Formaldehyde Reacts with Amino Acids and Peptides with a Potential Role in Acute Methanol Intoxication
Language English Country Great Britain, England Media print
Document type Journal Article
PubMed
32364609
DOI
10.1093/jat/bkaa039
PII: 5826074
Knihovny.cz E-resources
- MeSH
- Amino Acids chemistry MeSH
- Formaldehyde chemistry MeSH
- Humans MeSH
- Methanol poisoning MeSH
- Substance Abuse Detection methods MeSH
- Peptides chemistry MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Amino Acids MeSH
- Formaldehyde MeSH
- Methanol MeSH
- Peptides MeSH
Methanol, an aliphatic alcohol widely used in the industry, causes acute and chronic intoxications associated with severe long-term health damage, including permanent visual impairment, brain damage, mainly necrosis of the basal ganglia and high mortality due to cancer. However, the role of formaldehyde, an intermediate metabolite of methanol oxidation, in methanol toxicity remains unclear. Thus, we studied the reactivity of several amino acids and peptides in the presence of formaldehyde by identifying products by direct infusion electrospray high-resolution mass spectrometry (MS) and matrix-assisted laser desorption-ionization MS. Cysteine, homocysteine and two peptides, CG and CGAG, provided cyclic products with a +12 amu mass shift with respect to the original compounds. The proposed structures of the products were confirmed by high-resolution tandem MS. Moreover, the formation of the products with +12 amu mass shift was also shown for two biologically relevant peptides, fragments of ipilimumab, which is a human IgG1 monoclonal antibody against cytotoxic T-lymphocyte-associated protein 4. Overall, our experimental results indicate that formaldehyde reacts with some amino acids and peptides, yielding covalently modified structures. Such chemical modifications may induce undesirable changes in the properties and function of vital biomolecules (e.g., hormones, enzymes) and consequently pathogenesis.
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