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Synthesis and Antitumor Evaluation of Nitrovinyl Biphenyls: Anticancer Agents Based on Allocolchicines
Author(s) -
Jain Nishant,
Yada Divya,
Shaik Thokhir B.,
Vasantha Galanki,
Reddy P. Surendra,
Kalivendi Shasi V.,
Sreedhar B.
Publication year - 2011
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201100019
Subject(s) - tubulin , cell cycle , colchicine , cell cycle checkpoint , hela , mitosis , chemistry , cyclin b1 , flow cytometry , kinase , microbiology and biotechnology , microtubule , biochemistry , cell , biology , cyclin dependent kinase 1 , genetics
A new class of nitrovinyl biphenyl compounds based on the structures of colchicines and allocolchicines were designed, synthesized, and shown to inhibit tubulin polymerization and cause mitotic arrest. A majority of these compounds were found to possess potent anticancer properties, with IC 50 values in the range of 0.05–7 μ M , and are equally potent with colchicine in HeLa and MCF‐7 cells. Compounds 14 e and 14 f inhibited tubulin assembly by more than 60 %, and flow cytometry studies indicated growth arrest of cells in the G 2 /M phase of the cell cycle in a concentration‐dependent manner. Treatment of cells with 14 f resulted in upregulation of cyclin B1 and aurora kinase B mRNA levels, corresponding to growth arrest in the G 2 /M phase of the cell cycle as the mode of action.