Synthesis, Characterization, and Cytotoxicity of Platinum(IV) Carbamate Complexes
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-toly...
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| Format: | Article |
| Language: | en_US |
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American Chemical Society
2012
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| Online Access: | http://hdl.handle.net/1721.1/71116 https://orcid.org/0000-0002-2693-4982 |
| _version_ | 1811097882733838336 |
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| author | Wilson, Justin Jeff Lippard, Stephen J. |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Wilson, Justin Jeff Lippard, Stephen J. |
| author_sort | Wilson, Justin Jeff |
| collection | MIT |
| description | 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. |
| first_indexed | 2024-09-23T17:06:28Z |
| format | Article |
| id | mit-1721.1/71116 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T17:06:28Z |
| publishDate | 2012 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | mit-1721.1/711162022-09-29T23:43:16Z Synthesis, Characterization, and Cytotoxicity of Platinum(IV) Carbamate Complexes Wilson, Justin Jeff Lippard, Stephen J. Massachusetts Institute of Technology. Department of Chemistry Lippard, Stephen J. Wilson, Justin Jeff Lippard, Stephen J. 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. National Cancer Institute (U.S.) (Grant CA034992) 2012-06-06T19:41:53Z 2012-06-06T19:41:53Z 2011-03 Article http://purl.org/eprint/type/JournalArticle 0020-1669 1520-510X http://hdl.handle.net/1721.1/71116 Wilson, Justin J., and Stephen J. Lippard. “Synthesis, Characterization, and Cytotoxicity of Platinum(IV) Carbamate Complexes.” Inorganic Chemistry 50.7 (2011): 3103–3115. Web. https://orcid.org/0000-0002-2693-4982 en_US http://dx.doi.org/10.1021/ic2000816 Inorganic Chemistry Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society Prof. Lippard via Erja Kajosalo |
| spellingShingle | Wilson, Justin Jeff Lippard, Stephen J. Synthesis, Characterization, and Cytotoxicity of Platinum(IV) Carbamate Complexes |
| title | Synthesis, Characterization, and Cytotoxicity of Platinum(IV) Carbamate Complexes |
| title_full | Synthesis, Characterization, and Cytotoxicity of Platinum(IV) Carbamate Complexes |
| title_fullStr | Synthesis, Characterization, and Cytotoxicity of Platinum(IV) Carbamate Complexes |
| title_full_unstemmed | Synthesis, Characterization, and Cytotoxicity of Platinum(IV) Carbamate Complexes |
| title_short | Synthesis, Characterization, and Cytotoxicity of Platinum(IV) Carbamate Complexes |
| title_sort | synthesis characterization and cytotoxicity of platinum iv carbamate complexes |
| url | http://hdl.handle.net/1721.1/71116 https://orcid.org/0000-0002-2693-4982 |
| work_keys_str_mv | AT wilsonjustinjeff synthesischaracterizationandcytotoxicityofplatinumivcarbamatecomplexes AT lippardstephenj synthesischaracterizationandcytotoxicityofplatinumivcarbamatecomplexes |