Mitomycin C 自力霉素
CAS 50-07-7 MFCD00078109
化学结构图
SMILES: CO[C@@]12[C@H](COC(N)=O)C3=C(C(=O)C(C)=C(N)C3=O)N1C[C@@H]1N[C@@H]12
化学属性
| Mol. Formula | C15H18N4O5 |
|---|---|
| Mol. Weight | 334.33 |
| Melting Point | 360°C |
| Solubility | 360℃以上分解。溶于水、甲醇、丙醇、乙酸丁酯和环已酮，微溶于苯、四氯化碳和醚，几乎不溶于石油醚。其水溶液对酸、碱均不稳定。 |
| Appearance | 50 (大鼠，经口) 14mg/kg。试验表明本品对实验动物有潜在致癌作用。 powder 蓝紫色有光泽结晶或结晶性粉末。固体稳定，但在酸性和碱性溶液中易失活。Mp>;360℃；在甲醇中最大吸收波长为216nm、360nm和560nm，水溶液的最大吸收波长为365nm±2nm。本品溶于水、甲醇、丙酮和乙酸乙酯等有机溶剂，微溶于苯、乙醚和四氯化碳，不溶于石油醚。剧毒，LD |
| Density | 1.56 |
别名和识别编码
| Chemical Name | Mitomycin C |
|---|---|
| CAS Number | 50-07-7 |
| Synonym | )methyl)-1,1a,2,8,8a,8b-hexahydro-8-a-methoxy-5-methyl-,(1as-(1aalpha,8beta, 6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione carbamate (ester) 7-amino-9-alpha-methoxymitosane 8aalpha,8balpha))-(9ci) 8balpha)]-8aalph AMETYCIN Ametycine MITOCIN C MITOMYCIN MITOMYCIN C MITOMYCIN C, STREPTOMYCES CAESPITOSUS MMC MUTAMYCIN Mitocin C Mitocin-C MitocinC Mitomycin Mitomycin C Mitomycin-C Mitonco Mitoplus Mutamycin NSC 26980 NSC-26980 NSC26980 [1aR-(1aalpha,8beta,8aalpha,8balpha)]-6-Amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-alpha]indole-4,7-d |
| MDL Number | MFCD00078109 |
| PubChem Substance ID | 5746 |
| Beilstein Registry Number | 7231816 |
| EC Number | 200-008-6 |
| Chemical Name Translation | 自力霉素 |
| Merck Number | 6215 |
| Reaxys-RN | 3570056 |
| LabNetwork Molecule ID | LN01289085 |
| InChI | InChI=1S/C15H18N4O5/c1-5-9(16)12(21)8-6(4-24-14(17)22)15(23-2)13-7(18-13)3-19(15)10(8)11(5)20/h6-7,13,18H,3-4,16H2,1-2H3,(H2,17,22)/t6-,7+,13+,15-/m1/s1 |
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专业采购外包团队在线服务
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分类
- {SNA} Analytical Standards, EP Standards, EP Standards L - M, Pharmacopeia & Metrological Institutes Standards, 分析/色谱
- Antibiotic powders, Antibiotics, Antibiotics A to Z, Antibiotics G-M, Antibiotics by Application, Antibiotics for Scale-Up Cell Culture, Antineoplastic and Immunosuppressive Antibiotics, Aziridines, Bioactive Small Molecules, Cell Biology, Cell Culture, Cell Culture Supplies, Chemical Structure Class, Core Bioreagents, Culture, Dissociation, General Stem Cell Biology, Interferes with DNA Synthesis, Labware, Life Science Reagents for Cell Culture,
- {SNA} Antibiotic
产品应用
- DND合成、核分裂和癌细胞的抑制剂。该品和博来霉素及其衍生物派来霉素都是破坏DNA的抗生素类抗癌药，可使细胞DNA解聚，抑制增生细胞的DNA的复制。
相关文献及参考
- Sartorelli AC, et al., Mitomycin C: a prototype bioreductive agent Oncol. Res. 6 , 501-508, (1994) 摘要
- Merck: 14,6215
- Armstrong MJ, et al., A quantitative assessment of the cytotoxicity associated with chromosomal aberration detection in Chinese hamster ovary cells Mutat. Res. 265 , 45-60, (1992) 摘要
- Kinoshita, S., et al.: J. Med. Chem., 14, 13 (1971),
- Tomasz M, and Palom Y., The mitomycin bioreductive antitumor agents: cross-linking and alkylation of DNA as the molecular basis of their activity Pharmacol. Ther. 76 , 73-87, (1997) 摘要
- Beijnen, J.H., et al.: Anal. Profiles Drug Subs., 16, 361 (1986),
- Omoto M, et al., The use of human mesenchymal stem cell-derived feeder cells for the cultivation of transplantable epithelial sheets Invest. Ophthalmol. Vis. Sci. 50(5) , 2108-2115, (2009) 摘要
- Sugimura, S., et al., Interspecies somatic cell nucleus transfer with porcine oocytes as recipients: A novel bioassay system for assessing the competence of canine somatic cel
- Johnson WS, et al., Selective recognition of the m5CpG dinucleotide sequence in DNA by mitomycin C for alkylation and cross-linking Bioorg. Med. Chem. 3 , 851-860, (1995) 摘要
- Nieto A, et al., Effect of mitomycin-C on human foreskin fibroblasts used as feeders in human embryonic stem cells: immunocytochemistry MIB1 score and DNA ploidy and apoptosis evaluated by flow cytometry Cell Biol. Int. 31 , 269-278, (2007) 摘要
- Gao K, et al., Inhibitory effect of mesenchymal stem cells on lymphocyte proliferation Cell Biochem. Funct. 26 , 900-907, (2008) 摘要
- Tomasz M., Mitomycin C: small, fast and deadly (but very selective) Chem. Biol. 2 , 575-579, (1995) 摘要
安全信息
GHS Symbol
- P201 Obtain special instructions before use. 使用前获取专门指示。
- P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。
- P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
- P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
- P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
- P281 Use personal protective equipment as required. 使用所需的个人防护装备。
- P301+P310
- P301+P310+P330
- P301+P312+P330
- P308+P313
- P321 Specific treatment (see … on this label). 具体治疗（见本标签上的）。
- P330 Rinse mouth. 漱口
- P405 Store locked up. 上锁保管。
- P501 Dispose of contents/container to..… 处理内容物/容器.....
