Design and synthesis of minimalist terminal alkyne-containing diazirine photo-crosslinkers and their incorporation into kinase inhibitors for cell- and tissue-based proteome profiling

Angewandte Chemie - International Edition

Volumn 52, Issue 33, 2013, Pages 8551-8556

  Li, Zhengqiu ^a   Hao, Piliang ^b   Li, Lin ^a   Tan, Chelsea Y J ^a   Cheng, Xiamin ^a   Chen, Grace Y J ^a   Sze, Siu Kwan ^b   Shen, Han Ming ^a   Yao, Shao Q ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b NANYANG TECHNOLOGICAL UNIVERSITY   (Singapore)

Author keywords

affinity based probes; fluorescent probes; kinases; photo crosslinking; proteomics

Indexed keywords

CELLULAR KINASE; FLUORESCENT PROBES; KINASE INHIBITORS; KINASES; PHOTO-CROSSLINKER; PHOTOCROSS-LINKING; PROTEOME PROFILING; PROTEOMICS;

MOLECULAR BIOLOGY; PROBES;

ENZYME INHIBITION;

ALKYNE; CROSS LINKING REAGENT; DIAZOMETHANE; PROTEIN KINASE; PROTEIN KINASE INHIBITOR; PROTEOME;

AFFINITY-BASED PROBES; ARTICLE; CELL PROLIFERATION; CELL STRAIN HEPG2; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; DRUG EFFECT; FLUORESCENT ANTIBODY TECHNIQUE; FLUORESCENT PROBES; HUMAN; IC 50; KINASES; KINETICS; MASS SPECTROMETRY; METABOLISM; MOLECULAR PROBE; PHOTO-CROSSLINKING; PHOTOAFFINITY LABELING; PROTEOMICS; SYNTHESIS;

AFFINITY-BASED PROBES; FLUORESCENT PROBES; KINASES; PHOTO-CROSSLINKING; PROTEOMICS;

ALKYNES; CELL PROLIFERATION; CROSS-LINKING REAGENTS; DIAZOMETHANE; DRUG DESIGN; FLUORESCENT ANTIBODY TECHNIQUE; HEP G2 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; KINETICS; MOLECULAR PROBES; MOLECULAR STRUCTURE; PHOTOAFFINITY LABELS; PROTEIN KINASE INHIBITORS; PROTEIN KINASES; PROTEOME; PROTEOMICS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 84882441298     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201300683     Document Type: Article

References (29)

1. F. Kotzyba-Hibert, I. Kapfer, M. Goeldner, Angew. Chem. 1995, 107, 1391-1408
2. Angew. Chem. Int. Ed. Engl. 1995, 34, 1296-1312
3. B. J. Leslie, P. J. Hergenrother, Chem. Soc. Rev. 2008, 37, 1347-1360
4. J. Das, Chem. Rev. 2011, 111, 4405-4417
5. L. Dubinsky, B. P. Krom, M. M. Meijler, Bioorg. Med. Chem. 2012, 20, 554-570.
6. H. Shi, X.-M. Cheng, S. K. Sze, S. Q. Yao, Chem. Commun. 2011, 47, 11306-11308
7. H. Shi, C.-J. Zhang, G. Y. J. Chen, S. Q. Yao, J. Am. Chem. Soc. 2012, 134, 3001-3014.
8. P. Ranjitkar, B. G. K. Perera, D. Swaney, S. B. Hari, E. T. Larson, R. Merritt, E. A. Krishnamurty, J. Villén, D. J. Maly, J. Am. Chem. Soc. 2012, 134, 19017-19025
9. R. Krishnamurty, J. L. Brigham, S. E. Leonard, P. Ranjitkar, E. J. Dale, E. T. Larson, E. A. Merritt, D. J. Maly, Nat. Chem. Biol. 2013, 9, 43-50.
10. E. W. Chan, S. Chattopadhaya, R. C. Panicker, X. Huang, S. Q. Yao, J. Am. Chem. Soc. 2004, 126, 14435-14446
11. K. Liu, H. Shi, H. Xiao, A. G. L. Chong, X. Bi, Y. T. Chang, K. Tan, R. Y. Yada, S. Q. Yao, Angew. Chem. 2009, 121, 8443-8447
12. Angew. Chem. Int. Ed. 2009, 48, 8293-8297.
13. H. C. Kolb, K. B. Sharpless, Drug Discovery Today 2003, 8, 1128-1137
14. M. Meldal, C. W. Tornøe, Chem. Rev. 2008, 108, 2952-3015
15. E. M. Sletten, C. R. Bertozzi, Angew. Chem. 2009, 121, 7108-7133
16. Angew. Chem. Int. Ed. 2009, 48, 6974-6998
17. K. A. Kalesh, H. Shi, J. Ge, S. Q. Yao, Org. Biomol. Chem. 2010, 8, 1749-1762.
18. P.-Y. Yang, K. Liu, M. H. Ngai, M. J. Lear, M. R. Wenk, S. Q. Yao, J. Am. Chem. Soc. 2010, 132, 656-666.
19. J. Dancey, E. A. Sausville, Nat. Rev. Drug Discovery 2003, 2, 296-313.
20. T. Force, K. L. Kolaja, Nat. Rev. Drug Discovery 2011, 10, 111-126.
21. T. Anastassiadis, S. W. Deacon, K. Devarajan, H. Ma, J. R. Peterson, Nat. Biotechnol. 2011, 29, 1039-1045
22. M. I. Davis, J. P. Hunt, S. Herrgard, P. Ciceri, L. M. Wodicka, G. Pallares, M. Hocker, D. K. Treiber, P. P. Zarrinkar, Nat. Biotechnol. 2011, 29, 1046-1051
23. U. Rix, G. Superti-Furga, Nat. Chem. Biol. 2009, 5, 616-624.
24. E. Weisberg, P. W. Manley, S. W. Cowan-Jacob, A. Hochhaus, J. D. Griffin, Nat. Rev. Cancer 2007, 7, 345-356.
25. L. Dubinsky, L. M. Jarosz, N. Amara, P. Krief, V. V. Kravchenko, B. P. Krom, M. M. Meijler, Chem. Commun. 2009, 7378-7380.
26. J. J. Fischer, O. Y. Graebner, C. Dalhoff, S. Michaelis, A. K. Schrey, J. Ungewiss, K. Andrich, D. Jeske, F. Kroll, M. Glinski, M. Sefkow, M. Dreger, H. Koester, J. Proteome Res. 2010, 9, 806-817.
27. S. A. Sieber, S. Niessen, H. S. Hoover, B. F. Cravatt, Nat. Chem. Biol. 2006, 2, 274-281
28. H. Shi, M. Uttamchandani, S. Q. Yao, Chem. Asian J. 2011, 6, 2803-2815.
29. M. Bantscheff, D. Eberhard, Y. Abraham, S. Bastuck, M. Boesche, S. Hobson, T. Mathieson, J. Perrin, M. Raida, C. Rau, V. Reader, G. Sweetman, A. Bauer, T. Bouwmeester, C. Hopf, U. Kruse, G. Neubauer, N. Ramsden, J. Rick, B. Kuster, G. Drewes, Nat. Biotechnol. 2007, 25, 1035-1044.