Utilizing ¹⁹F NMR to investigate drug disposition early in drug discovery

References

• Beumer JH, Beijnen JH, Schellens JHM. (2006). Mass balance studies, with a focus on anticancer drugs. Clin Pharmacokinet 45:33–58
   PubMed Web of Science ®Google Scholar
• Bradley SA, Ouyang A, Purdie J, et al. (2010). Fermentanomics: monitoring mammalian cell cultures with NMR spectroscopy. J Am Chem Soc 132:9531–3
   PubMed Web of Science ®Google Scholar
• Cobas C, Sykora S. (2009). The bumpy road towards automatic global spectral deconvolution (GSD). Paper presented at the 50th Experimental NMR Conference, Asilomar, CA. Available from: http://www.ebyte.it/library/downloads/Poster_GSD_ENC09.pdf [last accessed 21 Apr 2015]
   Google Scholar
• Do NM, Oliver MA, Salisbury JJ, Wager CB. (2011). Application of quantitative 19F and 1H NMR for reaction monitoring and in situ yield determinations for an early stage pharmaceutical candidate. Anal Chem 83:8766–71
   PubMed Web of Science ®Google Scholar
• Espina R, Yu L, Wang J, et al. (2009). Nuclear magnetic resonance spectroscopy as a quantitative tool to determine the concentrations of biologically produced metabolites: implications in metabolites in safety testing. Chem Res Toxicol 22:299–310
   PubMed Web of Science ®Google Scholar
• Holzgrabe U, Deubner R, Schollmayer C, Waibel B. (2005). Quantitative NMR spectroscopy – application in drug analysis. J Pharm Biomed Anal 38:806–12
   PubMed Web of Science ®Google Scholar
• Hop CECA, Wang Z, Chen Q, Kwei G. (1998). Plasma-pooling methods to increase throughput for in vivo pharmacokinetic screening. J Pharm Sci 87:901–3
   PubMed Web of Science ®Google Scholar
• International Conference on Harmonisation (ICH). (2009). Guidance on nonclinical safety studies for the conduct of human clinical trials and marketing authorization for pharmaceuticals M3(R2). Available from: http://www.ich.org/fileadmin/Public_Web_Site/ICH_Products/Guidelines/Multidisciplinary/M3_R2/Step4/M3_R2__Guideline.pdf [last accessed 21 Apr 2015]
   Google Scholar
• Kenwright AM, Kuprov I, De Luca E, et al. (2008). 19F NMR based pH probes: lanthanide (III) complexes with pH-sensitive chemical shifts. Chem Commun 2514–16
   PubMed Web of Science ®Google Scholar
• Lindon JC, Nicholson JK, Holmes E, Everett JR. (2000). Metabolic processes studied by NMR spectroscopy of biofluids. Concepts Mag Res 12:289–320
   Web of Science ®Google Scholar
• Malet-Martino M, Gilard V, Desmoulin F, Martino R. (2005). Fluorine nuclear magnetic resonance spectroscopy of human biofluids in the field of metabolic studies of anticancer and antifungal fluoropyrimidine drugs. Clin Chim Acta 366:61–73
   PubMed Web of Science ®Google Scholar
• Martino R, Gilard V, Desmoulin F, Malet-Martino M. (2005). Fluorine-19 or phosphorous-31 NMR spectroscopy: a suitable analytical technique for quantitative in vitro metabolic studies of fluorinated or phosphorylated drugs. J Pharm Biomed Anal 38:871–91
   PubMed Web of Science ®Google Scholar
• Martino R, Gilard V, Desmoulin F, Malet-Martino M. (2006). Interest of fluorine-19 nuclear magnetic resonance spectroscopy in the detection, identification and quantification of metabolites of anticancer and antifungal fluoropyrimidine drugs in human biofluids. Chemotherapy 52:215–19
   PubMed Web of Science ®Google Scholar
• Miyataka H, Ozaki T, Himeno S. (2007). Effect of pH on 1H-NMR spectroscopy of mouse urine. Biol Pharm Bull 30:667–70
   PubMed Web of Science ®Google Scholar
• Muller N, Carr DT. (1963). Carbon-13 splittings in fluorine nuclear magnetic resonance spectra. J Phys Chem 67:112–15
   Web of Science ®Google Scholar
• Müller K, Faeh C, Diederich F. (2007). Fluorine in pharmaceuticals: looking beyond intuition. Science 317:1881–6
