Kinetic Modeling of Methionine Oxidation in Monoclonal Antibodies from Hydrogen Peroxide Spiking Studies

References

1. 1.↵
   1. Bertolotti-Ciarlet A.,
   2. Wang W.,
   3. Lownes R.,
   4. Pristatsky P.,
   5. Fang Y.,
   6. McKelvey T.,
   7. Li Y.,
   8. Drummond J.,
   9. Prueksaritanont T.,
   10. Vlasak J.

   Impact of methionine oxidation on the binding of human IgG1 to Fc Rn and Fc gamma receptors. Mol. Immunol. 2009, 46 (8–9), 1878–1882.

   OpenUrlCrossRefPubMed
2. 2.↵
   1. Chumsae C.,
   2. Gaza-Bulseco G.,
   3. Sun J.,
   4. Liu H.

   Comparison of methionine oxidation in thermal stability and chemically stressed samples of a fully human monoclonal antibody. J. Chromatogr., B 2007, 850 (1–2), 285–294.

   OpenUrlCrossRef
3. 3.↵
   1. Lam X. M.,
   2. Yang J. Y.,
   3. Cleland J. L.

   Antioxidants for prevention of methionine oxidation in recombinant monoclonal antibody HER2. J. Pharm. Sci. 1997, 86 (11), 1250–1255.

   OpenUrlCrossRefPubMed
4. 4.↵
   1. Loew C.,
   2. Knoblich C.,
   3. Fichtl J.,
   4. Alt N.,
   5. Diepold K.,
   6. Bulau P.,
   7. Goldbach P.,
   8. Adler M.,
   9. Mahler H. C.,
   10. Grauschopf U.

   Analytical protein a chromatography as a quantitative tool for the screening of methionine oxidation in monoclonal antibodies. J. Pharm. Sci. 2012, 101 (11), 4248–4257.

   OpenUrlPubMed
5. 5.↵
   1. Pan H.,
   2. Chen K.,
   3. Chu L.,
   4. Kinderman F.,
   5. Apostol I.,
   6. Huang G.

   Methionine oxidation in human IgG2 Fc decreases binding affinities to protein A and FcRn. Protein Sci. 2009, 18 (2), 424–433.

   OpenUrlCrossRefPubMedWeb of Science
6. 6.↵
   1. Wang W.,
   2. Vlasak J.,
   3. Li Y.,
   4. Pristatsky P.,
   5. Fang Y.,
   6. Pittman T.,
   7. Roman J.,
   8. Wang Y.,
   9. Prueksaritanont T.,
   10. Ionescu R.

   Impact of methionine oxidation in human IgG1 Fc on serum half-life of monoclonal antibodies. Mol. Immunol. 2011, 48 (6–7), 860–866.

   OpenUrlCrossRefPubMed
7. 7.↵
   1. Stracke J.,
   2. Emrich T.,
   3. Rueger P.,
   4. Schlothauer T.,
   5. Kling L.,
   6. Knaupp A.,
   7. Herternberger H.,
   8. Wolfert A.,
   9. Spick C.,
   10. Lau W.,
   11. Drabner G.,
   12. Reiff U.,
   13. Koll H.,
   14. Papadimitriou A.

   A novel approach to investigate the effect of methionine oxidation on pharmacokinetic properties of therapeutic antibodies. MAbs 2014, 6 (5), 1129–1242.

   OpenUrl
8. 8.↵
   1. Kabat E. A.,
   2. Wu T. T.,
   3. Perry H. M.,
   4. Gottesman K. S.,
   5. Foeller C.

   Sequences of proteins of immunological interest. 1991, NIH Publication no. 91-3242.
9. 9.↵
   1. Deisenhofer J.

   Crystallographic refinement and atomich models of human Fc fragment and its complex with fragment B of protein A from Staphylococcus aureus at 2.9- and 2.8-A resolution. Biochemistry 1981, 20 (9), 2361–2370.

   OpenUrlCrossRefPubMedWeb of Science
10. 10.↵
    1. Houde D.,
    2. Kauppinen P.,
    3. Mhatre R.,
    4. Lyuvarskaya Y.

