A rapid on-line method for mass spectrometric confirmation of a cysteine-conjugated antibody-drug-conjugate structure using multidimensional chromatography

References

• Senter PD. Potent antibody drug conjugates for cancer therapy. Curr Opin Chem Biol 2009; 13:235-44; http://dx.doi.org/10.1016/j.cbpa.2009.03.023
   PubMed Web of Science ®Google Scholar
• Chari RV. Targeted cancer therapy: conferring specificity to cytotoxic drugs. Acc Chem Res 2008; 41:98-107; PMID:17705444; http://dx.doi.org/10.1021/ar700108g
   PubMed Web of Science ®Google Scholar
• Lewis Phillips GD, Li G, Dugger DL, Crocker LM, Parsons KL, Mai E, Blättler WA, Lambert JM, Chari RV, Lutz RJ, et al. Targeting HER2-positive breast cancer with trastuzumab-DM1, an antibody-cytotoxic drug conjugate. Cancer Res 2008; 68:9280-90; PMID:19010901; http://dx.doi.org/10.1158/0008-5472.CAN-08-1776
   PubMed Web of Science ®Google Scholar
• Palanca-Wessels M, Press OW. Advances in the treatment of hematologic malignancies using immunoconjugates. Blood 2014; 123:2293-301; PMID:24578502; http://dx.doi.org/10.1182/blood-2013-10-492223
   PubMed Web of Science ®Google Scholar
• Ansell SM. Brentuximab vedotin. Blood 2014; 124:3197-200; PMID:25293772; http://dx.doi.org/10.1182/blood-2014-06-537514
   PubMed Web of Science ®Google Scholar
• Reichert JM, Rosensweig CJ, Faden LB, Dewitz MC. Monoclonal antibody successes in the clinic. Nat Biotech 2005; 23:1073-8; http://dx.doi.org/10.1038/nbt0905-1073
   PubMed Web of Science ®Google Scholar
• Wu AM, Senter PD. Arming antibodies: prospects and challenges for immunoconjugates. Nat Biotech 2005; 23:1137-46; http://dx.doi.org/10.1038/nbt1141
   PubMed Web of Science ®Google Scholar
• Lambert JM. Drug-conjugated monoclonal antibodies for the treatment of cancer. Curr Opin Pharmacol 2005; 5:543-9; http://dx.doi.org/10.1016/j.coph.2005.04.017
   PubMed Web of Science ®Google Scholar
• Pro B, Advani R, Brice P, Bartlett N, Rosenblatt J, Illidge T, Matous J, Ramchandren R, Fanale M, Connors JM, et al. Brentuximab Vedotin (SGN-35) in Patients With Relapsed or Refractory Systemic Anaplastic Large-Cell Lymphoma: Results of a Phase II Study. J Clin Onocol 2012; 30:2190-6; http://dx.doi.org/10.1200/JCO.2011.38.0402
   PubMed Web of Science ®Google Scholar
• Junutula JR, Raab H, Clark S, Bhakta S, Leipold DD, Weir S, Chen Y, Simpson M, Tsai SP, Dennis MS, et al. Site-specific conjugation of a cytotoxic drug to an antibody improves the therapeutic index. Nat Biotechnol 2008; 26:925-32; http://dx.doi.org/10.1038/nbt.1480
   PubMed Web of Science ®Google Scholar
• Wakankar A, Chen Y, Gokarn Y, Jacobson FS. Analytical methods for physicochemical characterization of antibody drug conjugates. Mabs 2011; 3:161-72; PMID:21441786; http://dx.doi.org/10.4161/mabs.3.2.14960
   PubMed Web of Science ®Google Scholar
• Sun MM, Beam KS, Cerveny CG, Hamblett KJ, Blackmore RS, Torgov MY, Handley FG, Ihle NC, Senter PD, Alley SC. Reduction-alkylation strategies for the modification of specific monoclonal antibody disulfides. Bioconjug Chem 2005; 16:1282-90; PMID:16173809; http://dx.doi.org/10.1021/bc050201y
   PubMed Web of Science ®Google Scholar
• Hamann PR, Hinman LM, Hollander I, Beyer CF, Lindh D, Holcomb R, Hallett W, Tsou HR, Upeslacis J, Shochat D, et al. Gemtuzumab Ozogamicin, A Potent and Selective Anti-CD33 Antibody-Calicheamicin Conjugate for Treatment of Acute Myeloid Leukemia. Bioconjugate Chemistry 2001; 13:47-58; http://dx.doi.org/10.1021/bc010021y
   Web of Science ®Google Scholar
• McDonagh CF, Turcott E, Westendorf L, Webster JB, Alley SC, Kim K, Andreyka J, Stone I, Hamblett KJ, Francisco JA, et al. Engineered antibody-drug conjugates with defined sites and stoichiometries of drug attachment. Protein Eng Des Sel 2006; 19:299-307; PMID:16644914; http://dx.doi.org/10.1093/protein/gzl013
