Citation: Tu Shuangyan, Xu Wushuang, Qi Fen, He Weijiang, Fei Baoli. 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 shu

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

Tu Shuangyan ^a ,
Xu Wushuang ^a ,
Qi Fen ^d ,
He Weijiang ^d,, ,
Fei Baoli ^a,b,c,,

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

Corresponding author: He Weijiang, hgfbl@njfu.edu.cn Fei Baoli, heweij69@nju.edu.cn
Received Date: 2 April 2019
Revised Date: 28 June 2019
Available Online: 17 November 2019
Fund Project: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University CMEMR2018-B13Project supported by the Major Projects of Natural Science Research in Jiangsu Higher Education Institutions (No. 18KJA150006), and State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University (No. CMEMR2018-B13)the Major Projects of Natural Science Research in Jiangsu Higher Education Institutions 18KJA150006

Figures(4)

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.
- dehydroabietylamine,
- heterocyclic compounds,
- DNA,
- biological activity
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