Solid-phase PEGylation of recombinant interferon α-2a for site-specific modification: Process performance, characterization, and in vitro bioactivity

Bioconjugate Chemistry

Volumn 18, Issue 6, 2007, Pages 1728-1734

  Byung, Kook Lee ^a   Jin, Sook Kwon ^a   Hyung, Jin Kim ^a   Yamamoto, Shuichi ^b   Lee, E K ^a  

^a Hanyang University   (South Korea)

^b YAMAGUCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; ANTIBIOTICS; BIOACTIVITY; CELL PROLIFERATION; GLYCOPROTEINS; MOLECULAR WEIGHT; MOLECULES; MONOCLONAL ANTIBODIES; SURFACE PLASMON RESONANCE;

IN-VITRO BIOACTIVITY; MODIFICATION PROCESS; N TERMINUS; PEGYLATION; PERFORMANCE CHARACTERIZATION; PROCESS PERFORMANCE; SITE-SPECIFIC MODIFICATIONS; SOLID PHASIS; SOLID-PHASE; SOLUTION PHASE;

PURIFICATION;

CATION EXCHANGE RESIN; RECOMBINANT ALPHA2A INTERFERON; TRYPSIN;

ALKYLATION; AMINO TERMINAL SEQUENCE; ANIMAL CELL; ANTIGEN BINDING; ANTIVIRAL ACTIVITY; ARTICLE; CELL PROLIFERATION; CHEMICAL MODIFICATION; CHROMATOGRAPHY; CONTROLLED STUDY; DRUG CONJUGATION; DRUG PURIFICATION; DRUG SPECIFICITY; IN VITRO STUDY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOLECULAR WEIGHT; NONHUMAN; SURFACE PLASMON RESONANCE; THERMOSTABILITY;

EID: 36849064395     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc060245m     Document Type: Article

References (36)

