SC 26196 - CAS 218136-59-5
Category: Inhibitor
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Molecular Formula:
C27H29N5
Molecular Weight:
423.55
COA:
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Targets:
Stearoyl-CoA Desaturase (SCD)
Description:
SC 26196 is a selective Δ6 desaturase inhibitor (IC50 = 0.2 μM in vitro) that displays >100 fold selectivity over Δ5 and Δ9 desaturases (IC50 >200 μM in vitro). SC 26196 completely inhibits the conversion of linoleic acid to arachidonic acid (AA). It exhibits anti-inflammatory properties in a mouse edema model.
Brife Description:
Δ6 desaturase inhibitor
Purity:
≥98% by HPLC
Synonyms:
α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile; PF-o6341724; FT-0674530
MSDS:
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InChIKey:
QFYKXKMYVYOUNJ-UHFFFAOYSA-N
InChI:
InChI=1S/C27H29N5/c28-23-27(25-10-3-1-4-11-25,26-12-5-2-6-13-26)14-8-16-31-17-19-32(20-18-31)30-22-24-9-7-15-29-21-24/h1-7,9-13,15,21-22H,8,14,16-20H2
Canonical SMILES:
C1CN(CCN1CCCC(C#N)(C2=CC=CC=C2)C3=CC=CC=C3)N=CC4=CN=CC=C4
1.Conjugated linoleic acid-induced fat loss dependence on Delta6-desaturase or cyclooxygenase.
Hargrave-Barnes KM;Azain MJ;Miner JL Obesity (Silver Spring). 2008 Oct;16(10):2245-52. doi: 10.1038/oby.2008.338. Epub 2008 Jul 24.
OBJECTIVE: ;To determine whether conjugated linoleic acid (CLA)-induced body fat loss is dependent upon metabolism of CLA by Delta6-desaturase, cyclooxygenase, or lipoxygenase.;METHODS AND PROCEDURES: ;Mice were fed diets with or without CLA and inhibitors to either Delta6-desaturase (SC-26196), cyclooxygenase (aspirin), or lipoxygenase (nordihydroguaiaretic acid (NDGA)) for 2 weeks. Body fat percent, lean mass, fat pad weights, liver weight, and fatty acid concentrations were determined. A Delta6-desaturase index was calculated, and adipose tissue prostaglandin E(2) (PGE(2)) and leukotriene B(4) (LTB(4)) concentrations were determined to confirm enzyme inhibition.;RESULTS: ;Inhibition of Delta6-desaturase and cyclooxygenase were confirmed. CLA caused a loss of body fat (P < 0.001). The body fat loss was blocked (P = 0.08) by the Delta6-desaturase inhibitor at a dose that decreased (P < 0.05) the calculated index. Aspirin and NDGA had no effect on body fat and did not interact with CLA.;DISCUSSION: ;Inhibition of Delta6-desaturase prevented CLA from being able to cause a body fat loss. Therefore, a desaturated metabolite of CLA appears to be involved in the CLA antiobesity effect. This effect of CLA does not seem dependent upon cyclooxygenase.
2.Selective inhibition of Delta-6 desaturase impedes intestinal tumorigenesis.
Hansen-Petrik MB;McEntee MF;Johnson BT;Obukowicz MG;Masferrer J;Zweifel B;Chiu CH;Whelan J Cancer Lett. 2002 Jan 25;175(2):157-63.
Arachidonic acid is an important polyunsaturated fatty acid involved in cell signaling. It is derived primarily from dietary linoleic acid, and the rate-limiting step in its biosynthesis is the initial desaturation of linoleic acid via Delta-6 desaturase. Evidence suggests that downstream metabolic products of arachidonic acid, e.g. prostaglandins, are involved in colorectal cancer, but involvement of the biosynthetic pathway of arachidonic acid has not been previously investigated. In the present study, we report the effects of a novel selective Delta-6 desaturase inhibitor, SC-26196, on tumorigenesis in two in vivo models of intestinal cancer. SC-26196 treatment resulted in 36-37% fewer tumors in Apc(Min/+) mice and 35% decrease in primary tumor size in nude mice bearing HT-29 human colon cancer cell xenografts (P<0.05). As expected, SC-26196 treatment resulted in significantly higher linoleic acid levels in tissue phospholipids and lower levels of arachidonic acid. The effects on both tissue fatty acid composition and tumorigenesis in Apc(Min/+) mice were abrogated by concomitant treatment with dietary arachidonic acid, indicating that the observed effects were due to interference with the biosynthetic pathway of arachidonic acid.
3.Lipid remodeling in mouse liver and plasma resulting from delta6 fatty acid desaturase inhibition.
Duffin KL;Obukowicz MG;Salsgiver WJ;Welsch DJ;Shieh C;Raz A;Needleman P Lipids. 2001 Nov;36(11):1203-8.
Electrospray/tandem mass spectrometry was used to quantify lipid remodeling in mouse liver and plasma during inhibition of polyunsaturated fatty acid synthesis by the delta6 fatty acid desaturase inhibitor, SC-26196. SC-26196 caused increases in linoleic acid and corresponding decreases in arachidonic acid and docosahexaenoic acid in select molecular species of phosphatidylcholine, phosphatidylethanolamine, and cholesterol esters but not in phosphatidylserine, phosphatidylinositol, or triglycerides. For linoleic acid-, arachidonic acid-, and docosahexaenoic acid-containing phospholipid species, this difference was, in part, determined by the fatty acid at the sn-1 position, namely, palmitic or stearic acid. An understanding of phospholipid remodeling mediated by delta6 desaturase inhibition should aid in clarifying the contribution of arachidonic acid derived via de novo synthesis or obtained directly in the diet during inflammatory responses.
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CAS 218136-59-5 SC 26196

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