Nuclear magnetic resonance spectroscopy as a quantitative tool to determine the concentrations of biologically produced metabolites: Implications in metabolites in safety testing

Chemical Research in Toxicology

Volumn 22, Issue 2, 2009, Pages 299-310

  Espina, Robert ^a   Yu, Linning ^a   Wang, Jianyao ^a   Tong, Zeen ^a   Vashishtha, Sarvesh ^a   Talaat, Rasmy ^a   Scatina, Joann ^a   Mutlib, Abdul ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG METABOLITE; LAURIC ACID DERIVATIVE; NORVERAPAMIL; PARACETAMOL; PARACETAMOL GLUCURONIDE; PROTOCATECHUATE N OXIDE; S 4 NITROBENZYLOXYCARBONYL GLUTATHIONE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; COMPARATIVE STUDY; CONTROLLED STUDY; DIAGNOSTIC ACCURACY; FOOD AND DRUG ADMINISTRATION; GRAVIMETRY; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; INFORMATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; PUBLICATION; QUALITATIVE ANALYSIS; QUANTITATIVE ANALYSIS; RAT; RELIABILITY; RISK ASSESSMENT; STANDARD; VALIDATION STUDY;

ACETAMINOPHEN; ANIMALS; CHROMATOGRAPHY, LIQUID; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PHARMACEUTICAL PREPARATIONS; PHENACETIN; RATS; TOXICITY TESTS;

EID: 62249210251     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx800251p     Document Type: Article

References (51)

