66584-72-3

• 常用中文名：安丝菌素P3
• 常用英文名：Ansamitocin P-3
• CAS号：66584-72-3
• 分子式：C₃₂H₄₃ClN₂O₉
• 分子量：635.145
• 相关类别： 原料药 抗寄生虫病药 抗蠕虫药
• 发布时间：2018-07-07 22:49:34
• 更新时间：2026-07-01 10:49:13
• Ansamitocin P-3 是一种微管 (microtubule)抑制剂。Ansamitocin P-3 是一种大环抗肿瘤抗生素。

名称

• 中文名: 安丝菌素P3
• 英文名: ansamitocin P3
• 中文别名: 安丝菌素 P 3,10 MM DMSO 溶液; 安沙菌素AP3; MICROTUBULE抑制剂(ANSAMITOCIN P-3); (14S,16S,32S,33S,2R,4S,10E,12E,14R)-86-氯-14-羟基-85,14-二甲氧基-33,2,7,10-四甲基-12,6-二氧代-7-氮杂-1(6,4)-OXAZINANA-3(2,3)-环氧乙烷-8(1,3)-苯环十四烷-10,12-二烯-4-基 异丁酸脂; Ansamitocin P-3试剂; 氨丝菌素P3; 安丝菌素P-3(AP3); 美登醇异丁酸酯; 安沙菌素P-3; 安丝菌素 P 3; 安丝菌素 P-3; 安赛霉素P3; Ansamitocin p-3 (Maytansinol isobutyrate, NSC292222) :安丝菌素P-3; 安丝菌素
• 英文别名: Tam; Propanoic acid, 2-methyl-, (1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1.0]hexacosa-10,12,1
 4(26),16,18-pentaen-6-yl ester; 11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.,14~.,5~]hexacosa-10,11,13,16,18-pentaen-6-yl 2-methylpropanoate; (1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-Chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1.0]hexacosa-10(26),11,13,16,18-pentaen-6-yl 2- methylpropanoate; Ansamitocin P-3 (Maytansinol butyrate); Ansamitocin P-3 (Antibiotic C 15003P3'; Ansamitocin p-3, 10 mM in DMSO; 3-Pyridinecboxylicacid,6-(1H-imidazol-3-yl); ANSAMITOCIN P-3; 2'-De[acetyl(methyl)amino]-2'-methylmaytansine; Anasamitocin P-3; (1S,2R,3R,5S,6S,16E,18E,20R,21S)-11-Chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1.0]hexacosa-10(26),11,13,16,18-pentaen-6-yl 2- methylpropanoate; Ansamitosin P 3; ANTIBIOTIC C 15003P3;MAYTANSINOL ISOBUTYRATE; US-DMF No.; Tam-330; ansamitocin P-3 //BP; Propanoic acid, 2-methyl-, (1S,2R,3R,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.1.0]hexacosa-10,12,1
 4(26),16,18-pentaen-6-yl ester; Ansamitocin p-3; Maytansinol isobutyrate; O3-isobutyryl-maytansinol; MTA/CBR32; (3E,5E,7R,84S)-14-chloro-10t,11c-epoxy-84-hydroxy-12c-isobutyryl-15,7r-dimethoxy-3,9c,11t,15-tetramethyl-(84r'H,86c'H)-15-aza-1(1,3)-benzena-8(4,6)-[1,3]oxazinana-cyclopentadecaphane-3,5-diene-82,14-dione; Trimethyloxazolidine-2; (14S,16S,32S,33S,2R,4S,10E,12E,14R)-86-Cchloro-14-hydroxy-85,14-dimethoxy-33,2,7,10-tetramethyl-12,6-dioxo-7-aza-1(6,4)-oxazinana-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-4-yl isobutyrate; Nsc292222; (14S,16S,32R,33S,2R,4S,10Z,12E,14R)-86-Chloro-14-hydroxy-85,14-dimethoxy-33,2,7,10-tetramethyl-12,6-dioxo-7-aza-1(6,4)-oxazinana-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-4-yl isobutyrate; 2'-De(acetylmethylamino)-2'-methylmaytansine; Ansamitocin P-3（Maytansinol isobutyrate）; Ansamitocin p-3 (Maytansinol isobutyrate, NSC292222)

物化性质

• 密度: 1.3±0.1 g/cm3
• 沸点: 833.1±65.0 °C at 760 mmHg
• 熔点: 190-192℃
• 分子式: C₃₂H₄₃ClN₂O₉
• 分子量: 635.145
• 闪点: 457.7±34.3 °C
• 精确质量: 634.265686
• PSA: 136.16000
• LogP: 5.09
• 蒸汽压: 0.0±3.2 mmHg at 25°C
• 折射率: 1.583
• 储存条件: 2-8°C

