Facile double-functionalization of designed ankyrin repeat proteins using click and thiol chemistries

Bioconjugate Chemistry

Volumn 23, Issue 2, 2012, Pages 279-286

  Simon, Manuel ^a,b   Zangemeister Wittke, Uwe ^a,b   Plückthun, Andreas ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b UNIVERSITY OF BERN   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CELL ADHESION; DISSOCIATION; ESCHERICHIA COLI; MEDICAL APPLICATIONS; MOLECULES; PROTEINS; SCAFFOLDS (BIOLOGY); SYNTHESIS (CHEMICAL); TUMORS;

ANKYRIN REPEATS; BINDING PROTEINS; C-TERMINUS; CLICK CHEMISTRY; FUNCTIONALIZATIONS; METHIONINE; REGIO-SELECTIVE; REPEAT PROTEINS; THERAPEUTIC PROTEIN; THIOL CHEMISTRY;

AMINO ACIDS;

ANKYRIN; EPITHELIAL CELL ADHESION MOLECULE; MACROGOL; THIOL DERIVATIVE;

ARTICLE; BINDING KINETICS; BIOMEDICINE; CLICK CHEMISTRY; CONTROLLED STUDY; DATA ANALYSIS; DISSOCIATION; FEMALE; HUMAN; HUMAN CELL; MEDICAL RECORD; PROTEIN FUNCTION; PROTEIN MODIFICATION; TUMOR; TUMOR CELL;

EID: 84855591894     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc200591x     Document Type: Article

References (37)

