Recombinant protein hydrazides: Application to site-specific protein PEGylation

Bioconjugate Chemistry

Volumn 22, Issue 6, 2011, Pages 1017-1020

  Thom, Jennifer ^a   Anderson, David ^a   McGregor, Joanne ^a   Cotton, Graham ^a  

^a Almac Sciences   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COVALENT BONDS; NITROGEN COMPOUNDS; SULFUR COMPOUNDS;

CHEMICAL CLEAVAGE; FUSION PROTEINS; HYDRAZONES; INTEINS; NOVEL METHODS; PEGYLATION; PROTEIN PEGYLATION; PROTEIN SEQUENCES; SITE-SPECIFIC; TERMINAL MODIFICATIONS;

RECOMBINANT PROTEINS;

HYDRAZIDE DERIVATIVE; HYDRAZONE DERIVATIVE; PEGINTERFERON; PEGINTERFERON ALPHA2B; PEGINTERFERON ALPHA2B HYDRAZIDE; PEGINTERFERON BETA1B HYDRAZIDE; RECOMBINANT PROTEIN; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CARBOXY TERMINAL SEQUENCE; CONTROLLED STUDY; DISULFIDE BOND; HUMAN; HUMAN CELL; NONHUMAN; PROTEIN ENGINEERING; PROTEIN MODIFICATION;

EID: 79959192999     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc2001374     Document Type: Article

References (24)

