Scavenging 4-Oxo-2-nonenal.
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.
Department of Pathology, Microbiology and Immunology, and ‡Division of Clinical Pharmacology Vanderbilt University Medical Center , Nashville, Tennessee 37232, United States.
Venkataraman
V
Amarnath
Department of Pathology, Microbiology and Immunology, and ‡Division of Clinical Pharmacology Vanderbilt University Medical Center , Nashville, Tennessee 37232, United States.
Kalyani
K
Amarnath
D000447:Aldehydes / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000737:chemistry*; D015227:Lipid Peroxidation; D008239:Lysine / Q000737:chemistry; D011506:Proteins / Q000737:chemistry / Q000378:metabolism; D011733:Pyridoxamine / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry
C403894:4-oxo-2-nonenal; D000447:Aldehydes; D016166:Free Radical Scavengers; D011506:Proteins; D011758:Pyrroles; D011733:Pyridoxamine; D008239:Lysine