   PubMed Web of Science ®Google Scholar
• Mutlib A, Espina R, Vishwanathan K, et al. (2011). Application of quantitative NMR in pharmacological evaluation of biologically generated metabolites: implications in drug discovery. Drug Metab Dispos 39:106–16
   PubMed Web of Science ®Google Scholar
• Mutlib A, Espina R, Atherton J, et al. (2012). Alternate strategies to obtain mass balance without the use of radiolabeled compounds: application of quantitative fluorine (19F) nuclear magnetic resonance (NMR) in metabolism studies. Chem Res Toxicol 25:572–83
   PubMed Web of Science ®Google Scholar
• Pauli GF, Gödecke T, Jaki BU, Lankin DC. (2012). Quantitative 1H NMR. Development and potential of an analytical method: an update. J Nat Prod 75:834–51
   PubMed Web of Science ®Google Scholar
• Penner N, Klunk LJ, Prakash C. (2009). Human radiolabeled mass balance studies: objectives, utilities and limitations. Biopharm Drug Dispos 30:185–203
   PubMed Web of Science ®Google Scholar
• Raufman JP, Xu S, Cheng K, et al. (2011). In vivo magnetic resonance imaging to detect biliary excretion of 19F-labeled drug in mice. Drug Metab Dispos 39:736–9
   PubMed Web of Science ®Google Scholar
• Roffey SJ, Obach RS, Gedge JI, Smith DA. (2007). What is the objective of the mass balance study? A retrospective analysis of data in animal and human excretion studies employing radiolabeled drugs. Drug Metab Rev 39:17–43
   PubMed Web of Science ®Google Scholar
• Sylvia LA, Gerig JT. (1993). Fluorine NMR studies of the metabolism of flumecinol (3-trifluromethyl-a-ethylbenzhydrol). Drug Metab Dispos 21:105–13
   PubMed Web of Science ®Google Scholar
• US Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research. (2008). Guidance for Industry. Safety Testing of Drug Metabolites. US FDA website. Available from: http://www.fda.gov [last accessed 21 Apr 2015]
   Google Scholar
• US Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research. (2012). Guidance for Industry. M3(R2) Nonclinical Safety Studies for the Conduct of Human Clinical Trials and Marketing Authorization for Pharmaceuticals. Questions and Answers. Available from: http://www.fda.gov/downloads/biologicsbloodvaccines/guidancecomplianceregulatoryinformation/guidances/general/ucm292164.pdf [last accessed 21 Apr 2015]
   Google Scholar
• Van Laarhoven HWM, Punt CJA, Kamm YJL, Heerschap A. (2005). Monitoring fluoropyrimidine metabolism in solid tumors with in vivo 19F magnetic resonance spectroscopy. Crit Rev Oncol Hematol 56:321–43
   PubMed Web of Science ®Google Scholar
• Vishwanathan K, Babalola K, Wang J, et al. (2009). Obtaining exposures of metabolites in preclinical species through plasma pooling and quantitative NMR: addressing metabolites in safety testing (MIST) guidance without using radiolabeled compounds and chemically synthesized metabolite standards. Chem Res Toxicol 22:311–22
   PubMed Web of Science ®Google Scholar
• Walker GS, Ryder TF, Sharma R, et al. (2011). Validation of isolated metabolites from drug metabolism studies as analytical standards by quantitative NMR. Drug Metab Dispos 39:433–40
   PubMed Web of Science ®Google Scholar
• Walker GS, Bauman JN, Ryder TF, et al. (2014). Biosynthesis of drug metabolites and quantitation using NMR spectroscopy for use in pharmacologic and drug metabolism studies. Drug Metab Dispos 42:1627–39
   PubMed Web of Science ®Google Scholar
• Wang J, Sánchez-Roselló M, Acena JL, et al. (2014). Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001–2011). Chem Rev 114:2432–506
   PubMed Web of Science ®Google Scholar
• Wider G, Dreier L. (2006). Measuring protein concentrations by NMR spectroscopy. J Am Chem Soc 128:2571–6
   PubMed Web of Science ®Google Scholar