Analytical protein a chromatography as a quantitative tool for the screening of methionine oxidation in monoclonal antibodies

Journal of Pharmaceutical Sciences

Volumn 101, Issue 11, 2012, Pages 4248-4257

  Loew, Caroline ^a   Knoblich, Constanze ^a   Fichtl, Jürgen ^b   Alt, Nadja ^b   Diepold, Katharina ^b   Bulau, Patrick ^b   Goldbach, Pierre ^a   Adler, Michael ^a   Mahler, Hanns Christian ^a   Grauschopf, Ulla ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

^b ROCHE DIAGNOSTICS GMBH   (Germany)

Author keywords

Analytical biochemistry; Antibody degradation; Bioanalysis; Fc domain; High throughput technologies; HPLC (high performance pressure liquid chromatography); Methionine; Oxidation; Protein A binding; Separation science

Indexed keywords

IMMUNOGLOBULIN FC FRAGMENT; METHIONINE; MONOCLONAL ANTIBODY; MONOCLONAL ANTIBODY 1; MONOCLONAL ANTIBODY 2; MONOCLONAL ANTIBODY 3; MONOCLONAL ANTIBODY 4; MONOCLONAL ANTIBODY 5; MONOCLONAL ANTIBODY 6; PROTEIN A; UNCLASSIFIED DRUG;

ARTICLE; CHROMATOGRAPHY; DRUG SCREENING; OXIDATION; PROTEIN ANALYSIS;

EID: 84866413853     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23286     Document Type: Article

References (33)

