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Synthesis and Biological Evaluation of Novel Genistein Amino Acid Ester Derivatives as Potential Anti‐Tumor Agents
Author(s) -
Long Xiaokang,
Liao LanQing,
Zeng YaoFu,
Zhang Ye,
Xiao Fang,
Li Chong,
Guo Yu
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900857
Subject(s) - genistein , hela , cytotoxicity , apoptosis , chemistry , amino acid , cell culture , cell cycle , stereochemistry , cell , biochemistry , in vitro , biology , genetics , endocrinology
Thirty‐one novel genistein amino acid ester derivatives were synthesized and evaluated for their anti‐proliferative activities against HUVEC cells and five cancer cells lines (HCT‐116, HeLa, HepG‐2, MCF‐7, MGC‐803). Most of the amino acid ester derivatives exhibited more inhibitory activity than their parent compound genistein. In particular, compound 8 j (methyl(4‐((5‐hydroxy‐3‐(4‐hydroxyphenyl)‐4‐oxo‐4H‐chromen‐7‐yl)oxy)butanoyl)tryptophanate) bearing tryptophan chain showed the most cytotoxicity against HCT‐116 cells with IC 50 value of 2.76 μM. Further mechanistic studies indicated that compound 8 j suppressed HCT‐116 cell metastasis and induced cell apoptosis in a dose‐dependent manner. Cell cycle assay showed that compound 8 j arrested the HCT‐116 cells to G1 phase. These studies suggested compound 8 j might be a potential candidate for developing new anticancer drugs.