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

被引:25
作者
Culbertson, SM [1 ]
Enright, GD [1 ]
Ingold, KU [1 ]
机构
[1] Natl Res Council Canada, Steacie Inst Mol Sci, Ottawa, ON K1A 0R6, Canada
关键词
D O I
10.1021/ol0348147
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] 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).
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收藏
页码:2659 / 2662
页数:4
相关论文
共 24 条
[1]   Glycoxidation and lipoxidation in atherogenesis [J].
Baynes, JW ;
Thorpe, SR .
FREE RADICAL BIOLOGY AND MEDICINE, 2000, 28 (12) :1708-1716
[2]   AGEs and their interaction with AGE-receptors in vascular disease and diabetes mellitus. I. The AGE concept [J].
Bierhaus, A ;
Hofmann, MA ;
Ziegler, R ;
Nawroth, PP .
CARDIOVASCULAR RESEARCH, 1998, 37 (03) :586-600
[3]   In vitro kinetic studies of formation of antigenic advanced glycation end products (AGEs) - Novel inhibition of post-Amadori glycation pathways [J].
Booth, AA ;
Khalifah, RG ;
Todd, P ;
Hudson, BG .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1997, 272 (09) :5430-5437
[4]  
Costantino L, 1999, MED RES REV, V19, P3, DOI 10.1002/(SICI)1098-1128(199901)19:1<3::AID-MED2>3.0.CO
[5]  
2-7
[6]   Antioxidant properties of aminoguanidine [J].
Courderot-Masuyer, C ;
Dalloz, F ;
Maupoil, V ;
Rochette, L .
FUNDAMENTAL & CLINICAL PHARMACOLOGY, 1999, 13 (05) :535-540
[7]   PHYCOERYTHRIN FLUORESCENCE-BASED ASSAY FOR PEROXY-RADICALS - A SCREEN FOR BIOLOGICALLY RELEVANT PROTECTIVE AGENTS [J].
DELANGE, RJ ;
GLAZER, AN .
ANALYTICAL BIOCHEMISTRY, 1989, 177 (02) :300-306
[8]   The advanced glycation end product, N-(epsilon)(carboxymethyl)lysine, is a product of both lipid peroxidation and glycoxidation reactions [J].
Fu, MX ;
Requena, JR ;
Jenkins, AJ ;
Lyons, TJ ;
Baynes, JW ;
Thorpe, SR .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1996, 271 (17) :9982-9986
[9]   Amadorins: Novel post-Amadori inhibitors of advanced glycation reactions [J].
Khalifah, RG ;
Baynes, JW ;
Hudson, BG .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1999, 257 (02) :251-258
[10]   SYNTHESIS AND PHYSICOCHEMICAL AND BIOLOGICAL PROPERTIES OF 6-HALOGEN-SUBSTITUTED VITAMIN-B6 ANALOGS [J].
KORYTNYK, W ;
SRIVASTAVA, SC .
JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (06) :638-642