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

Igor Schepetkin, Andrei Sergeevich Potapov, Andrey Ivanovich Khlebnikov, Elena Korotkova, Anna Lukina, Galina Malovichko, Lilia Kirpotina, Mark T. Quinn

Research output: Contribution to journalArticle

57 Citations (Scopus)

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) [CuL 1(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 H 2O2 (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.

Original languageEnglish
Pages (from-to)499-513
Number of pages15
JournalJournal of Biological Inorganic Chemistry
Volume11
Issue number4
DOIs
Publication statusPublished - 1 Jun 2006

Fingerprint

Methane
Copper
Reactive Oxygen Species
Decomposition
Ions
Superoxide Dismutase
Ligands
Alkanes
Peroxynitrous Acid
Spectroscopic analysis
Oxidants
Superoxides
Stoichiometry
Nitrates
Cyclic voltammetry
Paramagnetic resonance
Neutrophils
Blood
Antioxidants

Keywords

  • Copper complexes
  • Peroxynitrite
  • Pyrazole derivatives
  • Reactive oxygen species
  • Superoxide dismutase mimetics

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry

Cite this

Decomposition of reactive oxygen species by copper(II) bis(1-pyrazolyl) methane complexes. / Schepetkin, Igor; Potapov, Andrei Sergeevich; Khlebnikov, Andrey Ivanovich; Korotkova, Elena; Lukina, Anna; Malovichko, Galina; Kirpotina, Lilia; Quinn, Mark T.

In: Journal of Biological Inorganic Chemistry, Vol. 11, No. 4, 01.06.2006, p. 499-513.

Research output: Contribution to journalArticle

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AU - Schepetkin, Igor

AU - Potapov, Andrei Sergeevich

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AU - Korotkova, Elena

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AU - Quinn, Mark T.

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AB - 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) [CuL 1(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 H 2O2 (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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