Direct detection of the internal acyl migration reactions of benzoic acid 1-O-acylglucuronide by 13C-labeling and nuclear magnetic resonance spectroscopy

Journal of Pharmacological and Toxicological Methods

Volumn 37, Issue 4, 1997, Pages 237-243

  Akira, Kazuki ^a   Taira, Tadaaki ^a   Shinohara, Yoshihiko ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

13C Labeling; Acyl migration; Acylglucuronide; Benzoic acid; NMR

Indexed keywords

BENZOIC ACID; BENZOIC ACID DERIVATIVE; CARBON 13;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG GLUCURONIDATION; ISOTOPE LABELING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

BENZOATES; BENZOIC ACID; CARBON ISOTOPES; GLUCURONATES; ISOTOPE LABELING; MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN BINDING; SENSITIVITY AND SPECIFICITY; STEREOISOMERISM;

EID: 0030874692     PISSN: 10568719     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1056-8719(97)00035-X     Document Type: Article

References (40)

1. 13C-labeling and nuclear magnetic resonance spectroscopy to pharmacokinetic research: measurement of metabolic rate of benzoic acid to hippuric acid in the rat. Anal Biochem 210:86-90.
2. 13C-labeled ketoprofen glucuronides in human urine by nuclear magnetic resonance spectroscopy. Anal Chim Acta 334:67-74.
3. 13C-labelled (R)-and (S)-ketoprofens. J Labelled Compd Radiopharm 39:353-361.
4. 13C label-nuclear magnetic resonance (NMR) tracer techniques to clinical chemistry: metabolic rate of benzoic acid to hippuric acid. Yakugaku Zasshi 110:586-590.
5. 13C-labeling for pharmacokinetic research in man: detection of benzoic acid conversion to hippuric acid. Biol Pharm Bull 18:643-647.
6. α glucuronide in cholestasis and during storage in vitro: intramolecular rearrangement to positional isomers of glucuronic acid. Biochem J 171:203-214.
7. Boeckel CAA, Delbressine LPC and Kaspersen FM (1985) The synthesis of glucuronides derived from the antidepressant drugs mianserin and Org 3770. Recl Trav Chim Pays-Bas 104:259-265.
8. 9-11-carboxytetrahydrocannabinol glucuronide. Chem Res Toxicol 2:316-324.
9. Brusilow SW, Valle DL, Batshaw ML (1979) New pathways of nitrogen excretion in inborn errors of urea synthesis. Lancet II:452-454.
10. Dickinson RG, King, AR (1991) Studies on the reactivity of acyl glucuronides II: interaction of diflunisal acyl glucuronide and its isomers with human serum albumin in vitro. Biochem Pharmacol 42:2301-2306.
11. Ding A, Ojingwa JC, McDonagh AF, Burlingame AL, Benet LZ (1993) Evidence for covalent binding of acyl glucuronides to serum albumin via an imine mechanism as revealed by tandem mass spectrometry. Proc Natl Acad Sci USA 90:3797-3801.
12. Ding A, Zia-Amirhosseini P, McDonagh AF, Burlingame AL, Benet LZ (1995) Reactivity of tolmetin glucuronide with human serum albumin: identification of binding sites and mechanisms of reaction by tandem mass spectrometry. Drug Metab Dispos 23:369-376.
13. Dutton GJ (1980) Glucuronidation of drugs and other compounds. Boca Raton: CRC Press.
14. 1H NMR resonances from a mixture of transacylated ester glucuronic acid conjugates with the aid of oversampling and digital filtering during acquisition. J Pharm Biomed Anal 13:971-977.
15. Faed EM (1984) Properties of acyl glucuronides: implications for studies of the pharmacokinetics and metabolism of acidic drugs. Drug Metab Rev 15:1213-1249.
16. Fenselau C (1994) Acyl glucuronides as chemically reactive intermediates. In Handbook of Experimental Pharmacology, Volume 112. Conjugation-Deconjugation Reactions in Drug Metabolism and Toxicity. Ed., FC Kauffman. Berlin: Springer-Verlag, pp. 367-389.
17. Fischer E (1920) Migration of the acyl in glycerides. Chem Ber 53:1621-1633.
18. Goebel WF (1938) Derivatives of glucuronic acid VIII: the structure of benzoylglucuronic acid. J Biol Chem 122:649-653.
19. Hasegawa J, Smith PC, Benet LZ (1982) Apparent intramolecular acyl migration of zomepirac glucuronide. Drug Metab Dipos 10:469-473.
