Acifran - CAS 72420-38-3
Category: Inhibitor
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Molecular Formula:
C12H10O4
Molecular Weight:
218.21
COA:
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Targets:
nAChR
Description:
Acifran is a nicotinic acid receptor agonist with hypolipidemic effects, which shows higher potency than nicotinic acid and clofibrate. It is a potent and full agonist at the human orphan GPCR HM74A/GPR109A and GPR109B. It reduces circulating LDL-cholesterol and serum triglycerides in vivo without affecting liver enzymes or liver weight.
Purity:
≥99% by HPLC
Synonyms:
AY 25712; 4,5-Dihydro-5-methyl-4-oxo-5-phenyl-2-furancarboxylic acid; (±)-Acifran; Reductol
MSDS:
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InChIKey:
DFDGRKNOFOJBAJ-UHFFFAOYSA-N
InChI:
InChI=1S/C12H10O4/c1-12(8-5-3-2-4-6-8)10(13)7-9(16-12)11(14)15/h2-7H,1H3,(H,14,15)
Canonical SMILES:
CC1(C(=O)C=C(O1)C(=O)O)C2=CC=CC=C2
1.Niacin receptor activation improves human microvascular endothelial cell angiogenic function during lipotoxicity.
Hughes-Large JM;Pang DK;Robson DL;Chan P;Toma J;Borradaile NM Atherosclerosis. 2014 Dec;237(2):696-704. doi: 10.1016/j.atherosclerosis.2014.10.090. Epub 2014 Oct 28.
OBJECTIVE: ;Niacin (nicotinic acid) as a monotherapy can reduce vascular disease risk, but its mechanism of action remains controversial, and may not be dependent on systemic lipid modifying effects. Niacin has recently been shown to improve endothelial function and vascular regeneration, independent of correcting dyslipidemia, in rodent models of vascular injury and metabolic disease. As a potential biosynthetic precursor for NAD(+), niacin could elicit these vascular benefits through NAD(+)-dependent, sirtuin (SIRT) mediated responses. Alternatively, niacin may act through its receptor, GPR109A, to promote endothelial function, though endothelial cells are not known to express this receptor. We hypothesized that niacin directly improves endothelial cell function during exposure to lipotoxic conditions and sought to determine the potential mechanism(s) involved.;METHODS AND RESULTS: ;Angiogenic function in excess palmitate was assessed by tube formation following treatment of human microvascular endothelial cells (HMVEC) with either a relatively low concentration of niacin (10 μM), or nicotinamide mononucleotide (NMN) (1 μM), a direct NAD(+) precursor. Although both niacin and NMN improved HMVEC tube formation during palmitate overload, only NMN increased cellular NAD(+) and SIRT1 activity.
2.Niacin induces PPARgamma expression and transcriptional activation in macrophages via HM74 and HM74a-mediated induction of prostaglandin synthesis pathways.
Knowles HJ;te Poele RH;Workman P;Harris AL Biochem Pharmacol. 2006 Feb 28;71(5):646-56. Epub 2006 Jan 18.
HM74 and HM74a have been identified as receptors for niacin. HM74a mediates the pharmacological anti-lipolytic effects of niacin in adipocytes by reducing intracellular cyclic AMP (cAMP) and inhibiting release of free fatty acids into the circulation. In macrophages, niacin induces peroxisome proliferator-activated receptor gamma (PPARgamma)-dependent and cAMP-dependent expression of genes mediating reverse cholesterol transport, although via an unidentified receptor. We describe constitutive expression of HM74a mRNA and hypoxia- and IFNgamma-inducible expression of HM74 and HM74a in human monocytic cell lines and primary cells in culture. In U937 cells niacin-induced expression of 15-deoxy-Delta(12,14)-prostaglandin J(2) (15d-PGJ(2)), the most potent endogenous ligand of PPARgamma. Both niacin and the structurally distinct HM74/HM74a ligand acifran-induced nuclear expression of PPARgamma protein and enhanced PPARgamma transcriptional activity. Niacin-induced PPARgamma transcriptional activity was pertussis toxin sensitive and required activity of phospholipase A(2) (EC 3.1.1.4), cyclo-oxygenase (EC 1.14.99.1) and prostaglandin D(2) synthase (EC 5.3.99.2). Niacin also induced PPARgamma transcriptional activity in HM74 and HM74a CHO cell transfectants, although not in vector-only control cells.
3.Evaluation of the lipid-lowering activity of AY-25,712 in rats.
Cayen MN;Kallai-Sanfacon MA;Dubuc J;Greselin E;Dvornik D Atherosclerosis. 1982 Dec;45(3):267-79.
The effect of AY-25,712 (2-methyl-2-phenyl-3(2H)-furanone-5-carboxylic acid) on serum lipids, hepatic lipogenesis and biliary cholesterol was investigated in male rats. Based on one-week treatment, the minimal effective dose of AY-25,712 which lowered serum triglycerides was 1 mg/kg/day, and LDL-cholesterol, 5 mg/kg/day. Nicotinic acid produced a similar lipid-lowering profile albeit at 5 times higher doses. AY-25,712 at doses of 2 mg/kg/day and higher significantly increased the ratio of HDL to total cholesterol. Unlike clofibrate, AY-25,712 did not increase liver weight or liver mitochondrial alpha-glycerophosphate dehydrogenase, nor increase biliary cholesterol levels in rats fed a diet containing 2% cholesterol and 0.5% cholic acid. AY-25,712 lowered serum cholesterol, triglycerides and phospholipids in rats rendered hyperlipidemic with Triton WR-1339 and decreased the elevated serum triglycerides in streptozotocin-diabetic rats. [14C]Acetate incorporation into cholesterol by liver homogenate was suppressed in rats given AY-25,712 p.o. for 1 week. The results show that AY-25,712 is a potent LDL-cholesterol- and triglyceride-lowering agent in rats, and that its lipid-lowering profile differs from that of clofibrate but resembles that of nicotinic acid.
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CAS 72420-38-3 Acifran

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