Kinetic and J-resolved statistical total correlation NMR spectroscopy approaches to structural information recovery in complex reacting mixtures: Application to acyl glucuronide intramolecular transacylation reactions

Analytical Chemistry

Volumn 80, Issue 13, 2008, Pages 4886-4895

  Johnson, Caroline H ^a   Athersuch, Toby J ^a   Wilson, Ian D ^b   Iddon, Lisa ^c   Meng, Xiaoli ^c   Stachulski, Andrew V ^c   Lindon, John C ^a   Nicholson, Jeremy K ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; GLUCOSE; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYETHYLENE TEREPHTHALATES; REACTION KINETICS; RECOVERY; SHAPE OPTIMIZATION; STATISTICAL METHODS; STATISTICS;

(5Z) ISOMERS; ACYL MIGRATION; ALKALINE PH; ANOMERS; GLUCURONIC ACIDS; GLUCURONIDE; GLUCURONIDES; INTRAMOLECULAR TRANSACYLATION; KINETIC (POLYM.); NMR SPECTROS COPY; REACTING MIXTURES; REACTION MIXTURES; RING ISOMERS; SPECTROSCOPIC METHODS; STARTING MATERIALS; STRUCTURAL INFORMATIONS; TIME SCALING;

ISOMERS;

1 BETA O ACYL ALPHA METHYLPHENYLACETYL GLUCURONIDE; BUFFER; GLUCURONIC ACID; GLUCURONIDE; PHENYLACETIC ACID DERIVATIVE; SODIUM DIHYDROGEN PHOSPHATE;

ACYLATION; ALKALINITY; ANALYTIC METHOD; ARTICLE; HYDROLYSIS; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STATISTICAL ANALYSIS; STATISTICAL TOTAL CORRELATION SPECTROSCOPY;

ACYLATION; GLUCURONIDES; ISOMERISM; KINETICS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR;

EID: 46849112801     PISSN: 00032700     EISSN: None     Source Type: Journal    
DOI: 10.1021/ac702614t     Document Type: Article

References (50)

