Liquid chromatography coupled to mass spectrometry for metabolite profiling in the field of drug discovery

References

• Jia L, Liu X. The conduct of drug metabolism studies considered good practice (II): in vitro experiments. Curr Drug Metab. 2007;8:822–829.
   PubMed Web of Science ®Google Scholar
• Liu XD, Jia L. The conduct of drug metabolism studies considered good practice (I): analytical systems and in vivo studies. Curr Drug Metab. 2007;8:815–821.
   PubMed Web of Science ®Google Scholar
• Zhang ZP, Zhu MS, Tang W. Metabolite identification and profiling in drug design: current practice and future directions. Curr Pharm Design. 2009;15:2220–2235.
   PubMed Web of Science ®Google Scholar
• Prakash C, Shaffer CL, Nedderman A. Analytical strategies for identifying drug metabolites. Mass Spectrom Rev. 2007;26:340–369.
   PubMed Web of Science ®Google Scholar
• Prasad B, Garg A, Takwani H, et al. Metabolite identification by liquid chromatography-mass spectrometry. Trend Anal Chem. 2011;30:360–387.
   Web of Science ®Google Scholar
• Staack RF, Hopfgartner G. New analytical strategies in studying drug metabolism. Anal Bioanal Chem. 2007;388:1365–1380.
   PubMed Web of Science ®Google Scholar
• Saurina J, Sentellas S. Strategies for metabolite profiling based on liquid chromatography. J Chromatogr B Anal Technol Biomed Life Sci. 2017;1044:103–111.
   PubMed Web of Science ®Google Scholar
• Zhang DL, Zhang HY, Aranibar N, et al. Structural elucidation of human oxidative metabolites of muraglitazar: use of microbial bioreactors in the biosynthesis of metabolite standards. Drug Metab Dispos. 2006;34:267–280.
   PubMed Web of Science ®Google Scholar
• Geier M, Braun A, Emmerstorfer A, et al. Production of human cytochrome P450 2D6 drug metabolites with recombinant microbes - a comparative study. Biotechnol J. 2012;7:1346–1358.
   PubMed Web of Science ®Google Scholar
• Baumann A, Karst U. Online electrochemistry/mass spectrometry in drug metabolism studies: principles and applications. Expert Opin Drug Met. 2010;6:715–731.
   PubMed Web of Science ®Google Scholar
• Alvarez-Sanchez B, Priego-Capote F, Luque de Castro MD. Metabolomics analysis II. Preparation of biological samples prior to detection. Trends Anal Chem. 2010;29:120–127.
   Web of Science ®Google Scholar
• Darvesh AS, Carroll RT, Geldenhuys WJ, et al. In vivo brain microdialysis: advances in neuropsychopharmacology and drug discovery. Expert Opin Drug Discov. 2011;6:109–127.
   PubMed Web of Science ®Google Scholar
• David A, Abdul-Sada A, Lange A, et al. A new approach for plasma (xeno)metabolomics based on solid-phase extraction and nanoflow liquid chromatography-nanoelectrospray ionisation mass spectrometry. J Chromatogr A. 2014;1365:72–85.
   PubMed Web of Science ®Google Scholar
• Saunders KC, Ghanem A, Hon WB, et al. Separation and sample pre-treatment in bioanalysis using monolithic phases: A review. Anal Chim Acta. 2009;652:22–31.
   PubMed Web of Science ®Google Scholar
• Liang Y, Wang G, Xie L, et al. Recent development in liquid chromatography/mass spectrometry and emerging technologies for metabolite identification. Curr Drug Metab. 2011;12:329–344.
   PubMed Web of Science ®Google Scholar
• Kavanagh P, Grigoryev A, Melnik A, et al. Detection and tentative identification of urinary phase I metabolites of phenylacetylindole cannabimimetics JWH-203 and JWH-251, by GC-MS and LC-MS/MS. J Chromatogr B Anal Technol Biomed Life Sci. 2013;934:102–108.
