Synthesis and Antitumor Evaluation of Nitrovinyl Biphenyls: Anticancer Agents Based on Allocolchicines
- 6 April 2011
- journal article
- research article
- Published by Wiley in ChemMedChem
- Vol. 6 (5), 859-868
- https://doi.org/10.1002/cmdc.201100019
Abstract
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 IC50 values in the range of 0.05–7 μM, 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 G2/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 G2/M phase of the cell cycle as the mode of action.This publication has 41 references indexed in Scilit:
- Synthesis and biological evaluation of cinnamido linked pyrrolo[2,1-c][1,4]benzodiazepines as antimitotic agentsEuropean Journal of Medicinal Chemistry, 2010
- Cancer prevention research — then and nowNature Reviews Cancer, 2009
- An Overview of Syntheses of Apogalanthamine Analogues and 7‐Aza Derivatives of Steganacin and SteganoneEuropean Journal of Organic Chemistry, 2008
- Plk1-dependent phosphorylation of FoxM1 regulates a transcriptional programme required for mitotic progressionNature, 2008
- Allocolchicines via Intramolecular Nicholas Reactions: The Synthesis of NSC 51046Organic Letters, 2007
- Asymmetric Synthesis of Antimicrotubule Biaryl Hybrids of Allocolchicine and SteganacinChemistry – A European Journal, 2007
- Targeted cancer therapyNature, 2004
- Checking Out the CentrosomeCell Cycle, 2004
- New small-molecule tubulin inhibitorsPure and Applied Chemistry, 2001
- The Hallmarks of CancerCell, 2000