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Updated: Aug 14, 2025
Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
Published on: May 28, 2014
Anticancer Activity of Nonpolar Pt(CH3)2I2{bipy} is Found to be Superior among Four Similar Organoplatinum(IV)
Ameneh Arabi1, Marcus O Cogley1, Daniel Fabrizio1
1Department of Chemistry & Biochemistry, University of Alaska Fairbanks, 900 Yukon Drive, Fairbanks, Alaska 99775, United States.
Abstract:
The anticancer properties of well-defined molecules serve to bolster the field of metals in medicine. Such compounds, particularly those of platinum and their closely related structural analogs, continue to be potentially highly interesting to researchers and clinicians alike. The four octahedral organoplatinum(IV) compounds [Pt(CH3)2X2{bipy-R }] (X = Br, I; bipy-R = 2,2'-bipyridine, 2,2'-bipyridine-4,4'-dicarboxylic acid) have been isolated and structurally characterized by single-crystal X-ray diffraction. Nuclear magnetic resonance and infrared spectroscopic data are also tabulated as useful reference values. The anticancer potential of each compound was assessed via in vitro MTT assays, using human breast cancer cells (cell line ZR-75-1). EC50 values were determined as 11.5 μM for Pt(CH3)2Br2{bipy}; 3020 μM, for Pt(CH3)2Br2{bipy-(CO H) }; 6.1 μM, for Pt(CH3)2I2{bipy}; and 86.0 μM, for Pt(CH3)2I2{bipy-(CO H) }; for comparison, the EC50 value for cisplatin against the ZR-75-1 cells was 16.4 μM. The most cytotoxic of the four compounds Pt(CH3)2I2{bipy} undergoes reaction with glutathione in a THF/water mixture at 68°C very slowly.
