52934-83-5

• 常用中文名：七尾霉素
• 常用英文名：Nanafrocin
• CAS号：52934-83-5
• 分子式：C₁₆H₁₄O₆
• 分子量：302.279
• 相关类别： 信号通路 表观遗传学 DNA甲基转移酶
• 发布时间：2018-08-25 15:12:19
• 更新时间：2024-01-02 16:37:49
• Nanaomycin A 是第一个选择性 DNMT3B 抑制剂,IC50 为 500 nM。Nanaomycin A 是一种醌类抗生素,可重新激活人类癌细胞中沉默的抑癌基因。Nanaomycin A 抑制人疟原虫恶性疟原虫的体外生长,IC80 值为 33.1 nM。

名称

• 中文名: 七尾霉素
• 英文名: nanaomycin A
• 中文别名: 那罗星
• 英文别名: (1S-E)-3,4,5,10-Tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-1H-naphtho[2,3-c]pyran-3-acetic Acid; 4-deoxykalafunginic acid; 1H-Naphtho[2,3-c]pyran-3-acetic acid, 3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-, (1S,3R)-; dihydrokalafungin; 2-[(1S,3R)-9-hydroxy-1-methyl-5,10-dioxo-3,4-dihydro-1H-benzo[g]isochromen-3-yl]acetic acid; Rosanomycin A; Nanafrocine; Nanafrocinum; nanaomycin A; nanafrocinum [INN_la]; (1S,3R)-3,4,5,10-Tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-1H-naphtho[2,3-c]pyran-3-acetic Acid; OS 3966-A; [(1S,3R)-9-Hydroxy-1-methyl-5,10-dioxo-3,4,5,10-tetrahydro-1H-benzo[g]isochromen-3-yl]acetic acid; Nanafrocin

物化性质

• 密度: 1.5±0.1 g/cm3
• 沸点: 601.5±55.0 °C at 760 mmHg
• 分子式: C₁₆H₁₄O₆
• 分子量: 302.279
• 闪点: 229.0±25.0 °C
• 精确质量: 302.079041
• PSA: 100.90000
• LogP: 2.60
• 蒸汽压: 0.0±1.8 mmHg at 25°C
• 折射率: 1.649
• 储存条件: -20°C，干燥，密封

生物活性

• 描述: Nanaomycin A 是第一个选择性 DNMT3B 抑制剂,IC50 为 500 nM。Nanaomycin A 是一种醌类抗生素,可重新激活人类癌细胞中沉默的抑癌基因。Nanaomycin A 抑制人疟原虫恶性疟原虫的体外生长,IC80 值为 33.1 nM。
• 相关类别:
  研究领域 >> 癌症
  研究领域 >> 感染
  信号通路 >> 表观遗传学 >> DNA甲基转移酶
• 靶点:

  DNMT3B:500 nM (IC50)

• 体外研究: 纳诺霉素A(10-10000纳米；72小时)对所有三种细胞系都有明显的细胞毒性作用[1]。纳诺霉素A(0.5,5μM；72小时)诱导A549细胞RASSF1A蛋白表达[1]。纳诺霉素A(5μM；72小时)具有18倍的相对诱导率[1]。纳诺霉素A对DNMT1酶活性无影响[1]。细胞毒性试验[1]细胞株：HCT116(结肠)、A549(肺)、HL60(骨髓)人肿瘤细胞株浓度：10、100、1000、10000nm孵育时间：72h结果：三种细胞株均有明显的细胞毒性作用。Western Blot分析[1]细胞株：A549细胞浓度：0.5,5μM孵育时间：72h结果：RASSF1A蛋白表达诱导。RT-PCR[1]细胞株：A549细胞浓度：5μM孵育时间：72h结果：相对诱导率为18倍。
• 参考文献:

  [1]. Kuck D, et al.Nanaomycin A selectively inhibits DNMT3B and reactivates silenced tumor suppressor genes in human cancer cells.Mol Cancer Ther. 2010 Nov;9(11):3015-23.

  [2]. Tanaka Y, et al.Heme-dependent radical generation: possible involvement in antimalarial action of non-peroxide microbial metabolites, nanaomycin A and radicicol.J Antibiot (Tokyo). 1999 Oct;52(10):880-8.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : QL6127000 CHEMICAL NAME : 1H-Naphtho(2,3-c)pyran-3-acetic acid, 3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-, (1S-E)- CAS REGISTRY NUMBER : 52934-83-5 LAST UPDATED : 199306 DATA ITEMS CITED : 7 MOLECULAR FORMULA : C16-H14-O6 MOLECULAR WEIGHT : 302.30 WISWESSER LINE NOTATION : T C666 BV EO IVT&&J D1 F1VQ NQ HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD - Lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >200 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 33,728,1980 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 52 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 33,728,1980 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 290 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value 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: 28,860,1975 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Administration onto the skin SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 52 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 33,728,1980 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 28200 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value 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: 28,860,1975 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 56 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 33,728,1980 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 52 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 33,728,1980

安全

• 危害码 (欧洲): Xi
• 风险声明 (欧洲): 22-24
• 危险品运输编码: UN 2811 6.1/PG 3