1. U.S. Food and Drug Administration (2008) Guidance for Industry: Safety Testing of Drug Metabolites, U.S. Food and Drug Administration, Center for Drug Evaluation and Research (CDER), Rockville, MD.
2. Mutlib, A. E., and Shockcor, J. P. (2003) Application of LC/MS, LC/ NMR and stable isotopes in identifying and characterizing metabolites. In Drug Metabolizing Enzymes: Cytochrome P450 and Other Enzymes in Drug Discovery and Development (Lee, J. S., Obach, R. S., and Fisher, M. B., Eds.) pp 33-86, Fontsi Media and Marcel Dekker, New York, NY.
3. Warren, R. J., Zarembo, J. E., Staiger, D. B., and Post, A. (1976) Quantitative NMR analysis of a four-component mixture of phenylglycine derivatives. J. Pharm. Sci. 65, 738-740.
4. Vinson, J. A., and Kozak, D. M. (1978) Analysis of aspirin tablets using quantitative NMR. Am. J. Pharm. Educ. 42, 290-291.
5. Werner, I., Bacher, A., and Eisenreich, W. (1997) Retrobiosynthetci NMR studies with 13C-labeled glucose. Formation of gallic acid in plants and fungi. J. Biol. Chem. 272, 25474-25482.
6. Groen, D., Metternich, H. J., and Schoenfelder, W. (1998) Quantitative NMR-spectroscopic analysis of the compounds of glycerol esters of fatty acids. Lipid 100, 64-69.
7. Silvestre, V., Goupry, S., Trierweiler, M., Robins, R., and Akoka, S. (1862) (2001) Determination of substrate and product concentrations in lactic acid bacterial fermentations by proton NMR using the ERETIC method. Anal. Chem. 73, 1868.
8. Holzgrabe, U., Deubner, R., Schollmayer, C., and Waibel, B. (2005) quantitative NMR spectroscopy - Applications in drug analysis. J. Pharm. Biomed. Anal. 38, 806-812.
9. Rizzo, V., and Pinciroli, V. (2005) Quantitative NMR in synthetic and combinatorial chemistry. J. Pharm. Biomed. Anal. 38, 851-857.
10. Diehl, B. W. K., Malz, F., and Holzgrabe, U. (2007) Quantitative NMR spectroscopy in the quality evaluation of active pharmaceutical ingredients and excepients. Spec. Eur. 19, 15-19.
11. Pauli, G. F., Jaki, B., and Lankin, D. (2005) Quantitative 1H-NMR: Development and potential of a method for natural products analysis. J. Nat. Prod. 68, 133-149.
12. Pauli, G. F., Jaki, B. U., and Lankin, D. C. (2007) A routine experimental protocol for qHNMR illustrated with Taxol. J. Nat. Prod. 70, 589-595.
13. Shao, G., Kautz, R., Peng, S., Cui, G., and Giese, R. W. (2007) Calibration by NMR for quantitative analysis: p-Toluenesulfonic acid as a reference substance. J. Chromatogr. A 1138, 305-308.
14. Pauli, G. F., Jaki, B. U., Lankin, D. C., and Walter, J. A. (2008) Quantitative NMR of bioactive natural products. In Bioactive Natural Products: Detection, Isolation and Structural Determination (Colgate, S. M., and Molyneux, R. J., Eds.) pp 113-141, CRC Press, Boca Raton, FL.
15. Bernadou, J., Armand, J. P., Lopez, A., Malet-Martino, M. C., and Martino, R. (1985) Complete urinary excretion profile of 5-fluorouracil during a six-day chemotherapeutic schedule, as resolved by 19F nuclear magnetic resonance. Clin. Chem. 31, 846-848.
16. Malet-Martino, M. C., Armand, J. P., Lopez, A., Bernadou, J., Beteille, J. P., Bon, M., and Martino, R. (1986) Evidence for the importance of 5′-deoxy-5-fluorouridine catabolism in humans from 19F nuclear magnetic resonance spectroscopy. Cancer Res. 46, 2105-2112.
17. Mallet-Martino, M. C., and Martino, R. (1992) Magnetic resonance spectroscopy: A powerful tool for drug metabolism studies. Biochimie 74, 785-800.
18. Martino, R., Crasnier, F., Chouini-Llanne, N., Gilard, V., Niemeyer, U., De Forni, M., and Malet-Martino, M. C. (1992) A new approach to the study of ifosamide metabolism by the analysis of human body fluids with 31P nuclear magnetic resonance spectroscopy. J. Pharmacol. Exp. Ther. 260, 1133-1144.
19. Malet-Martino, M. C., and Martino, R. (1992) Magnetic resonance spectroscopy: A powerful tool for drug metabolism studies. Biochimie 74, 785-800.
20. Gilard, V., Malet-Martino, M. C., De Forni, M., Niemeyer, U., Ader, J. C., and Martino, R. (1993) Determination of the urinary excretion of ifosfamide and its phosporated metabolites by phosphorus-31 nuclear magnetic resonance spectroscopy. Cancer Chemother. Pharmacol. 31, 387-394.
21. Monte, S. Y., Ismail, I., Mallett, D. N., Matthews, C., and Tanner, R. J. N. (1994) The minimal metabolism of inhaled 1,1,1,2-tetrafluorethane to trifluoroaceticacid in man as determined by high sensitivity 19F nuclear magnetic resonance spectroscopy of urine samples. J. Pharm. Biomed. Anal. 12, 1489-1493.
22. Street, J. C., Mahmood, U., Matei, C., and Koutcher, J. A. (1995) In vivo and in vitro studies of cyclosphosphamide chemotherapy in a mouse mammary carcinoma by 31 P NMR spectroscopy. NMR Biomed. 8, 149-158.
23. Arellano, M., Malet-Martino, M., Martino, R., and Spector, T. (1997) E-Ethynyluracil (GW776): Effects on the formation of 5-fluorouracil, fluoroacetate and fluorohydroxypropionic acid in the isolated perfused rat liver model. Br. J. Cancer 76, 1170-1180.
24. Busse, D., Busch, F. W., Bohnenstengel, F., Eichelbaum, M., Fischer, P., Opalinska, J., Schumacher, K., Schweizer, E., and Kroemer, H. K. (1997) Dose escalation of cyclophosphamide in patients with breast cancer: Consequences for pharmacokinetics and metabolism. J. Clin. Oncol. 15, 1885-1896.
25. Judson, I. R., Beale, P. J., Trigo, J. M., Aherne, W., Crompton, T., Jones, D., Bush, E., and Reigner, B. (1999) A human capacitabine excretion balance and pharmacokinetic study after administration of a single oral dose of 14C-labelled drug. Invest. New Drugs 17, 49-56.