1. Shechter Y, Burstein Y, Patchornik A. 1975. Selective oxidation of methionine residues in proteins. Biochemistry 14(20):4497-4503.
2. Shechter Y. 1986. Selective oxidation and reduction of methionine residues in peptides and proteins by oxygen exchange between sulfoxide and sulfide. J Biol Chem 261(1):66-70.
3. Brot N, Weissbach H. 1983. Biochemistry and physiological role of methionine sulfoxide residues in proteins. Arch Biochem Biophys 223(1):271-281.
4. Ionescu R, Vlasak J. 2010. Kinetics of chemical degradation in monoclonal antibodies: Relationship between rates at the molecular and peptide levels. Anal Chem 82(8):3198-3206.
5. Ravi J, Hills AE, Cerasoli E, Rakowska PD, Ryadnov MG. 2011. FTIR markers of methionine oxidation for early detection of oxidized protein therapeutics. Eur Biophys J 40(3):339-345.
6. Pan H, Chen K, Chu L, Kinderman F, Apostol I, Huang G. 2009. Methionine oxidation in human IgG2 Fc decreases binding affinities to protein A and FcRn. Protein Sci 18(2):424-433.
7. Schoneich C. 2005. Methionine oxidation by reactive oxygen species: Reaction mechanisms and relevance to Alzheimer's disease. Biochim Biophys Acta 1703(2):111-119.
8. Stadtman ER, Moskovitz J, Levine RL. 2003. Oxidation of methionine residues of proteins: Biological consequences. Antioxid Redox Signal 5(5):577-582.
9. Wang W, Vlasak J, Li Y, Pristatsky P, Fang Y, Pittman T, Roman J, Wang Y, Prueksaritanont T, Ionescu R. 2011. Impact of methionine oxidation in human IgG1 Fc on serum half-life of monoclonal antibodies. Mol Immunol 48(6-7):860-866.
10. Kabat EA, Wu TT, Perry HM, Gottesman KS, Foeller C. 1991. Sequences of proteins of immunological interest. 5th ed. Washington, DC: Public Health Service NIH. NIH Publication No. 91-3242.
11. Lam XM, Yang JY, Cleland JL. 1997. Antioxidants for prevention of methionine oxidation in recombinant monoclonal antibody HER2. J Pharm Sci 86(11):1250-1255.
12. Chumsae C, Gaza-Bulseco G, Sun J, Liu H. 2007. Comparison of methionine oxidation in thermal stability and chemically stressed samples of a fully human monoclonal antibody. J Chromatogr B Analyt Technol Biomed Life Sci 850(1-2):285-294.
13. Deisenhofer J. 1981. Crystallographic refinement and atomic models of a human Fc fragment and its complex with fragment B of protein A from Staphylococcus aureus at 2.9- and 2.8-A resolution. Biochemistry 20(9):2361-2370.
14. Kronvall G, Frommel D. 1970. Definition of staphylococcal protein A reactivity for human immunoglobulin G fragments. Immunochemistry 7(1):124-127.
15. Hjelm H, Hjelm K, Sjoquist J. 1972. Protein A from Staphylococcus aureus. Its isolation by affinity chromatography and its use as an immunosorbent for isolation of immunoglobulins. FEBS Lett 28(1):73-76.
16. Goding JW. 1978. Use of staphylococcal protein A as an immunological reagent. J Immunol Methods 20:241-253.
17. Li R, Dowd V, Stewart DJ, Burton SJ, Lowe CR. 1998. Design, synthesis, and application of a protein A mimetic. Nat Biotechnol 16(2):190-195.
18. Sauer-Eriksson AE, Kleywegt GJ, Uhlen M, Jones TA. 1995. Crystal structure of the C2 fragment of streptococcal protein G in complex with the Fc domain of human IgG. Structure 3(3):265-278.
19. Ghose S, Allen M, Hubbard B, Brooks C, Cramer SM. 2005. Antibody variable region interactions with Protein A: Implications for the development of generic purification processes. Biotechnol Bioeng 92(6):665-673.
20. Michaelsen TE, Frangione B, Franklin EC. 1977. The amino acid sequence of a human immunoglobulin G3m(g) pFc' fragment. J Immunol 119(2):558-563.
21. Hamilton RG. 1987. The human IgG subclasses. Austin, Texas: Calbiochem-Novabiochem Corporation, pp 1-75.
22. Gaza-Bulseco G, Faldu S, Hurkmans K, Chumsae C, Liu H. 2008. Effect of methionine oxidation of a recombinant monoclonal antibody on the binding affinity to protein A and protein G. J Chromatogr B Analyt Technol Biomed Life Sci 870(1):55-62.
23. Liu H, Gaza-Bulseco G, Xiang T, Chumsae C. 2008. Structural effect of deglycosylation and methionine oxidation on a recombinant monoclonal antibody. Mol Immunol 45(3):701-708.
24. Hensel M, Steurer R, Fichtl J, Elger C, Wedekind F, Petzold A, Schlothauer T, Molhoj M, Reusch D, Bulau P. 2011. Identification of potential sites for tryptophan oxidation in recombinant antibodies using tert-butylhydroperoxide and quantitative LC-MS. PLoS One 6(3):e17708.
25. Diepold K, Bomans K, Wiedmann M, Zimmermann B, Petzold A, Schlothauer T, Mueller R, Moritz B, Stracke JO, Molhoj M, Reusch D, Bulau P. 2012. Simultaneous assessment of Asp isomerization and Asn deamidation in recombinant antibodies by LC-MS following incubation at elevated temperatures. PLoS One 7(1):e30295.
26. Baxter JH, Lai CS, Phillips RR, Dowlati L, Chio JJ, Luebbers ST, Dimler SR, Johns PW. 2007. Direct determination of methionine sulfoxide in milk proteins by enzyme hydrolysis/high-performance liquid chromatography. J Chromatogr A 1157(1-2):10-16.
27. Boyd D, Kaschak T, Yan B. 2011. HIC resolution of an IgG1 with an oxidized Trp in a complementarity determining region. J Chromatogr B Analyt Technol Biomed Life Sci 879(13-14):955-960.
28. Kishore RS, Kiese S, Fischer S, Pappenberger A, Grauschopf U, Mahler HC. 2011. The degradation of polysorbates 20 and 80 and its potential impact on the stability of biotherapeutics. Pharm Res 28(5):1194-1210.
29. Kishore RS, Pappenberger A, Dauphin IB, Ross A, Buergi B, Staempfli A, Mahler HC. 2011. Degradation of polysorbates 20 and 80: Studies on thermal autoxidation and hydrolysis. J Pharm Sci 100(2):721-731.
30. Wu Y, Levons J, Narang AS, Raghavan K, Rao VM. 2011. Reactive impurities in excipients: Profiling, identification and mitigation of drug-excipient incompatibility. AAPS PharmSciTech 12(4):1248-1263.
31. Fransson J, Hagman A. 1996. Oxidation of human insulin-like growth factor I in formulation studies, II. Effects of oxygen, visible light, and phosphate on methionine oxidation in aqueous solution and evaluation of possible mechanisms. Pharm Res 13(10):1476-1481.
32. Fransson J, Florin-Robertsson E, Axelsson K, Nyhlen C. 1996. Oxidation of human insulin-like growth factor I in formulation studies: Kinetics of methionine oxidation in aqueous solution and in solid state. Pharm Res 13(8):1252-1257.
33. Bjorck L, Kronvall G. 1984. Purification and some properties of streptococcal protein G, a novel IgG-binding reagent. J Immunol 133(2):969-974.