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Microwave-assisted synthesis of hydroxyphenyl nitrones with protective action against oxidative stress

AuthorsChavarría, Cecilia; Pérez, Daniel I.; Pérez, Concepción; Morales-García, José A. ; Alonso-Gil, Sandra ; Pérez Castillo, Ana ; Gil, Carmen ; Souza, José M.; Porcal, Williams
Issue Date2012
CitationEuropean Journal of Medicinal Chemistry 58: 44-49 (2012)
AbstractOxidative stress plays an important role in neuronal death in neurodegenerative disorders such as Parkinson's disease (PD). Hydroxyphenyl nitrones, derivatives of the nitrone spin trap alpha-phenyl-N-tert-butylnitrone (PBN), were synthesized and their antioxidant, anti-inflammatory and neuroprotective activity in neural cells evaluated. These hydroxyphenyl nitrones 5-7 were synthesized by reaction of the corresponding hydroxybenzaldehyde with N-tert-butyl hydroxylamine under microwave irradiation. They showed good peroxyl free radical scavenger capacities, analyzed by oxygen radical absorbance capacity (ORAC). Also inhibited peroxynitrite-mediated tyrosine nitration of alpha-synuclein in vitro and protected human neuroblastoma (SH-SY5Y) cells against SIN-1 and 6-OHDA toxicity when micromolar concentrations were used. Besides, the hydroxyphenyl nitrones evaluated showed anti-inflammatory activity modulating nitrite production in primary neural cell cultures of astrocytes and microglia treated with lipopolysaccharide (LPS), a potent inflammatory agent. These experimental data suggest a potential therapeutic use of these hydroxyphenyl nitrones against oxygen and nitrogen reactive species involved in neurodegenerative pathology. © 2012 Elsevier Masson SAS. All rights reserved.
Identifiersdoi: 10.1016/j.ejmech.2012.09.044
issn: 0223-5234
e-issn: 1768-3254
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