Scavenging 4-Oxo-2-nonenal.

Abstract

4-Oxo-2-nonenal (ONE), a product of cellular lipid oxidation, reacts nonspecifically with the lysine residues of proteins and is generated in increased amounts during degenerative diseases and cancer. We show that pyridoxamine, salicylamine, and related 2-aminomethylphenols react with ONE, to form pyrrolo[2,1-b][1,3]oxazines with the participation of both the amino and the phenolic groups. 2-Aminomethylphenols react with ONE as well as with the Michael adducts of ONE much more rapidly than lysine, suggesting their use for therapeutically scavenging ONE.

• Authors: Venkataraman Amarnath, Kalyani Amarnath
• Journal: Chemical research in toxicology (Chem Res Toxicol) Vol. 28 Issue 10 Pg. 1888-90 (Oct 19 2015) ISSN: 1520-5010 [Electronic] United States
• PMID: 26355561 (Publication Type: Journal Article, Research Support, N.I.H., Extramural)

Chemical References

• 4-oxo-2-nonenal
• Aldehydes
• Free Radical Scavengers
• Proteins
• Pyrroles
• Pyridoxamine
• Lysine

Topics

• Aldehydes (chemistry)
• Free Radical Scavengers (chemistry)
• Lipid Peroxidation
• Lysine (chemistry)
• Proteins (chemistry, metabolism)
• Pyridoxamine (chemistry)
• Pyrroles (chemistry)