12684-33-2

• 常用中文名：Sibiromycin
• 常用英文名：Sibiromycin
• CAS号：12684-33-2
• 分子式：C₂₄H₃₁N₃O₇
• 分子量：473.51900
• 相关类别： 信号通路 细胞周期/DNA损伤 DNA烷基化剂/交联剂
• 发布时间：2016-07-25 10:35:08
• 更新时间：2026-07-16 18:49:32
• 西布罗霉素是一种天然产生的糖基化吡咯苯二氮卓类(PBD)。西布罗霉素也是一种有效的抗肿瘤抗生素,与鸟嘌呤NH2小沟中的DNA共价结合[1][2]。

名称

• 中文名: 西伯利亚霉素
• 英文名: (6R,6aS)-2-[(2S,3R,4R,5S,6S)-3,4-dihydroxy-4,6-dimethyl-5-(methylamino)oxan-2-yl]oxy-4,6-dihydroxy-3-methyl-8-[(E)-prop-1-enyl]-5,6,6a,7-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one
• 中文别名: 西北利亚霉素
• 英文别名: Sybiromycin; (7S,8R)-13-{[(2S,3R,4R,5S,6S)-3,4-dihydroxy-4,6-dimethyl-5-(methylamino)oxan-2-yl]oxy}-8,11-dihydroxy-12-methyl-5-[(1E)-prop-1-en-1-yl]-3,9-diazatricyclo[8.4.0.03,]tetradeca-1,4,11,13-tetraen-2-one; 5H-Pyrrolo[2,1-c][1,4]benzodiazin-5-one, 7-[[4,6-dideoxy-3-C-methyl-4-(methylamino)-α-L-mannopyranosyl]oxy]-1,10,11,11a-tetrahydro-9,11-dihydroxy-8-methyl-2-(1E)-1-propen-1-yl-, (11R,11aS); 7-[(4,6-Dideoxy-3-methyl-4-methylamino-α-L-mannopyranosyl)oxy]-10,11-dihydro-9,11-dihydroxy-8-methyl-2-(1-propenyl)-5H-pyrrolo[2,1-c][1,4]benzodiazin-5-one; 5H-Pyrrolo(2,1-C)(1,4)benzodiazin-5-one, 7-((4,6-dideoxy-3-C-methyl-4-(methylamino)-alpha-L-mannopyranosyl)oxy)-1,10,11,11A-treahydro-9,11-dihydroxy-8-methyl-2-(1E)-1-propenyl-, (11R,11as); C24H31N3O7

物化性质

• 密度: 1.41g/cm3
• 沸点: 755.7ºC at 760 mmHg
• 分子式: C₂₄H₃₁N₃O₇
• 分子量: 473.51900
• 闪点: 410.8ºC
• 精确质量: 473.21600
• PSA: 145.44000
• LogP: 1.99250
• 蒸汽压: 5.32E-24mmHg at 25°C
• 折射率: 1.662

生物活性

• 描述: 西布罗霉素是一种天然产生的糖基化吡咯苯二氮卓类(PBD)。西布罗霉素也是一种有效的抗肿瘤抗生素,与鸟嘌呤NH2小沟中的DNA共价结合[1][2]。
• 相关类别:
  研究领域 >> 癌症
  信号通路 >> 细胞周期/DNA损伤 >> DNA烷基化剂/交联剂
• 体外研究: 吡咯苯二氮杂卓(PBD)是具有显著抗肿瘤活性的序列选择性DNA烷基化剂[1]。炭疽霉素、西伯利亚霉素和托霉素对DNA的烷基化具有序列特异性,结合偏好为5′-Pu-G-Pu>5′-Py-G-Pu>5′-Pu-G-Py>5′-Py-G-Py[1]。西布罗霉素对L1210(白血病)、ADJ/PC6(浆细胞瘤)和CH1(卵巢)细胞具有细胞毒性,IC50范围为0.000017~0.0029μM[1]。
• 参考文献:

  [1]. Gerratana B. Biosynthesis, synthesis, and biological activities of pyrrolobenzodiazepines. Med Res Rev. 2012;32(2):254-293.

  [2]. Li W, et al. Biosynthesis of sibiromycin, a potent antitumor antibiotic. Appl Environ Microbiol. 2009;75(9):2869-2878.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : UY8495000 CHEMICAL NAME : 5H-Pyrrolo(2,1-c)(1,4)benzodiazepin-5-one, 7-((4,6-dideoxy-3-(methyl-4-(methylamino)-beta- D-altropyranosyl)oxy))-10,11-dihydro-9,11-dihydroxy-8 -methyl-2-(1-propenyl )- CAS REGISTRY NUMBER : 12684-33-2 LAST UPDATED : 199609 DATA ITEMS CITED : 13 MOLECULAR FORMULA : C24-H31-N3-O7 MOLECULAR WEIGHT : 473.58 WISWESSER LINE NOTATION : T C576 BVN IM HHJ E1U2 HQ KQ L1 MO- BT6OTJ CQ DQ D1 EM1 F1 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 6 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 29 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 459 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 32 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 84 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 58 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD10 - Lethal Dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 5 ug/kg TOXIC EFFECTS : Cardiac - pericarditis Cardiac - other changes TYPE OF TEST : LD10 - Lethal Dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 12 ug/kg TOXIC EFFECTS : Blood - other changes TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 98 ug/kg/4D-I TOXIC EFFECTS : Related to Chronic Data - death TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 22500 ng/kg/30D-I TOXIC EFFECTS : Cardiac - cardiomyopathy including infarction Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 30 ug/kg/15D-I TOXIC EFFECTS : Kidney, Ureter, Bladder - other changes Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Related to Chronic Data - death MUTATION DATA TYPE OF TEST : Mutation test systems - not otherwise specified TEST SYSTEM : Rodent - mouse Ascites tumor DOSE/DURATION : 1 ug/L REFERENCE : NEOLA4 Neoplasma. (Karger-Libri, P.O. Box, CH-4009 Basel, Switzerland) V.4- 1957- Volume(issue)/page/year: 22,105,1975