Design, Synthesis, and Evaluation of Genistein Analogues as Anti-Cancer Agents

ISSN: 1875-5992 (Online)
ISSN: 1871-5206 (Print)

Volume 16, 12 Issues, 2016

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Anti-Cancer Agents in Medicinal Chemistry

Formerly: Current Medicinal Chemistry - Anti-Cancer Agents

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  • 27th of 59 in Chemistry, Medicinal

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Michelle Prudhomme
Universite Blaise Pascal - C.N.R.S
Aubiere Cedex

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Design, Synthesis, and Evaluation of Genistein Analogues as Anti-Cancer Agents

Anti-Cancer Agents in Medicinal Chemistry, 15(9): 1197-1203.

Author(s): Pahoua Xiong, Rubing Wang, Xiaojie Zhang, Eduardo DeLa Torre, Francisco Leon, Qiang Zhang, Shilong Zheng, Guangdi Wang and Qiao-Hong Chen.

Affiliation: Department of Chemistry, California State University Fresno, 2555 E. San Ramon Avenue M/S SB 70.


Genistein is a bioactive isoflavone derived from soybeans. The tie-in between the intake of genistein and the decreased incidence of some solid tumors (including prostate cancer) has been demonstrated by epidemiological studies. The potential of genistein in treating prostate cancer has also been displayed by in vitro cell-based and in vivo animal experiments. Genistein has entered clinical trials for both chemoprevention and potential treatment of prostate cancer. Even though the low oral bioavailability has presented the major challenges to genistein’s further clinical development, chemical modulation of genistein holds the promise to generate potential anti-prostate cancer agents with enhanced potency and/or better pharmacokinetic profiles than genistein. As part of our ongoing project to develop natural products-based anti-prostate cancer agents, the current study was undertaken to synthesize eight genistein analogues for cytotoxic evaluation in three prostate cancer cell lines (PC-3, DU-145, LNCaP; both androgen-sensitive and androgen-refractory cell lines), as well as one aggressive cervical cancer cell line (HeLa). Eight genistein analogues have been successfully synthesized with Suzuki-Miyaura coupling reaction as a key step. Their in vitro anti-cancer potential was evaluated by trypan blue exclusion assay and WST-1 cell proliferation assay against a panel of four human cancer cell lines. The acquired data suggest i) that the C-5 and C-7 hydroxyl groups in genistein are very important for the cytotoxicity and anti-proliferative activity; and ii) that 1-alkyl-1H-pyrazol-4-yl and pyridine-3-yl might act as good bioisosteres for the 4'-hydroxyphenyl moiety in genistein.


Cytotoxicity, genistein analogue, prostate cancer, structure-activity relationship, Suzuki-Miyaura coupling reaction.

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Article Details

Volume: 15
Issue Number: 9
First Page: 1197
Last Page: 1203
Page Count: 7
DOI: 10.2174/1871520615666150520142437
Price: $58

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