Modification of proteins and other biological molecules by acetaldehyde: Adduct structure and functional significance

Hydroxyethyl radicals in ethanol hepatotoxicity

“…Such immune reactions involve lymphocyte-mediated response to alcoholic hyalin (38) or liver autologous human hepatocytes (39) as well as the development of circulating antibodies against epitopes present on the surface of hepatocytes from ethanol-fed rabbits (40)(41), that trigger antibody-dependent immunotoxicity (42,43). These immunological reactions have been ascribed to the binding of acetaldehyde to proteins (44,45), since, either experimental animals exposed to alcohol (46) or alcoholic patients have high titres of immunoglobulins which react with acetaldehyde-protein adducts (47)(48)(49)(50)(51). Although the immunization with acetaldehyde-modified hemoglobin of ethanol-fed guinea pigs has been reported to reproduce experimentally some features of human alcoholic hepatitis (52), immune response toward acetaldehyde adducts can not completely explain the immunoallergic reactions associated to alcoholic liver disease, since antiacetaldehyde antibodies can also be found in patients with liver diseases unrelated to alcohol (53).…”

Determination of maternal-fetal biomarkers of prenatal exposure to ethanol: A review

“…However, acetaldehyde is rapidly converted to acetate by acetaldehyde dehydrogenase (ALDH) and it is a highly reactive molecule that tends to bind to cellular compounds [40][41][42]. In addition, acetaldehyde might react with the nucleophilic groups of proteins forming adducts with several proteins, some of which have already been identified: hemoglobin, albumin and other serum proteins, lipoproteins, tubulin, CYP450 2E1 and red blood cell membrane proteins.…”

Study on the relationship of the structure and toxicity of alcohols, aldehydes and acids

“…It is generally considered that the potential carcinogenic mechanism is that the aldehyde attacks guanosine on the N2 bits of DNA to form unstable Schiff base, then Schiff base restores to stable N2-ethyl-3'-deoxyguanosine adducts by the intracellular system [10]. Formation of DNA-protein crosslink and protein adducts of acetaldehyde has also been reported [13][14][15][16]. In addition, aldehydes also have narcotic effects, and the effect enhances with the increased number of carbon atoms, while its irritation correspondingly weakens and the toxicity reduces.…”