Electrophilic Modulation of the Superoxide Anion Radical Scavenging Ability of Copper(II) Complexes with 4-Methyl Imidazole
| Autor: | Pierre Florian, Arlette Richaud, Omar Noel Medina-Campos, Norah Barba-Behrens, Francisco Méndez, José Pedraza-Chaverri |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
010304 chemical physics biology Superoxide Active site 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Coordination complex Superoxide dismutase chemistry.chemical_compound chemistry Nucleophile 0103 physical sciences Electrophile biology.protein Imidazole Molecule Physical and Theoretical Chemistry |
| Zdroj: | The Journal of Physical Chemistry A. 125:2394-2401 |
| ISSN: | 1520-5215 1089-5639 |
| Popis: | Three Cu(II) coordination compounds with 4-methyl imidazole were obtained, such as [Cu(C4H6N2)4(NO3)2], [Cu(C4H6N2)4Br2], and [Cu(C4H6N2)4Cl2]. Crystallographic studies confirmed their structural similarity with Cu(II) in the active site of endogenous copper-zinc superoxide dismutase (CuZn-SOD). The superoxide anion radical (O2•-) scavenging activity was evaluated by the non-enzymatic experimental assay and followed the trend [Cu(C4H6N2)4(NO3)2] > [Cu(C4H6N2)4Br2] > [Cu(C4H6N2)4Cl2]. The density functional theory and the hard and soft acids and bases principle showed the importance of the electron-deficient character of Cu(II) in the chemical reactivity of the coordination compounds; Cu(II) is the softest site in the molecule and it is preferred for the nucleophilic and radical attacks of the soft O2•-. A simple rule was obtained: "the electron-deficient character of Cu(II) is the key index for the O2•- scavenging activity and is modulated by the electron-releasing counteranion effect on the coordination compound". |
| Databáze: | OpenAIRE |
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