   PubMed Web of Science ®Google Scholar
• Hamblett KJ, Senter PD, Chace DF, Sun MM, Lenox J, Cerveny CG, Kissler KM, Bernhardt SX, Kopcha AK, Zabinski RF, et al. Effects of drug loading on the antitumor activity of a monoclonal antibody drug conjugate. Clin Cancer Res 2004; 10:7063-70; PMID:15501986; http://dx.doi.org/10.1158/1078-0432.CCR-04-0789
   PubMed Web of Science ®Google Scholar
• Sanderson RJ, Hering MA, James SF, Sun MM, Doronina SO, Siadak AW, Senter PD, Wahl AF. In vivo drug-linker stability of an anti-CD30 dipeptide-linked auristatin immunoconjugate. Clin Cancer Res 2005; 11:843-52; PMID:15701875
   PubMed Web of Science ®Google Scholar
• Le LN, Moore JMR, Ouyang J, Chen X, Nguyen MDH, Galush WJ. Profiling Antibody Drug Conjugate Positional Isomers: A System-of-Equations Approach. Anal Chem 2012; 84:7479-86; PMID:22913809; http://dx.doi.org/10.1021/ac301568f
   PubMed Web of Science ®Google Scholar
• Valliere-Douglass J, Wallace A, Balland A. Separation of populations of antibody variants by fine tuning of hydrophobic-interaction chromatography operating conditions. J Chromatogr A 2008; 1214:81-9; http://dx.doi.org10.1016/j.chroma.2008.10.078
   PubMed Web of Science ®Google Scholar
• Boyd D, Kaschak T, Yan B. HIC resolution of an IgG1 with an oxidized Trp in a complementarity determining region. J Chromatogr B 2011; 879:955-60; http://dx.doi.org/10.1016/j.jchromb.2011.03.006
   PubMed Web of Science ®Google Scholar
• Cacia J, Keck R, Presta LG, Frenz J. Isomerization of an Aspartic Acid Residue in the Complementarity-Determining Regions of a Recombinant Antibody to Human IgE: Identification and Effect on Binding Affinity. Biochemistry 1996; 35:1897-903; PMID:8639672; http://dx.doi.org/10.1021/bi951526c
   PubMed Web of Science ®Google Scholar
• Lazar AC, Wang L, Blattler WA, Amphlett G, Lambert JM, Zhang W. Analysis of the composition of immunoconjugates using size-exclusion chromatography coupled to mass spectrometry. Rapid Commun Mass Spectrom 2005; 19:1806-14; PMID:15945030; http://dx.doi.org/10.1002/rcm.1987
   PubMed Web of Science ®Google Scholar
• Chen J, Yin S, Wu Y, Ouyang J. Development of a native nanoelectrospray mass spectrometry method for determination of the drug-to-antibody ratio of antibody-drug conjugates. Anal Chem 2013; 85:1699-704; PMID:23289544; http://dx.doi.org/10.1021/ac302959p
   PubMed Web of Science ®Google Scholar
• Valliere-Douglass JF, McFee WA, Salas-Solano O. Native Intact Mass Determination of Antibodies Conjugated with Monomethyl Auristatin E and F at Interchain Cysteine Residues. Anal Chem 2012; 84:2843-9; PMID:22384990; http://dx.doi.org/10.1021/ac203346c
   PubMed Web of Science ®Google Scholar
• Wagner-Rousset E, Janin-Bussat M, Colas O, Excoffier M, Ayoub D, Haeuw J, Rilatt I, Perez M, Corvaïa N, Beck A, et al. Antibody-drug conjugate model fast characterization by LC-MS following IdeS. Mabs 2014; 6:173-84; PMID:25006625; http://dx.doi.org/10.4161/mabs.26773
   PubMed Web of Science ®Google Scholar
• Debaene F, Boeuf A, Wagner-Rousset E, Colas O, Ayoub D, Corvaia N, Van Dorsselaer A, Beck A, Cianférani S. Innovative Native MS Methodologies for Antibody Drug Conjugate Characterization: High Resolution Native MS and IM-MS for Average DAR and DAR Distribution Assessment. Anal Chem 2014; 86:10674-83; PMID:25270580; http://dx.doi.org/10.1021/ac502593n
   PubMed Web of Science ®Google Scholar
• Debaene F, Wagner-Rousset E, Colas O, Ayoub D, Corvaia N, Van Dorsselaer A, Beck A, Cianférani S. Time Resolved Native Ion-Mobility Mass Spectrometry to Monitor Dynamics of IgG4 Fab Arm Exchange and “Bispecific” Monoclonal Antibody Formation. Anal Chem 2013; 85:9785-92; PMID:24007193; http://dx.doi.org/10.1021/ac402237v
