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

Organic Letters

Volumn 5, Issue 15, 2003, Pages 2659-2662

  Culbertson, Sean M ^a   Enright, Gary D ^a   Ingold, K U ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

6 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;

EID: 0141743450     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0348147     Document Type: Article

References (34)

1. ε -carboxymethyllysine; DTPA, diethylenetriaminepentaacetic acid; HNE, hydroxynonenal; IP, ionization potential; MDA, malondialdehyde; PM, pyridoxamine; PN, pyridoxine; SEC, size-exclusion chromatography; Tx, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox).
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28. PM incubated with APC and the absence of ABAP showed no quenching of APC fluorescence (i.e., result identical to No ABAP).
29. 4-hydroxyl group of dmaPN, 6.
30. HPLC conditions: Discovery C18 column, solvents A (water) and B (acetonitrile) both containing 0.1% heptafluorobutyric acid delivered at 1 mL/min as gradient; time (%A) 0 min (100); 30 (40). Quantification of inhibitors was at 293 nm UV against a calibration curve.
31. m = 660 nm) at 37°C was measured in a 1 cm cell just before addition of ABAP, and at 5 min intervals, on a Photon Technology International C-700 fluorescence lifetime system.
32. Conditions were 10 mg/mL BSA and 50 mM ribose in 0.2 M phosphate buffer pH 7.4 containing 1 mM DTPA and 1 mM phytic acid (chelators added after buffer was stored over Chelex-100 resin for 24 h).
33. (a) For more complete examination of dmaPM (11) and Tx in glycation models, see: Culbertson, S. M.; Vassilenko, E.; Morrison, L.; Ingold, K. U. manuscript submission to J. Biol. Chem. (b) For example, results from ribose derived pentosidine yields also support radical trapping activity for dmaPM, 11, and dmaPN, 6.
34. (a) For more complete examination of dmaPM (11) and Tx in glycation models, see: Culbertson, S. M.; Vassilenko, E.; Morrison, L.; Ingold, K. U. manuscript submission to J. Biol. Chem. (b) For example, results from ribose derived pentosidine yields also support radical trapping activity for dmaPM, 11, and dmaPN, 6.