   PubMed Web of Science ®Google Scholar
• Yang S, Lu JH, Xu YX, et al. New oxymesterone metabolites in human by gas chromatography-tandem mass spectrometry and their application for doping control. Drug Test Anal. 2016;8:633–643.
   PubMed Web of Science ®Google Scholar
• Matabosch X, Pozo OJ, Perez-Mana C, et al. Identification of budesonide metabolites in human urine after oral administration. Anal Bioanal Chem. 2012;404:325–340.
   PubMed Web of Science ®Google Scholar
• Wang X, Li KF, Adams E, et al. Capillary electrophoresis-mass spectrometry in metabolomics: the potential for driving drug discovery and development. Curr Drug Metabol. 2013;14:807–813.
   PubMed Web of Science ®Google Scholar
• Bytzek AK, Hartinger CG. Capillary electrophoretic methods in the development of metal-based therapeutics and diagnostics: new methodology and applications. Electrophoresis. 2012;33:622–634.
   PubMed Web of Science ®Google Scholar
• Potterat O, Hamburger M. Natural products in drug discovery - Concepts and approaches for tracking bioactivity. Curr Org Chem. 2006;10:899–920.
   Web of Science ®Google Scholar
• Lapthorn C, Pullen F, Chowdhry BZ. Ion mobility spectrometry-mass spectrometry (IMS-MS) of small molecules: separating and assigning structures to ions. Mass Spectrom Rev. 2013;32:43–71.
   PubMed Web of Science ®Google Scholar
• Taguchi K, Fukusaki E, Bamba T. Supercritical fluid chromatography/mass spectrometry in metabolite analysis. Bioanalysis. 2014;6:1679–1689.
   PubMed Web of Science ®Google Scholar
• Malherbe CJ, de Beer D, Joubert E. Development of on-line High Performance Liquid Chromatography (HPLC)-Biochemical detection methods as tools in the identification of bioactives. Int J Mol Sci. 2012;13:3101–3133.
   PubMed Web of Science ®Google Scholar
• Gika H, Theodoridis G. Sample preparation prior to the LC-MS-based metabolomics/metabonomics of blood-derived samples. Bioanalysis. 2011;3:1647–1661.
   PubMed Web of Science ®Google Scholar
• Kole PL, Venkatesh G, Kotecha J, et al. Recent advances in sample preparation techniques for effective bioanalytical methods. Biomed Chromatogr. 2011;25:199–217.
   PubMed Web of Science ®Google Scholar
• Raja M, Alberti J, Saurina J, et al. Liquid chromatography-mass spectrometry as a general approach for investigating covalent binding of drugs to DNA. Anal Bioanal Chem. 2016;408:3911–3922.
   PubMed Web of Science ®Google Scholar
• Roszkowska A, Miekus N, Baczek T. Application of solid-phase microextraction in current biomedical research. J Sep Sci. 2019;42:285–302.
   PubMed Web of Science ®Google Scholar
• Xu RNX, Fan LM, Rieser MJ, et al. Recent advances in high-throughput quantitative bioanalysis by LC-MS/MS. J Pharm Biomed Anal. 2007;44:342–355.
   PubMed Web of Science ®Google Scholar
• Tanaka N, McCalley DV. Core-shell, ultrasmall particles, monoliths, and other support materials in high-performance liquid chromatography. Anal Chem. 2016;88:279–298.
   PubMed Web of Science ®Google Scholar
• Marquez H, Alberti J, Salva M, et al. Development of a UHPLC method for the assessment of the metabolic profile of cinitapride. J Sep Sci. 2011;24:3502–3508.
   Google Scholar
• De Vos J, Broeckhoven K, Eeltink S. Advances in ultrahigh-pressure liquid chromatography technology and system design. Anal Chem. 2016;88:262–278.
   PubMed Web of Science ®Google Scholar
• Rodriguez-Cid L, Sentellas S, Saurina J. Voltammetric and electrogeneration approaches for the assessment of the oxidative drug metabolism. Anal Bioanal Chem. 2018;410:2229–2239.
