Nanaomycin | 52934-83-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异色满醌
• 英文名称: Nanaomycin
• 英文别名: 2-(9-hydroxy-1-methyl-5,10-dioxo-3,4-dihydro-1H-benzo[g]isochromen-3-yl)acetic acid
• CAS: 52934-83-5
• 化学式: C₁₆H₁₄O₆
• 分子量: 302.28
• InChiKey: ZCJHPTKRISJQTN-UHFFFAOYSA-N

物化性质

• 熔点：
  179°C
• 沸点：
  363.32°C (rough estimate)
• 密度：
  1.2514 (rough estimate)
• 溶解度：
  不溶于水； DMSO 中≥15.1 mg/mL； ≥31.07 mg/mL，乙醇溶液，超声波

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险类别码：
  R22,R24
• 危险品运输编号：
  UN 2811 6.1/PG 3

制备方法与用途

生物活性

Nanaomycin A 是第一个选择性 DNMT3B 抑制剂，IC50 为 500 nM。它是一种醌类抗生素，可重新激活人类癌细胞中沉默的抑癌基因。此外，Nanaomycin A 还能抑制体外恶性疟原虫的生长，IC80 值为 33.1 nM。

靶点

• DNMT3B：IC50 为 500 nM

体外研究

Nanaomycin A 在不同浓度 (10-10000 nM) 和时间 (72 小时) 下对三种细胞系均显示出显著的细胞毒性效应。

• Nanaomycin A（0.5, 5 μM；72 小时）诱导 A549 细胞中 RASSF1A 蛋白表达，具有 18 倍的相对诱导量。
• Nanaomycin A 不影响 DNMT1 的酶活性。

细胞毒性实验

• 细胞系：结肠癌 HCT116、肺癌 A549 和骨髓 HL60 人肿瘤细胞系
• 浓度：10, 100, 1000, 10000 nM
• 孵育时间：72 小时
• 结果：在所有三个细胞系中均显示出显著的细胞毒性效应。

蛋白质印迹分析

• 细胞系：A549 细胞
• 浓度：0.5, 5 μM
• 孵育时间：72 小时
• 结果：诱导 RASSF1A 蛋白表达。

RT-PCR 分析

• 细胞系：A549 细胞
• 浓度：5 μM
• 孵育时间：72 小时
• 结果：具有 18 倍的相对诱导量。

反应信息

• 作为产物：
  描述：

  cis-methyl <9-methoxy-1-methyl5,10-dioxo-3,4,5,10-tetrahydro-1H-naphtho<2,3-c>pyran-3-yl>acetate 生成 Nanaomycin
  参考文献：
  名称：

  MARUYAMA, KADZUXIRO;NARITA, JOSITOKU;UNO, XIDEHMITSU

  摘要：

  DOI：

文献信息

• Antibiotic nanaomycin E and a process for producing the same
  申请人：Kyowa Hakko Kogyo Kabushiki Kaisha

  公开号：US04296040A1

  公开（公告）日：1981-10-20

  The present invention teaches a new antibiotic nanaomycin E represented by the formula: ##STR1## Nanaomycin E is active against Gram-positive bacteria, Trichophyton and Mycoplasma and may be used as antibacterial and therapeutic agents for humans and animals. Nanaomycin E is also a useful starting maerial for the preparation of nanaomycin A which latter nanaomycin has the highest activity among the various nanaomycin-type compounds. Nanaomycin E is produced by fermentation of a microorganism belonging to the genus Streptomyces and capable of producing nanaomycin E, especially Streptomyces rosa variant notoensis (FERM-P 2209; ATCC 31135) and recovering the same from the fermented liquor.

  本发明教授了一种新的抗生素nanaomycin E，其化学式为：##STR1## Nanaomycin E对革兰氏阳性菌、毛癣菌和支原体具有活性，并可用作人类和动物的抗菌和治疗剂。Nanaomycin E还是制备nanaomycin A的有用起始材料，后者是各种nanaomycin型化合物中活性最高的。Nanaomycin E是通过发酵属于链霉菌属的微生物并能够产生nanaomycin E，特别是Streptomyces rosa变种notoensis（FERM-P 2209; ATCC 31135）并从发酵液中回收而得到的。
• Process for producing antibiotic nanaomycin E
  申请人：Kyowa Hakko Kogyo Kabushiki Kaisha

  公开号：US04353986A1

  公开（公告）日：1982-10-12

  The present invention teaches a new antibiotic nanaomycin E represented by the formula: ##STR1## Nanaomycin E is active against Gram-positive bacteria, Trichophyton and Mycoplasma and may be used as antibacterial and therapeutic agents for humans and animals. Nanaomycin E is also a useful starting material for the preparation of nanaomycin A which latter nanaomycin has the highest activity among the various nanaomycin-type compounds. Nanaomycin E is produced by fermentation of a microorganism belonging to the genus Streptomyces and capable of producing nanaomycin E, especially Streptomyces rosa variant notoensis (FERM-P 2209; ATCC 31135) and recovering the same from the fermented liquor.

  本发明教授了一种新的抗生素nanaomycin E，其化学式为：##STR1## Nanaomycin E对革兰氏阳性菌、毛癣菌和支原体具有活性，并可用作人类和动物的抗菌和治疗剂。Nanaomycin E也是制备nanaomycin A的有用起始材料，后者是各种nanaomycin型化合物中活性最高的一种。Nanaomycin E是通过发酵属于链霉菌属的微生物并能够产生nanaomycin E的菌株，特别是Streptomyces rosa variant notoensis (FERM-P 2209; ATCC 31135)，并从发酵液中回收而得到的。
• NOVEL METHODOLOGY FOR IDENTIFYING ANTI-PERSISTER ACTIVITY AND ANTIMICROBIAL SUSCEPTIBILITY FOR BORRELIA BURGDORFERI AND OTHER BACTERIA
  申请人：ZHANG YING

  公开号：US20170058314A1

  公开（公告）日：2017-03-02

  The presently disclosed subject matter provides methods, compositions, and kits for assessing the viability of bacteria from a selected genus, assessing the antibiotic susceptibility of bacteria from the selected genus, and identifying compounds with anti-persister activity for bacteria from the selected genus. The bacteria include, but are not limited to, Borrelia burgdorferi, Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Acinetobacter baumanii , and Mycobacterium tuberculosis . Compositions include compounds with high activity against Borrelia persisters and their combinations with current Lyme antibiotics for more effect treatment of Lyme disease. Methods for inhibiting the growth and/or survival of bacteria from the Borrelia genus and for treating Lyme disease using appropriate drug combinations in a subject are also provided.
• MARUYAMA, KADZUXIRO;NARITA, JOSITOKU;UNO, XIDEHMITSU
  作者：MARUYAMA, KADZUXIRO、NARITA, JOSITOKU、UNO, XIDEHMITSU

  DOI：——

  日期：——