA (Synonyms: Alk-16)

Catalog No.GC12757

17-ODYA, a non-selective inhibitor of both ω-hydroxylation and epoxygenation of arachidonic acid via cytochrome P450 (IC50<100nM).

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17-ODYA Chemical Structure

Cas No.: 34450-18-5

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1mg
$20.00
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5mg
$85.00
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10mg
$147.00
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100mg
$1,098.00
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Sample solution is provided at 25 µL, 10mM.

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Description of 17-ODYA

17-ODYA, a non-selective inhibitor of both ω-hydroxylation and epoxygenation of arachidonic acid via cytochrome P450 (IC50<100nM). 17-ODYA effectively suppressed the production of 20-hydroxyeicosatetraenoic acid, epoxyeicosatrienoic acids, and dihydroxyeicosatrienoic acids by rat renal cortical microsomes when exposed to arachidonic acid[1,2].

17-ODYA as the highest unique metabolite in periapical abscesses, acts an essential role in the Pathogenesis of Periapical Abscesses, one of the most frequent pathologic lesions in the alveolar bone. 17-ODYA caused significant up-regulation of interleukin-1α, interleukin-1β, interleukin-6, matrix metalloproteinase-1, monocyte chemoattractant protein-1 and platelet-derived growth factor alpha and vascular endothelial growth factor alpha at 10μmol/L in periodontal ligament fibroblasts.1μmol/L 17-ODYA caused the same effect in peripheral blood mononuclear cells. These affected cytokines have important biological activities in coordinating the body's response to infection[3].

17-ODYA delivered via the superfusate for 45mins at 10mmol/l, inhibits both local and conducted responses of microiontophoresis of ACh evoked vasodilation that conducted along arterioles in C57Bl6 mice[4].

References:
[1] Zou A P, Ma Y H, Sui Z H, et al. Effects of 17-octadecynoic acid, a suicide-substrate inhibitor of cytochrome P450 fatty acid omega-hydroxylase, on renal function in rats[J]. Journal of Pharmacology and Experimental Therapeutics, 1994, 268(1): 474-481.
[2] Manicam C, Ginter N, Li H, et al. Compensatory vasodilator mechanisms in the ophthalmic artery of endothelial nitric oxide synthase gene knockout mice[J]. Scientific reports, 2017, 7(1): 7111.
[3] Altaie A M, Mohammad M G, Madkour M I, et al. The essential role of 17-octadecynoic acid in the pathogenesis of periapical abscesses[J]. Journal of Endodontics, 2023, 49(2): 169-177. e3.
[4] Hnngerford J E, Sessa W C, Segal S S. Vasomotor control in arterioles of the mouse cremaster muscle[J]. The FASEB journal, 2000, 14(1): 197-207.

Protocol of 17-ODYA

Cell experiment [1]:

Cell lines

Human neutrophils

Preparation Method

Pre-warmed human neutrophil suspensions (37°C, 5 million cells/ml in HBSS containing 1.6 mM CaCl2) were incubated 5 minutes with vehicle (DMSO), PF-4708671 (30μM, 5 minutes), or 17-ODYA (30μM, 30 minutes), then treated with 1μM of LTB4 for the indicated times. Samples then were processed and analyzed for LTB4 biosynthesis, then performing kinetic experiments in which neutrophils were incubated with 1μM LTB4.

Reaction Conditions

30μM 17-ODYA for 30 minutes

Applications

17-ODYA increased LTB4 half-life by 5 folds, from ~10 sminutes to ~50 minutes. In comparison, PF-4708671 increased the half-life of LTB4 by 7.5 folds, from ~20 minutes to ~150 minutes.
Animal experiment [2]:

Animal models

Male Sprague-Dawley rats (9-12 week old)

Preparation Method

Rats (n=9) were pretreated 30 mins before subarachnoid hemorrhage (SAH) with N-hydroxy-N'-(4-butyl-2-methylphenyl) formamidine (HET0016) (10mg/kg iv) or 17-ODYA (1.5nmol intrathecally) (n=7 each) or vehicle (n=15). An additional control group of rats (n=9) received an infusion of an equal volume of artificial cerebrospinal fluid in the cisterna magna SAH was induced by injecting 0.3 mL of blood into the cisterna magna over a 10-min period. The effects of two inhibitors on the changes on regional cerebral blood flow (rCBF) after induction of SAH were measured with laser-Doppler flowmetry.

Dosage form

1.5nM, 50μL, cisterna magna injection

Applications

Both 17-ODYA and HET0016 attenuated fall in rCBF recorded at 10mins after induction of SAH by 40%, and rCBF completely recovered within 60mins after induction of SAH in rats treated with 17-ODYA and within 90mins in rats treated with HET0016.

References:

[1] Archambault A S, Turcotte C, Martin C, et al. Leukotriene B₄ Metabolism and p70S6 Kinase 1 Inhibitors: PF-4708671 but Not LY2584702 Inhibits CYP4F3A and the ω-Oxidation of Leukotriene B₄ In Vitro and In Cellulo[J]. Plos one, 2017, 12(1): e0169804.
[2] Kehl F, Cambj-Sapunar L, Maier K G, et al. 20-HETE contributes to the acute fall in cerebral blood flow after subarachnoid hemorrhage in the rat[J]. American Journal of Physiology-Heart and Circulatory Physiology, 2002, 282(4): H1556-H1565.

Chemical Properties of 17-ODYA

Cas No. 34450-18-5 SDF
Synonyms Alk-16
Chemical Name octadec-17-ynoic acid
Canonical SMILES OC(CCCCCCCCCCCCCCCC#C)=O
Formula C18H32O2 M.Wt 280.45
Solubility 1 mg/mL in DMSO, 10mg/mL in DMF,10mg/mL in ethanol Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of 17-ODYA

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1 mg 5 mg 10 mg
1 mM 3.5657 mL 17.8285 mL 35.657 mL
5 mM 0.7131 mL 3.5657 mL 7.1314 mL
10 mM 0.3566 mL 1.7828 mL 3.5657 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 11 reference(s) in Google Scholar.)

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