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Document type
články
články
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Source: BMČ - články
Title
Formaldehyde Reacts with Amino Acids and Peptides with a Potential Role in Acute Methanol Intoxication / D. Sýkora, J. Jindřich, V. Král, M. Jakubek, A. Tatar, Z. Kejík, P. Martásek, S. Zakharov,
Author
Sýkora, David
University of Chemistry and Technology Prague, Department of Analytical Chemistry, Technicka 5, 166 28 Prague, Czech Republic.

Jindřich, Jindřich
Charles University, Faculty of Science, Department of Organic Chemistry, Hlavova 8, 128 43 Prague, Czech Republic.

Král, Vladimír
University of Chemistry and Technology Prague, Department of Analytical Chemistry, Technicka 5, 166 28 Prague, Czech Republic. BIOCEV, Charles University, First Faculty of Medicine, Katerinská 32, 121 08 Prague, Czech Republic.

Jakubek, Milan
University of Chemistry and Technology Prague, Department of Analytical Chemistry, Technicka 5, 166 28 Prague, Czech Republic. BIOCEV, Charles University, First Faculty of Medicine, Katerinská 32, 121 08 Prague, Czech Republic. Charles University, First Faculty of Medicine and General University Hospital, Department of Pediatrics and Adolescent Medicine, Katerinská 32, 121 08 Prague, Czech Republic.

Tatar, Ameneh
University of Chemistry and Technology Prague, Department of Analytical Chemistry, Technicka 5, 166 28 Prague, Czech Republic. Charles University, First Faculty of Medicine and General University Hospital, Department of Pediatrics and Adolescent Medicine, Katerinská 32, 121 08 Prague, Czech Republic.

Kejík, Zdeněk
University of Chemistry and Technology Prague, Department of Analytical Chemistry, Technicka 5, 166 28 Prague, Czech Republic. BIOCEV, Charles University, First Faculty of Medicine, Katerinská 32, 121 08 Prague, Czech Republic. Charles University, First Faculty of Medicine and General University Hospital, Department of Pediatrics and Adolescent Medicine, Katerinská 32, 121 08 Prague, Czech Republic.

Martásek, Pavel
Charles University, First Faculty of Medicine and General University Hospital, Department of Pediatrics and Adolescent Medicine, Katerinská 32, 121 08 Prague, Czech Republic.

Zakharov, Sergey
Charles University, First Faculty of Medicine and General University Hospital, Department of Occupational Medicine, Na Bojisti 1, 120 00 Prague, Czech Republic.

Cited source
Journal of analytical toxicology. 2020, roč. 44, č. 8, s. 880-885. ISSN: 0146-4760; 1945-2403 (online).
Date of issue
2020
Language
angličtina
Country
Spojené království
Document type
články
DOI
Pubmed ID
Link
Record number
bmc20027580
Persistent link
MESH descriptor
methanol (otrava)
aminokyseliny (chemie)
formaldehyd (chemie)
lidé
peptidy (chemie)
odhalování abúzu drog (metody)
Genre
English Abstract
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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