Using Mass Spectrometry for Drug Metabolism Studies

Strategies and Techniques for Bioanalytical Assays as Part of New Drug Discovery, Walter A. Korfmacher The Drug Discovery Process: From Molecules to Drugs, Mike S. Lee and Steven E. Klohr PK Principles and PK/PD Applications, Hong Mei and Richard A. Morrison Mass Spectrometry for In Vitro ADME Screening, Inhou Chu Metabolite Identification Strategies and Procedures, Ragu Ramanathan, S. Nilgun Comezog lu, and W. Griffith Humphreys Reactive Metabolite Screening and Covalent-Binding Assays, Gerard Hopfgartner Fast Metabolite Screening in a Discovery Setting, Xiaoying Xu Fast Chromatography with UPLC and Other Techniques, Sam Wainhaus Supercritical Fluid Chromatography-Mass Spectrometry, Yunsheng Hsieh Biomarkers of Efficacy and Toxicity: Discovery and Assay, Joanna R. Pols Imaging Mass Spectrometry for Small Molecules, Fangbiao Li MALDI IMS for Proteins and Biomarkers, Michelle L. Reyzer and Richard M. Caprioli Ambient Ionization Methods and Their Early Applications in ADME Studies, Jing-Tao Wu Pharmaceutical Applications of Accelerator Mass Spectrometry, Lan Gao and Swapan Chowdhury

[1]  S. Ito,et al.  Matrix effect and correction by standard addition in quantitative liquid chromatographic-mass spectrometric analysis of diarrhetic shellfish poisoning toxins. , 2002, Journal of chromatography. A.

[2]  C. Enke,et al.  A predictive model for matrix and analyte effects in electrospray ionization of singly-charged ionic analytes. , 1997, Analytical chemistry.

[3]  D. A. Wells,et al.  96-Well plate products for solid-phase extraction , 1999 .

[4]  R. Fisk,et al.  Performance of an ultra-low elution-volume 96-well plate: drug discovery and development applications. , 2003, Rapid communications in mass spectrometry : RCM.

[5]  J. Gebler,et al.  Analysis of native and chemically modified oligonucleotides by tandem ion-pair reversed-phase high-performance liquid chromatography/electrospray ionization mass spectrometry. , 2003, Rapid communications in mass spectrometry : RCM.

[6]  C. Enke,et al.  Relating electrospray ionization response to nonpolar character of small peptides. , 2000, Analytical chemistry.

[7]  D. Wu,et al.  High throughput liquid chromatography/mass spectrometry bioanalysis using 96-well disk solid phase extraction plate for the sample preparation. , 1998, Rapid communications in mass spectrometry : RCM.

[8]  T. D. Parker,et al.  Automated sample preparation for drugs in plasma using a solid-phase extraction workstation. , 1998, Journal of pharmaceutical and biomedical analysis.

[9]  D. A. Wells.  Accessory products for SPE using 96-well plates , 1999 .

[10]  Shaolian Zhou,et al.  Protonation in electrospray mass spectrometry: Wrong-way-round or right-way-round? , 2000, Journal of the American Society for Mass Spectrometry.

[11]  Dieter Zimmer,et al.  Matrix effects during analysis of plasma samples by electrospray and atmospheric pressure chemical ionization mass spectrometry: practical approaches to their elimination. , 2003, Rapid communications in mass spectrometry : RCM.

[12]  C. Enke,et al.  Importance of gas-phase proton affinities in determining the electrospray ionization response for analytes and solvents. , 2000, Journal of mass spectrometry : JMS.

[13]  W S Hancock,et al.  Analysis of Oligonucleotides by HPLC-Electrospray Ionization Mass Spectrometry. , 1997, Analytical chemistry.

[14]  P. Kebarle,et al.  Effect of the conductivity of the electrosprayed solution on the electrospray current. Factors determining analyte sensitivity in electrospray mass spectrometry , 1991 .