1. Corssmit, E. P. M., Metz, J. D., Sauerwein, H. P., and Romun, J. A. (2000) Biologic responses to IFN-a administration in humans. J. Interferon Cytokine Res. 20, 1039-1047.
2. Potera, C. (2003) Pegylation for improving polypeptide drugs. Genet. Eng. News 23, 58-60.
3. Perry, C. M., and Blair, J. (2001) Peginterferon-alpha-2a (40kD). Drugs 61, 2263-2288.
4. Bailon, P., Palleroni, A., Schaffer, C. A., Spence, C. L., Fung, W. J., Porter, J. E., Ehrlich, G. K., Pan, W., Xu, Z. X., Modi, M. W., Farid, A., and Berthold, W. (2001) Rational design of a potent, long-lasting form of interferon: A 40 kDa branched polyethylene glycol-conjugated interferon alpha 2a for the treatment of Hepatitis C. Bioconjugate Chem. 12, 195-202.
5. Harris, J. M., Martin, N. E., and Modi, M. (2001) PEGylation: A novel process for modifying pharmacokinetics. Clin. Pharmacokinet. 40, 539-551.
6. Liptakova, H., and Kontsek, P. (1990) Problem of recombinant interferon alpha 2-immunogenicity in therapy. Do Redakcie Doslo 100, 139-143.
7. Reddy, K. R., Wright, T. L., Pockros, P. J., Shiffman, M., Eversom, G., Reindollar, R., Fride, M. W., Purdum III, P. P., Jensen, D., Smith, C., Lee, W. M., Boyer, T. D., Lin, A., Pedder, S., and Depamphilis, J. (2001) Efficacy and safety of PEGylated (40 kDa) interferon alpha 2a compared with interferon alpha 2a in noncirrhotic patients with chronic Hepatitis C. Hepatology 33, 433-438.
8. Pepinsky, R. B., Doreen, J. L., and Alan, G. (2001) Improved pharmacokinetic properties of a polyethylene glycol modified form of interferon-beta-1a with preserved in vitro bioactivity. J. Pharmacol. Exp. Ther. 297, 1059-1066.
9. Bailon, P., and Berthold, W. (1998) Polyethylene glycol-conjugated pharmaceutical proteins. P. S. T. T. 1, 352-356.
10. Hinds, K. D., and Kim, S. W. (2002) Effect of PEG conjugation on insulin properties. Adv. Drug Delivery Rev. 54, 505-530.
11. Kodera, Y., Matsushima, A., Hiroto, M., Nishimura, H., Ishii, A., Ueno, T., and Inada, Y. (1998) PEGylation of proteins and bioactive substances for medical and technical applications. Prog. Polymer. Sci. 23, 1233-1271.
12. Zalipsky, S. (1995) Chemistry of polyethylene glycol conjugates with biologically active molecules. Adv. Drug Delivery Rev. 16, 157-182.
13. Conover, C. D., Greenwald, R. B., Pendri, A., and Shum, K. L. (1999) Camptothecin delivery systems: the utility of amino acid spacers for the conjugation of camptothecin with polyethylene glycol to create prodrugs. Anti-Cancer Drug Des. 14, 499-506.
14. Means, G. E., and Feeney, R. E. (1995) Reductive alkylation of proteins. Anal. Biochem. 224, 1-16.
15. Kinstler, O. B., Brems, D. N., Lauren, S. L., Paige, A. G., Hamburger, J. B., and Treuheit, M. J. (1996) Characterization and stability of N-terminally PEGylated rhG-CSF. Pharmacol. Res. 13, 996-1002.
16. Kinstler, O. B. (1998) U.S. Patent 19, 5824784.
17. Kinstler, O., Molineux, G., Treuheit, M., Ladd, D., and Gegg, C. (2002) Mono-N-terminal poly(ethylene glycol)-protein conjugates. Adv. Drug Delivery Rev. 54, 477-485.
18. Yamamoto, Y., Tsutsumi, Y., Yoshioka, Y., Nishibata, T., Kobayashi, K., Okamoto, T., Mukai, Y., Shimizu, T., Nakagawa, S., Nagata, S., and Mayumi, T. (2003) Site-specific PEGylation of a lysine-deficient TNF-alpha with full bioactivity. Nat. Biotechnol. 21, 546-552.
19. Fee, C. J., and Alstine, J. M. V. (2006) PEG-protein: reaction engineering and separation issues. Chem. Eng. Sci. 61, 924-939.
20. Harris, J. M. and Zalipsky, S. (1997) Poly(ethylene glycol) Chemistry and Biological Application, pp 207-216, American Chemical Society, Washington, DC,
21. Lee, B. K., Lee, J. D. and Lee, E. K. (2004) Solid-Phase, N-Terminus-Specific, Mono-PEGylation of Recombinant Interferon-α-2a: Purification, Characterization, and Bioactivity, presented at ISPPP 2004, Aachen, Germany.
22. Lee, E. K. (2004) Korean Patent #0453185.
23. Takacs, M. A., Jacobs, S. J., Bordens, R. M., and Swanson., S. J. (1999) Detention and characterization of antibodies to PEG-IFN-alpha 2b using surface plasmon resonance. J. Interferon Cytokine Res. 19, 781-789.
24. Rubinstein, S., Familletti, P. C., and Pestaka, S. (1981) Convenient assay for interferons. J. Virol. 37, 755-758.
25. Gillis, E. H., Gosling, J. P., Sreenan, J. M., and Kane, M. (2002) Development and validation of a biosensor-based immunoassay for progesterone in bovine milk. J. Immunol. Methods 267, 131-138.
26. Lofas, S., Malmqvist, M., Ronnberg, I., and Stenberg, E. (1991) Bioanalysis with surface plasmon resonance. Sens. Actuators, B 5, 79-84.
27. Hellman, U., Wernstedt, C., Gonez, J., and Heldin, C. (1995) Improvement of an "In-Gel" digestion procedure for the micropreparation of internal protein fragments for amino acid sequencing. Anal. Biochem. 224, 451-455.
28. Ghorbel, B., Kamoun, A. S., and Nasri, M. (2003) Stability studies of protease from bacillus cereus BG1. Enzyme Microb. Technol. 6261, 1-6.
29. Allen, D., Baffi, R., Bausch, J., Bongers, J., Costello, M., Dougherty, J., Federici, M., Jr., Garnick, R., Peterson, S., Riggins, R., Sewerin, K., and Tuls, J. (1996) Validation of peptide mapping for protein identity and genetic stability. Biologicals 24, 255-275.
30. Seely, J. E., Buckel, S. D., Green, P. D., and Richey, C. W. (2005) Making site-specific PEGylation work. BioPharm Int. March, 30-41.
31. Kim, C. S., and Lee, E. K. (2000) Effects of operating parameters in in vitro renaturation of a fusion protein of human growth hormone and glutathione S transferase from inclusion body. Process Biochem. 36, 111-117.
32. Fee, C. J. and Mason, S. (2004) Charge-pH Behaviour of PEGylated Proteins: Consequences for Downstream Processing, Bioseparation, 2004, Uminonakamichi, Japan, Oct 15-16.
33. Fee, C. J. (2003) Size-exclusion reaction chromatography (SERC): A new technique for protein PEGylation. Biotechnol. Bioeng. 82, 200-206.
34. Foster, S., Schacher, A., Weyer, K. A., Brugger, D., Dietel, E., Marti, S., and Schreitmuller, T. (2003) Isolaration, Structural characterization, and antiviral activity of positional isomers of monopegylated interferon α-2a (PEGASYS). Protein Expression Purif. 30, 78-87.
35. Monkaesh, S. P., Ma, Y., Aglione, A., Bailon, P., Ciolek, D., Barbieri, B. D., Graves, M. C., Hollfelder, K., Michel, H., Palleroni, A., Porter, J. E., Russoman, E., Roy, S., and Pan, Y. E. (1996) Positional isomers of monopegylated interferon α-2a: Isolation, characterization, and biological activity. Anal. Biochem. 247, 434-440.
36. Yamaoka, T., Tabata, Y., and Ikada, Y. (1994) Distribution and tissue uptake of poly(ethylene) glycol with different molecular weights after intravenous administration to mice. J. Pharm. Sci. 83, 601-606.