    Determination of protein oxidation by mass spectrometry and method transfer to quality control. J. Chromatogr., A 2006, 1123 (2), 189–198.

    OpenUrlCrossRefPubMedWeb of Science
11. 11.↵
    1. Ji J. A.,
    2. Zhang B.,
    3. Cheng W.,
    4. Wang Y. J.

    Methionine, tryptophan, and histidine oxidation in a model protein, PTH: mechanisms and stabilization. J. Pharm. Sci. 2009, 98 (12), 4485–4500.

    OpenUrlCrossRefPubMed
12. 12.↵
    1. Keck R. G.

    The use of t-butyl hydroperoxide as a probe for methionine oxidation in proteins. Anal. Biochem. 1996, 236 (1), 56–62.

    OpenUrlCrossRefPubMedWeb of Science
13. 13.↵
    1. Manning M. C.,
    2. Patel K.,
    3. Borchardt R. T.

    Stability of protein pharmaceuticals. Pharm. Res. 1989, 6 (11), 903–918.

    OpenUrlCrossRefPubMedWeb of Science
14. 14.↵
    1. Marshak D. R

    1. Shen F. J.,
    2. Kwong M. Y.,
    3. Keck R. G.,
    4. Harris R. J.

    The Application of tert-Butylhydroperoxide Oxidation to Study Sites of Potential Methionine Oxidation in a Recombinant Antibody. In Techniques in Protein Chemistry VII; Marshak D. R, Ed.; Academic Press: San Diego, CA, 1996; pp 275–284.
15. 15.↵
    1. Bounoure F.,
    2. Fiquet H.,
    3. Arnaud P.

    Comparison of hydrogen peroxide and peracetic acid as isolator sterilization in a hospital pharmacy. Am. J. Health-Syst. Pharm. 2006, 63 (5), 451–455.

    OpenUrlAbstract/FREE Full Text
16. 16.↵
    1. Krishna A. K.,
    2. Lodhi S. A.,
    3. Harris M. R.

    Isolation technology for research and development applications: from concept to production. Pharm. Dev. Technol. 2000, 5 (4), 507–520.

    OpenUrlPubMed
17. 17.↵
    1. Schoneich C.,
    2. Zhao F.,
    3. Wilson G. S.,
    4. Borchardt R. T.

    Iron-thiolate induced oxidation of methionine to methionine sulfoxide in small model peptides. Intramolecular catalysis by histidine. Biochim. Biophys. Acta 1993, 1158 (3), 307–322.

    OpenUrlPubMed
18. 18.↵
    1. Kharasch N.,
    2. Meyers C. Y.

    1. Barnard D.,
    2. Bateman L.,
    3. Cuneen J. L.

    The Chemistry of Organic Sulfur Compounds. In Kharasch N., Meyers C. Y., Eds. Pergamon Press: New York, 1961; Vol. 1, pp 229–247.
19. 19.↵
    1. Nguyen T. H.,
    2. Burnier J.,
    3. Meng W.

    The kinetics of relaxin oxidation by hydrogen peroxide. Pharm. Res. 1993, 10 (11), 1563–1571.

    OpenUrlPubMed
20. 20.↵
    1. Chu J. W.,
    2. Brooks B. R.,
    3. Trout B. L.

    Oxidation of methionine residues in aqueous solutions: free methionine and methionine in granulocyte colony-stimulationg factor. J. Am. Chem. Soc. 2004, 126 (50), 16601–16607.

    OpenUrlPubMed
21. 21.↵
    1. Liu D.,
    2. Ren D.,
    3. Huang H.,
    4. Dankberg J.,
    5. Rosenfeld R.,
    6. Cocco M. J.,
    7. Li L.,
    8. Brems D. N.,
    9. Remmele R. L. J.

    Structure and stability changes of human IgG1 Fc as a consequence of methionine oxidation. Biochem. 2008, 47 (18), 5088–5100.

    OpenUrlCrossRefPubMedWeb of Science