[15]  C. James,et al.  Quantitative determination of paclitaxel in human plasma using semi-automated liquid-liquid extraction in conjunction with liquid chromatography/tandem mass spectrometry. , 2003, Journal of pharmaceutical and biomedical analysis.

[16]  M. Sandahl,et al.  On-line automated sample preparation for liquid chromatography using parallel supported liquid membrane extraction and microporous membrane liquid-liquid extraction. , 2002, Journal of chromatography. A.

[17]  D. Hercules,et al.  LC-MS/MS signal suppression effects in the analysis of pesticides in complex environmental matrices , 2001, Fresenius' journal of analytical chemistry.

[18]  K. Boos,et al.  Multidimensional on-line solid-phase extraction (SPE) using restricted access materials (RAM) in combination with molecular imprinted polymers (MIP) , 2001, Fresenius' journal of analytical chemistry.

[19]  T. D. Parker,et al.  Design and evaluation of an automated solid-phase extraction method development system for use with biological fluids. , 1996, Analytical chemistry.

[20]  K. Markides,et al.  Factors influencing the determination of analyte ion surface partitioning coefficients in electrosprayed droplets , 2001 .

[21]  Jack D. Henion,et al.  Ion spray interface for combined liquid chromatography/atmospheric pressure ionization mass spectrometry , 1987 .

[22]  P. Kebarle.  A brief overview of the present status of the mechanisms involved in electrospray mass spectrometry. , 2000, Journal of mass spectrometry : JMS.

[23]  R. Majors.  A review of modern solid-phase extraction , 1998 .

[24]  U. Neue,et al.  A new approach to the effective preparation of plasma samples for rapid drug quantitation using on-line solid phase extraction mass spectrometry. , 1999, Rapid Communications in Mass Spectrometry.

[25]  A. Jaffrezic,et al.  Correlation Between Solvation Energies and Electrospray Mass Spectrometric Response Factors. Study by Electrospray Mass Spectrometry of Supramolecular Complexes in Thermodynamic Equilibrium in Solution , 1996 .

[26]  N. Spooner,et al.  Reduction of signal suppression effects in ESI-MS using a nanosplitting device. , 2001, Analytical chemistry.

[27]  Liang Li,et al.  Lithium and transition metal ions enable low energy collision-induced dissociation of polyglycols in electrospray ionization mass spectrometry , 2001, Journal of the American Society for Mass Spectrometry.

[28]  Vinod P. Shah,et al.  Bioanalytical Method Validation—A Revisit with a Decade of Progress , 2000, Pharmaceutical Research.

[29]  R. C. Mobley,et al.  Molecular Beams of Macroions , 1968 .

[30]  P. Kebarle,et al.  FROM IONS IN SOLUTION TO IONS IN THE GAS PHASE , 1993 .

[31]  R. Grant,et al.  Generic serial and parallel on-line direct-injection using turbulent flow liquid chromatography/tandem mass spectrometry. , 2002, Rapid communications in mass spectrometry : RCM.

[32]  C. Enke,et al.  Practical implications of some recent studies in electrospray ionization fundamentals. , 2001, Mass spectrometry reviews.

[33]  J. V. Iribarne,et al.  Atmospheric pressure ion evaporation-mass spectrometry , 1983 .

[34]  T. Koal,et al.  On the signal response of various pesticides in electrospray and atmospheric pressure chemical ionization depending on the flow-rate of eluent applied in liquid chromatography-tandem mass spectrometry. , 2001, Journal of chromatography. A.

[35]  F. Hsu,et al.  Distinction among isomeric unsaturated fatty acids as lithiated adducts by electrospray ionization mass spectrometry using low energy collisionally activated dissociation on a triple stage quadrupole instrument , 1999, Journal of the American Society for Mass Spectrometry.

[36]  Patrick R Griffin,et al.  Effect of signal interference from dosing excipients on pharmacokinetic screening of drug candidates by liquid chromatography/mass spectrometry. , 2002, Analytical chemistry.

