Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (11): 3269-3276.DOI: 10.6023/cjoc201904003 Previous Articles     Next Articles


屠双燕a, 徐武双a, 齐芬d, 何卫江d*(), 费宝丽abc*()   

  1. 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 发布日期:2019-07-17
  • 通讯作者: 何卫江,费宝丽;
  • 基金资助:

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

Tu Shuangyana, Xu Wushuanga, Qi Fend, He Weijiangd*(), Fei Baoliabc*()   

  1. 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:2019-04-02 Published:2019-07-17
  • Contact: He Weijiang,Fei Baoli;
  • 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)

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