Synthesis of peptide-protein conjugates using N-succinimidyl carbamate chemistry

Bioconjugate Chemistry

Volumn 21, Issue 2, 2010, Pages 219-228

  Mhidia, Reda ^a   Vallin, Aurélie ^a   Ollivier, Nathalie ^a   Blanpain, Annick ^a   Shi, Getao ^b,c   Christiano, Romain ^b,c   Johannes, Ludger ^b   Melnyk, Oleg ^a  

^a UNIV LILLE   (France)

^b INSTITUT CURIE   (France)

^c INSTITUT CURIE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BIOSYNTHESIS; CELL MEMBRANES; CHEMICAL BONDS; ENZYMES; UREA;

BIOLOGICAL MECHANISMS; CARBAMATE DERIVATIVES; LYSINE RESIDUES; MODEL PROTEINS; PEPTIDE PROTEINS; PEPTIDE SUBSTRATES; PROTEIN CONJUGATES; RP-HPLC; SEMICARBAZONES; SYNTHESISED;

PEPTIDES;

CARBAMIC ACID DERIVATIVE; DISSUCINIMIDYLCARBONATE; LYSINE; LYSOZYME; N SUCCINIMIDYLCARBAMATE; PEPTIDE; PEPTIDE PROTEIN CONJUGATE; PROTEIN; SEMICARBAZIDE DERIVATIVE; SHIGA TOXIN; SHIGA TOXIN B; SULFOTRANSFERASE; TYROSYLPROTEIN SULFOTRANSFERASE SHIGA TOXIN B CONJUGATE; UNCLASSIFIED DRUG; UREA;

ALKALINITY; AMINO ACID SEQUENCE; ARTICLE; CONJUGATE; GOLGI COMPLEX; ONE POT SYNTHESIS; PEPTIDE SYNTHESIS; PROTEIN TRANSPORT; REACTION ANALYSIS; SEQUENCE ANALYSIS; SYNTHESIS;

EID: 77049093038     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc900154r     Document Type: Article

References (42)

