Synthesis, Characterization, and Cytotoxicity of Platinum(IV) Carbamate Complexes
Name
Wilson and Lippard Inorg Chem.pdf
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3.58 MB
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Author(s)
Wilson, Justin Jeff
Lippard, Stephen J.
Date Issued
March 2011
Journal
Inorganic Chemistry
Publisher
American Chemical Society
Citation
Wilson, Justin J., and Stephen J. Lippard. “Synthesis, Characterization, and Cytotoxicity of Platinum(IV) Carbamate Complexes.” Inorganic Chemistry 50.7 (2011): 3103–3115. Web.
Version
Author's final manuscript
Abstract
The synthesis, characterization, and cytotoxicity of eight new platinum(IV) complexes having the general formula cis,cis,trans-[Pt(NH[subscript 3)[subscript 2]Cl[subscript 2](O[subscript 2]CNHR)[subscript 2]] are reported, where R = tert-butyl (4), cyclopentyl (5), cyclohexyl (6), phenyl (7), p-tolyl (8), p-anisole (9), 4-fluorophenyl (10), or 1-naphthyl (11). These compounds were synthesized by reacting organic isocyanates with the platinum(IV) complex cis,cis,trans-[Pt(NH[subscript 3])[subscript 2]Cl[subscript 2](OH)[subscript 2]]. The electrochemistry of the compounds was investigated by cyclic voltammetry. The aryl carbamate complexes 7−11 exhibit reduction peak potentials near −720 mV vs Ag/AgCl, whereas the alkyl carbamate complexes display reduction peak potentials between −820 and −850 mV vs Ag/AgCl. The cyclic voltammograms of cis,cis,trans-[Pt(NH[subscript 3])[subscript 2]Cl[subscript 2](O[subscript 2]CCH[subscript 3])[subscript 2]] (1), cis,cis,trans-[Pt(NH[subscript 3])[subscript 2]Cl[subscript 2](O[subscript 2]CCF[subscript 3])[subscript 2]] (2), and cis-[Pt(NH3)[subscript 2]Cl[subscript 4]] (3) were measured for comparison. Density functional theory studies were undertaken to investigate the electronic structures of 1−11 and to determine their adiabatic electron affinities. A linear correlation (R2 = 0.887) between computed adiabatic electron affinities and measured reduction peak potentials was discovered. The biological activity of 4−11 and, for comparison, cisplatin was evaluated in human lung cancer A549 and normal MRC-5 cells by the MTT assay. The compounds exhibit comparable or slightly better activity than cisplatin against the A549 cells. In MRC-5 cells, all are equally or slightly less cytotoxic than cisplatin, except for 4 and 5, which are more toxic.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ic2000816
