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Novel Oxaliplatin Derivatives with 1‐(Substituted Benzyl)azetidine‐3,3‐dicarboxylate Anions. Synthesis, Cytotoxicity, and Interaction with DNA
Author(s) -
Sun Yanyan,
Cao Zhe,
Gou Shaohua,
Hu Tingting
Publication year - 2014
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201300092
Subject(s) - chemistry , oxaliplatin , cytotoxicity , carboplatin , dna , agarose gel electrophoresis , stereochemistry , azetidine , medicinal chemistry , in vitro , biochemistry , cancer , medicine , colorectal cancer , surgery , chemotherapy , cisplatin
A series of oxaliplatin derivatives with (1 R ,2 R )‐ N 1 ‐alkyl‐1,2‐cyclohexane‐1,2‐diamine (alkyl=Bu or i Pr) as carrier ligands and 1‐(methoxy‐ or methyl‐substituted benzyl)azetidine‐3,3‐dicarboxylate anions as leaving groups were synthesized and spectrally characterized. Generally, Complexes 10 – 15 with an i Pr substituent at N(1) showed higher activities in vitro than carboplatin against MCF‐7 human breast carcinoma and A549 human non‐small‐cell lung cell lines, although they were less potent than oxaliplatin. The typical complex 14 exhibited cytotoxicity superior to that of carboplatin and comparable to that of oxaliplatin against two selected tumor cell lines. Additionally, agarose gel electrophoresis was applied to investigate the DNA‐cleavage ability of complex 14 , which demonstrated that it has a different mode of DNA distortion from that of oxaliplatin.