1. Amessou, M., Popoff, V., Yelamos, B., Saint-Pol, A., Johannes, L. (2006) Measuring retrograde transport to the trans-Golgi network. In Current Protocols in Cell Biology (Bonifacino, J. S., Dasso, M., Harford, J. B., Lippincott-Schwartz, J., Yamada, K. M., Eds.) Chapter 15, Unit 15.10.1 15.10.21, John Wiley & Sons, Inc.
2. Stoddart, C. A., Nault, G., Galkina, S. A., Thibaudeau, K., Bakis, P., Bousquet-Gagnon, N., Robitaille, M., Bellomo, M., Paradis, V., Liscourt, P., Lobach, A., Rivard, M. E., Ptak, R. G., Mankowski, M. K., Bridon, D., and Quraishi, O. (2008) Albumin-conjugated C34 peptide HIV-1 fusion inhibitor: equipotent to C34 and T-20 in vitro with sustained activity in SCIDhu Thy/Liv mice. J. Biol. Chem. 283, 34045-34052
3. Dixon, H. B. (1964) Removal of the N-terminal residue of a peptide after transamination. Biochem. J. 90, 2C-3C.
4. Geoghegan, K. F., and Stroh, J. G. (1992) Site-directed conjugation of nonpeptide groups to peptides and proteins via periodate oxidation of a 2-amino alcohol. Application to modification at N-terminal serine. Bioconjugate Chem. 3, 138-146
5. Werlen, R. C., Offord, R. E., Blakey, D. C., East, S. J., Melton, R. G., and Rose, K. (1995) In vitro and in vivo comparison of a randomly coupled antibody fragment-enzyme conjugate with a site-specific conjugate. Biomed. Pept. Proteins Nucleic Acids 1, 251-254
6. Wang, L., Zhang, Z., Brock, A., and Schultz, P. G. (2003) Addition of the keto functional group to the genetic code of Escherichia coli. Proc. Natl. Acad. Sci. U.S.A. 100, 56-61.
7. Kafi, K., Betting, D. J., Yamada, R. E., Bacica, M., Steward, K. K., and Timmerman, J. M. (2009) Maleimide conjugation markedly enhances the immunogenicity of both human and murine idiotype-KLH vaccines. Mol. Immunol. 46, 448-456
8. Temming, K., Meyer, D. L., Zabinski, R., Senter, P. D., Poelstra, K., Molema, G., and Kok, R. J. (2007) Improved efficacy of alphavbeta3-targeted albumin conjugates by conjugation of a novel auristatin derivative. Mol. Pharmacol. 4, 686-694
9. Kumaresan, P. R., Luo, J., Song, A., Marik, J., and Lam, K. S. (2008) Evaluation of ketone-oxime method for developing therapeutic on-demand cleavable immunoconjugates. Bioconjugate Chem. 19, 1313-1318
10. Kalkhof, S., and Sinz, A. (2008) Chances and pitfalls of chemical cross-linking with amine-reactive N-hydroxysuccinimide esters. Anal. Bioanal. Chem. 392, 305-312
11. Kida, S., Maeda, M., Hojo, K., Eto, Y., Gao, J. Q., Kurachi, S., Mizuguchi, H., Hayakawa, T., Mayumi, T., Nakagawa, S., and Kawasaki, K. (2006) Design and synthesis of a Tat-related gene transporter: a tool for carrying the adenovirus vector into cells. Bioorg. Med. Chem. Lett. 16, 743-745
12. Inglese, J., and Glickman, J. F. (1999) Radiolabeling of receptor ligands by chemical incorporation of phosphorylation sites. Anal. Biochem. 274, 104-109
13. Morpurgo, M., Bayer, E. A., and Wilchek, M. (1999) N-hydroxysuccinimide carbonates and carbamates are useful reactive reagents for coupling ligands to lysines on proteins. J. Biochem. Biophys. Methods 38, 17-28.
14. Clave, G., Boutal, H., Hoang, A., Perraut, F., Volland, H., Renard, P. Y., and Romieu, A. (2008) A novel heterotrifunctional peptide-based cross-linking reagent for facile access to bioconjugates. Applications to peptide fluorescent labelling and immobilisation. Org. Biomol. Chem. 6, 3065-3078
15. Pasut, G., Mero, A., Caboi, F., Scaramuzza, S., Sollai, L., and Veronese, F. M. (2008) A new PEG-beta-alanine active derivative for releasable protein conjugation. Bioconjugate Chem. 19, 2427-2431
16. Pina, D. G., and Johannes, L. (2005) Cholera and Shiga toxin B-subunits: thermodynamic and structural considerations for function and biomedical applications. Toxicon 45, 389-393
17. Mallard, F., and Johannes, L. (2003) Shiga toxin B-subunit as a tool to study retrograde transport. Methods Mol. Med. 73, 209-220
18. Walker, J. M. (1994) The bicinchoninic acid (BCA) assay for protein quantitation. Methods Mol. Biol. 32, 5-8.
19. Ollivier, N., Besret, S., Blanpain, A., and Melnyk, O. (2009) Silver- catalyzed azaGly ligation. Application to the synthesis of azapeptides and of lipid-peptide conjugates. Bioconjugate Chem. 20, 1397-1403
20. Smith, M. J., Carvalho, H. M., Melton-Celsa, A. R., and O'Brien, A. D. (2006) The 13C4 monoclonal antibody that neutralizes Shiga toxin Type 1 (Stx1) recognizes three regions on the Stx1 B subunit and prevents Stx1 from binding to its eukaryotic receptor globotriaosylceramide. Infect. Immunol. 74, 6992-6998