   PubMed Web of Science ®Google Scholar
• Jiang HP, Chu JM, Lan MD, et al. Comprehensive profiling of ribonucleosides modification by affinity zirconium oxide-silica composite monolithic column online solid-phase microextraction - Mass spectrometry analysis. J Chromatogr A. 2016;1462:90–99.
   PubMed Web of Science ®Google Scholar
• Wickremsinhe ER, Singh G, Ackermann BL, et al. A review of nanoelectrospray ionization applications for drug metabolism and pharmacokinetics. Curr Drug Metabol. 2006;7:913–928.
   PubMed Web of Science ®Google Scholar
• Caspar AT, Meyer MR, Westphal F, et al. Nano liquid chromatography-high-resolution mass spectrometry for the identification of metabolites of the two new psychoactive substances N-(ortho-methoxybenzyl)-3,4-dimethoxyamphetamine and N-(ortho-methoxybenzyl)-4-methylmethamphetamine. Talanta. 2018;188:111–123.
   PubMed Web of Science ®Google Scholar
• Liu J, Zhao Z, Teffera Y. Application of on-line nano-liquid chromatography/mass spectrometry in metabolite identification studies. Rapid Commun Mass Spectrom. 2012;26:320–326.
   PubMed Web of Science ®Google Scholar
• Jones DR, Boysen G, Miller GP. Novel multi-mode ultra performance liquid chromatography-tandem mass spectrometry assay for profiling enantiomeric hydroxywarfarins and warfarin in human plasma. J Chromatogr B Anal Technol Biomed Life Sci. 2011;879:1056–1062.
   PubMed Web of Science ®Google Scholar
• Hlabangana L, Hernandez-Cassou S, Saurina J. Determination of biogenic amines in wines by ion-pair liquid chromatography and post-column derivatization with 1,2-naphthoquinone-4-sulphonate. J Chromatogr A. 2006;1130:130–136.
   PubMed Web of Science ®Google Scholar
• Liu A, Lute J, Gu H, et al. Challenges and solutions in the bioanalysis of BMS-986094 and its metabolites including a highly polar, active nucleoside triphosphate in plasma and tissues using LC-MS/MS. J Chromatogr B Anal Technol Biomed Life Sci. 2015;1000:29–40.
   PubMed Web of Science ®Google Scholar
• Pecher D, Dokupilova S, Zelinkova Z, et al. Analytical and sample preparation protocol for therapeutic drug monitoring of 12 thiopurine metabolites related to clinical treatment of inflammatory bowel disease. Molecules. 2018;23:1744.
   Web of Science ®Google Scholar
• Onorato JM, Langish R, Bellamine A, et al. Applications of HILIC for targeted and non-targeted LC/MS analyses in drug discovery. J Sep Sci. 2010;33:923–929.
   PubMed Web of Science ®Google Scholar
• Li Z, Han J, Sun SA, et al. Hydrophilic interaction liquid chromatography tandem mass spectrometry: an attractive and prospective method for quantitative bioanalysis in drug metabolism. Curr Drug Metabol. 2016;17:386–400.
   PubMed Web of Science ®Google Scholar
• Kusumoto K, Nagao T, Ogihara T. A new high-throughput analysis for drug metabolism profiling using liquid chromatography coupled with tandem mass spectrometry. Drug Res. 2013;63:171–176.
   Google Scholar
• Khreit OIG, Grant HM, Henderson C, et al. Identification of novel metabolic pathways of sitagliptin (STG) by LC/MS and LC/MS2 after incubations with rat hepatocytes. J Drug Metabol Toxicol. 2016;7:220/1–220/7.
   PubMedGoogle Scholar
• Tarascou I, Mazauric JP, Meudec E, et al. Characterisation of genuine and derived cranberry proanthocyanidins by LC-ESI-MS. Food Chem. 2011;128:802–810.
