Evaluation of sulfatase-directed quinone methide traps for proteomics

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 2, 2012, Pages 622-627

  Lenger, Janina ^a,b   Schröder, Marius ^a   Ennemann, Eva C ^a   Müller, Benjamin ^a   Wong, Chi Huey ^b   Noll, Thomas ^a   Dierks, Thomas ^a   Hanson, Sarah R ^a,b   Sewald, Norbert ^a  

^a BIELEFELD UNIVERSITY   (Germany)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Activity based proteomics; Enzyme inhibitor; Quinone methide; Suicide inhibitor; Sulfatase probe

Indexed keywords

4 FLUOROMETHYLPHENYL SULFATE; ARYLSULFATASE; DIFLUOROMETHYLPHENYL SULFATE; ENZYME INHIBITOR; MONOFLUOROMETHYLPHENYL SULFATE; PROTEOME; QUINONE METHIDE; STERYL SULFATASE; SULFATE; UNCLASSIFIED DRUG;

ACTIVITY BASED PROTEOMIC PROBE; ARTICLE; CHEMICAL LABELING; CONTROLLED STUDY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME INACTIVATION; ENZYME PURIFICATION; ENZYME SPECIFICITY; ENZYME SUBSTRATE; ENZYME SUBSTRATE COMPLEX; FUNCTIONAL PROTEOMICS; KLEBSIELLA PNEUMONIAE; MOLECULAR PROBE; PSEUDOMONAS AERUGINOSA;

BACTERIAL PROTEINS; ELECTROPHORESIS, GEL, TWO-DIMENSIONAL; ENZYME INHIBITORS; FLUORESCENT DYES; HUMANS; INDOLEQUINONES; KLEBSIELLA PNEUMONIAE; PROTEOMICS; PSEUDOMONAS AERUGINOSA; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; STERYL-SULFATASE; SULFATASES;

BACTERIA (MICROORGANISMS); KLEBSIELLA PNEUMONIAE; PSEUDOMONAS AERUGINOSA;

EID: 84855812463     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.04.044     Document Type: Article

References (43)

