Comparison of LC-NMR and conventional NMR for structure elucidation in drug metabolism studies

Bibliography

• Watanabe N, Niki E. Direct-coupling of FT-NMR to high performance liquid chromatography. Proc Jpn Acad Ser B 1978;54(4):194-9
   Web of Science ®Google Scholar
• Yang Z. Online hyphenated liquid chromatography-nuclear magnetic resonance spectroscopy-mass spectrometry for drug metabolite and nature product analysis. J Pharm Biomed Anal 2006;40(3):516-27
   PubMed Web of Science ®Google Scholar
• Shockcor JP. Application of on-line LC-NMR and related techniques to drug metabolism studies. In: Klaus Albert, editor, on-line LC-NMR related techniques. John Wiley and Sons; 2002. p. 89-108
   Google Scholar
• Albert K, Kunst M, Bayer E, et al. Investigation of a cyclopropyl-containing drug by On-line high-performance liquid chromatography/nuclear magnetic resonance. Anal Chem 1989;61(7):772-5
   Web of Science ®Google Scholar
• Durand S, Sancelme M, Delort AM, et al. Study by NMR and LC/ESI-MS of the biodegradative pathway of mesotrione. Environ. Fate Ecol. Eff. Pestic. Symp. Pestic. Chem. 13th, Symposium Pesticide Chemistry; 2007 September 3 – 6; Piacenza, Italy
   Google Scholar
• Roberts JK, Smith RJ. Use of liquid chromatography-nuclear magnetic resonance spectroscopy for the identification of impurities in drug substances. J Chromatogr A 1994;677(2):385-9
   Web of Science ®Google Scholar
• Potts BCM, Albizati K, Johnson M, et al. Application of LC-NMR to the identification of bulk drug impurities in GART inhibitor AG2034. Magn Reson Chem 1999;37(6):393-400
   Web of Science ®Google Scholar
• Prakash C, Shaffer CL, Nedderman A. Analytical strategies for identifying drug metabolites. Mass Spectrom Rev 2007;26(3):340-69
   PubMed Web of Science ®Google Scholar
• Wolfender JL, Queiroz EF, Hostettmann K. Development and application of LC-NMR techniques to the identification of bioactive natural products. In: Steven Colgate, editor, Bioact Nat Prod. 2nd edition. CRC Press; 2008. p. 143-90
   Google Scholar
• Ramanathan R, Chowdhury SK, Alton KB. Oxidative metabolites of drugs and xenobiotics: LC-MS methods to identify and characterize in biological matrices. Prog Pharm Biomed Anal 2005;6:225-76
   Google Scholar
• Tomer KB, Parker CE. Biochemical applications of liquid chromatography-mass spectrometry. J Chromatogr 1989;492:189-221
   PubMed Web of Science ®Google Scholar
• Spraul M, Hoemann M, Dvortsak P, et al. Liquid chromatography coupled with high-field proton NMR for profiling human urine for endogenous compounds and drug metabolites. J Pharm Biomed Anal 1992;10(8):601-5
   PubMed Web of Science ®Google Scholar
• Braumann U, Spraul M. LC-NMR: automation. In: Klaus Albert, editor, on-line LC-NMR related techniques. John Wiely and Sons; 2002. p. 23-43
   Google Scholar
• Spraul M, Hofmann M. 750 MHz NMR spectroscopy and food-related LC-NMR applications. Spec Publ R Soc Chem 1995;157:77-92
   Google Scholar
• Dear GJ, Plumb RS, Sweatman BC, et al. Use of directly coupled ion-exchange liquid chromatography-mass spectrometry and liquid chromatography-nuclear magnetic resonance spectroscopy as a strategy for polar metabolite identification. J Chromatogr B Biomed Sci Appl 2000;748(1):295-309
   PubMed Web of Science ®Google Scholar
• Wolfender JL, Rodriguez S, Hostettmann K. Liquid chromatography coupled to mass spectrometry and nuclear magnetic resonance spectroscopy for the screening of plant constituents. J Chromatogr A 1998;794(1 + 2):299-316
   Web of Science ®Google Scholar
