Synthesis of a novel radical trapping and carbonyl group trapping anti-AGE agent: A pyridoxamine analogue for inhibiting advanced glycation (AGE) and lipoxidation (ALE) end products

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DOIResolve DOI: http://doi.org/10.1021/ol0348147
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TypeArticle
Journal titleOrganic Letters
ISSN1523-7060
Volume5
Issue15
Pages26592662; # of pages: 4
Subject6 dimethylaminopyridoxamine; drug analog; pyridoxamine; trolox C; unclassified drug; article; 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
Abstract(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).
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC); NRC Steacie Institute for Molecular Sciences (SIMS-ISSM)
Peer reviewedYes
NPARC number21276488
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Record identifier62b3802d-a8ae-4f51-a0e5-f33e4657e452
Record created2015-10-13
Record modified2016-05-09
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