セルレニン 化学特性,用途語,生産方法
外観
白色〜うすい褐色, 結晶性粉末〜粉末
溶解性
水、エタノール及びアセトンに溶ける。本品20mg＋メタノール1mlで可溶。
用途
阻害剤、薬理研究用。
使用上の注意
不活性ガス封入
説明
Cerulenin is a fungal metabolite originally isolated from
C. caerulens that has diverse biological activities. It is active against a variety of bacteria, including
B. subtilis,
E. coli,
B. megaterium, and
B. anthracis (MICs = 12.5, 12.5, 50, and 50 μg/ml, respectively) and fungi, including strains of
C. albicans,
T. rubrum, and
A. fumigatus (MICs = 0.8-3.7, 3.1-6.2 and 12.5-50 μg/ml, respectively). Cerulenin is an inhibitor of fatty acid synthase type I (FAS-I) and FAS-II (IC
50s = 3 and 20 μM, respectively, for the
E. coli enzymes). It inhibits fatty acid synthesis in a panel of human cancer cell lines, including breast, ovarian, and endometrial cancer cells, as well as reduces tumor growth in a OVCAR-3 mouse xenograft model.
化学的特性
White powder
使用
Cerulenin is an epoxy fatty acid amide isolated from the fungus Cephalosporium caerulens and identified as an antifungal in the 1960s. Over the past 40 years, cerulenin has found broad application in lipid biochemistry as an inhibitor fatty acid and sterol biosynthesis. Cerulenin binds to β-keto-acyl-ACP synthase blocking the interaction of malonyl CoA. Cerulenin also an inhibits bacterial fatty acid synthesis, acting on the FabH, FabB and FabF condensation enzymes. Cerulenin stimulates fatty acid oxidation and inhibits HMG-CoA synthetase activity.
定義
ChEBI: An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.
一般的な説明
An anti-fungal antibiotic that inhibits fatty acid biosynthesis by binding, in equimolar ratio, to β-keto-acyl-ACP synthase. Also inhibits sterol synthesis by blocking the activity of HMG-CoA synthetase activity. Systemic and intracerebroventricular of this compound reduces feeding and induces weight loss.
純化方法
It forms white needles from *C6H6. It has also been purified by repeated chromatography through Florisil and silica gel. It is soluble in EtOH, MeOH, *C6H6, slightly soluble in H2O and pet ether. The dl-form has m 40-42o (from *C6H6/hexane), and the 2R,3S-tetrahydrocerulenin has m 86-87o, [] 20 +44.4 (c 0.25, MeOH after 24hours). [Ohrui & Emato Tetrahedron Lett 2095 1978, Sneda et al. Tetrahedron Lett 2039 1979, Broeckman & Thomas J Am Chem Soc 99 2805 1977, Jakubowski et al. J Org Chem 47 1221 1982, Beilstein 18/2 V 201.]
セルレニン 上流と下流の製品情報
原材料
準備製品