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Chinese Journal of Organic Chemistry >

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

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

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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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

Cite this article

Shuangyan Tu , Wushuang Xu , Fen Qi , Weijiang He , Baoli Fei . Interaction of Optically Pure Dehydroabietylamine Heterocyclic Derivatives with DNA and Preliminary Cytotoxic Activity[J]. Chinese Journal of Organic Chemistry, 2019 , 39(11) : 3269 -3276 . DOI: 10.6023/cjoc201904003

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