20. Hansen-Moller J, Cornett C, Dalgaard L, Hansen SH (1988) Isolation and identification of the rearrangement products of diflunisal 1-O-acyl glucuronide. J Pharm Biomed Anal 6:229-240.
21. Hyneck ML, Smith PC, Munafo A, McDonagh AF, Benet LZ (1988) Disposition and irreversible plasma protein binding of tolmetin in humans. Clin Pharmacol Ther 44:107-114.
22. Illing HPA, Wilson ID (1981) pH-Dependent formation of β-glucuronidase resistent conjugates from the biosynthetic ester glucuronide of isoxepac. Biochem Pharmacol 30:3381-3384.
23. Iwakawa S, Spahn H, Benet LZ, Lin ET (1990) Stereoselective binding of the glucuronide conjugates of carprofen enantiomers to human serum-albumin. Biochem Pharmacol 39:949-953.
24. Janssen FW, Kirkman SK, Fenselau C, Stogniew M, Hofmann BR, Young EM, Ruelius HW (1982) Metabolic formation of N-and O-glucuronides of 3-(p-chlorophenyl)thiazolo[3,2-α]benzimidazole-2-acetic acid: rearrangement of the 1-O-acyl glucuronide. Drug Metab Dispos 10:599-604.
25. Kretz-Rommel A, and Boelsterli UA (1994) Mechanism of covalent adduct formation of diclofenac to rat hepatic microsomal proteins: retention of the glucuronic acid moiety in the adduct. Drug Metab Dispos 22:956-961.
26. McKinnon GE, Dickinson RG (1989) Covalent binding of diflunisal and probenecid to plasma protein in humans: persistence to the adducts in the circulation. Res Commun Chem Pathol Pharmacol 66:339-354.
27. Musson DG, Lin JH, Lyon KA, Tocco DJ and Yeh KC (1985) Assay methodology for quantification of the ester and ether glucuronide conjugates of diflunisal in human urine. Chromatogr 337:363-378.
28. Nicholls AW, Akira K, Lindon JC, Farrant RD, Wilson ID, Harding J, Killick DA, Nicholson JK (1996) 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. Chem Res Toxicol 9:1414-1424.
29. Ruelius HW, Young EM, Kirkman SK, Schillings RT, Sisenwine SF, Janssen FW (1985) Biological fate of glucuronides in the rat. Biochem Pharmacol 34:451-452.
30. Schachter D (1956) The chemical estimation of acyl glucuronides and its application to studies on the metabolism of benzoate and salicylate in man. J Clin Invest 36:297-302.
31. Schmidt RR (1986) New methods for the synthesis of glycosides and Oligosaccharides. Are there alternatives to the Koenigs-Knorr method? Angew Chem Int Ed Engl 25:212-235.
32. Sidelmann UG, Hansen SH, Gavaghan C, Carless HAJ, Lindon JC, Farrant RD, Wilson ID and Nicholson JK (1996) Measurement of internal acyl migration reaction kinetics using directly coupled HPLC-NMR: application for the positional isomers of synthetic (2-fluorobenzoyl)-D-glucopyranuronic acid. Anal Chem 68:2564-2572.
33. Smith PC, Benet LZ (1986) Characterization of the isomeric esters of zomepirac glucuronide by proton NMR. Drug Metab Dispos 14: 503-505.
34. Smith PC, McDonagh AF, Benet LZ (1986) Irreversible binding of zomepirac to plasma protein in vitro and in vivo. J Clin Invest 77:934-939.
35. Smith PC, Benet LZ, McDonagh AF (1990) Covalent binding of zomepirac glucuronide to proteins: evidence for a schiff base mechanism. Drug Metab Dispos 18:639-644.
36. Smith PC, Song WQ, Rodriguez RJ (1992) Covalent binding of etodolac acyl glucuronide to albumin in vitro. Drug Metab Dispos 20:962-965.
37. Smith PC, Liu JH (1995) Covalent binding of suprofen to renal tissue of rat correlates with excretion of its acyl glucuronide. Xenobiotica 25:531-540.
38. Spahn-Langguth H, Benet LZ (1992) Acyl glucuronides revisited: is the glucuronidation process a toxification as well as a detoxification mechanism? Drug Metab Rev 24:5-48.
39. Volland C, Sun H, Dammeyer J, Benet LZ (1991) Stereoselective degradation of the fenoprofen acyl glucuronide enantiomers and irreversible binding to plasma protein. Drug Metab Dispos 19:1080-1086.
40. Watt JA, Dickinson RG (1990) Reactivity of diflunisal acyl glucuronide in human and rat plasma and albumin solutions. Biochem Pharmacol 39:1067-1075.