[37]  L. Romanyshyn,et al.  Ultra-fast gradient vs. fast isocratic chromatography in bioanalytical quantification by liquid chromatography/tandem mass spectrometry. , 2001, Rapid communications in mass spectrometry : RCM.

[38]  P. Kebarle,et al.  On the mechanisms by which the charged droplets produced by electrospray lead to gas phase ions , 2000 .

[39]  J. Foley,et al.  Reduction in matrix-related signal suppression effects in electrospray ionization mass spectrometry using on-line two-dimensional liquid chromatography. , 2001, Analytical chemistry.

[40]  C. Enke,et al.  Effects of salt concentration on analyte response using electrospray ionization mass spectrometry , 1999, Journal of the American Society for Mass Spectrometry.

[41]  G. A. Smith,et al.  Automated solid-phase extraction and sample preparation - finding the right solution for your laboratory , 1998 .

[42]  F. Beaudry,et al.  In vivo pharmacokinetic screening in cassette dosing experiments; the use of on-line Pprospekt liquid chromatography/atmospheric pressure chemical ionization tandem mass spectrometry technology in drug discovery. , 1998, Rapid communications in mass spectrometry : RCM.

[43]  Michael Karas,et al.  Nanoelectrospray—More than just a minimized-flow electrospray ionization source , 1999, Journal of the American Society for Mass Spectrometry.

[44]  J. Herman.  Generic method for on-line extraction of drug substances in the presence of biological matrices using turbulent flow chromatography. , 2002, Rapid communications in mass spectrometry : RCM.

[45]  S. A. McLuckey,et al.  Ion/ion proton transfer reactions for protein mixture analysis. , 1996, Analytical chemistry.

[46]  D. T. Rossi,et al.  Automating solid-phase extraction: current aspects and future prospects. , 2000, Journal of chromatography. A.

[47]  N. Ogawa,et al.  Identification of rat urinary and biliary metabolites of esonarimod, a novel antirheumatic drug, using liquid chromatography/electrospray ionization tandem mass spectrometry with postcolumn addition of 2-(2-methoxyethoxy)ethanol, a signal-enhancing modifier. , 2001, Drug metabolism and disposition: the biological fate of chemicals.

[48]  M. J. Avery.  Quantitative characterization of differential ion suppression on liquid chromatography/atmospheric pressure ionization mass spectrometric bioanalytical methods. , 2003, Rapid communications in mass spectrometry : RCM.

[49]  F. Tse,et al.  Liquid-liquid extraction using 96-well plate format in conjunction with liquid chromatography/tandem mass spectrometry for quantitative determination of methylphenidate (Ritalin) in human plasma. , 2000, Rapid communications in mass spectrometry : RCM.

[50]  L. Andersson,et al.  Molecular imprinting for drug bioanalysis. A review on the application of imprinted polymers to solid-phase extraction and binding assay. , 2000, Journal of chromatography. B, Biomedical sciences and applications.

[51]  Timothy Olah,et al.  Mechanistic investigation of ionization suppression in electrospray ionization , 2000, Journal of the American Society for Mass Spectrometry.

[52]  R L Foltz,et al.  Ionization enhancement in atmospheric pressure chemical ionization and suppression in electrospray ionization between target drugs and stable-isotope-labeled internal standards in quantitative liquid chromatography/tandem mass spectrometry. , 2003, Rapid communications in mass spectrometry : RCM.

[53]  Z. Ouyang,et al.  High performance liquid chromatography mobile phase composition optimization for the quantitative determination of a carboxylic acid compound in human plasma by negative ion electrospray high performance liquid chromatography tandem mass spectrometry. , 1998, Rapid communications in mass spectrometry : RCM.

[54]  Richard D. Smith,et al.  Physical/chemical separations in the break-up of highly charged droplets from electrosprays , 2001, Journal of the American Society for Mass Spectrometry.

[55]  Luis E Sojo,et al.  Internal standard signal suppression by co-eluting analyte in isotope dilution LC-ESI-MS. , 2003, The Analyst.

