Therapeutic properties, SOD and catecholase mimetic activities of novel ternary copper(II) complexes of the anti-inflammatory drug Fenoprofen with imidazole and caffeine

The copper(II) ternary complexes of the non-steroidal anti-inflammatory drug Fenoprofen (Hfen) and the biologically relevant molecules imidazole (im) and caffeine (cat) as auxiliary ligands were investigated as novel anti-inflammatory agents. The new copper(II) complexes with formula [Cu(fen)(2)(im)(2)] (1) and Cu-2(fen)(4)(caf)(2) (2) were synthesized from the dinuclear complex [Cu-2(fen)(4)(dmf)(2)] and characterized by IR, UV-Vis, EPR spectral and elemental analysis. The molecular structure of complex 1 was determined by X-ray crystallography. Both complexes 1 and 2 present enhanced and prolongued anti-inflammatory properties against the parent drug calcium Fenoprofenate, Ca(fen)(2)center dot 2H(2)O, with a better performance for complex 1. Ternary complexes are potential models for several mono and poly-nuclear metal enzymes. The measured superoxide dismutase (SOD) mimetic activities of the complexes indicated a higher SOD mimic activity for complex 2(IC50 of 0.24 mu M) than complex 1 (IC50 of 0.70 mu M), and also than the native enzyme evaluated by the same method (IC50 of 0.480 mu M). The catecholase activity of the complexes toward the aerobic oxidation of 3,5-di-tert-butylcatechol (dtbc) onto 3,5-di-tert-butylquinone (dtbq) showed that both complexes have moderate catalytic oxidase activity. (C) 2011 Elsevier Ltd. All rights reserved.