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2019 , Vol. 39 >Issue 11: 3269 - 3276

DOI: https://doi.org/10.6023/cjoc201904003

研究简报

光学纯脱氢枞胺杂环衍生物与DNA作用及初步细胞毒活性

  • 屠双燕 ,
  • 徐武双 ,
  • 齐芬 ,
  • 何卫江 ,
  • 费宝丽
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  • a南京林业大学 江苏省生物质绿色燃料与化学品重点实验室 南京 210037
    b 广西师范大学 省部共建药用资源化学与药物分子工程国家重点实验室 广西桂林 541006
    c 南京林业大学 林业资源高效加工利用协同创新中心 南京 210037
    d 南京大学化学化工学院 南京 210037

收稿日期: 2019-04-02

  网络出版日期: 2019-07-17

基金资助

江苏省高等学校自然科学研究重大项目(18KJA150006);广西师范大学省部共建药用资源化学与药物分子工程国家重点实验室(CMEMR2018-B13)

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Interaction of Optically Pure Dehydroabietylamine Heterocyclic Derivatives with DNA and Preliminary Cytotoxic Activity

  • Shuangyan Tu ,
  • Wushuang Xu ,
  • Fen Qi ,
  • Weijiang He ,
  • Baoli Fei
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  • a Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, Nanjing Forestry University, Nanjing 210037
    b State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University, Guilin, Gungxi 541006
    c Collaborative Innovation Center for Efficient Processing and Utilization of Forestry Resources, Nanjing Forestry University, Nanjing 210037
    d College of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210037

Received date: 2019-04-02

  Online published: 2019-07-17

Supported by

the Major Projects of Natural Science Research in Jiangsu Higher Education Institutions(18KJA150006);State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University(CMEMR2018-B13)

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摘要

根据活性叠加原理，在天然产物松香的改性产品光学纯脱氢枞胺（1）的B环和C环中引入不同的芳香杂环，合成了三个光学纯脱氢枞基杂环衍生物，乙酰脱氢枞胺-6，7-（3-巯基）-1，2，4-三嗪（5）、乙酰脱氢枞胺-6，7-吲哚（7）和12-（2-氨基噻唑）乙酰脱氢枞胺（10）.荧光光谱和圆二色谱分析证明，化合物5、7和10均能够与DNA发生作用，且作用强度为5 > 10 > 7.凝胶电泳实验结果表明，5、7和10都能够对pBR 322质粒DNA进行单链切割且5的切割能力最强.另外，脱氢枞胺及化合物5、7和10与氯化铜的复配物（32 μmol/L）对人乳腺肿瘤细胞MCF-7的增殖抑制率，分别为86.0%（1），86.7%（5），34.4%（7）和0（10）.

关键词： 脱氢枞胺; 杂环化合物; DNA; 生物活性

本文引用格式

屠双燕 , 徐武双 , 齐芬 , 何卫江 , 费宝丽 . 光学纯脱氢枞胺杂环衍生物与DNA作用及初步细胞毒活性[J]. 有机化学, 2019 , 39(11) : 3269 -3276 . DOI: 10.6023/cjoc201904003

Abstract

Three optically pure dehydroabietylamine derivatives, acetyldehydroabietylamine-6, 7-(3-mercapto)-1, 2, 4-triazine (5), acetyldehydroabietylamine-6, 7-indole (7) and 12-(2-aminothiazole)-acetyldehydroabietylamine (10), were obtained by introducing different aromatic heterocycles into the B and C rings of optically pure dehydroabietylamine, which is derived from natural product of rosin, according to superposition principle of activity groups. The results of fluorescence spectroscopy and circular dichroism studies indicate that 5, 7 and 10 could interact with DNA, and the binding ability followed the order 5 > 10 > 7. Gel electrophoresis experiments suggest that 5, 7 and 10 could scissor pBR 322 plasmid DNA into single strands and 5 was the strongest cutter. In addition, the inhibitory rates of dehydroabietylamine and its derivatives 5, 7 and 10 combined with copper chloride (32 μmol·L-1) on the proliferation of human breast cancer cells MCF-7 were 86.0% (1), 86.7% (5), 34.4% (7) and 0 (10), respectively.

Key words： dehydroabietylamine; heterocyclic compounds; DNA; biological activity

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