Identification of deamidation and isomerization sites on pharmaceutical recombinant antibody using H218O

Analytical Biochemistry

Volumn 368, Issue 1, 2007, Pages 49-60

  Terashima, Isamu ^a   Koga, Akiko ^a   Nagai, Hiroshi ^a  

^a Analytical Technology Research Department   (Japan)

Author keywords

18O; Antibody; Deamidation; High performance liquid chromatography; Isomerization; Mass spectrometry; Peptide mapping

Indexed keywords

AMINO ACIDS; ANTIBODIES; DRUG PRODUCTS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERS; MAPPING; MASS SPECTROMETRY; MONOCLONAL ANTIBODIES; PEPTIDES;

DEAMIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY-MASS SPECTROMETRIES; HUMANIZED MONOCLONAL ANTIBODY; PEPTIDE MAPPING; PHARMACEUTICAL PROTEIN; RECOMBINANT ANTIBODY; TANDEM MASS SPECTROMETRY; ^18O;

ISOMERIZATION;

ASPARAGINE; ASPARTIC ACID; MONOCLONAL ANTIBODY; OXYGEN 18; RECOMBINANT ANTIBODY; TRYPSIN;

ARTICLE; CHEMICAL REACTION; DEAMINATION; FREEZE DRYING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERIZATION; PEPTIDE MAPPING; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY;

EID: 34447307909     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2007.05.012     Document Type: Article

References (23)

1. Brekke O.H., and Sandlie I. Therapeutic antibodies for human diseases at the dawn of the twenty-first century. Nat. Rev. Drug Discov. 2 (2003) 52-62
2. Harris R.J., Shire S.J., and Winter C. Commercial manufacturing scale formulation and analytical characterization of therapeutic recombinant antibodies. Drug Dev. Rev. 61 (2004) 137-154
3. Harris R.J. Processing of C-terminal lysine and arginine residues of proteins isolated from mammalian cell culture. J. Chromatogr. A 1 (1995) 129-134
4. Powell M.F. A compendium and hydropathy flexibility analysis of common reactive sites in proteins: Reactivity at Asn, Asp, Gln, and Met motifsin neutral pH solution. In: Pearlman R., and Wang Y.J. (Eds). Formulation, Characterization, and Stability of Protein Drugs vol. 9 (1996), Plenum, New York 1-81
5. Harris R.J. Heterogeneity of recombinant antibodies: Linking structure to function. Dev. Biol. 122 (2005) 117-127
6. Cacia J., Keck R., Presta L.G., and 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 35 (1996) 1897-1903
7. Harris R.J., Kabakoff B., Macchi F.D., Shen F.J., Kwong M., Andya J.D., Shire S.J., Bjork N., Totpal K., and Chen A.B. Identification of multiple sources of charge heterogeneity in a recombinant antibody. J. Chromatogr. B 752 (2001) 233-245
8. Patel K., and Borchardt R.T. Chemical pathways of peptide degradation: II. Kinetics of deamidation of an asparaginyl residue in a model hexapeptide. Pharm. Res. 7 (1990) 703-711
9. Patel K., and Borchardt R.T. Chemical pathways of peptide degradation: III. Effect of primary sequence on the pathways of deamidation of asparaginyl residues in hexapeptides. Pharm. Res. 7 (1990) 787-793
10. Oliyai C., and Borchardt R.T. Chemical pathways of peptide degradation: IV. Pathways, kinetics, and mechanism of degradation of an aspartyl residue in a model hexapeptide. Pharm. Res. 10 (1993) 95-102
11. Oliyai C., and Borchardt R.T. Chemical pathways of peptide degradation: VI. Effect of the primary sequence on the pathways of degradation of aspartyl residues in model hexapeptides. Pharm. Res. 5 (1994) 751-758
12. Geiger T., and Clarke S.J. Deamidation, isomerization, and racemization at asparaginyl and aspartyl residues in peptides: Succinimide-linked reactions that contribute to protein degradation. Biol. Chem. 262 (1987) 785-794
13. Tyler-Cross R., and Schirch V. Effects of amino acid sequence, buffers, and ionic strength on the rate and mechanism of deamidation of asparagine residues in small peptides. J. Biol. Chem. 266 (1991) 22549-22556
14. Kosky A.A., Razzaq U.O., Treuheit M.J., and Brems D.N. The effects of α-helix on the stability of Asn residues: Deamidation rates in peptides of varying helicity. Protein Sci. 8 (1999) 2519-2523
15. Robinson N.E., and Robinson A.B. Prediction of protein deamidation rates from primary and three-dimensional structure. Proc. Natl. Acad. Sci. USA 98 (2001) 4367-4372
16. Chelius D., Rehder D.S., and Bondarenko P.V. Identification and characterization of deamidation sites in the conserved regions of human immunoglobulin gamma antibodies. Anal. Chem. 77 (2005) 6004-6011
17. Grossenbacher H., Marki W., Coulot M., Muller D., and Richter W.J. Characterization of succinimide-type dehydration products of recombinant hirudin variant 1 by electrospray tandem mass spectrometry. Rapid Commun. Mass Spectrom. 12 (1993) 1082-1085
18. Huang L., Lu J., Wroblewski V.J., Beals J.M., and Riggin R.M. In vivo deamidation characterization of monoclonal antibody by LC/MS/MS. Anal. Chem. 77 (2005) 1432-1439
19. Aswad D.W., Paranandi M.V., and Schurter B.T. Isoaspartate in peptides and proteins: Formation, significance, and analysis. Pharm. Biomed. Anal. 6 (2000) 1129-1136
20. Lehmann W.D., Schlosser A., Erben G., Pipkorn R., Bossemeyer D., and Kinzel V. Analysis of isoaspartate in peptides by electrospray tandem mass spectrometry. Protein Sci. 11 (2000) 2260-2268
21. MacCoss M.J., and Matthews D.E. Quantitative MS for proteomics: Teaching a new dog old tricks. Anal. Chem. 77 (2005) 294A-302A
22. 18 O-labeled water. Anal. Biochem. 205 (1992) 151-158
23. Rose K., Simona M.G., Offord R.E., Prior C.P., Otto B., and Thatcher D.R. A new mass-spectrometric C-terminal sequencing technique finds a similarity between γ-interferon and α-2-interferon and identifies a proteolytically clipped γ-interferon that retains full antiviral activity. Biochem. J. 215 (1983) 273-277