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Decomposition of reactive oxygen species by copper(II) bis(1-pyrazolyl)methane complexes

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Abstract

Two bis(1-pyrazolyl)alkane ligands, bis(3,5-dimethyl-1-pyrazolyl)methane and bis(4-iodo-3,5-dimethyl-1-pyrazolyl)methane, and their copper(II) complexes, bis(3,5-dimethyl-1-pyrazolyl)methanedinitratocopper(II) [CuL1(NO3)2] and bis(4-iodo-3,5-dimethyl-1-pyrazolyl)methanedinitratocopper(II) [CuL2(NO3)2]·2H2O, were prepared. Physiochemical properties of the copper(II) complexes were studied by spectroscopic (UV–vis, IR, EPR) techniques and cyclic voltammetry. Spectroscopic analysis revealed a 1:1 stoichiometry of ligand:copper(II) ion and a bindentate coordination mode for the nitrate ions in both of the complexes. According to experimental and theoretical ab initio data, the copper(II) ion is located in an octahedral hexacoordinated environment. Both complexes were able to catalyze the dismutation of superoxide anion (\( {\text{O}}^{{\bullet - }}_{{\text{2}}} \)) (pH 7.5) and decomposition of H2O2 (pH 7.5) and peroxynitrite (pH 10.9). In addition, both complexes exhibited superoxide dismutase (SOD) like activity toward extracellular and intracellular reactive oxygen species produced by activated human neutrophils in whole blood. Thus, these complexes represent useful SOD mimetics with a broad range of antioxidant activity toward a variety of reactive oxidants.

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Acknowledgements

We would like to thank Mark Munro and Valentin Grachev, Department of Physics, Montana State University, Bozeman, MT, USA, for help with EPR measurements and EPR spectra analysis, respectively. This work was supported in part by Department of Defense grant W9113M-04-1-0001, NIH grants AR42426 and RR020185, and the Montana State University Agricultural Experimental Station. The US Army Space and Missile Defense Command, 64 Thomas Drive, Frederick, MD 21702, USA, is the awarding and administering acquisition office. The content of this report does not necessarily reflect the position or policy of the US Government.

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Authors and Affiliations

  1. Department of Veterinary Molecular Biology, Montana State University, Bozeman, MT, 59717, USA

    Igor Schepetkin, Lilia Kirpotina & Mark T. Quinn

  2. Department of Chemistry, Altai State Technical University, Barnaul, Russia

    Andrei Potapov & Andrei Khlebnikov

  3. Department of Chemical Technology, Tomsk Polytechnic University, Tomsk, Russia

    Elena Korotkova & Anna Lukina

  4. Department of Physics, Montana State University, Bozeman, MT, 59717, USA

    Galina Malovichko

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  1. Igor Schepetkin
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Correspondence to Mark T. Quinn.

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Schepetkin, I., Potapov, A., Khlebnikov, A. et al. Decomposition of reactive oxygen species by copper(II) bis(1-pyrazolyl)methane complexes. J Biol Inorg Chem 11, 499–513 (2006). https://doi.org/10.1007/s00775-006-0101-1

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  • DOI: https://doi.org/10.1007/s00775-006-0101-1

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