   Web of Science ®Google Scholar
• van Dooren I, Foubert K, Theunis M, et al. Advantages of a validated UPLC-MS/MS standard addition method for the quantification of A-type dimeric and trimeric proanthocyanidins in cranberry extracts in comparison with well-known quantification methods. J Pharm Biomed Anal. 2018;148:32–41.
   PubMed Web of Science ®Google Scholar
• Jenkins S, Fischer SM, Chen L, et al. Global LC/MS metabolomics profiling of calcium stressed and immunosuppressant drug treated Saccharomyces cerevisiae. Metabolites. 2013;3:1102–1117.
   PubMedGoogle Scholar
• Wang X, Zeng S. Stereoselective metabolic and pharmacokinetic analysis of the chiral active components from herbal medicines. Curr Pharm Anal. 2010;6:39–52.
   Web of Science ®Google Scholar
• Mesaros C, Blair IA. Targeted chiral analysis of bioactive arachidonic acid metabolites using liquid-chromatography-mass spectrometry. Metabolites. 2012;2:337–365.
   PubMedGoogle Scholar
• Li J, Liu Y, Wei JQ, et al. Isolation and identification of phase 1 metabolites of curcuminoids in rats. Planta Med. 2012;78:1351–1356.
   PubMed Web of Science ®Google Scholar
• Bakhytkyzy I, Nunez O, Saurina J. Size exclusion coupled to reversed phase liquid chromatography for the characterization of cranberry products. Food Anal Methods. 2018. DOI:10.1007/s12161-018-1390-z
   Web of Science ®Google Scholar
• Yao CL, Pan HQ, Wang H, et al. Global profiling combined with predicted metabolites screening for discovery of natural compounds: characterization of ginsenosides in the leaves of Panax notoginseng as a case study. J Chromatogr A. 2018;1538:34–44.
   PubMed Web of Science ®Google Scholar
• Bankefors J, Nord LI, Kenne L. Multidimensional profiling of components in complex mixtures of natural products for metabolic analysis, proof of concept: application to Quillaja saponins. J Chromatogr B Anal Technol Biomed Life Sci. 2010;878:471–476.
   PubMed Web of Science ®Google Scholar
• Fitzsimmons ME, Sun G, Kuksa V, et al. Disposition, profiling and identification of emixustat and its metabolites in humans. Xenobiotica. 2018;48:592–604.
   PubMed Web of Science ®Google Scholar
• Belaz KRA, Pereira-Filho ER, Oliveira RV. Development of achiral and chiral 2D HPLC methods for analysis of albendazole metabolites in microsomal fractions using multivariate analysis for the in vitro metabolism. J Chromatogr B Anal Technol Biomed Life Sci. 2013;932:26–33.
   PubMed Web of Science ®Google Scholar
• Hernandez-Cassou S, Saurina J. Derivatization strategies for the determination of biogenic amines in wines by chromatographic and electrophoretic techniques. J Chromatogr B Anal Technol Biomed Life Sci. 2011;879:1270–1281.
   PubMed Web of Science ®Google Scholar
• Qi BL, Liu P, Wang QY, et al. Derivatization for liquid chromatography-mass spectrometry. Trends Anal Chem. 2014;59:121–132.
   Web of Science ®Google Scholar
• Perez-Rafols C, Vinas D, Hernandez-Cassou S, et al. Experimental design for the determination of polyphenols by liquid chromatography: application to the chemometric characterization and classification of beers. Anal Methods. 2015;7:3283–3290.
   Web of Science ®Google Scholar
• Klencsar B, Li SW, Balcaen L, et al. High-performance liquid chromatography coupled to inductively coupled plasma - Mass spectrometry (HPLC-ICP-MS) for quantitative metabolite profiling of non-metal drugs. Trends Anal Chem. 2018;104:118–134.
   Web of Science ®Google Scholar
• Losada C, Alberti JJ, Saurina J, et al. Determination of S-containing drug metabolites from in vitro and in vivo metabolism studies by using LC-ICP/MS. Anal Bioanal Chem. 2012;404:539–551.