- H300 Fatal if swallowed 吞食致命
- H351 Suspected of causing cancer 怀疑致癌
- S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
- S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
- S28 After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) 皮肤接触后，立即用大量…（由生产厂家指定）冲洗；
- S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置；
- S22 Do not breathe dust 不要吸入粉尘；
- R25 Toxic if swallowed 吞咽有毒
- R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
- R22 Harmful if swallowed 吞咽有害
其他信息
- 毒性分级:剧毒
- 储运特性:库房通风低温干燥
- 灭火剂:干粉、泡沫、砂土、二氧化碳, 雾状水
- Mitomycin C is part of a family of azidine natural products. It is a DNA crosslinking and damaging agent, making it a useful antibiotic and antitumor compound. When crosslinking, Mitomycin C displays absolute specificity and high efficiency for the CpG sequence. Mammalian Cells treated with Mitomycin C (0.4 mg/mL for 5 min) can undergo apoptosis through upregulation of Bad, Fas, FasL and phosphorylated p53 along with activation of caspase-3, caspase-8, and caspase-9 activating both the intrinsic and extrinsic pathway for apoptosis.
- 类别:有毒物品
- 360℃以上分解。溶于水、甲醇、丙醇、乙酸丁酯和环已酮，微溶于苯、四氯化碳和醚，几乎不溶于石油醚。其水溶液对酸、碱均不稳定。
- 方法二:用发酵方法生产。自放线菌（Strepto-myces caespitosus）培养液可提出丝裂霉素A、B、C。我国从自己分离的放线菌H2760菌株中提取，又称自力霉素，与国外报道的丝裂霉素C相同。
- Acros Organics:丝裂霉素 C MitomycinC,contains2mgMitomycinCand48mgNaCl(50-07-7)
- 参考质量标准:含量≥90%；mp>360℃；比旋光度+195°；要求溶解度、稳定性、薄层层析、元素分析及显色反应均合格。
- MSDS 信息:[1aR-(1aalpha,8beta,8aalpha,8balpha)]-6-Amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-5-methylazirino[2',3':3,4]pyrrolo[1,2-alpha]indole-4,7-dione(50-07-7).msds
- MOL 文件:50-07-7.mol
- 方法一:土壤中分离的放线菌菌株培养液经分离纯化制得。
- Sigma Aldrich:50-07-7(sigmaaldrich)
- 可燃性危险特性:可燃;燃烧产生有毒氮氧化物烟雾
- 用途一:细胞分裂抑制剂、核酸抑制剂和噬菌体诱导剂；临床作为抗肿瘤药物。
- F:8-10
- 具有抗癌作用:丝裂霉素C是从链霉菌的细
- 上游原料:二氯甲烷 --> 放线菌
- 急性毒性:口服-大鼠LD50: 30 毫克公斤; 口服-小鼠LD50: 23 毫克/公斤
- 丝裂霉素 C价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 66004480 丝裂霉素C（剧毒）(+4℃) 2mg 1500元 2010/06/21 226940020 丝裂霉素 C Mitomycin C , contains 2 mg Mitomycin C and 48 mg NaCl 2 MG 1217元
- 用途二:该品抗瘤谱较广，用于胃癌、乳腺癌效果好。对肺癌、肝癌、恶性化淋巴瘤、何杰金氏病、网状细胞肉瘤、子宫癌、白血病、肠道癌和胰腺癌等均有一定疗效，但缓解期较短。与尿激酶合用可提高疗效，该品作用迅速，但治疗接线员数不高，毒性大。该品和博来霉素及其衍生物派来霉素都是破坏DNA的抗生素类抗癌药，可使细胞DNA解聚，抑制增生细胞的DNA的复制。小鼠静脉注射LD50为5ml/kg。