   PubMed Web of Science ®Google Scholar
• Pacholarz KJ, Porrini M, Garlish RA, Burnley RJ, Taylor RJ, Henry AJ, Barran PE. Dynamics of Intact Immunoglobulin G Explored by Drift-Tube Ion-Mobility Mass Spectrometry and Molecular Modeling. Angew Chem Int Ed Engl 2014; 53:7765-9; http://dx.doi.org/10.1002/anie.201402863
   PubMed Web of Science ®Google Scholar
• Beck A, Wagner-Rousset E, Ayoub D, Van Dorsselaer A, Sanglier-Cianferani S. Characterization of Therapeutic Antibodies and Related Products. Anal Chem 2013; 85:715-36; PMID:23134362; http://dx.doi.org/10.1021/ac3032355
   PubMed Web of Science ®Google Scholar
• Beck A, Sanglier-Cianferani S, Van Dorsselaer A. Biosimilar, Biobetter, and Next Generation Antibody Characterization by Mass Spectrometry. Anal Chem 2012; 84:4637-46; PMID:22510259; http://dx.doi.org/10.1021/ac3002885
   PubMed Web of Science ®Google Scholar
• Janin-Bussat MC, Dillenbourg M, Corvaia N, Beck A, Klinguer-Hamour C. Characterization of antibody drug conjugate positional isomers at cysteine residues by peptide mapping LC-MS analysis. J Chromatogr B Analyt Technol Biomed Life Sci 2014; 981-982:9-13; PMID:25596378
   PubMed Web of Science ®Google Scholar
• Zhang K, Li Y, Tsang M, Chetwyn NP. Analysis of pharmaceutical impurities using multi-heartcutting 2D LC coupled with UV-charged aerosol MS detection. J Sep Sci 2013; 36:2986-92; PMID:23821312
   PubMed Web of Science ®Google Scholar
• Gilar M, Yu Y-Q, Ahn J, Xie H, Han H, Ying W, Gilar M, Yu YQ, Ahn J, Xie H, Han H, Ying W. Characterization of glycoprotein digests with hydrophilic interaction chromatography and mass spectrometry. Anal Biochem 2011; 417:80-8; PMID:21689629; http://dx.doi.org/10.1016/j.ab.2011.05.028
   PubMed Web of Science ®Google Scholar
• Doneanu C, Xenopoulos A, Fadgen K, Murphy J, Skilton SJ, Prentice H, Stapels M, Chen W. Analysis of host-cell proteins in biotherapeutic proteins by comprehensive online two-dimensional liquid chromatography/mass spectrometry. Mabs 2012; 4:24-44; PMID:22327428; http://dx.doi.org/10.4161/mabs.4.1.18748
   PubMed Web of Science ®Google Scholar
• Li Y, Hewitt D, Lentz YK, Ji JA, Zhang TY, Zhang K. Characterization and Stability Study of Polysorbate 20 in Therapeutic Monoclonal Antibody Formulation by Multidimensional Ultrahigh-Performance Liquid Chromatography-Charged Aerosol Detection-Mass Spectrometry. Anal Chem 2014; 86:5150-7; PMID:24749737; http://dx.doi.org/10.1021/ac5009628
   PubMed Web of Science ®Google Scholar
• Annesley T. Ion Suppresion in Mass Spectrometry. Clin Chem 2003; 49:1041-4; PMID:12816898; http://dx.doi.org/10.1373/49.7.1041
   PubMed Web of Science ®Google Scholar
• King R, Bonfiglio R, Fernandez-Metzler C, Miller-Stein C, Olah T. Mechanistic investigation of ionization suppression in electrospray ionization. J Am Soc Mass Spectrom 2000; 11:942-50; http://dx.doi.org/10.1016/S1044-0305(00)00163-X]
   PubMed Web of Science ®Google Scholar
• Lyon RP, Setter JR, Bovee TD, Doronina SO, Hunter JH, Anderson ME, Balasubramanian CL, Duniho SM, Leiske CI, Li F, et al. Self-hydrolyzing maleimides improve the stability and pharmacological properties of antibody-drug conjugates. Nat Biotechol 2014; 32:1059-62; http://dx.doi.org/10.1038/nbt.2968
   PubMed Web of Science ®Google Scholar
• Panowski S, Bhakta S, Raab H, Polakis P, Junutula JR. Site-specific antibody drug conjugates for cancer therapy. Mabs 2014; 6:34-45; PMID:24423619; http://dx.doi.org/10.4161/mabs.27022
   PubMed Web of Science ®Google Scholar
• Behrens CR, Liu B. Methods for site-specific drug conjugation to antibodies. Mabs 2014; 6:46-53; PMID:24135651; http://dx.doi.org/10.4161/mabs.26632
   PubMed Web of Science ®Google Scholar