Polyamine-Derived Aminoaldehydes and Acrolein: Cytotoxicity, Reactivity and Analysis of the Induced Protein Modifications

Polyamines participate in the processes of cell growth and development. The degradation branch of their metabolism involves amine oxidases. The oxidation of spermine, spermidine and putrescine releases hydrogen peroxide and the corresponding aminoaldehyde. Polyamine-derived aminoaldehydes have been...

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Main Authors: Marek Šebela, Michaela Rašková
Format: Article
Language:English
Published: MDPI AG 2023-11-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/28/21/7429
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author Marek Šebela
Michaela Rašková
author_facet Marek Šebela
Michaela Rašková
author_sort Marek Šebela
collection DOAJ
description Polyamines participate in the processes of cell growth and development. The degradation branch of their metabolism involves amine oxidases. The oxidation of spermine, spermidine and putrescine releases hydrogen peroxide and the corresponding aminoaldehyde. Polyamine-derived aminoaldehydes have been found to be cytotoxic, and they represent the subject of this review. 3-aminopropanal disrupts the lysosomal membrane and triggers apoptosis or necrosis in the damaged cells. It is implicated in the pathogenesis of cerebral ischemia. Furthermore, 3-aminopropanal yields acrolein through the elimination of ammonia. This reactive aldehyde is also generated by the decomposition of aminoaldehydes produced in the reaction of serum amine oxidase with spermidine or spermine. In addition, acrolein is a common environmental pollutant. It causes covalent modifications of proteins, including carbonylation, the production of Michael-type adducts and cross-linking, and it has been associated with inflammation-related diseases. APAL and acrolein are detoxified by aldehyde dehydrogenases and other mechanisms. High-performance liquid chromatography, immunochemistry and mass spectrometry have been largely used to analyze the presence of polyamine-derived aminoaldehydes and protein modifications elicited by their effect. However, the main and still open challenge is to find clues for discovering clear linkages between aldehyde-induced modifications of specific proteins and the development of various diseases.
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spelling doaj.art-8adb1beb88db4ce2832ce1a3ff2484302023-11-10T15:08:58ZengMDPI AGMolecules1420-30492023-11-012821742910.3390/molecules28217429Polyamine-Derived Aminoaldehydes and Acrolein: Cytotoxicity, Reactivity and Analysis of the Induced Protein ModificationsMarek Šebela0Michaela Rašková1Department of Biochemistry, Faculty of Science, Palacký University, Šlechtitelů 27, 783 71 Olomouc, Czech RepublicDepartment of Biochemistry, Faculty of Science, Palacký University, Šlechtitelů 27, 783 71 Olomouc, Czech RepublicPolyamines participate in the processes of cell growth and development. The degradation branch of their metabolism involves amine oxidases. The oxidation of spermine, spermidine and putrescine releases hydrogen peroxide and the corresponding aminoaldehyde. Polyamine-derived aminoaldehydes have been found to be cytotoxic, and they represent the subject of this review. 3-aminopropanal disrupts the lysosomal membrane and triggers apoptosis or necrosis in the damaged cells. It is implicated in the pathogenesis of cerebral ischemia. Furthermore, 3-aminopropanal yields acrolein through the elimination of ammonia. This reactive aldehyde is also generated by the decomposition of aminoaldehydes produced in the reaction of serum amine oxidase with spermidine or spermine. In addition, acrolein is a common environmental pollutant. It causes covalent modifications of proteins, including carbonylation, the production of Michael-type adducts and cross-linking, and it has been associated with inflammation-related diseases. APAL and acrolein are detoxified by aldehyde dehydrogenases and other mechanisms. High-performance liquid chromatography, immunochemistry and mass spectrometry have been largely used to analyze the presence of polyamine-derived aminoaldehydes and protein modifications elicited by their effect. However, the main and still open challenge is to find clues for discovering clear linkages between aldehyde-induced modifications of specific proteins and the development of various diseases.https://www.mdpi.com/1420-3049/28/21/7429acroleinaldehyde dehydrogenaseamine oxidaseaminoaldehyde3-aminopropanalcytotoxicity
spellingShingle Marek Šebela
Michaela Rašková
Polyamine-Derived Aminoaldehydes and Acrolein: Cytotoxicity, Reactivity and Analysis of the Induced Protein Modifications
Molecules
acrolein
aldehyde dehydrogenase
amine oxidase
aminoaldehyde
3-aminopropanal
cytotoxicity
title Polyamine-Derived Aminoaldehydes and Acrolein: Cytotoxicity, Reactivity and Analysis of the Induced Protein Modifications
title_full Polyamine-Derived Aminoaldehydes and Acrolein: Cytotoxicity, Reactivity and Analysis of the Induced Protein Modifications
title_fullStr Polyamine-Derived Aminoaldehydes and Acrolein: Cytotoxicity, Reactivity and Analysis of the Induced Protein Modifications
title_full_unstemmed Polyamine-Derived Aminoaldehydes and Acrolein: Cytotoxicity, Reactivity and Analysis of the Induced Protein Modifications
title_short Polyamine-Derived Aminoaldehydes and Acrolein: Cytotoxicity, Reactivity and Analysis of the Induced Protein Modifications
title_sort polyamine derived aminoaldehydes and acrolein cytotoxicity reactivity and analysis of the induced protein modifications
topic acrolein
aldehyde dehydrogenase
amine oxidase
aminoaldehyde
3-aminopropanal
cytotoxicity
url https://www.mdpi.com/1420-3049/28/21/7429
work_keys_str_mv AT mareksebela polyaminederivedaminoaldehydesandacroleincytotoxicityreactivityandanalysisoftheinducedproteinmodifications
AT michaelaraskova polyaminederivedaminoaldehydesandacroleincytotoxicityreactivityandanalysisoftheinducedproteinmodifications