[56]  Wilson Z Shou,et al.  Post-column infusion study of the 'dosing vehicle effect' in the liquid chromatography/tandem mass spectrometric analysis of discovery pharmacokinetic samples. , 2003, Rapid communications in mass spectrometry : RCM.

[57]  C. M. Jones,et al.  Use of reduced sorbent bed and disk membrane solid-phase extraction for the analysis of pharmaceutical compounds in biological fluids, with applications in the 96-well format. , 1997, Journal of chromatography. B, Biomedical sciences and applications.

[58]  B. Chait,et al.  Effects of anions on the positive ion electrospray ionization mass spectra of peptides and proteins. , 1994, Analytical chemistry.

[59]  B. Matuszewski,et al.  Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS. , 2003, Analytical chemistry.

[60]  J. Janiszewski,et al.  High-throughput method development approaches for bioanalytical mass spectrometry. , 2000, Journal of chromatographic science.

[61]  Kenneth R Wehmeyer,et al.  Semi-automated liquid--liquid back-extraction in a 96-well format to decrease sample preparation time for the determination of dextromethorphan and dextrorphan in human plasma. , 2002, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[62]  S X Peng,et al.  Fully automated 96-well liquid-liquid extraction for analysis of biological samples by liquid chromatography with tandem mass spectrometry. , 2001, Analytical chemistry.

[63]  T. Olah,et al.  Determination of L-654,066, a new 5 alpha-reductase inhibitor in plasma by liquid chromatography/atmospheric pressure chemical ionization mass spectrometry. , 1992, Biological mass spectrometry.

[64]  Walter A. Korfmacher,et al.  Investigation of matrix effects in bioanalytical high-performance liquid chromatography/tandem mass spectrometric assays: application to drug discovery. , 2003, Rapid communications in mass spectrometry : RCM.

[65]  R. Cole,et al.  Disparity between solution‐phase equilibria and charge state distributions in positive‐ion electrospray mass spectrometry , 1994 .

[66]  M. Wilm,et al.  Analytical properties of the nanoelectrospray ion source. , 1996, Analytical chemistry.

[67]  S. Jingu,et al.  Utility of postcolumn addition of 2-(2-methoxyethoxy)ethanol, a signal-enhancing modifier, for metabolite screening with liquid chromatography and negative ion electrospray ionization mass spectrometry. , 1999, Analytical chemistry.

[68]  Stefan Fischer,et al.  Enhanced sensitivity for peptide mapping with electrospray liquid chromatography-mass spectrometry in the presence of signal suppression due to trifluoroacetic acid-containing mobile phases. , 1995, Journal of chromatography. A.

[69]  S. Fischer,et al.  Signal enhancement for gradient reverse-phase high-performance liquid chromatography-electrospray ionization mass spectrometry analysis with trifluoroacetic and other strong acid modifiers by postcolumn addition of propionic acid and isopropanol , 1995, Journal of the American Society for Mass Spectrometry.

[70]  B. Matuszewski,et al.  Matrix effect in quantitative LC/MS/MS analyses of biological fluids: a method for determination of finasteride in human plasma at picogram per milliliter concentrations. , 1998, Analytical chemistry.

[71]  C. Enke,et al.  Effect of affinity for droplet surfaces on the fraction of analyte molecules charged during electrospray droplet fission. , 2001, Analytical chemistry.

[72]  T. Olah,et al.  The effects of sample preparation methods on the variability of the electrospray ionization response for model drug compounds. , 1999, Rapid communications in mass spectrometry : RCM.

[73]  K. Hoffman,et al.  Semi-automated 96-well liquid-liquid extraction for quantitation of drugs in biological fluids. , 2000, Journal of pharmaceutical and biomedical analysis.

[74]  J. Fenn,et al.  Ion formation from charged droplets: Roles of geometry, energy, and time , 1993, Journal of the American Society for Mass Spectrometry.