   PubMed Web of Science ®Google Scholar
• Cuyckens F, Koppen V, Kembuegler R, et al. Improved liquid chromatography-Online radioactivity detection for metabolite profiling. J Chromatogr A. 2008;1209:128–135.
   PubMed Web of Science ®Google Scholar
• Wishart DS. Quantitative metabolomics using NMR. Trends Anal Chem. 2008;27:228–237.
   Web of Science ®Google Scholar
• Zhang SC, Gowda GAN, Ye T, et al. Advances in NMR-based biofluid analysis and metabolite profiling. Analyst. 2010;135:1490–1498.
   PubMed Web of Science ®Google Scholar
• Beckonert O, Keun HC, Ebbels TMD, et al. Metabolic profiling, metabolomic and metabonomic procedures for NMR spectroscopy of urine, plasma, serum and tissue extracts. Nat Protocols. 2007;2:2692–2703.
   PubMed Web of Science ®Google Scholar
• Lindon JC, Holmes E, Nicholson JK. Metabonomics techniques and applications to pharmaceutical research & development. Pharm Res. 2006;23:1075–1088.
   PubMed Web of Science ®Google Scholar
• Lindon JC, Nicholson JK, Wilson ID. Directly coupled HPLC-NMR and HPLC-NMR-MS in pharmaceutical research and development. J Chromatogr B. 2000;748:233–258.
   PubMed Web of Science ®Google Scholar
• Wen B, Zhu M. Applications of mass spectrometry in drug metabolism: 50 years of progress. Drug Metabol Rev. 2015;47:71–87.
   PubMed Web of Science ®Google Scholar
• Spaggiari D, Geiser L, Rudaz S. Coupling ultra-high-pressure liquid chromatography with mass spectrometry for in-vitro drug-metabolism studies. Trends Anal Chem. 2014;63:129–139.
   Web of Science ®Google Scholar
• Bhatnagar A, McKay MJ, Crumbaker M, et al. Quantitation of the anticancer drug abiraterone and its metabolite Delta(4)-abiraterone in human plasma using high-resolution mass spectrometry. J Pharm Biomed Anal. 2018;154:66–74.
   PubMed Web of Science ®Google Scholar
• Shah Y, Iqbal Z, Ahmad L, et al. Determination of rosuvastatin and its metabolite N-desmethyl rosuvastatin in human plasma by liquid chromatography-high resolution mass spectrometry: method development, validation, and application to pharmacokinetic study. J Liq Chromatogr Rel Technol. 2015;38:863–873.
   Web of Science ®Google Scholar
• Sun Y, Wang S, Ji J, et al. Metabolite identification of the antimalarial naphthoquine using liquid chromatography-tandem high-resolution mass spectrometry in combination with multiple data-mining tools. Biomed Chromatogr. 2018;32:n/a.
   Web of Science ®Google Scholar
• Bandu R, Lee HJ, Lee HM, et al. Liquid chromatography/mass spectrometry-based plasma metabolic profiling study of escitalopram in subjects with major depressive disorder. J Mass Spectrom. 2018;53:385–399.
   PubMed Web of Science ®Google Scholar
• Xian F, Hendrickson CL, Marshall AG. High resolution mass spectrometry. Anal Chem. 2012;84:708–719.
   PubMedGoogle Scholar
• Kaufmann A. Analytical performance of various acquisition modes in orbitrap MS and MS/MS. J Mass Spectrom. 2018;53:725–738.
   PubMed Web of Science ®Google Scholar
• Lin L, Lin H, Zhang M, et al. Types, principle, and characteristics of tandem high-resolution mass spectrometry and its applications. RSC Adv. 2015;5:107623–107636.
   Web of Science ®Google Scholar
• Gao D, Chen XW, Yang XM, et al. Stable isotope labeling strategy for curcumin metabolite study in human liver microsomes by liquid chromatography-tandem mass spectrometry. J Am Soc Mass Spectrom. 2015;26:686–694.