26. Reigner, B., et al. (1999) Influence of the antacid Maalox on the pharmacokinetics of capecitabine in cancer patients. Cancer Chemother. Pharmcol. 43, 309-315.
27. Desmoulin, F., Gilard, V., Malet-Martino, M., and Martino, R. (2002) Metabolism of capecitabine, an oral fluorouracil prodrug: 19F NMR studies in animal models and human urine. Drug Metab. Dispos. 30, 1221-12229.
28. Le Belle, J. E., Harris, N. G., Williams, S. R., and Bhakoo, K. K. (2002) A comparison of cell and tissue extraction techniques using high-resolution 1H-NMR spectroscopy. NMR Biomed. 15, 37-44.
29. Lenz, E. M., Wilson, I. D., Wright, B., Partridge, E. A., Rodgers, C. T., Haycock, P. R., Lindon, J. C., and Nicholson, J. K. (2002) A comparison of quantitative NMR and radiolabelling studies of the metabolism and excretion of Statil (3-(4-bromo-2-fluorobenzyl)-4-oxo-3H-phthalazin-1-ylacetic acid) in the rat. J. Pharm. Biomed. Anal. 28, 31-43.
30. Sullentrop, F., Moka, D., Neubauer, S., Haupt, G., Engelmann, U., Hahn, J., and Schicha (2002) 31P NMR spectroscopy of blood plasma: Determination and quantitation of phospholipids classes in patients with renal cell carcinoma. NMR Biomed. 15, 60-68.
31. Lutz, N. W., Naser-Hijazi, B., Koroma, S., Berger, M. R., and Hull, W. E. (2004) Fluoropyrimidine chemotherapy in a rat model: comparison of fluorouracil metabolite profiles determined by high-field 19F-NMR spectroscopy of tissues ex vivo with therapy response and toxicity for locoregional vs. systemic infusion protocols. NMR Biomed. 17, 101-131.
32. Orhan, H., Commandeur, J. N. M., Sahin, G., Aypar, U., Sahin, A., and Vermeulen, N. P. E. (2004) Use of 19F-nuclear magnetic resonance and gas chromatography-electron capture detection in the quantitative analysis of fluorine-containing metabolites in urine of sevoflurane-anaesthetized patients. Xenobiotica 34, 301-316.
33. Skordi, E., Wilson, I. D., Lindon, J. C., and Nicholson, J. K. (2004) Characterization and quantification of metabolites of racemic ketoprofen excreted in urine following oral administration to man by 1H-NMR spectroscopy, directly coupled HPLC-MS and HPLC-NMR, and circular dichroism. Xenobiotica 24, 1075-1089.
34. Martino, R., Guard, V., Desmoulin, F., and Malet-Martino, M. (2005) Fluorine-19 or phosphorus-31 NMR spectroscopy: A suitable analytical technique for quantitative in vitro metabolic studies of fluorinated or phosphorylated drugs. J. Pharm. Biomed. Anal. 38, 871-891.
35. Moazzami, A. A., erson, R. E., and Kamal-Eldin, A. (2007) Quantitative NMR analysis of a sesamin catechol metabolite in human urine. J. Nutr. 137, 940-944.
36. Henderson, T. J. (2002) Quantitative NMR spectroscopy using coaxial inserts containing a reference standard: Purity determinations for military nerve agents. Anal. Chem. 74, 191-198.
37. Hays, P. A. (2005) Proton nuclear magnetic resonance spectroscopy (NMR) methods for determining the purity of reference drug standards and illicit forensic drug seizures. J. Forensic Sci. 50, 1342-1360.
38. Malz, F., and Jancke, H. (2006) Purity assessment problem in quantitative NMR-impurity resonance overlaps with monitor signal multiplets from stereoisomers. Anal. Bioanal. Chem. 385, 760-765.
39. Wevers, R. A., Engelke, U. F. H., Moolenaar, S. H., Brautigam, C., De Jong, J. G. N., Duran, R., DeAbreu, R. A., and van Gennip, A. H. (1999) 1H-NMR spectroscopy of body fluids: Inborn errors of purine and pyrimidine metabolism. Clin. Chem. 45, 539-548.
40. Moolenaar, S. H., Gohlich-Ratmann, G., Engelke, U. F., Spraul, M., Humpfer, E., Dvortsak, P., Voit, T., Hoffmann, G. F., Brautigam, C., van Kuilenberg, A. B., van Gennip, A., Vreken, P., and Wevers, R. A. (2001) β-Ureidopropionase deficiency: A novel inborn error of metabolism discovered using NMR spectroscopy on urine. Magn. Reson. Med. 46, 1014-1017.
41. Serkova, N. J., and Christians, U. (2005) Biomarkers for toxicodynamic monitoring of immunosuppressants: NMR-based quantitative meta-bonomics of the blood. Ther. Drug Monit. 27, 733-737.
42. Lindon, J. C., Nicholson, J. K., and Hohnes, E. (2005) NMR spectroscopy of biofluids. In Metabonomics in Toxicity Assessment (Robertson, D. G., and Lindon, J., Eds.) pp 105-172, Taylor and Francis, Boca Raton, FL.
43. Lindon, J. C., Holmes, E., and Nicholson, J. K. (2006) Recent developments and applications of NMR-based metabonomics. Bopuxue Zazhi 23, 101-127.
44. Wilson, I. D., and Nicholson, J. K. (2006) Metabonomics. In Comprehensive Medicinal Chemistry II (Taylor, I. B., and Triggle, D. J., Eds.) pp 989-1007, Elsevier, Oxford, United Kingdom.
45. Mackenzie, I. S. (1984) Theoretical aspects of quantitative NMR. Anal. Proc. 21, 500-502.
46. Evilia, R. F. (2001) Quantitative NMR spectroscopy. Anal. Lett. 34, 2227-2236.
47. Malz, F., and Jancke, H. (2005) Validation of quantitative NMR. J. Pharm. Biomed. Anal. 38, 813-823.
48. Burton, I. W., Quilliam, M. A., and Walter, J. A. (2005) Quantitative 1H-NMR with external standards: Use in preparation of calibration solutions for algal toxins and other natural products. Anal. Chem. 77, 3123-3131.
49. U.S. Food and Drug Administration (2001) Guidance for Industry: Bioanalytical Method Validation. U.S. Food and Drug Administration, Center for Drug Evaluation and Research (CDER), Rockville, MD.
50. Rabenstein, D. L. (2001) NMR spectroscopy: Past and present. Anal. Chem. 73, 214A-223A.
51. 1H NMR. Org. Proc. Res. Dev. 8, 381-384.