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Ternary copper(II) complexes with hippurate derivatives and 1,10-phenanthroline: Synthesis and biological activity |
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| Authors: | Miquel Barceló-Oliver Ángel Terrón Elies Molins Virtudes Moreno Victoria Lladó Antonio Gutiérrez |
| Institution: | a Departament de Química, Grup de Química Bioinorgànica i Bioorgànica, IUNICS, Universitat de les Illes Balears, Campus UIB, Carretera Valldemossa km. 7.5, Palma de Mallorca E-07122, I. Balears, Spain b Institut de Ciència dels Materials de Barcelona (CSIC), Campus de la Universitat Autònoma, Cerdanyola E-08193, Spain c Departments of Inorganic Chemistry and Microbiology, Faculty of Chemistry, Universitat de Barcelona, Barcelona E-08028, Spain d Servei d’Hematologia, Hospital Universitari de Son Dureta, Palma de Mallorca, Spain e Department of Biology, Laboratory of Molecular and Cellular Biomedicine, IUNICS (CSIC associated unit), Universitat de les Illes Balears, Campus UIB, Carretera Valldemossa km. 7.5, Palma de Mallorca E-07122, Spain |
| Abstract: | Several new Cu-hippurate derivative-phenanthroline ternary complexes have been prepared. The X-ray structure of one of them, Cu(hip)(phen)2]+·(hip−) (2) (where hip is hippurate and phen is 1,10-phenanthroline) has been solved. The structure of this new compound shows important differences (3D-pattern) to other similar related complexes (2D-pattern). A study of the biological activity of Cu(hip)(phen)2]+·(hip−)·2H2O (2), Cu(BGG)(phen)2]+·(BGG−)·6H2O (3), Cu(BIGG)2(phen)](H2O) (4) and Cu(I-hip)(bpy)2]+·(I-hip−)·3.5H2O (5) (where I-hip is ortho-iodohippurate, BGG corresponds to benzoylglycilglycine, and BIGG is ortho-iodobenzoylglycilglycine) is included and compared with the anti-proliferative activity of Cu(I-hip)(phen)2]+·(I-hip−)·7H2O (1) previously described, resulting in a greater cytotoxic activity of the compounds with 1,10-phenanthroline instead of those with 2,2′-bipyridyl, in the same way that removing iodine substitution or lengthening the peptidic chain diminishes the activity of compounds compared with 1. The presence of an ortho-iodine group and the direct bond between Ar-CO and glycine moieties yield to the best results. |
| Keywords: | Ternary complexes Hippuric acid Copper X-ray structure C-H?π?π?H-C interactions Cytotoxic activity |
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