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 language | English |
|---|---|
| Pages (from-to) | 499-513 |
| Number of pages | 15 |
| Journal | Journal of Biological Inorganic Chemistry |
| Volume | 11 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 1 Jun 2006 |
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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 journal › Article
}
TY - JOUR
T1 - Decomposition of reactive oxygen species by copper(II) bis(1-pyrazolyl) methane complexes
AU - Schepetkin, Igor
AU - Potapov, Andrei Sergeevich
AU - Khlebnikov, Andrey Ivanovich
AU - Korotkova, Elena
AU - Lukina, Anna
AU - Malovichko, Galina
AU - Kirpotina, Lilia
AU - Quinn, Mark T.
PY - 2006/6/1
Y1 - 2006/6/1
N2 - 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.
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.
KW - Copper complexes
KW - Peroxynitrite
KW - Pyrazole derivatives
KW - Reactive oxygen species
KW - Superoxide dismutase mimetics
UR - http://www.scopus.com/inward/record.url?scp=33745753533&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33745753533&partnerID=8YFLogxK
U2 - 10.1007/s00775-006-0101-1
DO - 10.1007/s00775-006-0101-1
M3 - Article
C2 - 16680452
AN - SCOPUS:33745753533
VL - 11
SP - 499
EP - 513
JO - Journal of Biological Inorganic Chemistry
JF - Journal of Biological Inorganic Chemistry
SN - 0949-8257
IS - 4
ER -