Aerobic co-oxidation of hemoglobin and aminoacetone
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2022
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REUNIAO ANUAL DA SBQ, 45.
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Aminoacetone (1-aminopropan-2-one), a putative minor biological source of methylglyoxal, reacts like other
-aminoketones such as 6-aminolevulinic acid (first heme precursor) yielding electrophilic -oxoaldehydes,
ammonium ion and reactive oxygen species by metal- and hemeprotein catalyzed aerobic oxidation 1,2. A
wealth of reports implicates methylglyoxal in protein crosslinking and DNA addition, leading to age-related
disorders, including diabetes 3,4. Importantly, methylglyoxal-treated hemoglobin adds four water-exposed
arginine residues, which may compromise its physiological role and potentially serve as biomarkers for
diabetes 5. In this work, we investigate the co-oxidation of aminoacetone and oxyhemoglobin in normally
aerated phosphate buffer, leading to structural changes in hemoglobin, which might reportedly be attributed
to the addition of aminoacetone-generated methylglyoxal to the protein. Hydroxyl radical-promoted chemical
damage to hemoglobin may also occur in parallel, which is suggested by EPR-spin trapping studies with
5,5-dimethyl-1-pyrroline-N-oxide and ethanol. Concomitantly, oxyhemoglobin is oxidized to methemoglobin,
as indicated by characteristic CD spectral changes in the absorption Soret and visible regions. Overall,
these findings may contribute to elucidate the molecular mechanisms underlying human diseases
associated with hemoglobin dysfunctions (e.g., diabetes) and with aminoacetone in metabolic alterations
related to excess of glycine and threonine (e.g., threoninemia, cri-du-chat syndrome).
Como referenciar
RAMOS, LUIZ D.; MANTOVANI, MARIANA C.; SARTORI, ADRIANO; DUTRA, FERNANDO; STEVANI, CASSIUS V.; BECHARA, ETELVINO J.H. Aerobic co-oxidation of hemoglobin and aminoacetone. In: SILVA, FERNANDO de C. da (org.). In: REUNIAO ANUAL DA SBQ, 45., 31 de maio - 3 de junho, 2022, Maceió, AL. Resumo... São Carlos, SP: Aptor Software, 2022. p. 164-164. Disponível em: http://repositorio.ipen.br/handle/123456789/33966. Acesso em: 20 Mar 2026.
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