Alpha-phenyl-N-tert-butyl nitrone (PBN) derivatives: synthesis and protective action against microvascular damages induced by ischemia/reperfusion.
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.
Kim
Sothea
S
UMR 152, IRD-Université Paul Sabatier, Pharmacochimie des Substances Naturelles et Pharmacophore Redox, Faculté de Pharmacie, 35, ch. des Maraîchers, 31062 Toulouse Cedex 9, France.
de A Vilela
Guilherme V M
GV
Bouajila
Jalloul
J
Dias
Ayres G
AG
Cyrino
Fatima Z G A
FZ
Bouskela
Eliete
E
Costa
Paulo R R
PR
Nepveu
Françoise
F
D000818:Animals; D002196:Capillaries / Q000187:drug effects / Q000473:pathology; D002851:Chromatography, High Pressure Liquid; D006224:Cricetinae; D003497:Cyclic N-Oxides / Q000138:chemical synthesis* / Q000494:pharmacology*; D004578:Electron Spin Resonance Spectroscopy; D005456:Fluorescent Dyes; D007202:Indicators and Reagents; D008297:Male; D008647:Mesocricetus; D009061:Mouth Mucosa / Q000098:blood supply / Q000473:pathology; D012039:Regional Blood Flow / Q000187:drug effects; D015427:Reperfusion Injury / Q000473:pathology* / Q000517:prevention & control*; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship
D003497:Cyclic N-Oxides; D005456:Fluorescent Dyes; D007202:Indicators and Reagents; C029217:phenyl-N-tert-butylnitrone