• Backer AE, Thorbert S, Rakotonirainy O, et al. Liquid chromatography “on-flow” 1H nuclear magnetic resonance on native glycosphingolipid mixtures together with gas chromatography/mass spectrometry on the released oligosaccharides for screening and characterization of carbohydrate-based antigens from pig lungs. Glycoconj J 1999;16(1):45-58
   PubMed Web of Science ®Google Scholar
• Shockcor JP, Unger SE, Savina P, et al. Application of directly coupled LC-NMR-MS to the structural elucidation of metabolites of the HIV-1 reverse-transcriptase inhibitor BW935U83. J Chromatogr B Biomed Sci Appl 2000;748(1):269-79
   PubMed Web of Science ®Google Scholar
• Dear GJ, Plumb RS, Sweatman BC, et al. Mass directed peak selection, an efficient method of drug metabolite identification using directly coupled liquid chromatography-mass spectrometry-nuclear magnetic resonance spectroscopy. J Chromatogr B Biomed Sci Appl 2000;748(1):281-93
   PubMed Web of Science ®Google Scholar
• Nicholson JK, Lindon JC, Holmes E. “Metabonomics”: understanding the metabolic responses of living systems to pathophysiological stimuli via multivariate statistical analysis of biological NMR spectroscopic data. Xenobiotica 1999;29(11):1181-9
   PubMed Web of Science ®Google Scholar
• Stockman BJ. Flow NMR spectroscopy in drug discovery. Curr Opin Drug Discov Devel 2000;3(3):269-74
   PubMedGoogle Scholar
• Smallcombe SH, Patt SL, Keifer A. WET solvent suppression and its applications to LC NMR and high-resolution NMR spectroscopy. J Magn Reson Ser A 1995;117(2):295-303
   Web of Science ®Google Scholar
• Hofmann M, Spraul M. Method and apparatus for coupling a liquid chromatograph and an NMR spectrometer. Patent Application: DE 91-4101473; 1992
   Google Scholar
• Spraul M, Hofmann M, Dvortsak P, et al. High-performance liquid chromatography coupled to high-field proton nuclear magnetic resonance spectroscopy: application to the urinary metabolites of ibuprofen. Anal Chem 1993;65(4):327-30
   PubMed Web of Science ®Google Scholar
• Lenz EM, Greatbanks D, Wilson ID, et al. Direct characterization of drug glucuronide isomers in human urine by HPLC-NMR spectroscopy: application to the positional isomers of 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetic acid glucuronide. Anal Chem 1996;68(17):2832-7
   PubMed Web of Science ®Google Scholar
• Corcoran O, Spraul M. LC-NMR-MS in drug discovery. Drug Discov Today 2003;8(14):624-31
   PubMed Web of Science ®Google Scholar
• Spraul M, Braumann U, Hofmann M, et al. From LC-NMR to LC-NMR/MS under full automation. Abstracts of Papers, 221st ACS National Meeting; 1 – 5 April 2001; San Diego, CA, United States
   Google Scholar
• Mutlib AE, Strupczewski JT, Chesson SM. Application of hyphenated LC/NMR and LC/MS techniques in rapid identification of in vitro and in vivo metabolites of iloperidone. Drug Metab Dispos 1995;23(9):951-64
   PubMed Web of Science ®Google Scholar
• Holt RM, Newman MJ, Pullen FS, et al. High-performance liquid chromatography/NMR spectrometry/mass spectrometry: further advances in hyphenated technology. J Mass Spectrom 1997;32(1):64-70
   PubMed Web of Science ®Google Scholar
• Cummings G, Offen P, Olsen MA, et al. LC/MS, LC/NMR, FTIR: an integrated approach to impurity identification in pharmaceutical development and formulation. Am Pharm Rev 2003;6(3):88-92
   Google Scholar
• Norwood DL, Mullis JO, Feinberg TN. Hyphenated techniques. Sep Sci Technol (San Diego, CA, US) 2007;8:189-235
   Google Scholar
• Spraul M. Developments in NMR hyphenation for pharmaceutical industry. Mod Magn Reson 2006;2:1203-10
   Google Scholar
