Synthesis and application of a N-1′ fluorescent biotinyl derivative inducing the specific carboxy-terminal dual labeling of a novel RhoB-selective scFv

Bioconjugate Chemistry

Volumn 20, Issue 5, 2009, Pages 847-855

  Chaisemartin, L ^a   Chinestra, P ^a   Favre, G ^a   Blonski, C ^b   Faye, J C ^a  

^a INSTITUT CLAUDIUS REGAUD   (France)

^b UPS)   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CHEMICAL DETECTION; ESCHERICHIA COLI; PURIFICATION;

AMINO-ACIDS; BIOCHEMICAL METHODS; COVALENT LABELING; DUAL LABELING; IMMUNOCHEMICAL METHODS; INTEINS; LABELINGS; PHAGE DISPLAY LIBRARIES; PHAGE LIBRARIES; SITE-SPECIFIC;

FLUORESCENCE;

AMINO ACID; ANTIBODY; BIOTIN; BIOTIN DERIVATIVE; CYSTEINE DERIVATIVE; FLUORESCEIN; INTEIN; RHOB GUANINE NUCLEOTIDE BINDING PROTEIN; THIOL; CYSTEINE; ESTER; FLUORESCENT DYE; NITROGEN; SINGLE CHAIN FRAGMENT VARIABLE ANTIBODY;

ANTIBODY DETECTION; ARTICLE; BIOTINYLATION; CARBOXY TERMINAL SEQUENCE; ESCHERICHIA COLI; FEMALE; HUMAN; HUMAN CELL; IMMUNOFLUORESCENCE; PHAGE DISPLAY; PROTEIN PROCESSING; PROTEIN PURIFICATION; SYNTHESIS; ANTIBODY SPECIFICITY; BINDING SITE; CHEMISTRY; ENZYME SPECIFICITY; FLUORESCENT ANTIBODY TECHNIQUE; HELA CELL LINE; IMMUNOLOGY; METABOLISM; PROCEDURES; STAINING;

ANTIBODY SPECIFICITY; BINDING SITES; BIOTIN; CYSTEINE; ESTERS; FLUORESCENT ANTIBODY TECHNIQUE; FLUORESCENT DYES; HELA CELLS; HUMANS; INTEINS; NITROGEN; PROTEIN SPLICING; RHOB GTP-BINDING PROTEIN; SINGLE-CHAIN ANTIBODIES; STAINING AND LABELING; SUBSTRATE SPECIFICITY;

EID: 66149189323     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc800272r     Document Type: Article

References (44)

1. Griffiths, A. D. (1993) Production of human antibodies using bacteriophage. Curr. Opin. Immunol. 5, 263-267 (Pubitemid 23125303)
2. Griffiths, A. D., Williams, S. C., Hartley, O., Tomlinson, I. M., Waterhouse, P., Crosby, W. L., Kontermann, R. E., Jones, P. T., Low, N. M., Allison, T. J., et al. (1994) Isolation of high affinity human antibodies directly from large synthetic repertoires. EMBO J. 13, 3245-3260 (Pubitemid 24226939)
3. Hayden, M. S., Gilliland, L. K., and Ledbetter, J. A. (1997) Antibody engineering. Curr. Opin. Immunol. 9, 201-212 (Pubitemid 27190119)
4. Santamaria, H. (2003) [Phage display applications in clinical diagnosis]. Rev. Invest. Clin. 55, 711-718
5. Paschke, M. (2006) Phage display systems and their applications. Appl. Microbiol. Biotechnol. 70, 2-11. (Pubitemid 43234524)
6. Olichon, A., and Surrey, T. (2007) Selection of genetically encoded fluorescent single domain antibodies engineered for efficient expression in Escherichia coli. J. Biol. Chem. 282, 36314-36320
7. Ayriss, J., Woods, T., Bradbury, A., and Pavlik, P. (2007) High-throughput screening of single-chain antibodies using multiplexed flow cytometry. J. Proteome Res. 6, 1072-1082 (Pubitemid 46480471)
8. Antos, J. M., and Francis, M. B. (2006) Transition metal catalyzed methods for site-selective protein modification. Curr. Opin. Chem. Biol. 10, 253-262 (Pubitemid 43815783)
9. Agard, N. J., Prescher, J. A., and Bertozzi, C. R. (2004) A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. J. Am. Chem. Soc. 126, 15046-15047 (Pubitemid 39557262)
10. Bader, B., Kuhn, K., Owen, D. J., Waldmann, H., Wittinghofer, A., and Kuhlmann, J. (2000) Bioorganic synthesis of lipid-modified proteins for the study of signal transduction. Nature (London) 403, 223-226 (Pubitemid 30050969)
11. Hofmann, R. M., and Muir, T. W. (2002) Recent advances in the application of expressed protein ligation to protein engineering. Curr. Opin. Biotechnol. 13, 297-303. (Pubitemid 35254085)
12. Guignet, E. G., Segura, J. M., Hovius, R., and Vogel, H. (2007) Repetitive reversible labeling of proteins at polyhistidine sequences for single-molecule imaging in live cells. ChemPhysChem 8, 1221-1227
13. Hauser, C. T., and Tsien, R. Y. (2007) A hexahistidine-Zn2+-dye label reveals STIM1 surface exposure. Proc. Natl. Acad. Sci. U.S.A. 104, 3693-3697 (Pubitemid 47181517)
14. Juillerat, A., Heinis, C., Sielaff, I., Barnikow, J., Jaccard, H., Kunz, B., Terskikh, A., and Johnsson, K. (2005) Engineering substrate specificity of O6-alkylguanine-DNA alkyltransferase for specific protein labeling in living cells. Chembiochem 6, 1263-1269 (Pubitemid 40978188)
15. Yin, J., Lin, A. J., Golan, D. E., and Walsh, C. T. (2006) Site-specific protein labeling by Sfp phosphopantetheinyl transferase. Nat. Protoc. 1, 280-285
16. Machleidt, T., Robers, M., and Hanson, G. T. (2007) Protein labeling with FlAsH and ReAsH. Methods Mol. Biol. 356, 209-220
17. Los, G. V., Encell, L. P., McDougall, M. G., Hartzell, D. D., Karassina, N., Zimprich, C., Wood, M. G., Learish, R., Ohana, R. F., Urh, M., Simpson, D., Mendez, J., Zimmerman, K., Otto, P., Vidugiris, G., Zhu, J., Darzins, A., Klaubert, D. H., Bulleit, R. F., and Wood, K. V. (2008) HaloTag: a novel protein labeling technology for cell imaging and protein analysis. ACS Chem. Biol. 3, 373-382
18. Los, G. V., and Wood, K. (2007) The HaloTag: a novel technology for cell imaging and protein analysis. Methods Mol. Biol. 356, 195-208.
19. Zhang, Y., So, M. K., Loening, A. M., Yao, H., Gambhir, S. S., and Rao, J. (2006) HaloTag protein-mediated site-specific conjugation of bioluminescent proteins to quantum dots. Angew. Chem., Int. Ed. 45, 4936-4940 (Pubitemid 44166123)
20. Adams, S. R., Campbell, R. E., Gross, L. A., Martin, B. R., Walkup, G. K., Yao, Y., Llopis, J., and Tsien, R. Y. (2002) New biarsenical ligands and tetracysteine motifs for protein labeling in vitro and in vivo: synthesis and biological applications. J. Am. Chem. Soc. 124, 6063-6076 (Pubitemid 34552852)
21. Adams, S. R., and Tsien, R. Y. (2008) Preparation of the membrane-permeant biarsenicals FlAsH-EDT2 and ReAsH-EDT2 for fluorescent labeling of tetracysteine-tagged proteins. Nat. Protoc. 3, 1527-1534
22. Chen, B., Cao, H., Yan, P., Mayer, M. U., and Squier, T. C. (2007) Identification of an orthogonal peptide binding motif for biarsenical multiuse affinity probes. Bioconjugate Chem. 18, 1259-1265 (Pubitemid 47122649)
23. Martin, L. J., Hahnke, M. J., Nitz, M., Wohnert, J., Silvaggi, N. R., Allen, K. N., Schwalbe, H., and Imperiali, B. (2007) Double-lanthanide-binding tags: design, photophysical properties, and NMR applications. J. Am. Chem. Soc. 129, 7106-7113 (Pubitemid 46903275)
24. Nitz, M., Franz, K. J., Maglathlin, R. L., and Imperiali, B. (2003) A powerful combinatorial screen to identify high-affinity terbium(III)-binding peptides. Chembiochem 4, 272-276 (Pubitemid 36505197)
25. 3+ luminescence at longer wavelengths. Bioconjugate Chem. 19, 588-591
26. Sculimbrene, B. R., and Imperiali, B. (2006) Lanthanide-binding tags as luminescent probes for studying protein interactions. J. Am. Chem. Soc. 128, 7346-7352 (Pubitemid 43849137)
27. So, M. K., Yao, H., and Rao, J. (2008) HaloTag protein-mediated specific labeling of living cells with quantum dots. Biochem. Biophys. Res. Commun. 374, 419-423
28. Wohnert, J., Franz, K. J., Nitz, M., Imperiali, B., and Schwalbe, H. (2003) Protein alignment by a coexpressed lanthanide-binding tag for the measurement of residual dipolar couplings. J. Am. Chem. Soc. 125, 13338-13339 (Pubitemid 37352103)
29. Lin, M. Z., Glenn, J. S., and Tsien, R. Y. (2008) A drug-controllable tag for visualizing newly synthesized proteins in cells and whole animals. Proc. Natl. Acad. Sci. U.S.A. 105, 7744-7749
30. Tan, L. P., Chen, G. Y., and Yao, S. Q. (2004) Expanding the scope of site-specific protein biotinylation strategies using small molecules. Bioorg. Med. Chem. Lett. 14, 5735-5738 (Pubitemid 39421510)
31. Tan, L. P., Lue, R. Y., Chen, G. Y., and Yao, S. Q. (2004) Improving the intein-mediated, site-specific protein biotinylation strategies both in vitro and in vivo. Bioorg. Med. Chem. Lett. 14, 6067-6070 (Pubitemid 39531273)
32. Wood, R. J., Pascoe, D. D., Brown, Z. K., Medlicott, E. M., Kriek, M., Neylon, C., and Roach, P. L. (2004) Optimized conjugation of a fluorescent label to proteins via intein-mediated activation and ligation. Bioconjugate Chem. 15, 366-372 (Pubitemid 38365197)
33. Lue, R. Y., Chen, G. Y., Hu, Y., Zhu, Q., and Yao, S. Q. (2004) Versatile protein biotinylation strategies for potential high-throughput proteomics. J. Am. Chem. Soc. 126, 1055-1062 (Pubitemid 38140735)
34. Lesaicherre, M. L., Lue, R. Y., Chen, G. Y., Zhu, Q., and Yao, S. Q. (2002) Intein-mediated biotinylation of proteins and its application in a protein microarray. J. Am. Chem. Soc. 124, 8768-8769
35. Inard, C., Fourcade, E., Baron, R., Tovar, D., Chaisemartin, L., Blonski, C., and Faye, J. C. (2006) Syntheses of functionalized biotin N-1′ derivatives: new tools for the control of gene expression with small molecules. Bioconjugate Chem. 17, 1030-1035 (Pubitemid 44162623)
36. Lee, J. W., and L. Fuchs, P. L. (1999) Reduction of Azides to Primary Amines in Substrates Bearing Labile Ester Functionality. Synthesis of a PEG-Solubilized, "Y"-Shaped Iminodiacetic Acid Reagent for Preparation of Folate-Tethered Drugs. Org. Lett. 1, 179-182.
37. Schwabacher, A. W., Lane, J. W., Schiesher, M. W., Leigh, K. M., and Johnson, C. W. (1998) Desymmetrization Reactions: Efficient Preparation of Unsymmetrically Substituted Linker Molecules. J. Org. Chem. 63, 1727-1729.
38. MRC Centre for Protein Engineering, [http://www.mrc-cpe.cam. ac.uk/]. Accessed April 1999.
39. Goffinet, M., Chinestra, P., Lajoie-Mazenc, I., Medale-Giamarchi, C., Favre, G., and Faye, J. C. (2008) Identification of a GTP-bound Rho specific scFv molecular sensor by phage display selection. BMC Biotechnol. 8, 34.
40. Cui, C., Zhao, W., Chen, J., Wang, J., and Li, Q. (2006) Elimination of in vivo cleavage between target protein and intein in the intein-mediated protein purification systems. Protein Expr. Purif. 50, 74-81. (Pubitemid 44648744)
41. Lajoie-Mazenc, I., Tovar, D., Penary, M., Lortal, B., Allart, S., Favard, C., Brihoum, M., Pradines, A., and Favre, G. (2007) MAP1A light chain-2 interacts with GTP-RHOB to control EGF-dependent EGF-R signaling. J. Biol. Chem. 283, 4155-4164
42. Bucourt, R., Vignau, M., and Torelli, V. (1978) New biospecific adsorbents for the purification of estradiol receptor. J. Biol. Chem. 253, 8221-8228 (Pubitemid 9073721)
43. Xu, M. Q., and Evans, T. C., Jr. (2001) Intein-mediated ligation and cyclization of expressed proteins. Methods 24, 257-277
44. Tolbert, T., and Wong, C. H. (2000) Intein-Mediated Synthesis of Proteins Containing Carbohydrates and Other Molecular Probes. J. Am. Chem. Soc. 122, 5421-5428. (Pubitemid 30431058)