浅蓝菌素

中文名称:

浅蓝菌素

中文同义词:

2,3-环氧-4-氧-7,10-十二碳二烯酰胺;变蓝菌素;天蓝菌素;浅蓝菌素;2,3-环氧-4-氧-7,10-十二碳二烯酰胺/变蓝菌素/天蓝菌素

英文名称:

CERULENIN

英文同义词:

CERULENIN FROM CEPHALOSPORIUM CAERULENS;[2R-[2.alpha.,3.alpha.(4E,7E)]]-3-(1-Oxo-4,7-nonadienyl)oxiranecarboxamide;2,3-EPOXY-4-OXO-7,10-DODECADIENAMIDE;(2R,3S,E,E)-2,3-EPOXY-4-OXO-7,10-DODECADIENAMIDE;2R,3S-EPOXY-4-OXO-7,10-DODECADIENAMIDE;[2R-[2alpha,3alpha(4E,7E)]]-3-(1-oxonona-4,7-dienyl)oxirane-2-carboxamide;2,3-epoxy-4-oxo-10-dodecadienamide;3-(1-oxo-4,7-nonadienyl)-,(2r-(2-alpha,3-alpha(4e,7e)))-oxiranecarboxamid

CAS号:

17397-89-6

分子式:

C12H17NO3

分子量:

223.27

EINECS号:

241-424-8

相关类别:

微生物代谢物;抗生素;生化试剂;医药原料;antibiotic

Mol文件:

17397-89-6.mol

熔点

93.5℃

比旋光度

D16 +63° (c = 2 in methanol)

沸点

bp 120° (10-8 mm)

密度

1.1223 (rough estimate)

折射率

1.5300 (estimate)

储存条件

−20°C

溶解度

acetone: 20 mg/mL, clear, colorless to yellow

形态

White to off-white solid

酸度系数(pKa)

15.19±0.40(Predicted)

Merck

13,2014

BRN

4140423

生物活性

Cerulenin 是一种广泛使用的天然脂肪酸合成酶 (FASN) 抑制剂。Cerulenin 是由真菌 Cephalosporium caeruleus 产生的。

靶点

Fatty acid synthase (FASN)

体外研究

Cerulenin covalently binds to the catalytic site of FAS and disrupts the condensation reaction of acetyl-COA and malonyl-COA, inhibiting the biosynthesis of fatty acids and sterols in yeast. The Flavonoids quercetin and trans-Chalcone are effective against T. rubrum , with MICs of 125 and 7.5 μg/mL for the wild-type strain (MYA3108) and of 63 and 1.9 μg/mL for the ABC transporter mutant strain (Δ TruMDR2 ), respectively. The MICs of the Fluconazole and Cerulenin controls are 63 and 125 μg/mL for the wild-type strain and 30 and 15 μg/mL for the mutant strain, respectively. To explore the underlying mechanism of Steroidogenic acute regulatory protein (StAR)’s protective effect on endothelial dysfunction model, the inhibitor of fatty acid synthase and HMG-CoA reductase, Cerulenin ( 5 μg/mL) and Lovastatin, are used before palmitic acid (PA) added. The mRNA expression of IL-1β, TNFα, VCAM-1 and IL-6 are reduced while NO production is recovered with inhibitor treatment.

体内研究

Cerulenin treatment of ob/ob mice has obvious effects on body weight. With 2 days of treatment, body weight in treated mice is decreased compared to a 5.7% weight gain in the controls. With prolonged (7 days) treatment, no body weight loss is observed, but body weight gain is slowed. In all groups, 60 mg/kg of Cerulenin is more effective than 30 mg/kg in inhibiting weight gain. If given daily or every other day, ATP content are increased 58.1% and 61.5% respectively by 7-day treatment of 60 mg/kg Cerulenin. Significant ATP elevation is also observed with only 2 days of treatment with 60 mg/kg Cerulenin. In contrast, 30 mg/kg Cerulenin, given either 2 or 7 days, does not show any significant effect on cellular ATP content.

危险品标志

危险类别码

安全说明

24/25

WGK Germany

RTECS号

JR1670000

10-21

海关编码

29419090

毒性

LD50 in mice (mg/kg): 154 i.v.; 211 i.p.; 547 orally (Matsumae 1964)