National Research Council of Canada. NRC Steacie Institute for Molecular Sciences
6 dimethylaminopyridoxamine; drug analog; pyridoxamine; trolox C; unclassified drug; drug activity; drug efficacy; drug structure; drug synthesis; glycation; lipid oxidation; protein cross linking; structure analysis; substitution reaction; antioxidants; cross-linking reagents; free radicals; glycosylation end products, advanced; lipid peroxidation; proteins; pyridoxamine; ribose; spectrometry, fluorescence
(Matrix presented) Pyridoxamine is known to be an effective inhibitor of both advanced glycation (AGE) and advanced lipoxidation (ALE) end products. The synthesis of a novel multifunctional AGE and ALE inhibitor, 6-dimethylaminopyridoxamine (dmaPM, 11) is described. The 6-dimethylamino substituent increases the radical trapping ability of pyridoxamine's phenolic group. Results obtained during ribose glycations show that both the new dmaPM and a known strong radical trapping agent, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), prevent intermolecular protein cross-linking more effectively than pyridoxamine (PM).