• Exarchou V, Krucker M, van Beek TA, et al. LC-NMR coupling technology: recent advancements and applications in natural products analysis. Magn Reson Chem 2005;43(9):681-7
   PubMed Web of Science ®Google Scholar
• Bari SB, Kadam BR, Jaiswal YS, et al. Impurity profile: significance in active pharmaceutical ingredient. Eurasian J Anal Chem 2007;2(1):32-53
   Google Scholar
• Qiu F, Norwood DL. Identification of pharmaceutical impurities. J Liq Chromatogr Relat Technol 2007;30(5-7):877-935
   Web of Science ®Google Scholar
• Norwood DL, Qiu F. Strategies for the analysis of pharmaceutical excipients and their trace level impurities. Am Pharm Rev 2004;7(5):92,94,96-9
   Google Scholar
• Martin GE. Applications of cryogenic NMR probe technology for the identification of low-level impurities in pharmaceuticals. Mod Magn Reson 2006;2:1187-94
   Google Scholar
• Kovacs H, Moskau D, Spraul M. Cryogenically cooled probes-a leap in NMR technology. Prog Nucl Magn Reson Spectrosc 2005;46(2-3):131-55
   Web of Science ®Google Scholar
• Russell DJ, Hadden CE, Martin GE, et al. A Comparison of inverse-detected heteronuclear NMR performance: conventional vs cryogenic microprobe performance. J Nat Prod 2000;63(8):1047-9
   PubMed Web of Science ®Google Scholar
• Spraul M, Freund AS, Nast RE, et al. Advancing NMR sensitivity for LC-NMR-MS using a cryoflow probe: application to the analysis of acetaminophen metabolites in urine. Anal Chem 2003;75(6):1536-41
   PubMed Web of Science ®Google Scholar
• Exarchou V, Godejohann M, Van Beek TA, et al. LC-UV-solid-phase extraction-NMR-MS combined with a cryogenic flow probe and its application to the identification of compounds present in Greek Oregano. Anal Chem 2003;75(22):6288-94
   PubMed Web of Science ®Google Scholar
• Griffiths L, Horton R. Optimization of LC-NMR. III. Increased signal-to-noise ratio through column trapping. Magn Reson Chem 1998;36(2):104-9
   Web of Science ®Google Scholar
• Olson DL, Peck TL, Webb AG, et al. High-resolution microcoil 1H-NMR for mass-limited, nanoliter-volume samples. Science (Washington, DC) 1995;270(5244):1967-70
   Web of Science ®Google Scholar
• Subramanian R, Kelley WP, Floyd PD, et al. A microcoil NMR probe for coupling microscale HPLC with on-line NMR spectroscopy. Anal Chem 1999;71(23):5335-9
   PubMed Web of Science ®Google Scholar
• Olson DL, Lacey ME, Sweedler JV. High-resolution microcoil NMR for analysis of mass-limited, nanoliter samples. Anal Chem 1998;70(3):645-50
   PubMed Web of Science ®Google Scholar
• Schlotterbeck G, Ross A, Hochstrasser R, et al. High-resolution capillary tube NMR. A miniaturized 5-uL high-sensitivity TXI probe for mass-limited samples, off-line LC NMR, and HT NMR. Anal Chem 2002:4464-71
   PubMed Web of Science ®Google Scholar
• Obach RS, Reed-Hagen AE, Krueger SS, et al. Metabolism and disposition of varenicline, a selective a4b2 acetylcholine receptor partial agonist, in vivo and in vitro. Drug Metab Dispos 2006;34(1):121-30
   PubMed Web of Science ®Google Scholar
• Shaffer CL, Gunduz M, Scialis RJ, et al. Metabolism and disposition of a selective a7 nicotinic acetylcholine receptor agonist in humans. Drug Metab Dispos 2007;35(7):1188-95
   PubMed Web of Science ®Google Scholar
• Iversen LL, Woodruff GN, Kemp JA, et al. Pharmacology and neuroprotective effects of the NMDA antagonist MK-801. International Congress Series 1987;750:117-20
   Google Scholar
• Walker GS, Thornburgh BA, Fate GD. Structural characterization of P450 mediated metabolites of MK-801 in the rat. SMASH Conference, Arrgone National Laboratories: Illinois; 2000
   Google Scholar