1. Finn, M. G. and Fokin, V. V. (2010) Click chemistry: function follows form Chem. Soc. Rev. 39, 1231-1232
2. Nwe, K. and Brechbiel, M. W. (2009) Growing applications of "click chemistry" for bioconjugation in contemporary biomedical research. Cancer Biother. Radiopharm. 24, 289 - 302.
3. Lutz, J.-F. and Zarafshani, Z. (2008) Efficient construction of therapeutics, bioconjugates, biomaterials and bioactive surfaces using azide-alkyne "click" chemistry Adv. Drug Delivery Rev. 60, 958-970
4. Veronese, F. M. and Pasut, G. (2005) PEGylation, successful approach to drug delivery Drug Discovery Today 10, 1451-1458 (Pubitemid 41483874)
5. Caliceti, P. and Veronese, F. (2003) Pharmacokinetic and biodistribution properties of poly(ethylene glycol)-protein conjugates Adv. Drug Delivery Rev. 55, 1261-1277 (Pubitemid 37464561)
6. 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. 14, 5743-5745 (Pubitemid 39421512)
7. Sletten, E. M. and Bertozzi, C. R. (2008) A hydrophilic azacyclooctyne for Cu-free click chemistry Org. Lett. 10, 3097-3099
8. Baskin, J. M., Prescher, J. A., Laughlin, S. T., Agard, N. J., Chang, P. V., Miller, I. A., Lo, A., Codelli, J. A., and Bertozzi, C. R. (2007) Copper-free click chemistry for dynamic in vivo imaging Proc. Natl. Acad. Sci. U.S.A. 104, 16793-16797 (Pubitemid 350210944)
9. Debets, M. F., van Berkel, S. S., Schoffelen, S., Rutjes, F. P. J. T., van Hest, J. C. M., and van Delft, F. L. (2010) Aza-dibenzocyclooctynes for fast and efficient enzyme PEGylation via copper-free (3 + 2) cycloaddition Chem. Commun. 46, 97-99
10. Boersma, Y. L. and Plückthun, A. (2011) DARPins and other repeat protein scaffolds: advances in engineering and applications Curr. Opin. Biotechnol. 22, 849-857
11. Binz, H. K., Stumpp, M. T., Forrer, P., Amstutz, P., and Plückthun, A. (2003) Designing Repeat Proteins: Well-expressed, soluble and stable proteins from combinatorial libraries of consensus ankyrin repeat proteins J. Mol. Biol. 332, 489-503 (Pubitemid 37020959)
12. Steiner, D., Forrer, P., and Plückthun, A. (2008) Efficient selection of DARPins with sub-nanomolar affinities using SRP phage display J. Mol. Biol. 382, 1211-1227
13. Zahnd, C., Kawe, M., Stumpp, M. T., de Pasquale, C., Tamaskovic, R., Nagy-Davidescu, G., Dreier, B., Schibli, R., Binz, H. K., Waibel, R., and Plückthun, A. (2010) Efficient tumor targeting with high-affinity designed ankyrin repeat proteins: effects of affinity and molecular size Cancer Res. 70, 1595-1605
14. Zahnd, C., Pecorari, F., Straumann, N., Wyler, E., and Plückthun, A. (2006) Selection and characterization of Her2-binding Designed Ankyrin Repeat Proteins J. Biol. Chem. 281, 35167-35175 (Pubitemid 46036556)
15. Martin-Killias, P., Stefan, N., Rothschild, S., Plückthun, A., and Zangemeister-Wittke, U. (2011) A novel fusion toxin derived from an EpCAM-specific designed ankyrin repeat protein has potent antitumor activity Clin. Cancer Res. 17, 100-110
16. Stefan, N., Martin-Killias, P., Wyss-Stoeckle, S., Honegger, A., Zangemeister-Wittke, U., and Plückthun, A. (2011) DARPins recognizing the tumor-associated antigen EpCAM selected by phage and ribosome display and engineered for multivalency J. Mol. Biol. 413, 826-843
17. Hirel, P., Schmitter, J., Dessen, P., Fayat, G., and Blanquet, S. (1989) Extent of N-terminal methionine excision from Escherichia coli proteins is governed by the side-chain length of the penultimate amino acid Proc. Natl. Acad. Sci. U.S.A. 86, 8247-8251 (Pubitemid 19286036)
18. Wang, A., Winblade Nairn, N., Johnson, R. S., Tirrell, D. A., and Grabstein, K. (2008) Processing of N-terminal unnatural amino acids in recombinant human interferon-beta in Escherichia coli ChemBioChem 9, 324-330 (Pubitemid 351196801)
19. Kubetzko, S., Sarkar, C. A., and Plückthun, A. (2005) Protein PEGylation decreases observed target association rates via a dual blocking mechanism Mol. Pharmacol. 68, 1439-1454 (Pubitemid 41540000)
20. Tamaskovic, R., Simon, M., Stefan, N., Schwill, M., and Plückthun, A. (2012) Designed Ankyrin Repeat Proteins (DARPins): From research to therapy. Methods Enzymol 503, 101 - 134.
21. Wetzel, S. K., Settanni, G., Kenig, M., Binz, H. K., and Plückthun, A. (2008) Folding and unfolding mechanism of highly stable full-consensus ankyrin repeat proteins J. Mol. Biol. 376, 241-257
22. Seely, J. E. and Richey, C. W. (2001) Use of ion-exchange chromatography and hydrophobic interaction chromatography in the preparation and recovery of polyethylene glycol-linked proteins J. Chromatogr. 908, 235-241 (Pubitemid 32332934)
23. Yang, K., Basu, A., Wang, M., Chintala, R., Hsieh, M. C., Liu, S., Hua, J., Zhang, Z., Zhou, J., Li, M., Phyu, H., Petti, G., Mendez, M., Janjua, H., Peng, P., Longley, C., Borowski, V., Mehlig, M., and Filpula, D. (2003) Tailoring structure-function and pharmacokinetic properties of single-chain Fv proteins by site-specific PEGylation Protein Eng. Des. Sel. 16, 761-770 (Pubitemid 37442447)
24. Binz, H. K., Amstutz, P., and Plückthun, A. (2005) Engineering novel binding proteins from nonimmunoglobulin domains Nat. Biotechnol. 23, 1257-1268 (Pubitemid 41486853)
25. Stumpp, M. T., Binz, H. K., and Amstutz, P. (2008) DARPins: A new generation of protein therapeutics Drug Discovery Today 13, 695-701
26. Hermanson, G. T. (2008) Bioconjugate Techniques, 2 nd ed. Academic Press, London.
27. 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 (Pubitemid 34615544)
28. Selvakumar, E., Rameshkumar, N., Lee, S.-G., Lee, S.-J., and Park, H.-S. (2010) In vivo production of functional single-chain Fv fragment with an N-terminal-specific bio-orthogonal reactive group ChemBioChem 11, 498-501
29. Bundy, B. C. and Swartz, J. R. (2010) Site-specific incorporation of p-propargyloxyphenylalanine in a cell-free environment for direct protein-protein click conjugation Bioconjugate Chem. 21, 255-263
30. Jewett, J. C. and Bertozzi, C. R. (2010) Cu-free click cycloaddition reactions in chemical biology Chem. Soc. Rev. 39, 1272-1279
31. Laughlin, S. T. and Bertozzi, C. R. (2009) In vivo imaging of Caenorhabditis elegans glycans ACS Chem. Biol. 4, 1068-1072
32. Schoffelen, S., Lambermon, M. H. L., Eldijk, M. B. V., and Hest, J. C. M. V. (2008) Site-specific modification of Candida antarctica Lipase B via residue-specific incorporation of a non-canonical amino acid Bioconjugate Chem. 19, 1127-1131 (Pubitemid 351874933)
33. de Graaf, A. J., Kooijman, M., Hennink, W. E., and Mastrobattista, E. (2009) Nonnatural amino acids for site-specific protein conjugation Bioconjugate Chem. 20, 1281-1295
34. Patel, K. G. and Swartz, J. R. (2011) Surface functionalization of virus-like particles by direct conjugation using azide-alkyne click chemistry Bioconjugate Chem. 22, 376-387
35. Ledin, P. A., Friscourt, F., Guo, J., and Boons, G.-J. (2011) Convergent assembly and surface modification of multifunctional dendrimers by three consecutive click reactions Chem.-Eur. J. 17, 839-846
36. Bouvet, V. and Wuest, M. (2011) Copper-free click chemistry with the short-lived positron emitter fluorine-18 Org. Biomol. Chem. 9, 7393-7399
37. Qi, J., Han, M.-S., Chang, Y.-C., and Tung, C.-H. (2011) Developing visible fluorogenic "click-on" dyes for cellular imaging Bioconjugate Chem. 22, 1758-1762