Alpha-phenyl-N-tert-butyl nitrone (PBN) derivatives: synthesis and protective action against microvascular damages induced by ischemia/reperfusion |
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| Authors: | Kim Sothea de A Vilela Guilherme V M Bouajila Jalloul Dias Ayres G Cyrino Fatima Z G A Bouskela Eliete Costa Paulo R R Nepveu Françoise |
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| Institution: | 1. UMR 152, IRD—Université Paul Sabatier, Pharmacochimie des Substances Naturelles et Pharmacophore Redox, Faculté de Pharmacie, 35, ch. des Mara??chers, 31062 Toulouse Cedex 9, France;2. Laboratório de Química Bioorgânica, Núcleo de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, bloco H, Ilha da Cidade Universitária, Universidade Federal do Rio de Janeiro, 21941 590 RJ, Brazil;3. Instituto de Química, Universidade do Estado do Rio de Janeiro, Brazil;4. Laboratório de Pesquisas em Microcirculação, Instituto de Biologia Roberto Alcântara Gomes, Universidade do Estado do Rio de Janeiro, Brazil |
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| Abstract: | Nitrones 4-7, structurally related to PBN (1), were prepared by reaction of the corresponding aromatic aldehydes with N-tert-butyl hydroxylamine. The protective effects of these nitrones against microvascular damages in ischemia/reperfusion in the 'hamster cheek pouch' assay were studied and 1, as well as 4a, 4b, and 7 (derived from piperonal, O-benzyl vanillin, and furfural, respectively), showed to be more active than shark cartilage or alpha-tocopherol. No correlation was found between the protective effect of these nitrones and their logP (partition coefficient) or their capacity to trap (*)OH and (*)CH(3) radicals. |
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