1. Veronese, F. M. and Mero, A. (2008) The impact of PEGylation on biological therapies BioDrugs 22, 315-329
2. Jevsevar, S., Kunstelj, M., and Porekar, V. G. (2010) PEGylation of therapeutic proteins Biotechnol. J. 5, 113-128
3. Wang, Y. S., Youngster, S., Grace, M., Bausch, J., Bordens, R., and Wyss, D. F. (2002) Structural and biological characterization of pegylated recombinant interferon alpha-2b and its therapeutic implications Adv. Drug Delivery Rev. 54, 547-570 (Pubitemid 34618512)
4. Brocchini, S., Godwin, A., Balan, S., Choi, J. W., Zloh, M., and Shaunak, S. (2008) Disulfide bridge based PEGylation of proteins Adv. Drug Delivery Rev. 60, 3-12 (Pubitemid 350181163)
5. DeFrees, S., Wang, Z. G., Xing, R., Scott, A. E., Wang, J., Zopf, D., Gouty, D. L., Sjoberg, E. R., Panneerselvam, K., Brinkman-Van der Linden, E. C., Bayer, R. J., Tarp, M. A., and Clausen, H. (2006) GlycoPEGylation of recombinant therapeutic proteins produced in Escherichia coli Glycobiology 16, 833-843 (Pubitemid 44390927)
6. Xie, J. and Schultz, P. G. (2006) A chemical toolkit for proteins-an expanded genetic code Nat. Rev. Mol. Cell Biol. 7, 775-782 (Pubitemid 44450461)
7. Muir, T. W., Sondhi, D., and Cole, P. A. (1998) Expressed protein ligation: a general method for protein engineering Proc. Natl. Acad. Sci. U.S.A. 95, 6705-6710 (Pubitemid 28278044)
8. Muir, T. W. (2001) Development and application of expressed protein ligation Synlett. 6, 733-740 (Pubitemid 32505788)
9. Dawson, P. E., Muir, T. W., Clark-Lewis, I., and Kent, S. B. (1994) Synthesis of proteins by native chemical ligation Science 266, 776-779 (Pubitemid 24359280)
10. Weikart, N. D. and Mootz, H. D. (2010) Generation of site-specific and enzymatically stable conjugates of recombinant proteins with ubiquitin-like modifiers by the Cu(I)-catalyzed azide-alkyne cycloaddition ChemBioChem 11, 774-777
11. Yi, L., Sun, H., Wu, Y. W., Triola, G., Waldmann, H., and Goody, R. S. (2010) A highly efficient strategy for modification of proteins at the C terminus Angew. Chem., Int. Ed. Engl. 49, 9417-9421
12. Kalia, J. and Raines, R. T. (2006) Reactivity of intein thioesters: appending a functional group to a protein ChemBioChem 7, 1375-1383 (Pubitemid 44369089)
13. Cheriyan, M. and Perler, F. B. (2009) Protein splicing: A versatile tool for drug discovery Adv. Drug Delivery Rev. 61, 899-907
14. Gaertner, H. F., Offord, R. E., Cotton, R., Timms, D., Camble, R., and Rose, K. (1994) Chemo-enzymic backbone engineering of proteins. Site-specific incorporation of synthetic peptides that mimic the 64-74 disulfide loop of granulocyte colony-stimulating factor J. Biol. Chem. 269, 7224-7230
15. Gaertner, H. F., Rose, K., Cotton, R., Timms, D., Camble, R., and Offord, R. E. (1992) Construction of protein analogues by site-specific condensation of unprotected fragments Bioconjugate Chem. 3, 262-268
16. Bourel-Bonnet, L., Pecheur, E. I., Grandjean, C., Blanpain, A., Baust, T., Melnyk, O., Hoflack, B., and Gras-Masse, H. (2005) Anchorage of synthetic peptides onto liposomes via hydrazone and alpha-oxo hydrazone bonds, preliminary functional investigations Bioconjugate Chem. 16, 450-457 (Pubitemid 40388221)
17. Kochendoerfer, G. G., Tack, J. M., and Cressman, S. (2002) Total chemical synthesis of a 27 kDa TASP protein derived from the MscL ion channel of M. tuberculosis by ketoxime-forming ligation Bioconjugate Chem. 13, 474-480 (Pubitemid 34527509)
18. Fine, H. A., Wen, P. Y., Robertson, M., O'Neill, A., Kowal, J., Loeffler, J. S., and Black, P. M. (1997) A phase I trial of a new recombinant human beta-interferon (BG9015) for the treatment of patients with recurrent gliomas Clin. Cancer Res. 3, 381-387 (Pubitemid 27158061)
19. Fukutomi, T., Nakamuta, M., Fukutomi, M., Iwao, M., Watanabe, H., Hiroshige, K., Tanabe, Y., and Nawata, H. (2001) Decline of hepatitis C virus load in serum during the first 24 h after administration of interferon-beta as a predictor of the efficacy of therapy J. Hepatol. 34, 100-107 (Pubitemid 32102558)
20. Malucchi, S., Sala, A., Gilli, F., Bottero, R., Di Sapio, A., Capobianco, M., and Bertolotto, A. (2004) Neutralizing antibodies reduce the efficacy of betaIFN during treatment of multiple sclerosis Neurology 62, 2031-2037 (Pubitemid 38738217)
21. Filpula, D., Yang, K., Basu, A., and Wang, M. (2005) WO2005/084303A2 Interferon beta polymer conjugates. PCT/US2005/006575.
22. Basu, A., Yang, K., Wang, M., Liu, S., Chintala, R., Palm, T., Zhao, H., Peng, P., Wu, D., Zhang, Z., Hua, J., Hsieh, M. C., Zhou, J., Petti, G., Li, X., Janjua, A., Mendez, M., Liu, J., Longley, C., Zhang, Z., Mehlig, M., Borowski, V., Viswanathan, M., and Filpula, D. (2006) Structure-function engineering of interferon-beta-1b for improving stability, solubility, potency, immunogenicity, and pharmacokinetic properties by site-selective mono-PEGylation Bioconjugate Chem. 17, 618-630 (Pubitemid 43794371)
23. Zhao, H., Yang, K., Martinez, A., Basu, A., Chintala, R., Liu, H. C., Janjua, A., Wang, M., and Filpula, D. (2006) Linear and branched bicin linkers for releasable PEGylation of macromolecules: controlled release in vivo and in vitro from mono- and multi-PEGylated proteins Bioconjugate Chem. 17, 341-351
24. Gitlin, G., Tsarbopoulos, A., Patel, S. T., Sydor, W., Pramanik, B. N., Jacobs, S., Westreich, L., Mittelman, S., and Bausch, J. N. (1996) Isolation and characterization of a monomethioninesulfoxide variant of interferon alpha-2b Pharm. Res. 13, 762-769 (Pubitemid 26156227)