Acrolein and other α,β-unsaturated carbonyl compounds

Acrolein and other α,β-unsaturated carbonyl compounds are small, electrophilic, unsaturated aldehydes and ketones resulting from environmental exposure (e.g., combustion of organic materials) and endogenous lipid peroxidation during oxidative stress. They are not classical biological targets (such as receptors or enzymes), but rather, are highly reactive toxicants that covalently modify nucleophilic sites (especially cysteine thiols) in proteins and DNA via Michael-type addition. This leads to protein dysfunction, cellular stress, neurotoxicity (nerve terminal damage), inflammation, and in some cases, genotoxicity and carcinogenesis. Because these molecules disrupt many molecular pathways through non-specific covalent modification, they are generally considered harmful reactive species rather than druggable therapeutic targets

Other names

Acroleinα,β-unsaturated aldehydesacrylic aldehydeacrylaldehyde2-propenalpropenaldehydeacrolein-type aldehydesconjugated enalsmethyl vinyl ketone (MVK)4-hydroxy-2-nonenal (HNE)

Drugs like Mesna work as nucleophilic thiol donors, inactivating acrolein by covalent scavenging (neutralization of Michael acceptors)