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

doi:10.6023/cjoc201904003

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

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^a, 徐武双^a, 齐芬^d, 何卫江^d*(), 费宝丽^a^b^c*()

^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 E-mail:hgfbl@njfu.edu.cn;heweij69@nju.edu.cn
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)

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

Received:2019-04-02 Published:2019-07-17
Contact: He Weijiang,Fei Baoli E-mail:hgfbl@njfu.edu.cn;heweij69@nju.edu.cn
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

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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.

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Fig. & Tab. 4

Scheme 1. Synthesis route of target compounds

Figure 1. Effects of compounds on fluorescence spectra of salmon sperm DNA-EB system

Figure 2. Effects of compounds on CD spectra of salmon Sperm solution

Figure 3. Gel electrophoresis patterns of compounds cleaved pBR 322 plasmid DNA Lane 1: DNA; Lane 2: DNA+50 μmol?L－1 compounds 5, 6, 7 and 10; Lane 3: DNA+100 μmol?L－1 compounds 5, 6, 7 and 10; Lane 4: DNA+150 μmol? L－1 compounds 5, 6, 7 and 10

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光学纯脱氢枞胺杂环衍生物与DNA作用及初步细胞毒活性

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

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