Cysteine-specific PEGylation of rhG-CSF via selenylsulfide Bond

Bioconjugate Chemistry

Volumn 24, Issue 6, 2013, Pages 889-896

  Kunstelj, Menči ^a   Fidler, Katarina ^a   Škrajnar, Špela ^a   Kenig, Maja ^a   Smilović, Vanja ^a   Kusterle, Mateja ^a   Caserman, Simon ^b   Zore, Irena ^a   Porekar, Vladka Gaberc ^b   Jevševar, Simona ^a  

^a Lek Pharmaceuticals Dd   (Slovenia)

^b NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

BIOACTIVITY; REACTION RATES; RECOMBINANT PROTEINS; SELENIUM COMPOUNDS; SULFUR COMPOUNDS;

FREE THIOL GROUP; IN-VITRO; IN-VIVO; MALEIMIDES; PEGYLATION; PERFORMANCE; REACTIONS RATES; RECOMBINANT HUMAN GRANULOCYTE COLONY STIMULATING FACTORS; SELECTIVE MODIFICATION; SYNTHESISED;

AMINO ACIDS;

CYSTEINE; MACROGOL; MALEIMIDE; N HYDROXYSUCCINIMIDE; RECOMBINANT GRANULOCYTE COLONY STIMULATING FACTOR; SELENIUM; THIOL;

ARTICLE; BIOLOGICAL ACTIVITY; CONFORMATIONAL TRANSITION; CONJUGATE; DRUG STABILITY; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN;

EID: 84879336036     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc3005232     Document Type: Article

References (44)

