HPLC/1H NMR spectroscopic studies of the reactive α-1-O-acyl isomer formed during acyl migration of S-naproxen β-1-O-acyl glucuronide

Chemical Research in Toxicology

Volumn 14, Issue 10, 2001, Pages 1363-1370

  Corcoran, O ^a   Mortensen, R W ^b   Hansen, S H ^b   Troke, J ^a   Nicholson, J K ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

NAPROXEN BETA 1 O ACYL GLUCURONIDE; NAPROXEN DERIVATIVE; UNCLASSIFIED DRUG; DRUG DERIVATIVE; GLUCURONIDE; NAPROXEN; NAPROXEN GLUCURONIDE; NONSTEROID ANTIINFLAMMATORY AGENT;

ACYLATION; ARTICLE; DRUG GLUCURONIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; URINE; CHEMISTRY; ISOMERISM; KINETICS; MASS SPECTROMETRY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ACYLATION; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLUCURONIDES; ISOMERISM; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; NAPROXEN;

EID: 0034740588     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx010015q     Document Type: Article

References (25)

1. Properties of acyl glucuronides: Implications for studies of the pharmacokinetics and metabolism of acidic drugs
2. Acyl glucuronides revisited: Is the glucuronidation process a toxification as well as a detoxification mechanism?
3. Acyl glucuronides as chemically reactive intermediates. Conjugation-deconjugation reactions in drug metabolism and toxicity
4. Disposition and covalent binding of diflunisal and diflunisal acyl glucuronide in the isolated perfused rat liver
5. Cyclitols. XVIII. Acetyl migration equilibrium between axial and equatorial acetates
6. Identification of the positional isomers of 2-fluorobenzoic acid 1-O-acyl glucuronide by directly coupled HPLC-NMR
7. 750 MHz directly coupled HPLC-NMR: Application to the sequential characterization of the positional isomers and anomers of 2-, 3- and 4-fluorobenzoic acid glucuronides in equilibrium mixtures
8. Measurement of internal acyl migration reaction kinetics using directly coupled HPLC-NMR: Application for the positional isomers of synthetic (2-fluorobenzoyl)-D-glucopyranuronic acid
9. Isolation and identification of the rearrangement products of diflunisal 1-O-acyl glucuronide
10. Selective protein adduct formation of diclofenac glucuronide is critically dependent on the rat canalicular conjugate export pump (Mrp2)
11. A rapid method for the isolation and identification of drug metabolites from human urine using solid-phase extraction and proton NMR spectroscopy
12. 1H NMR used for determination of the elution order of S-naproxen glucuronide isomers in two isocratic reversed-phase HPLC-systems
13. 13C NMR spectroscopy of human blood plasma
14. A review of the methods of chemical synthesis of sulphate and glucuronide conjugates
15. Relative reactivities of hydroxyl groups in carbohydrates
16. Dispiroketals in synthesis. 2. A new group for the selective protection of diequatorial vicinal diols in carbohydrates
17. Base-catalysed acyl migrations in myo-inositol dibenzoates
18. Anomeric and exo-anomeric effects in carbohydrate chemistry
19. NMR spectroscopic and theoretical chemistry studies on the internal acyl migration reactions of the 1-O-acyl-β-D-glucopyranuronate conjugates of 2-, 3-, and 4-(trifluoromethyl)benzoic acids
20. 13C labelling and nuclear magnetic resonance spectroscopy
21. Kinetic analysis by HPLC-electrospray mass spectrometry of the pH-dependent acyl migration and solvolysis as the decomposition pathways of ifetroban 1-O-acyl glucuronide
22. Reactivity considerations in the analysis of glucuronide and sulphate conjugates of diflunisal
23. In vitro regioselective stability of β-1-O- and 2-O-acyl glucuronides of naproxen and their covalent binding to human serum albumin