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Antioxidant Potential of New Pyrazoline Derivatives to Prevent Oxidative Damage
Author(s) -
Martins Daniele M.,
Torres Bruna G.,
Spohr Patrícia R.,
Machado Pablo,
Bonacorso Helio G.,
Zanatta Nilo,
Martins Marcos A. P.,
Emanuelli Tatiana
Publication year - 2009
Publication title -
basic and clinical pharmacology and toxicology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.805
H-Index - 90
eISSN - 1742-7843
pISSN - 1742-7835
DOI - 10.1111/j.1742-7843.2008.00346.x
Subject(s) - trifluoromethyl , chemistry , lipid peroxidation , pyrazole , antioxidant , dpph , medicinal chemistry , pyrazoline , glutathione , toluene , organic chemistry , alkyl , enzyme
The antioxidant capacity of a series of six novel synthetic pyrazoline derivatives (i) 5‐hydroxy‐3‐methyl‐5‐trifluoromethyl‐4,5‐dihydro‐1 H ‐carbaldehyde‐pyrazole, (ii) 5‐hydroxy‐3‐methyl‐5‐trifluoromethyl‐4,5‐dihydro‐1 H ‐1‐acetyl‐pyrazole, (iii) 5‐hydroxy‐3‐methyl‐5‐trifluoromethyl‐4,5‐dihydro‐1 H ‐carboxyamide‐pyrazole, (iv) 5‐hydroxy‐3‐methyl‐5‐trifluoromethyl‐4,5‐dihydro‐1 H ‐1‐benzoyl‐pyrazole, (v) 5‐hydroxy‐3‐methyl‐5‐trifluoromethyl‐4,5‐dihydro‐1 H ‐1‐(2‐hydroxybenzoyl)‐pyrazole and (vi) 5‐hydroxy‐3‐methyl‐5‐trifluoromethyl‐4,5‐dihydro‐1 H ‐1‐(4‐methoxybenzoyl)‐pyrazole was evaluated as the capacity of compounds to transfer a hydrogen atom (protection against brain lipid peroxidation and glutathione oxidation) and their capacity to transfer a single electron [ferric‐reducing antioxidant power (FRAP) and 1,1‐diphenyl‐2‐picrylhydrazyl radical scavenging (DPPH) assays]. Compound 5 had the highest free radical scavenging capacity in the DPPH assay, while compound 2 had the highest FRAP value (P < 0.05). Only compounds 1, 4 and 5 protected against lipid peroxidation in rat brain homogenate. However, compound 5 was the most effective to prevent basal and iron‐, sodium nitroprusside‐ and H 2 O 2 ‐stimulated lipid peroxidation (IC 50 < 15 µM) and the only one effective to block glutathione oxidation‐mediated by H 2 O 2 (at 150 µM). Our results indicate that compound 5 has the greatest potential to prevent oxidative damage in brain homogenates.