1. Jevsevar, S., Kunstelj, M., and Porekar, V. G. (2010) PEGylation of therapeutic proteins Biotechnol. J. 5, 113-128
2. Caliceti, P. and Veronese, F. M. (2003) Pharmacokinetic and biodistribution properties of poly(ethylene glycol)-protein conjugates Adv. Drug Delivery Rev. 55, 1261-1277
3. Veronese, F. M. and Pasut, G. (2005) PEGylation, successful approach to drug delivery Drug Discov. Today 10, 1451-1458
4. Kinstler, O. B., Gabriel, N. E., arrar, N. E., and Prince, R. B. (1999) N-terminally chemically modified protein compositions and methods. Patent no. US 5,985,265, Nov 16, 1999. Patent application no. 08/879,760, 20. Jun. 1997.
5. Crawford, J. (2002) Pegfilgrastim administered once per cycle reduces incidence of chemotherapy-induced neutropenia Drugs 62, 89-98
6. Molineux, G. (2004) The design and development of pegfilgrastim (PEG-rmetHuG-CSF, Neulasta) Curr. Pharm. Des. 10, 1235-1244
7. Rajan, R. S., Li, T., Aras, M., Sloey, C., Sutherland, W., Arai, H., Briddell, R., Kinstler, O., Lueras, A. M., Zhang, Y., Yeghnazar, H., Treuheit, M., and Brems, D. N. (2006) Modulation of protein aggregation by polyethylene glycol conjugation: GCSF as a case study Protein Sci. 15, 1063-1075
8. 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
9. Deiters, A., Cropp, T. A., Summerer, D., Mukherji, M., and Schultz, P. G. (2004) Site-specific PEGylation of proteins containing unnatural amino acids Bioorg. Med. Chem. Lett. 14, 5743-5745
10. Vanwetswinkel, S., Plaisance, S., Zhi-Yong, Z., Vanlinthout, I., Brepoels, K., Collen, D., and Jespers, L. (2000) Pharmacokinetic and thrombolytic properties of cysteine-linked polyethylene glycol derivatives of staphylokinase Blood 95, 936-942
11. Carlsson, J., Drevin, H., and Axen, R. (1978) Protein thiolation and reversible protein-protein conjugation. N-Succinimidyl 3-(2-pyridyldithio) propionate, a new heterobifunctional reagent Biochem. J. 173, 723-737
12. Saito, G., Swanson, J. A., and Lee, K. D. (2003) Drug delivery strategy utilizing conjugation via reversible disulfide linkages: role and site of cellular reducing activities Adv. Drug Delivery Rev. 55, 199-215
13. Johansson, L., Gafvelin, G., and Arner, E. S. (2005) Selenocysteine in proteins-properties and biotechnological use Biochim. Biophys. Acta 1726, 1-13
14. Huber, R. E. and Criddle, R. S. (1967) Comparison of the chemical properties of selenocysteine and selenocystine with their sulfur analogs Arch. Biochem. Biophys. 122, 164-173
15. Besse, D., Siedler, F., Diercks, T., Kessler, H., and Moroder, L. (1997) The redox potential of selenocystine in unconstrained cyclic peptides Angew. Chem., Int. Ed. Engl. 36, 883-885
16. Crich, D., Krishnamurthy, V., and Hutton, T. K. (2006) Allylic selenosulfide rearrangement: A method for chemical ligation to cysteine and other thiols J. Am. Chem. Soc. 128, 2544-2545
17. Gieselman, M. D., Zhu, Y., Zhou, H., Galonic, D., and van der Donk, W. A. (2002) Selenocysteine derivatives for chemoselective ligations ChemBioChem 3, 709-716
18. Hondal, R. J., Nilsson, B. L., and Raines, R. T. (2001) Selenocysteine in native chemical ligation and expressed protein ligation J. Am. Chem. Soc. 123, 5140-5141
19. Quaderer, R., Sewing, A., and Hilvert, D. (2001) Selenocysteine-mediated native chemical ligation Helv. Chim. Acta 84, 1197-1206
20. Gamblin, D. P., Garnier, P., van, K. S., Oldham, N. J., Fairbanks, A. J., and Davis, B. G. (2004) Glyco-SeS: selenenylsulfide-mediated protein glycoconjugation - a new strategy in post-translational modification Angew. Chem., Int. Ed. 43, 828-833
21. Kubota, N., Orita, T., Hattori, K., Oh-eda, M., Ochi, N., and Yamazaki, T. (1990) Structural characterization of natural and recombinant human granulocyte colony-stimulating factors J. Biochem. 107, 486-492
22. Hill, C. P., Osslund, T. D., and Eisenberg, D. (1993) The structure of granulocyte-colony-stimulating factor and its relationship to other growth factors Proc. Natl. Acad. Sci. U.S.A. 90, 5167-5171
23. Arakawa, T., Prestrelski, S. J., Narhi, L. O., Boone, T. C., and Kenney, W. C. (1993) Cysteine 17 of recombinant human granulocyte-colony stimulating factor is partially solvent-exposed J. Protein Chem. 12, 525-531
24. Demetri, G. D. and Griffin, J. D. (1991) Granulocyte colony-stimulating factor and its receptor Blood 78, 2791-2808
25. Basu, S., Hodgson, G., Katz, M., and Dunn, A. R. (2002) Evaluation of role of G-CSF in the production, survival, and release of neutrophils from bone marrow into circulation Blood 100, 854-861
26. Veronese, F. M., Mero, A., Caboi, F., Sergi, M., Marongiu, C., and Pasut, G. (2007) Site-specific pegylation of G-CSF by reversible denaturation Bioconjugate Chem. 18, 1824-1830
27. Salmaso, S., Bersani, S., Scomparin, A., Mastrotto, F., Scherpfer, R., and Tonon, G. (2009) Tailored PEG for rh-G-CSF analogue site-specific conjugation Bioconjugate Chem. 20, 1179-1185
28. Russell-Jones, G. J., Westwood, S. W., and Habberfield, A. D. (1995) Vitamin B12 mediated oral delivery systems for granulocyte-colony stimulating factor and erythropoietin Bioconjugate Chem. 6, 459-465
29. Jevsevar, S., Gaberc-Porekar, V., Fonda, I., Podobnik, B., Grdadolnik, J., and Menart, V. (2005) Production of nonclassical inclusion bodies from which correctly folded protein can be extracted Biotechnol. Prog. 21, 632-639
30. Menart, V., Gaberc Porekar, V., and Jevsevar, S. (2004) Process for the production of a heterologous protein. International publication no. WO 2004/015124 A1, Feb 19, 2004; International patent application no. PCT/EP2003/006134, Jun 11, 2003.
31. Jevsevar, S. and Menart, V. (2004) Synthetic gene coding for human granulocyte-colony stimulating factor for the expression in E. coli; International patent publication no. WO 2004/013175, Feb 12, 2004; International patent application no. PCT/EP2003/008308, Jul 28, 2003.
32. Neulasta® is the Amgen Inc. trademark for pegfilgrastim.
33. Skrajnar, S., Lasnik, M. A., and Zavec, A. B. (2009) A flow cytometric method for determination of the blood neutrophil fraction in rats JAALAS 48, 152-156
34. Fidler, K., Jevsevar, S., Milunovic, T., Skrajnar, S., Premzl, A., Kunstelj, M., Zore, I., Podobnik, B., Kusterle, M., Caserman, S., Kenig, M., Smilovic, V., and Gaberc Porekar, V. (2011) The characterization and potential use of G-CSF dimers and their pegylated conjugates Acta Chim. Slov. 58, 1-8
35. Huston, A. and Lyman, G. H. (2007) Agents under investigation for the treatment and prevention of neutropenia Expert Opin. Invest. Drugs 16, 1831-1840
36. Roberts, M. J., Bentley, M. D., and Harris, J. M. (2002) Chemistry for peptide and protein PEGylation Adv. Drug Delivery Rev. 54, 459-476
37. Cox, G. N., Smith, D. J., Carlson, S. J., Bendele, A. M., Chlipala, E. A., and Doherty, D. H. (2004) Enhanced circulating half-life and hematopoietic properties of a human granulocyte colony-stimulating factor/immunoglobulin fusion protein Exp. Hematol. 32, 441-449
38. Jain, S., Laing, P., and Gregoriadis, G. (2009) Derivatisation of colony-stimulating factor, Patent no. EP 2041167, Apr 1, 2009; Patent application no. EP20070789047, Jul 25, 2007.
39. Choi, S. H. and Park, T. G. (2006) G-CSF loaded biodegradable PLGA nanoparticles prepared by a single oil-in-water emulsion method Int. J. Pharm. 311, 223-228
40. Fishburn, C. S. (2008) The pharmacology of PEGylation: balancing PD with PK to generate novel therapeutics J. Pharm. Sci. 97, 4167-4183
41. Arpicco, S., Dosio, F., Brusa, P., Crosasso, P., and Cattel, L. (1997) New coupling reagents for the preparation of disulfide cross-linked conjugates with increased stability Bioconjugate Chem. 8, 327-337
42. Dosio, F., Arpicco, S., Adobati, E., Canevari, S., Brusa, P., De, S. R., Parente, D., Pignanelli, P., Negri, D. R., Colnaghi, M. I., and Cattel, L. (1998) Role of cross-linking agents in determining the biochemical and pharmacokinetic properties of Mgr6-clavin immunotoxins Bioconjugate Chem. 9, 372-381
43. Bhabak, K. P. and Mugesh, G. (2010) Functional mimics of glutathione peroxidase: Bioinspired synthetic antioxidants Acc. Chem. Res. 43, 1408-1419
44. Xu, K., Zhang, Y., Tang, B., Laskin, J., Roach, P. J., and Chen, H. (2010) Study of highly selective and efficient thiol derivatization using selenium reagents by mass spectrometry Anal. Chem. 82, 6926-6932