1. Spahn-Langguth, H.; Benet, L. Z. Drug Metab. Rev. 1992, 24, 5-48.
2. Mulder, G. J. Annu. Rev. Pharmacol. Toxicol. 1992, 32, 25-49.
3. Faed, E. M. Drug Metab. Rev. 1984, 15, 1213-1249.
4. Fenselau, C. In Conjugation-deconjugation reactions in drug metabolism and toxicity; Kauffman, F. C., Ed.; Spring-Verlag: Berlin, 1994; pp 367-389.
5. Gibson, G. G.; Skett, P. Introduction to drug metabolism, 3rd ed.; Nelson Thornes: Cheltenham, U.K, 2001.
6. Nicholls, A. W.; Akira, K.; Lindon, J. C.; Farrant, R. D.; Wilson, I. D.; Harding, J.; Killick, D. A.; Nicholson, J. K. Chem. Res. Toxicol. 1996, 9, 1414-1424.
7. Vanderhoeven, S. J.; Troke, J.; Tranter, G. E.; Wilson, I. D.; Nicholson, J. K.; Lindon, J. C. Xenobiotica 2004, 34, 889-900.
8. Hasegawa, J.; Smith, P. C.; Benet, L. Z. Drug Metab. Dispos. 1982, 10, 469-473.
9. Samuel, S. A. N. Engl. J. Med. 1981, 304, 978.
10. Herxheimer, A. Drug Ther. Bull. 1968, 6, 48.
11. Castillo, M.; Smith, P. C. Drug Metab. Dispos. 1995, 23, 566-572.
12. Hyneck, M. L.; Smith, P. C.; Munafo, A.; McDonagh, A. F.; Benet, L. Z. Clin. Pharmacol. Ther. 1988, 44, 107-114,
13. Stachulski, A. V.; Harding, J. R.; Lindon, J. C.; Maggs, J. L.; Park, B. K.; Wilson, I. D. J. Med. Chem. 2006, 49, 6931-6945.
14. Bischer, A.; Zia-Amirhosseini, P.; Iwaki, M.; McDonagh, A. F.; Benet, L. Z. J Pharmacokinet. Biopharm. 1995, 23, 379-395.
15. Ruelius, H. W.; Young, E. M.; Kirkman, S. K.; Schillings, R. T.; Sisenwine, S. F.; Janssen, F. W. Biochem. Pharmacol. 1985, 34, 451-452.
16. Mortensen, R. W.; Sidelmann, U. G.; Tjornelund, J.; Hansen, S. H. Chirality 2002, 14, 305-312.
17. Volland, C.; Sun, H.; Dammeyer, J.; Benet, L. Z. Drug Metab. Dispos. 1991, 19, 1080-1086.
18. Benet, L. Z.; Spahn-Langguth, H.; Iwakawa, S.; Volland, C.; Mizuma, T.; Mayer, S.; Mutschler, E.; Lin, E. T. Life Sci. 1993, 53, PL141-146.
19. Spahn, H.; Iwakawa, S.; Lin, E. T.; Benet, L. Z. Pharm. Res. 1989, 6, 125-132.
20. Spahn, H. J. Chromatogr. 1988, 430, 368-375.
21. Smith, P. C.; Liu, J. H. Xenobiotica 1993, 23, 337-348.
22. Gavaghan, C. Ph.D. Thesis, Birkbeck College, University of London, 1997.
23. Vanderhoeven, S. J.; Lindon, J. C.; Troke, J.; Nicholson, J. K.; Wilson, I. D. J. Pharm. Biomed. Anal. 2006, 41, 1002-1006.
24. Sidelmann, U. G.; Hansen, S. H.; Gavaghan, C.; Carless, H. A. J.; Undon, J. C.; Farrant, R. D.; Wilson, I. D.; Nicholson, J. K. Anal. Chem. 1996, 68, 2564-2572.
25. Johnson, C. H.; Wilson, I. D.; Harding, J. R.; Stachulski, A. V.; Iddon, L.; Nicholson, J. K.; Undon, J. C. Anal. Chem. 2007, 79, 8720-8727.
26. Corcoran, O.; Mortensen, R. W.; Hansen, S. H.; Troke, J.; Nicholson, J. K. Chem. Res. Toxicol. 2001, 14, 1363-1370.
27. Farrant, R. D.; Spraul, M.; Wilson, I. D.; Nicholls, A. W.; Nicholson, J. K.; Undon, J. C. J. Pharm. Biomed. Anal. 1995, 13, 971-977.
28. Akira, K.; Taira, T.; Hasegawa, H.; Sakuma, C.; Shinohara, Y. Drug Metab. Dispos. 1998, 26, 457-464.
29. Akira, K.; Taira, T.; Shinohara, Y. J. Pharmacol. Toxicol. Methods 1997, 37, 237-243.
30. Mortensen, R. W.; Corcoran, O.; Cornett, C.; Sidelmann, U. G.; Lindon, J. C.; Nicholson, J. K.; Hansen, S. H. Drug Metab. Dispos. 2001, 29, 375-380.
31. Undon, J. C.; Holmes, E.; Nicholson, J. K. FEBS J. 2007, 274, 1140-1151.
32. Keun, H. C.; Beckonert, O.; Griffin, J. L.; Richter, C.; Moskau, D.; Lindon, J. C.; Nicholson, J. K. Anal. Chem. 2002, 74, 4588-4593.
33. Aue, W. P.; Karhan, J.; Ernst, R. R. J. Chem. Phys. 1976, 64, 4226-4227.
34. Tomlins, A. M.; Foxall, P. J. D.; Lynch, M. J.; Parkinson, J.; Everett, J. R.; Nicholson, J. K. Biochim. Biophys. Acta 1998, 1379, 367-380.
35. Foxall, P. J. D.; Parkinson, J. A.; Sadler, I. H.; Lindon, J. C.; Nicholson, J. K. J. Pharm. Biomed. Anal. 1993, 11, 21-31.
36. Nicholson, J. K.; Foxall, P. J.; Spraul, M.; Farrant, R. D.; Undon, J. C. Anal. Chem. 1995, 67, 793-811.
37. Lynch, M. J.; Masters, J.; Pryor, J. P.; Undon, J. C.; Spraul, M.; Foxall, P. J. D.; Nicholson, J. K. J. Pharm. Biomed. Anal. 1994, 12, 5-19.
38. Sweatman, B. C.; Farrant, R. D.; Holmes, E.; Ghauri, F. Y.; Nicholson, J. K.; Undon, J. C. J. Pharm. Biomed. Anal. 1993, 11, 651-664.
39. Wang, Y.; Cloarec, O.; Tang, H.; Undon, J. C.; Holmes, E.; Kochhar, S.; Nicholson, J. K. Anal. Chem. 2008, 80, 1058-1066.
40. Cloarec, O.; Dumas, M. E.; Craig, A.; Barton, R. H.; Trygg, J.; Hudson, J.; Blancher, C.; Gauguier, D.; Undon, J. C.; Holmes, E.; Nicholson, J. K. Anal. Chem. 2005, 77, 1282-1289.
41. Smith, L. M.; Maher, A D.; Cloarec, O.; Rantalainen, M.; Tang, H.; Elliott, P.; Stamler, J.; Undon, J. C.; Holmes, E.; Nicholson, J. K. Anal. Chem. 2007, 79, 5682-5689.
42. Coen, M.; Hong, Y. S.; Cloarec, O.; Rhode, C. M.; Reily, M. D.; Robertson, D. G.; Holmes, E.; Lindon, J. C.; Nicholson, J. K. Anal. Chem. 2007, 79, 8956-8966.
43. Holmes, E.; Loo, R. L.; Cloarec, O.; Coen, M.; Tang, H. R.; Maibaum, E.; Bruce, S.; Chan, Q.; Elliott, P.; Stamler, J.; Wilson, I. D.; Lindon, J. C.; Nicholson, J. K. Anal. Chem. 2007, 79, 2629-2640.
44. Cloarec, O.; Campbell, A.; Tseng, L. H.; Braumann, U.; Spraul, M.; Scarfe, G.; Weaver, R.; Nicholson, J. K. Anal. Chem. 2007, 79, 3304-3311.
45. Keun, H. C.; Athersuch, T. J.; Beckonert, O.; Wang, Y.; Saric, J.; Shockcor, J. P.; Lindon, J. C.; Wilson, I. D.; Holmes, E.; Nicholson, J. K. Anal. Chem. 2008, 80, 1073-1079.
46. Bruschweiler, R. J. Chem. Php. 2004, 121, 409-414.
47. Bruschweiler, R.; Zhang, F. J. Chem. Phys. 2004, 120, 5253-5260.
48. Perrie, J. A.; Harding, J. R.; Holt, D. W.; Johnston, A.; Meath, P.; Stachulski, A. V. Org. Lett. 2005, 7, 2591-2594.
49. Bowkett, E. R.; Harding, J. R.; Maggs, J. L.; Park, B. K.; Perrie, J. A.; Stachulski, A. V. Tetrahedron 2007, 63, 7596-7605.
50. Sidelmann, U. G.; Gavaghan, C.; Carless, H. A. J.; Farrant, R. D.; Lindon, J. C.; Wilson, I. D.; Nicholson, J. K. Anal. Chem. 1995, 67, 3401-3404.