Relative reactivity of dihydropyridine derivatives to electrogenerated superoxide ion in DMSO solutions: a voltammetric approach.

Purpose: To evaluate the reaction of a large series of pharmacologically significant 1,4-dihydropyridine (1,4-DHP) compounds with superoxide (O2.-) in dimethylsulfoxide using differential pulse voltammetry and controlled potential electrolysis.

Methods: Differential pulse voltammetry was used to track the consumption of O2.-, and controlled potential electrolysis was used to electrogenerate O2.-.

Results: With the addition of 1,4-DHP, the oxidation peak current of O2.- decreased concentration dependently, suggesting that 1,4-DHP reacts with O2.-, that is, 1,4-DHP scavenges O2.- in dimethylsulfoxide.

Conclusions: very easy and direct voltammetric procedure to study the relative reactivity of different 1,4-DHP with O2.- is proposed. Using the proposed method we have found that all commercial 1,4-DHP reacts with O2.-. The following order of rates was obtained: felodipine > or = vitamin E > isradipine > nimodipine > furnidipine > nitrendipine > nisoldipine > nifedipine. Furthermore, it was demonstrated that the hydrogen at the N-position of 1,4-DHP compounds could be released as a proton in the presence of O2.-, thus the electrogenerated O2.- worked as a proton acceptor to 1,4-DHP.