Chemical modifications of therapeutic proteins induced by residual ethylene oxide

Journal of Pharmaceutical Sciences

Volumn 104, Issue 2, 2015, Pages 731-739

  Chen, Louise ^a   Sloey, Christopher ^a   Zhang, Zhongqi ^a   Bondarenko, Pavel V ^a   Kim, Hyojin ^a   Ren, Da ^a   Kanapuram, Sekhar ^a  

^a AMGEN INC   (United States)

Author keywords

Analytical biochemistry; Chromatography; Drug delivery systems; Formulation; HPLC; Injectables; Mass spectrometry; Peptides; Protein delivery; Proteins

Indexed keywords

ETHYLENE OXIDE; HUMAN SERUM ALBUMIN; METHIONINE; PEGFILGRASTIM; RECOMBINANT ERYTHROPOIETIN; RESIDUAL ETHYLENE OXIDE; UNCLASSIFIED DRUG; DRUG; EPO PROTEIN, HUMAN; ERYTHROPOIETIN; GRANULOCYTE COLONY STIMULATING FACTOR; SERUM ALBUMIN;

ALKYLATION; ARTICLE; CATION EXCHANGE; COLLISIONALLY ACTIVATED DISSOCIATION; CONTROLLED STUDY; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYDROPHOBICITY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OXIDATION; PEPTIDE MAPPING; PROTEIN MODIFICATION; TANDEM MASS SPECTROMETRY; AMINO ACID SEQUENCE; CHEMISTRY; GENETICS; MOLECULAR GENETICS;

AMINO ACID SEQUENCE; ERYTHROPOIETIN; ETHYLENE OXIDE; GRANULOCYTE COLONY-STIMULATING FACTOR; HUMANS; MOLECULAR SEQUENCE DATA; PHARMACEUTICAL PREPARATIONS; SERUM ALBUMIN;

EID: 84922894725     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.24257     Document Type: Article

References (15)

1. Windmueller HG, Ackerman CJ, Engel RW. 1958. Reaction of ethylene oxide with histidine, methionine and cysteine. J Biol Chem 234(4):895-899.
2. Kelsey JC. 1961. Sterilization by ethylene oxide. J Clin Pathol 14:59-61.
3. Ford DJ. 1976. The effect of methods of sterilization on the nutritive value of protein in a commercial rat diet. Br J Nutr 35:267-276.
4. Wu KY, Chiang SY, Shih WC, Huang CC, Chen MF, Swenberg JA. 2011. The application of mass spectrometry in molecular dosimetry: Ethylene oxide as an example. Mass Spectrom Rev 30(5):733-756.
5. Mendes GCC, Brandao TRS, Silva CLM. 2007. Ethylene oxide sterilization of medical devices: A review. Am J Infect Control 35:574-581.
6. Nakata S, Umeshita K, Ueyama H, Takashina M, Noguchi S, Murata A, Ochi T. 2000. Aeration time following ethylene oxide sterilization for reusable rigid sterilization containers: Concentration of gaseous ethylene oxide in containers. Biomed Instrum Technol 34:121-124.
7. Lucas AD, Merritt K, Hitchins VM, Woods TO, McNamee SG, Lyle DB, Brown SA. 2003. Residual ethylene oxide in medical devices and device material. J Biomed Mater Res Part B 66B:548-552.
8. Buben L, Melichercikova V, Novotna N, Svitakova R. 1999. Problems associated with sterilization using ethylene oxide residues in treated materials. Centr Eur J Publ Hlth 7(4):197-202.
9. Dias FN, Ishii M, Nogaroto Sl, Piccini B, Penna TCV. 2009. Sterilization of medical devices by ethylene oxide, determination of the dissipation of residues, and use of green fluorescent protein as an indicator of process control. J Biomed Mater Res Part B 91B:626-630.
10. Pan B, Abel J, Ricci M, Brems D, Wang D, Trout B. 2006. Comparative oxidation studies of methionine residues reflect a structural effect on chemical kinetics in rhG-CSF. Biochemistry 45:15430-15443.
11. Chu J, Yin J, Wang D, Trout B. 2004. Molecular dynamics simulations and oxidation rates of methionine residues of Granulocyte colony-stimulating factor at different pH values. Biochemistry 43:1019-1029.
12. Jiang X, Smith JB, Abraham EC. 1996. Identification of a MS-MS fragment diagnostic for methionine sulfoxide. J Mass Spectrom 31(11):1309-1310.
13. Zhang Z. 2011. Prediction of collision-induced-dissociation spectra of peptides with post-translational or process-induced modifications. Anal Chem 83:8642-8651.
14. Beck JL, Ambahera S, Yong SR, Sheil MM, de Jersey J, Ralph SF. 2004. Direct observation of covalent adducts with Cys34 of human serum albumin using mass spectrometry. Anal Biochem 325(2):326-336.
15. Grammer LC, Patterson R. 1987. IgE against ethylene-altered human serum albumin (EtO-HSA) as an etiologic agent in allergic reactions of hemodialysis patients. Artif Organs 11:97-99.