Chinese Journal of Organic Chemistry >
Study on the Synthesis and Anti-tumor Activities of Rhein-Amino Acid Conjugates
Received date: 2016-07-12
Revised date: 2016-08-20
Online 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
Zhou Changjian , Xie Jianwei , Zhang Jie , Dai Bin . Study on the Synthesis and Anti-tumor Activities of Rhein-Amino Acid Conjugates[J]. Chinese Journal of Organic Chemistry, 2017 , 37(1) : 122 -132 . DOI: 10.6023/cjoc201607020
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