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

<abstract language="eng">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), ac...

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Main Authors: Fernando Dutra, Etelvino J. H. Bechara
Format: Article
Language:English
Published: Sociedade Brasileira de Química 2005-06-01
Series:Química Nova
Subjects:
Online Access:http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422005000300021
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author Fernando Dutra
Etelvino J. H. Bechara
author_facet Fernando Dutra
Etelvino J. H. Bechara
author_sort Fernando Dutra
collection DOAJ
description <abstract language="eng">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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spelling doaj.art-cc01b271a1bc4f0da02b2cbaefb494282022-12-21T17:57:53ZengSociedade Brasileira de QuímicaQuímica Nova0100-40421678-70642005-06-0128348349110.1590/S0100-40422005000300021Bioquímica e ação citotóxica de alfa-aminocetonas endógenas Biochemistry and cytotoxicity of alpha-aminoketonesFernando DutraEtelvino J. H. Bechara<abstract language="eng">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.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-404220050003000215-aminolevulinic acidaminoacetonehexosamines
spellingShingle Fernando Dutra
Etelvino J. H. Bechara
Bioquímica e ação citotóxica de alfa-aminocetonas endógenas Biochemistry and cytotoxicity of alpha-aminoketones
Química Nova
5-aminolevulinic acid
aminoacetone
hexosamines
title Bioquímica e ação citotóxica de alfa-aminocetonas endógenas Biochemistry and cytotoxicity of alpha-aminoketones
title_full Bioquímica e ação citotóxica de alfa-aminocetonas endógenas Biochemistry and cytotoxicity of alpha-aminoketones
title_fullStr Bioquímica e ação citotóxica de alfa-aminocetonas endógenas Biochemistry and cytotoxicity of alpha-aminoketones
title_full_unstemmed Bioquímica e ação citotóxica de alfa-aminocetonas endógenas Biochemistry and cytotoxicity of alpha-aminoketones
title_short Bioquímica e ação citotóxica de alfa-aminocetonas endógenas Biochemistry and cytotoxicity of alpha-aminoketones
title_sort bioquimica e acao citotoxica de alfa aminocetonas endogenas biochemistry and cytotoxicity of alpha aminoketones
topic 5-aminolevulinic acid
aminoacetone
hexosamines
url http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422005000300021
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