   PubMed Web of Science ®Google Scholar
• Leeming MG, Isaac AP, Pope BJ, et al. High-resolution twin-ion metabolite extraction (HiTIME) mass spectrometry: nontargeted detection of unknown drug metabolites by isotope labeling, liquid chromatography mass spectrometry, and automated high-performance computing. Anal Chem. 2015;87:4104–4109.
   PubMed Web of Science ®Google Scholar
• Rani PJ, Vishnuvardhan C, Nimbalkar RD, et al. Metabolite characterization of ambrisentan, in in vitro and in vivo matrices by UHPLC/QTOF/MS/MS: detection of glutathione conjugate of epoxide metabolite evidenced by in vitro GSH trapping assay. J Pharm Biom Anal. 2018;155:320–328.
   PubMed Web of Science ®Google Scholar
• Diao Z, Li J, Liu Q, et al. In-vivo metabolite profiling of chicoric acid in rat plasma, urine and feces after oral administration using liquid chromatography quadrupole time of flight mass spectrometry. J Chromatogr B Anal Technol Biomed Life Sci. 2018;1081:8–14.
   PubMed Web of Science ®Google Scholar
• Zhang Y, Sun Y, Mu X, et al. Identification of metabolites of vindoline in rats using ultra-high performance liquid chromatography/quadrupole time-of-flight mass spectrometry. J Chromatogr B Anal Technol Biomed Life Sci. 2017;1060:126–137.
   PubMed Web of Science ®Google Scholar
• Rashid M, Lee H, Jung BH. Metabolite identification and pharmacokinetic profiling of PP242, an ATPcompetitive inhibitor of mTOR using ultra high-performance liquid chromatography and mass spectrometry. J Chromatogr B Anal Technol Biomed Life Sci. 2018;1072:244–251.
   PubMed Web of Science ®Google Scholar
• Liu S, Che Y, Wang F, et al. Identification of metabolites of 6ʹ-Hydroxy-3,4,5,2ʹ,4ʹ-pentamethoxychalcone in rats by a combination of ultra-high-performance liquid chromatography with linear ion trap-orbitrap mass spectrometry based on multiple data processing techniques. Molecules. 2016;21:1266–1279.
   Web of Science ®Google Scholar
• Shang Z, Xin Q, Zhao W, et al. Rapid profiling and identification of puerarin metabolites in rat urine and plasma after oral administration by UHPLC-LTQ-Orbitrap mass spectrometer. J Chromatogr B Anal Technol Biomed Life Sci. 2017;1068–1069:180–192.
   PubMed Web of Science ®Google Scholar
• Shang Z, Wang F, Dai S, et al. Profiling and identification of (-)-epicatechin metabolites in rats using ultra-high performance liquid chromatography coupled with linear trap-Orbitrap mass spectrometer. Drug Test Anal. 2017;9:1224–1235.
   PubMed Web of Science ®Google Scholar
• Nikolaev EN, Kostyukevich YI, Vladimirov GN. Fourier transform ion cyclotron resonance (FT ICR) mass spectrometry: theory and simulations. Mass Spectrom Rev. 2016;35:219–258.
   PubMed Web of Science ®Google Scholar
• Li BL, Zhou H, Yang GC, et al. In vivo study of erysolin metabolic profile by ultrahigh performance liquid chromatography coupleded to Fourier transform ion cyclotron resonance mass spectrometry. Anal Technol Biomed Life Sci. 2018;1072:173–181.
   PubMed Web of Science ®Google Scholar
• Wu WY, Chu YJ, Wang SX, et al. Investigation of metabolic profile of pimavanserin in rats by ultrahigh-performance liquid chromatography combined with Fourier transform ion cyclotron resonance mass spectrometry. Rapid Commun Mass Spectrom. 2018;32:269–276.
   PubMed Web of Science ®Google Scholar
• Zhang JD, Zhang XX, Zhao YY, et al. Metabolic profile of Kudiezi injection in rats by UHPLC coupled with Fourier transform ion cyclotron resonance mass spectrometry. J Sep Sci. 2018;41:774–788.
   PubMed Web of Science ®Google Scholar