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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

From National Research Council Canada

DOIResolve DOI: https://doi.org/10.1021/ol0348147
AuthorSearch for: 1; Search for: 1; Search for: 1
Affiliation
  1. National Research Council of Canada. NRC Steacie Institute for Molecular Sciences
FormatText, Article
Subject6 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
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
In
  • Organic Letters 5, no. 15 (2003): 2659–2662.
LanguageEnglish
Peer reviewedYes
NPARC number21276488
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Record identifier62b3802d-a8ae-4f51-a0e5-f33e4657e452
Record created2015-10-13
Record modified2020-04-02
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