Ternary copper(II) complexes with hippurate derivatives and 1,10-phenanthroline: Synthesis and biological activity

Several new Cu-hippurate derivative-phenanthroline ternary complexes have been prepared. The X-ray structure of one of them, [Cu(hip)(phen)(2)](+)center dot(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)](+)center dot(hip)center dot 2H(2)O (2), [Cu(BGG)(phen)(2)](+)center dot(BGG)center dot 6H(2)O (3), [Cu(B(I)GG)(2)(phen)](H2O) (4) and [Cu(I-hip)(bpy)(2)](+)center dot(I-hip)center dot 3.5H(2)O (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](+)center dot(I-hip)center dot 7H(2)O (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. (C) 2009 Elsevier B. V. All rights reserved.