Scavenging activity of C4-hydroxyphenyl- and polyhydroxyphenyl-1,4-dihydropyridines toward free radicals

Salazar, R; Pardo-Jimenez, V; SQUELLA, J. A.; Nuñez-Vergara, L. J.; Navarrete-Encina P.A.; Camargo C.


The radical-scavenging ability of synthesized C4-phenolic-substituted 1,4-dihydropyridines (1,4-DHPs) toward 2,2-diphenyl-1-picrylhydrazyl (DPPH ) and alkyl/alkylperoxyl ABAP-derived radicals at pH 7.4 was assessed by UV-visible spectroscopy. Reactivity of 1,4-DHPs toward DPPH was measured by following the decay of the absorption corresponding to the radical ? max at 525 nm, permitting the calculation of EC 50, t EC50, and antiradical efficiency values. Pseudo-first-order kinetic rate constants for the reactivity between the C4-phenolic-substituted 1,4-DHP compounds and alkyl/alkylperoxyl ABAP-derived radicals were followed by the decrease in ? max at 356 nm corresponding to 1,4-DHP moiety. C4-phenolic-substituted 1,4-DHPs were more reactive toward alkyl free radicals than the other tested radicals. The 3,4,5-trihydroxyphenyl-1,4-DHP was the most reactive derivative toward this radical with a kinetic rate constant value of 513.2 s -1. Also, this derivative was the most effective toward the DPPH radical with the lowest EC 50 value (5.08 ?M). Comparative studies revealed that synthesized 1,4-DHPs were more reactive than commercial 1,4-DHPs. The scavenging mechanism involves the contribution of both pharmacophores, that is, hydroxyphenyl and 1,4-DHP rings, which was supported by the identification of the reaction products. © 2012 Wiley Periodicals, Inc.

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Editorial: John Wiley & Sons Inc.
Fecha de publicación: 2012