Abstract

NIUFAR, Noah N. et al. Reduction Potentials of Conjugated Aliphatic Ketones, Oximes, and Imines: Correlation with Structure and Bioactivity. Rev. Soc. Quím. Méx [online]. 2002, vol.46, n.4, pp.307-312. ISSN 0583-7693.

To determine which structural features may favor electron transfer in biological systems, cyclic voltammetric studies were carried out on conjugated aliphatic ketone, oxime, and imine species at pH levels 2 through 7 in most cases. The nature of the conjugated substituents strongly influenced the reduction potentials. The dione samples were most easily reduced, followed by the diimine and then the mono- and di-oxime analogs. The reduction potentials for all compounds were pH-dependent, with the most favorable potentials occurring at the lower pH values. The possible roles of protonation, hydrogen bonding, the captodative effect, and other aspects were considered. The favorable reduction potentials of the compounds ex-hibiting bioactivity suggest that in vivo electron transfer and oxidative stress may be involved in various types of biological processes.

Keywords : Cyclic voltammetry; diones; diimines; dioximes; bioactive; electron transfer; oxidative stress.

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