Potentiometric, spectroscopic and antioxidant activity studies of SOD mimics containing carnosine

Raffaele P. Bonomo; Valeria Bruno; Enrico Conte; Guido De Guidi; Diego La Mendola; Giuseppe Maccarrone; Ferdinando Nicoletti; Enrico Rizzarelli; Salvatore Sortino; Graziella Vecchio

doi:10.1039/B308168K

Potentiometric, spectroscopic and antioxidant activity studies of SOD mimics containing carnosine†

Raffaele P. Bonomo,^a Valeria Bruno,^bc Enrico Conte,^a Guido De Guidi,^a Diego La Mendola,^d Giuseppe Maccarrone,^a Ferdinando Nicoletti,^bc Enrico Rizzarelli,*^ad Salvatore Sortino^a and Graziella Vecchio^a

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* Corresponding authors

^a Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria 6, 95125 Catania, Italy
E-mail: erizzarelli@unict.it

^b Dipartimento di Fisiologia Umana e Farmacologia, Università di Roma “La Sapienza”, Piazzale A. Moro 5, 00185 Roma, Italy

^c Dipartimento di Neuroscienze, I. N. M. Neuromed, Località Camerelle, 86077 Pozzilli, Italy

^d Istituto di Biostrutture e Bioimmagini-Sez. di Catania, CNR, Viale A. Doria 6, 95125 Catania, Italy

Abstract

Stability constant values and bonding details of the copper(II) complexes of the β-cyclodextrin functionalized with the carnosine dipeptide (β-alanyl-L-histidine) at its narrow (CDAH6) or at its wide (CDAH3) rim were determined in aqueous solution. The potentiometric and spectroscopic data (UV-vis, CD and EPR) show that the involvement of a secondary OH group induces drastic differences in the coordination properties of CDAH3, in comparison with those of CDAH6. Direct and indirect assays were carried out showing that the copper(II) complexes with the two cyclodextrin derivatives are SOD-mimics with high catalytic activity. In addition the complex species are scavenger compounds towards ˙OH radicals, giving rise to a particular kind of copper(II) complexes with a combined activity against two toxic radical species, O₂˙⁻ and ˙OH. The cyclodextrin moiety contributes to the scavenger activity, without damaging the cellular membranes of neuronal and red blood cells.

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Potentiometric, spectroscopic and antioxidant activity studies of SOD mimics containing carnosine†

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