Química Nova (Jun 2005)

Bioquímica e ação citotóxica de alfa-aminocetonas endógenas Biochemistry and cytotoxicity of alpha-aminoketones

  • Fernando Dutra,
  • Etelvino J. H. Bechara

DOI
https://doi.org/10.1590/S0100-40422005000300021
Journal volume & issue
Vol. 28, no. 3
pp. 483 – 491

Abstract

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alpha-Aminoketones are expected to undergo enolization and subsequent aerobic oxidation yielding oxyradicals and highly toxic a-oxoaldehydes. Our interest has been focused on two endogenous a-aminoketones: 5-aminolevulinic acid (ALA) and aminoacetone (AA), accumulated in porphyrias and diabetes mellitus, respectively, and recently implicated as contributing sources of oxyradicals in these diseases. The final oxidation product of ALA, 4,5-dioxovaleric acid (DOVA), is able to alkylate DNA guanine moieties and expected to promote protein cross-linking. Methylglyoxal (MG), the final oxidation product of AA, is also highly cytotoxic and able to aggregate protein molecules. This review covers chemical and biochemical aspects of these alpha-aminoketones and their putative roles in the oxidative stress associated with porphyric disorders and diabetes.

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