[75]  Walter A. Korfmacher,et al.  Quantitative screening and matrix effect studies of drug discovery compounds in monkey plasma using fast-gradient liquid chromatography/tandem mass spectrometry. , 2001, Rapid communications in mass spectrometry : RCM.

[76]  Walter A. Korfmacher,et al.  Direct analysis of plasma samples for drug discovery compounds using mixed-function column liquid chromatography tandem mass spectrometry. , 2000, Rapid communications in mass spectrometry : RCM.

[77]  P. Kebarle,et al.  Dependence of ion intensity in electrospray mass spectrometry on the concentration of the analytes in the electrosprayed solution , 1993 .

[78]  H. Lingeman,et al.  Particle-loaded membranes for sample concentration and/or clean-up in bioanalysis. , 1997, Journal of chromatography. B, Biomedical sciences and applications.

[79]  D. Hercules,et al.  Effect of liquid chromatography separation of complex matrices on liquid chromatography-tandem mass spectrometry signal suppression. , 2001, Journal of chromatography. A.

[80]  M. Karas,et al.  High-sensitivity analysis of neutral underivatized oligosaccharides by nanoelectrospray mass spectrometry. , 1997, Analytical chemistry.

[81]  F. Hsu,et al.  Formation of lithiated adducts of glycerophosphocholine lipids facilitates their identification by electrospray ionization tandem mass spectrometry , 1998, Journal of the American Society for Mass Spectrometry.

[82]  M. Karas,et al.  Effect of different solution flow rates on analyte ion signals in nano-ESI MS, or: when does ESI turn into nano-ESI? , 2003, Journal of the American Society for Mass Spectrometry.

[83]  C. Lipinski.  Drug-like properties and the causes of poor solubility and poor permeability. , 2000, Journal of pharmacological and toxicological methods.

[84]  P. Kebarle,et al.  Characterization of the reaction products of deoxyguanosine with the anticancer agent BFNU and BFNU-1,1,1',1'-d4 in different buffers by high-performance liquid chromatography/atmospheric pressure ionization tandem mass spectrometry. , 1990, Biomedical & environmental mass spectrometry.

[85]  S. Chowdhury,et al.  Factors affecting electrospray ionization of effluents containing trifluoroacetic acid for high-performance liquid chromatography/mass spectrometry. , 1993, Analytical chemistry.

[86]  S. A. McLuckey,et al.  Counting basic sites in oligopeptides via gas-phase ion chemistry. , 1997, Analytical chemistry.

[87]  A P Watt,et al.  Higher throughput bioanalysis by automation of a protein precipitation assay using a 96-well format with detection by LC-MS/MS. , 2000, Analytical chemistry.

[88]  Shaolian Zhou,et al.  A mechanistic study of electrospray mass spectrometry: Charge gradients within electrospray droplets and their influence on ion response , 2001, Journal of the American Society for Mass Spectrometry.

[89]  F. Hsu,et al.  Characterization of phosphatidylethanolamine as a lithiated adduct by triple quadrupole tandem mass spectrometry with electrospray ionization. , 2000, Journal of mass spectrometry : JMS.

[90]  M. Karas,et al.  Nano-electrospray ionization mass spectrometry: addressing analytical problems beyond routine , 2000, Fresenius' journal of analytical chemistry.

[91]  Walter A. Korfmacher,et al.  Cassette-accelerated rapid rat screen: a systematic procedure for the dosing and liquid chromatography/atmospheric pressure ionization tandem mass spectrometric analysis of new chemical entities as part of new drug discovery. , 2001, Rapid communications in mass spectrometry : RCM.

[92]  R. Plumb,et al.  Optimisation and routine use of generic ultra-high flow-rate liquid chromatography with mass spectrometric detection for the direct on-line analysis of pharmaceuticals in plasma. , 1998, Journal of chromatography. A.

[93]  C. Enke,et al.  Predicting electrospray response from chromatographic retention time. , 2001, Analytical chemistry.