Preparation and investigation of vitamin B6-derived aminopyridinol antioxidants.

Serwa R, Nam TG, Valgimigli L, Culbertson S, Rector CL, Jeong BS, Pratt DA, Porter NA
Chemistry. 2010 16 (47): 14106-14

PMID: 20967898 · DOI:10.1002/chem.201001382

3-Pyridinols bearing amine substitution para to the hydroxylic moiety have previously been shown to inhibit lipid peroxidation more effectively than typical phenolic antioxidants, for example, α-tocopherol. We report here high-yielding, large-scale syntheses of mono- and bicyclic aminopyridinols from pyridoxine hydrochloride (i.e., vitamin B(6)). This approach provides straightforward, scaleable access to novel, potent, molecular scaffolds whose antioxidant properties have been investigated in homogeneous solutions and in liposomal vesicles. These molecular aggregates mimic cell membranes that are the targets of oxidative damage in vivo.

MeSH Terms (10)

alpha-Tocopherol Amino Alcohols Aminopyridines Antioxidants Free Radical Scavengers Humans Lipid Peroxidation Molecular Structure Oxidation-Reduction Vitamin B 6

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