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蝴蝶霉素

蝴蝶霉素用途

Rebeccamycin,一种抗肿瘤抗生素,抑制 DNA 拓扑异构酶 I (DNA topoisomerase I)。Rebeccamycin 通过毒害拓扑异构酶 I 发挥其主要的抗肿瘤作用,对蛋白激酶 C 和拓扑异构酶 Ⅱ 的作用较小。

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蝴蝶霉素名称

[ CAS 号 ]:
93908-02-2

[ 中文名 ]:
蝴蝶霉素

[ 英文名 ]:
Rebeccamycin

[英文别名 ]:

AmbotzLS-1199
MFCD01718312

蝴蝶霉素生物活性

[ 描述 ]:

[ 相关类别 ]:

研究领域 >> 癌症

信号通路 >> 细胞周期/DNA损伤 >> 拓扑异构酶

信号通路 >> 抗体- 药物偶联物 >> ADC细胞毒素

[ 靶点 ]

Topoisomerase I

Traditional Cytotoxic Agents

[体外研究]

瑞贝霉素是一种抗肿瘤抗生素,由放线菌Saccharotrix aerocolonigenes产生,对多种人类肿瘤细胞系,包括A549(肺腺癌)、HCT-116(结肠癌)和KB(鼻咽癌)具有活性[1]。瑞贝霉素对几种革兰氏阳性菌,包括金黄色葡萄球菌和粪链球菌具有抗菌活性[3]。

[体内研究]

瑞贝霉素(2-256 mg/kg；i.p.；每日9天)延长B16黑色素瘤、L1210白血病的生存期[2]。动物模型：CDF1小鼠(B16黑色素瘤,L1210白血病)[2]剂量：2,4,8,16,32,64,128,256 mg/kg给药：I.p.；每日9天结果：8-256 mg/kg剂量水平延长小鼠存活时间。

[参考文献]

[1]. Merchant J, et al. Phase I clinical and pharmacokinetic study of NSC 655649, a rebeccamycin analogue, given in both single-dose and multiple-dose formats. Clin Cancer Res. 2002 Jul;8(7):2193-201.

[2]. Bush JA, et al. Production and biological activity of rebeccamycin, a novel antitumor agent. J Antibiot (Tokyo). 1987 May;40(5):668-78.

[3]. Sánchez C, et al. The biosynthetic gene cluster for the antitumor rebeccamycin: characterization and generation of indolocarbazole derivatives. Chem Biol. 2002 Apr;9(4):519-31.

蝴蝶霉素物理化学性质

[ 密度 ]:
1.87g/cm3

[ 分子式 ]:
C₂₇H₂₁Cl₂N₃O₇

[ 分子量 ]:
570.37800

[ 精确质量 ]:
569.07600

[ PSA ]:
150.37000

[ 折射率 ]:
1.844

[ 储存条件 ]:
-20°C，密闭，干燥

蝴蝶霉素毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NM3455000

CHEMICAL NAME :: 5H-Indolo(2,3-a)pyrrolo(3,4-c)carbazole-5,7(6H)-dione , 1,11-dichloro-12,13-dihydro-12-(4-O- methyl-beta-D-glucopyranosyl)-

CAS REGISTRY NUMBER :: 93908-02-2

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C27-H21-Cl2-N3-O7

MOLECULAR WEIGHT :: 570.41

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Human Cells - not otherwise specified

DOSE/DURATION :: 3 mg/L

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 40,668,1987

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蝴蝶霉素安全信息

[ 危险品运输编码 ]:
NONH for all modes of transport

蝴蝶霉素合成路线

详细合成路线

蝴蝶霉素上下游产品

蝴蝶霉素上游产品

蝴蝶霉素下游产品

蝴蝶霉素文献

Structure and mechanism of the rebeccamycin sugar 4'-O-methyltransferase RebM.

J. Biol. Chem. 283(33) , 22628-36, (2008)

The 2.65-angstroms crystal structure of the rebeccamycin 4'-O-methyltransferase RebM in complex with S-adenosyl-l-homocysteine revealed RebM to adopt a typical S-adenosylmethionine-binding fold of sma...

Natural product diversification using a non-natural cofactor analogue of S-adenosyl-L-methionine.

J. Am. Chem. Soc. 128(9) , 2760-1, (2006)

Adenosine analogues bearing either 5'-aziridine or 5'-N-mustard electrophiles are methyltransferase-dependent DNA alkylating agents. We present here a novel synthetic cofactor bearing a pendant 5'-ami...

Engineering biosynthetic pathways to generate antitumor indolocarbazole derivatives.

J. Ind. Microbiol. Biotechnol. 33(7) , 560-8, (2006)

The indolocarbazole family of natural products is a source of lead compounds with potential therapeutic applications in the treatment of cancer and neurodegenerative disorders. Rebeccamycin and stauro...

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