21. Mallard, F., Antony, C., Tenza, D., Salamero, J., Goud, B., and Johannes, L. (1998) Direct pathway from early/recycling endosomes to the Golgi apparatus revealed through the study of shiga toxin B-fragment transport. J. Cell. Biol. 143, 973-990
22. Johannes, L., Tenza, D., Antony, C., and Goud, B. (1997) Retrograde transport of KDEL-bearing B-fragment of Shiga toxin. J. Biol. Chem. 272, 19554-19561
23. Liao, H. J., and Carpenter, G. (2007) Role of the Sec61 translocon in EGF receptor trafficking to the nucleus and gene expression. Mol. Biol. Cell 18, 1064-1072
24. Niehrs, C., Huttner, W. B., and Ruther, U. (1992) In vivo expression and stoichiometric sulfation of the artificial protein sulfophilin, a polymer of tyrosine sulfation sites. J. Biol. Chem. 267, 15938-15942
25. Hong, G., Chappey, O., Niel, E., and Scherrmann, J. M. (2000) Enhanced cellular uptake and transport of polyclonal immunoglobulin G and fab after their cationization. J. Drug Targeting 8, 67-77.
26. Pardridge, W. M., Bickel, U., Buciak, J., Yang, J., Diagne, A., and Aepinus, C. (1994) Cationization of a monoclonal antibody to the human immunodeficiency virus REV protein enhances cellular uptake but does not impair antigen binding of the antibody. Immunol. Lett. 42, 191-195
27. Pardridge, W. M., Kang, Y. S., Yang, J., and Buciak, J. L. (1995) Enhanced cellular uptake and in vivo biodistribution of a monoclonal antibody following cationization. J. Pharm. Sci. 84, 943-948
28. Ryser, H. J., Drummond, I., and Shen, W. C. (1982) The cellular uptake of horseradish peroxidase and its poly(lysine) conjugate by cultured fibroblasts is qualitatively similar despite a 900-fold difference in rate. J. Cell. Physiol. 113, 167-178
29. Kohn, W. D., Micanovic, R., Myers, S. L., Vick, A. M., Kahl, S. D., Zhang, L., Strifler, B. A., Li, S., Shang, J., Beals, J. M., Mayer, J. P., and DiMarchi, R. D. (2007) pI-shifted insulin analogs with extended in vivo time action and favorable receptor selectivity. Peptides 28, 935-948
30. Monsigny, M., Sene, C., Obrenovitch, A., Roche, A. C., Delmotte, F., and Boschetti, E. (1979) Properties of succinylated wheat-germ agglutinin. Eur. J. Biochem. 98, 39-45.
31. Nakashima, H., Hashimoto, M., Sadakane, Y., Tomohiro, T., and Hatanaka, Y. (2006) Simple and versatile method for tagging phenyldiazirine photophores. J. Am. Chem. Soc. 128, 15092-15093
32. Gassman, J. M., and Magrath, J. (1996) An active-site titrant for chymotrypsin, and evidence that azapeptide esters are less susceptible to nucleophilic attack than ordinary esters. Bioorg. Med. Chem. Lett. 6, 1771-1774.
33. Abello, N., Kerstjens, H. A., Postma, D. S., and Bischoff, R. (2007) Selective acylation of primary amines in peptides and proteins. J. Proteome Res. 6, 4770-4776
34. Brown, W. E., Green, A. H., Cedel, T. E., and Cairns, J. (1987) Biochemistry of protein-isocyanate interactions: a comparison of the effects of aryl vs. alkyl isocyanates. Environ. Health Perspect. 72, 5-11.
35. Sandvig, K., Dubinina, E., Garred, O., Prydz, K., Kozlov, J. V., Hansen, S. H., and van Deurs, B. (1992) Protein toxins: mode of action and cell entry. Biochem. Soc. Trans. 20, 724-727
36. Nakamura, N., Rabouille, C., Watson, R., Nilsson, T., Hui, N., Slusarewicz, P., Kreis, T. E., and Warren, G. (1995) Characterization of a cis-Golgi matrix protein, GM130. J. Cell. Biol. 131, 1715-1726
37. Niehrs, C., Kraft, M., Lee, R. W., and Huttner, W. B. (1990) Analysis of the substrate specificity of tyrosylprotein sulfotransferase using synthetic peptides. J. Biol. Chem. 265, 8525-8532
38. Niehrs, C., and Huttner, W. B. (1990) Purification and characterization of tyrosylprotein sulfotransferase. Embo J. 9, 35-42.
39. Carion, O., Souplet, V., Olivier, C., Maillet, C., Medard, N., El-Mahdi, O., Durand, J. O., and Melnyk, O. (2007) Chemical micropatterning of polycarbonate for site-specific peptide immobilization and biomolecular interactions. ChemBioChem 8, 315-322.
40. Duburcq, X., Olivier, C., Malingue, F., Desmet, R., Bouzidi, A., Zhou, F., Auriault, C., Gras-Masse, H., and Melnyk, O. (2004) Peptide-protein microarrays for the simultaneous detection of pathogen infections. Bioconjugate Chem. 15, 307-316
41. Duburcq, X., Olivier, C., Desmet, R., Halasa, M., Carion, O., Grandidier, B., Heim, T., Stievenard, D., Auriault, C., and Melnyk, O. (2004) Polypeptide semicarbazide glass slide microarrays: characterization and comparison with amine slides in serodetection studies. Bioconjugate Chem. 15, 317-325
42. Olivier, C., Hot, D., Huot, L., Ollivier, N., El-Mahdi, O., Gouyette, C., Huynh-Dinh, T., Gras-Masse, H., Lemoine, Y., and Melnyk, O. (2003) Alpha-oxo semicarbazone peptide or oligodeoxynucleotide microarrays. Bioconjugate Chem. 14, 430-439