生物活性

• 描述: Ansamitocin P-3 是一种微管 (microtubule)抑制剂。Ansamitocin P-3 是一种大环抗肿瘤抗生素。
• 相关类别:
  信号通路 >> 抗体- 药物偶联物 >> ADC细胞毒素
  信号通路 >> 细胞周期/DNA损伤 >> 微管/微管蛋白
  信号通路 >> 细胞骨架 >> 微管/微管蛋白
  天然产物 >> 其他
  研究领域 >> 癌症
• 靶点:

  Microtubule[1]

• 体外研究: Ansamitocin P3有效抑制培养中MCF-7,HeLa,EMT-6/AR1和MDA-MB-231细胞的增殖,半数最大抑制浓度为20±3,50±0.5,140±17和150± 1.1 pM,分别。此外,发现Ansamitocin P3在体外与纯化的微管蛋白结合,解离常数(Kd)为1.3±0.7μM。 Ansamitocin P3的结合诱导微管蛋白的构象变化。 Ansamitocin P3以浓度依赖性方式抑制培养物中MCF-7,HeLa,EMT-6/AR1和MDA-MB-231细胞的增殖。 PI染色细胞的流式细胞术分析表明,Ansamitocin P3抑制G2/M期MCF-7细胞的细胞周期进程。例如,在不存在和存在50和100pM Ansamitocin P3的情况下,发现26％,50％和70％的细胞处于G2/M期[2]。
• 细胞实验: 将MCF-7，EMT-6 / AR1，HeLa和MDA-MB-231细胞接种在96孔板中。随后，将细胞与载体（0.1％DMSO）或不同浓度（1-1000pM）的Ansamitocin P3在MCF-7细胞中孵育48小时，并将EMT-6 / AR1，HeLa和MDA-MB-231细胞孵育24小时。 ， 分别。通过磺酰罗丹明B测定法测定Ansamitocin P3的半数最大抑制浓度的细胞增殖（IC50）。在MCF-7细胞中进行四个独立实验，并在EMT-6 / AR1，HeLa和MDA-MB-231细胞中进行三组独立的实验[2]。
• 参考文献:

  [1]. Kiso T, et al. Screening for microtubule-disrupting antifungal agents by using a mitotic-arrest mutant of Aspergillus nidulans and novel action of phenylalanine derivatives accompanying tubulin loss. Antimicrob Agents Chemother. 2004 May;48(5):1739-48.

  [2]. Venghateri JB, et al. Ansamitocin P3 depolymerizes microtubules and induces apoptosis by binding to tubulin at thevinblastine site. PLoS One. 2013 Oct 4;8(10):e75182.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : OQ2291000 CHEMICAL NAME : Maytansine, 2'-de(acetylmethylamino)-2'-methyl- CAS REGISTRY NUMBER : 66584-72-3 LAST UPDATED : 199401 DATA ITEMS CITED : 4 MOLECULAR FORMULA : C32-H43-Cl-N2-O9 MOLECULAR WEIGHT : 635.22 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 625 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value MUTATION DATA TYPE OF TEST : Cytogenetic analysis TEST SYSTEM : Rodent - mouse Ascites tumor DOSE/DURATION : 4 ug/kg REFERENCE : CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 40,1707,1980

安全

• 符号: GHS07
• 信号词: Warning
• 危害声明: H302-H315-H319-H332-H335
• 警示性声明: P261-P305 + P351 + P338
• 个人防护装备: dust mask type N95 (US);Eyeshields;Gloves
• 危害码 (欧洲): Xn
• 风险声明 (欧洲): 20/22-36/37/38
• 安全声明 (欧洲): 26-36
• 危险品运输编码: NONH for all modes of transport
• RTECS号: OQ2293000

合成路线

93175-87-2 ~% 66584-72-3

文献：Akimoto; Kawai; Hashimoto; Nomura Chemical and Pharmaceutical Bulletin, 1984 , vol. 32, # 7 p. 2565 - 2570

78760-20-0 ~% 66584-72-3

文献：Chemical and Pharmaceutical Bulletin, , vol. 32, # 7 p. 2565 - 2570

57103-68-1 ~% 66584-72-3

文献：Chemical and Pharmaceutical Bulletin, , vol. 32, # 7 p. 2565 - 2570

75340-68-0 ~% 66584-72-3

文献：Chemical and Pharmaceutical Bulletin, , vol. 32, # 7 p. 2565 - 2570

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