Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents |
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| Authors: | Michael G. Apps Ben W. Johnson Oliver B. Sutcliffe Sarah D. Brown Nial J. Wheate |
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| Affiliation: | 1.Faculty of Pharmacy, The University of Sydney;2.School of Science and Health, University of Western Sydney;3.Division of Chemistry and Environmental Science, School of Science and the Environment, Manchester Metropolitan University;4.Nature Publishing Group |
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| Abstract: | Amide coupling reactions can be used to synthesize bispyridine-based ligands for use as bridging linkers in multinuclear platinum anticancer drugs. Isonicotinic acid, or its derivatives, are coupled to variable length diaminoalkane chains under an inert atmosphere in anhydrous DMF or DMSO with the use of a weak base, triethylamine, and a coupling agent, 1-propylphosphonic anhydride. The products precipitate from solution upon formation or can be precipitated by the addition of water. If desired, the ligands can be further purified by recrystallization from hot water. Dinuclear platinum complex synthesis using the bispyridine ligands is done in hot water using transplatin. The most informative of the chemical characterization techniques to determine the structure and gross purity of both the bispyridine ligands and the final platinum complexes is 1H NMR with particular analysis of the aromatic region of the spectra (7-9 ppm). The platinum complexes have potential application as anticancer agents and the synthesis method can be modified to produce trinuclear and other multinuclear complexes with different hydrogen bonding functionality in the bridging ligand. |
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| Keywords: | Chemistry Issue 87 BBR3464 picoplatin bispyridine amide coupling inorganic synthesis cancer |
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