1. T. Böttcher, M. Pitscheider, and S.A. Sieber Angew. Chem. 122 2010 2740
2. T. Böttcher, M. Pitscheider, and S.A. Sieber Angew. Chem., Int. Ed. 49 2010 2680
3. P.F. van Swieten, M.A. Leeuwenburgh, B.M. Kessler, and H.S. Overkleeft Org. Biomol. Chem. 3 2005 20
4. A.W. Puri, and M. Bogyo ACS Chem. Biol. 4 2009 603
5. M. Fonovic, and M. Bogyo Expert Rev. Proteomics 5 2010 721
6. M.C. Hagenstein, and N. Sewald J. Biotechnol. 124 2006 56
7. B.F. Cravatt, A.T. Wright, and J.W. Kozarich Annu. Rev. Biochem. 77 2008 383
8. D.K. Nomura, M.M. Dix, and B.F. Cravatt Nat. Rev. Cancer 10 2010 630
9. S.R. Hanson, M.D. Best, and C.-H. Wong Angew. Chem. 116 2004 5858
10. S.R. Hanson, M.D. Best, and C.-H. Wong Angew. Chem., Int. Ed. 43 2004 5736
11. M. Sardiello, I. Annunziata, G. Roma, and A. Ballabio Hum. Mol. Genet. 14 2005 3203
12. P. Bojarova, and S.J. Williams Curr. Opin. Chem. Biol. 12 2008 573
13. G. Diez-Roux, and A. Ballabio Annu. Rev. Genomics Hum. Genet. 6 2005 355
14. A.M. Roberton, R. Wiggins, P.H. Horner, R. Greenwood, T. Crowley, A. Fernandes, M. Berry, and A.P. Corfield J. Clin. Microbiol. 43 1999 5504
15. Y. Dai, Y. Yang, V. MacLeod, X. Yue, A.C. Rapraeger, Z. Shriver, G. Venkataraman, R. Sasisekharan, and R.D. Sanderson J. Biol. Chem. 280 2005 40066
16. M. Morimoto-Tomita, K. Uchimura, A. Bistrup, D.H. Lum, M. Egeblad, N. Boudreau, Z. Werb, and S.D. Rosen Neoplasia 7 2005 1001
17. K. Narita, J. Staub, J. Chien, K. Meyer, M. Bauer, A. Friedl, S. Ramakrishnan, and V. Shridhar Cancer Res. 66 2006 6025
18. K. Narita, J. Chien, S.A. Mullany, J. Staub, X. Qian, W.L. Lingle, and V. Shridhar J. Biol. Chem. 282 2007 14413
19. R. Nawroth, A. van Zante, S. Cervantes, M. McManus, M. Hebrok, and S.D. Rosen PLoS ONE 2 2007 e392
20. S. Otsuki, N. Taniguchi, S.P. Grogan, D. D'Lima, M. Kinoshita, and M. Lotz Arthritis Res. Ther. 10 2008 R61
21. S. Otsuki, S.R. Hanson, S. Miyaki, S.P. Grogan, M. Kinoshita, H. Asahara, C.-H. Wong, and M.K. Lotz Proc. Natl. Acad. Sci. U.S.A. 107 2010 10202
22. M.J. Reed, A. Purohit, L.W.L. Woo, S.P. Newman, and B.V.L. Potter Endocr. Rev. 26 2005 171
23. S.R. Hanson, L.J. Whalen, and C.-H. Wong Bioorg. Med. Chem. 14 2006 8386
24. L.-C. Lo, T.-L. Pang, C.-H. Kuo, Y.-L. Chiang, H.-Y. Wang, and J.-J. Lin J. Proteome Res. 1 2002 35
25. C.-S. Tsai, Y.-K. Li, and L.-C. Lo Org. Lett. 4 2002 3607
26. Q. Zhu, A. Girish, S. Chattopadhaya, and S.Q. Yao Chem. Commun. 13 2004 1512
27. C.-P. Lu, C.-T. Ren, Y.-N. Lai, S.-H. Wu, W.-M. Wang, J.-Y. Chen, and L.-C. Lo Angew. Chem. 117 2005 7048
28. C.-P. Lu, C.-T. Ren, Y.-N. Lai, S.-H. Wu, W.-M. Wang, J.-Y. Chen, and L.-C. Lo Angew. Chem., Int. Ed. 44 2005 6888
29. C.-P. Lu, C.-T. Ren, S.-H. Wu, C.-Y. Chu, and L.-C. Lo ChemBioChem 8 2007 2187
30. V. Ahmed, Y. Liu, and S.D. Taylor ChemBioChem 10 2009 1457
31. L.-C. Lo, C.-H.L. Lo, and K.D. Janda Bioorg. Med. Chem. Lett. 6 1996 2117
32. L.-C. Lo, Y.-L. Chiang, C.-H. Kuo, H.-K. Liao, Y.-J. Chen, and J.-J. Lin Biochem. Biophys. Res. Commun. 326 2005 30
33. M. Uttamchandani, J. Li, H. Sun, and S.Q. Yao ChemBioChem 9 2008 667
34. Q. Wang, U. Dechert, F. Jirik, and S.G. Withers Biochem. Biophys. Res. Commun. 200 1994 577
35. R. Kitz, and I.B. Wilson J. Biol. Chem. 237 1962 3245
36. T.L. Born, J.K. Myers, T.S. Widlanski, and F. Rusnak J. Biol. Chem. 270 1995 25651
37. C. Szameit, C. Miech, M. Balleinigner, B. Schmidt, K. von Figura, and T. Dierks J. Biol. Chem. 274 1999 15375
38. M.-A. Frese, S. Schulz, and T. Dierks J. Biol. Chem. 283 2008 11388
39. M. Mariappan, S.L. Gande, K. Radhakrishnan, B. Schmidt, T. Dierks, and K. von Figura J. Biol. Chem. 283 2008 11556
40. J. Conary, A. Nauerth, G. Burns, A. Hasilik, and K. von Figura Eur. J. Biochem. 158 1986 71
41. H.M. Awad, M.G. Boersma, S. Boeren, P.J. van Bladeren, and I.M. Rietjens Chem. Res. Toxicol. 14 2001 398
42. K.A. Kalesh, L.P. Tan, K. Lu, L. Gao, J. Wang, and S.Q. Yao Chem. Commun. 46 2010 589
43. C. Miech, T. Dierks, T. Selmer, K. von Figura, and B. Schmidt J. Biol. Chem. 273 1998 4835