Mass spectral analyses of hydroxymethylvinyl ketone-hemoglobin adducts formed after in vivo exposure of Sprague-Dawley rats to 3-butene-1,2-diol.

ABSTRACT: 3-Butene-1,2-diol (BDD), a known in vivo metabolite of 1,3-butadiene, is oxidized to a reactive Michael acceptor, hydroxymethylvinyl ketone (HMVK). Previously, we characterized the formation of three HMVK-amino acid monoadducts when HMVK was incubated in vitro with N-acetyl-l-cysteine, l-valinamide, and N-acetyl-l-lysine (NAL) at physiological conditions. One HMVK-NAL cyclic diadduct (cyclic diadduct 1) also formed by sequential Michael addition reactions of two HMVK molecules with the epsilon-amino group of NAL followed by enolization and cyclization. Loss of a water molecule and autoxidation convert cyclic diadduct 1 to a more stable cyclic diadduct 2. In the present study, we used multiple mass spectrometry techniques to investigate the formation of HMVK adducts with nucleophilic residu

SUBMITTER: Barshteyn N 

PROVIDER: S-EPMC2696584 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature