Development of an indole-based chemically cleavable linker concept for immobilizing bait compounds for protein pull-down experiments

Bioconjugate Chemistry

Volumn 22, Issue 2, 2011, Pages 211-217

  Sturm, Martin ^a,b   Leitner, Alexander ^a,c   Lindner, Wolfgang ^a  

^a UNIVERSITY OF VIENNA   (Austria)

^b Austrian Research Institute for Chemistry and Technology   (Austria)

^c ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CONDENSATION REACTIONS; ENZYMES; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULES;

ACRYLAMIDES; AGAROSE; INTERACTION STUDIES; MALONDIALDEHYDE; PYRROLIDINES; SOLID SUPPORTS; TARGET MOLECULE; TARGETED PROTEINS; TRYPTOPHAN RESIDUES; TYROSINE KINASE INHIBITOR;

POLYCYCLIC AROMATIC HYDROCARBONS;

ACRYLAMIDE; AGAROSE; BOSUTINIB; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE INHIBITOR; INDOLE; LINK PROTEIN; MALONALDEHYDE; PEPTIDE; PYRROLIDINE DERIVATIVE; SCAFFOLD PROTEIN; TRYPTOPHAN;

ARTICLE; BINDING AFFINITY; CELL LYSATE; CONTROLLED STUDY; ELUTION; HUMAN; HUMAN CELL; HYDROLYSIS; LIQUID CHROMATOGRAPHY; MOLECULE; PROTEIN ANALYSIS; PROTEIN CLEAVAGE; PROTEIN DEGRADATION; PROTEIN HYDROLYSIS; PROTEIN INTERACTION; PROTEIN PURIFICATION; PROTEIN TARGETING; PURIFICATION; SOLID; TANDEM MASS SPECTROMETRY;

EID: 79951686304     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc100330a     Document Type: Article

References (18)

1. Rix, U. and Superti-Furga, J. (2009) Target profiling of small molecules in chemical proteomics Nat. Chem. Biol. 5, 616-624
2. Landi, F., Johansson, C. M., Campopiano, D. J., and Hulme, A. N. (2010) Synthesis and application of a new cleavable linker for "click"-based affinity chromatography Org. Biomol. Chem. 8, 56-59
3. Ovaa, H. and van Leeuwen, F. (2008) Chemical biology approaches to probe the proteome ChemBioChem 9, 2913-2919
4. Santala, V. and Savirantal, P. (2004) Affinity-independent elution of antibody-displaying phages using cleavable DNA linker containing streptavidin beads J. Immunol. Methods 284, 159-163
5. Verhelst, S. H. L., Fonovic, M., and Bogyo, M. (2007) A mild chemically cleavable linker system for functional proteomic applications Angew. Chem., Intl. Ed. Engl. 46, 1284-1286
6. Cho, S., Lee, S.-H., Chung, W.-J., Kim, Y.-K., Lee, Y.-S., and Kim, B.-G. (2004) Microbead-based affinity chromatography chip using RNA aptamer modified with photocleavable linker Electrophoresis 25, 3730-3739
7. Foettinger, A., Leitner, A., and Lindner, W. (2007) Selective enrichment of tryptophan-containing peptides from protein digests employing a reversible derivatization with malondialdehyde and solid-phase capture on hydrazide beads J. Proteome Res. 6, 3827-3834
8. Foettinger, A., Melmer, M., Leitner, A., and Lindner, W. (2007) Reaction of the indole group with malondialdehyde: Application for the derivatization of tryptophan residues in peptides Bioconjugate Chem. 18, 1678-1683
9. Rix, U., Hantschel, O., Duernberger, G., Remsing-Rix, L. L., Planyavsky, M., Fernbach, N. V., Kaupe, I., Bennett, K. L., Valent, P., Colinge, J., Köcher, T., and Superti-Furga, G. (2007) Chemical proteomic profiles of the BCR-ABL inhibitors imatinib, nilotinib, and dasatinib reveal novel kinase and nonkinase targets Blood 110, 4055-4063
10. Fernbach, N. V., Planyasky, M., Mueller, A., Breitwieser, F. P., Colinge, J., Rix, U., and Bennett, K. L. (2009) Acid elution and one-dimensional shotgun analysis on an Orbitrap mass spectrometer: an application to drug affinity chromatography J. Proteome Res. 8, 4753-4765
11. Teuber, H. J., Glosauer, O., and Hochmuth, U. (1964) Ein neues Kondensationsprodukt aus Tryptamin und Acetessigaldehyd Chem. Ber. 97, 557-562
12. Dirksen, A., Dirksen, S., Hackeng, T. M., and Dawson, P. E. (2006) Nucleophilic catalysis of hydrazone formation and transimination: Implications for dynamic covalent chemistry J. Am. Chem. Soc. 128, 15602-15603
13. Bhat, V. T., Caniard, A. M., Luksch, T., Brenk, R., Campopiano, D. J., and Greaney, M. F. (2010) Nucleophilic catalysis of acylhydrazone equilibration for protein-directed dynamic covalent chemistry Nat. Chem. 2, 490-497
14. Kunishima, M., Kawachi, C., Morita, J., Terao, K., Iwasaki, F., and Tani, S. (1999) 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholinium chloride: An efficient condensing agent leading to the formation of amides and esters Tetrahedron 55, 13159-13170
15. Vultur, A., Buettner, R., Kowolik, C., Liang, W., Smith, D., Boschelli, F., and Jove, R. (2008) SKI-606 (bosutinib), a novel Src kinase inhibitor, suppresses migration and invasion of human breast cancer cells Mol. Cancer Ther. 7, 1185-1194
16. Remsing-Rix, L. L., Rix, U., Colinge, J., Hantschel, O., Bennett, K. L., Stranzl, T., Mueller, A., Baumgartner, C., Valent, P., Augustin, M., Till, J. H., and Superti-Furga, J. (2009) Global target profile of the kinase inhibitor bosutinib in primary chronic myeloid leukemia cells Leukemia 23, 477-485
17. Bantscheff, M., Eberhard, D., Abraham, Y., Bastuck, S., Boesche, M., Hobson, S., Mathieson, T., Raida, M., Rau, C., Reader, V., Sweetman, G., Bauer, A., Bouwmeester, T., Hopf, C., Kruse, U., Neubauer, G., Ramsden, N., Rick, J., Kuster, B., and Drewes, G. (2007) Quantitative chemical proteomics reveals mechanisms of action of clinical ABL kinase inhibitors Nat. Biotechnol. 25, 1035-1044
18. Geurink, P. P., Florea, B. I., Li, N., Witte, M. D., Verasdonck, J., Kuo, C.-L., van der Marel, G. A., and Overkleeft, H. S. (2010) A cleavable linker based on the levulinoyl ester for activity-based protein profiling Angew. Chem., Int. Ed. 49, 6802-6805