Study on the Synthesis and Anti-tumor Activities of Rhein-Amino Acid Conjugates

doi:10.6023/cjoc201607020

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (1): 122-132.DOI: 10.6023/cjoc201607020 Previous Articles Next Articles

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大黄酸-氨基酸缀合物的合成及初步抗肿瘤活性研究

周昌健^a, 谢建伟^a, 张洁^a, 代斌^a

a 石河子大学化学化工学院新疆兵团化工绿色过程重点实验室-省部共建国家重点实验室培育基地石河子 832003

收稿日期:2016-07-12 修回日期:2016-08-20 发布日期:2016-09-12
通讯作者: 谢建伟, 张洁 E-mail:cesxjw@foxmail.com;zhangjie-xj@163.com

Study on the Synthesis and Anti-tumor Activities of Rhein-Amino Acid Conjugates

Zhou Changjian^a, Xie Jianwei^a, Zhang Jie^a, Dai Bin^a

a School of Chemistry and Chemical Engineering and Key Laboratory for Green Processing of Chemical Engineering of Xin-jiang Bingtuan, Shihezi University, Shihezi 832003

Received:2016-07-12 Revised:2016-08-20 Published:2016-09-12

20 novel rhein-amino acid conjugates were designed and synthesized from the rhein via esterification,etherification,hydrolysis,condensation and salification.Their structures were confirmed by ¹H NMR,¹³C NMR and HRMS.All the target compounds were tested for cytotoxic activity against five cancer cell lines including Hela,MCF-7,HepG2,KB and HEK293T by methyl thiazolyl tetrazolium(MTT) method in vitro.The results showed that sodium(4,5-bis(benzyloxy)-9,10-dioxo-9,10-dihydroanthracene-2-carbonyl) leucinate(6eb) demonstrated moderate cytotoxic activities(IC₅₀<50 μmol·L^-1).The fluorescence of compounds sodium(4,5-dibutoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbonyl) leucinate(6db) and 6eb could be both quenched by DNA.It was speculated that compound 6db interacted with DNA by the static attraction or was partially embedded into DNA.

Key words: rhein, amino acid, antitumor activity, structure-activity relationships

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Zhou Changjian, Xie Jianwei, Zhang Jie, Dai Bin. Study on the Synthesis and Anti-tumor Activities of Rhein-Amino Acid Conjugates[J]. Chin. J. Org. Chem., 2017, 37(1): 122-132.

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大黄酸-氨基酸缀合物的合成及初步抗肿瘤活性研究

Study on the Synthesis and Anti-tumor Activities of Rhein-Amino Acid Conjugates

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