Development of tag-free photoprobes for studies aimed at identifying the target of novel Group A Streptococcus antivirulence agents

Bioorganic and Medicinal Chemistry Letters

Volumn 24, Issue 6, 2014, Pages 1538-1544

  Yestrepsky, Bryan D ^a   Kretz, Colin A ^b   Xu, Yuanxi ^c   Holmes, Autumn ^b   Sun, Hongmin ^c   Ginsburg, David ^b   Larsen, Scott D ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

^c University of Missouri   (United States)

Author keywords

Antibiotic; Click chemistry; Group A Streptococcus; Phenotypic screening; Photo crosslinking; Streptokinase; Tag free photoprobes; Target identification; Virulence inhibitor

Indexed keywords

ANTIINFECTIVE AGENT; FLUORESCENT DYE; TAG FREE PHOTOPROBE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; NONHUMAN; POLYACRYLAMIDE GEL ELECTROPHORESIS; STREPTOCOCCUS GROUP A; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

STREPTOCOCCUS SP. 'GROUP A';

ANTIBIOTIC; CLICK CHEMISTRY; GROUP A STREPTOCOCCUS; PHENOTYPIC SCREENING; PHOTO-CROSSLINKING; STREPTOKINASE; TAG-FREE PHOTOPROBES; TARGET IDENTIFICATION; VIRULENCE INHIBITOR;

ANTI-BACTERIAL AGENTS; AZIDES; BENZOPHENONES; CLICK CHEMISTRY; MOLECULAR PROBES; STREPTOCOCCUS PYOGENES; STRUCTURE-ACTIVITY RELATIONSHIP; VIRULENCE FACTORS;

EID: 84895825987     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2014.01.079     Document Type: Article

References (38)

1. M. Otto Sci. Trans. Med. 5 2013 184fs17
2. D.A. Rasko, and V. Sperandio Nat. Rev. Drug Disc. 9 2010 117
3. H. Sun, U. Ringdahl, J.W. Homeister, W.P. Fay, N.C. Engleberg, A.Y. Yang, L.S. Rozek, X. Wang, U. Sjobring, and D. Ginsburg Science 305 2004 1283
4. H. Sun, Y. Xu, I. Sitkiewicz, Y. Ma, X. Wang, B.D. Yestrepsky, Y. Huang, M.C. Lapadatescu, M.J. Larsen, S.D. Larsen, J.M. Musser, and D. Ginsburg PNAS 109 2012 3469
5. B.D. Yestrepsky, Y. Xu, M.E. Breen, X. Li, W.G. Rajeswaran, J.G. Ryu, R.J. Sorenson, Y. Tsume, M.W. Wilson, W. Zhang, D. Sun, H. Sun, and S.D. Larsen Bioorg. Med. Chem. 21 2013 1880
6. B.R. Stockwell Nature 432 2004 846
7. D.C. Swinney, and J. Anthony Nat. Rev. Drug Disc. 10 2011 507
8. D.J. Payne, M.N. Gwynn, D.J. Holmes, and D.L. Pompliano Nat. Rev. Drug Disc. 6 2007 29
9. B. Kreikemeyer, K.S. McIver, and A. Podbielski Trends Microbiol. 11 2003 224
10. K.S. McIver, and J.R. Scott J. Bacteriol. 179 1997 5178
11. M.S. Chaussee, D. Ajdic, and J.J. Ferretti Infect. Immun. 67 1999 1715
12. M.S. Chaussee, G.L. Sylva, D.E. Sturdevant, L.M. Smoot, M.R. Graham, R.O. Watson, and J.M. Musser Infect. Immun. 70 2002 762
13. A. Heath, V.J. DiRita, N.L. Barg, and N.C. Engleberg Infect. Immun. 67 1999 5298
14. S.B. Beres, G.L. Sylva, K.D. Barbian, B. Lei, J.S. Hoff, N.D. Mammarella, M.-Y. Liu, J.C. Smoot, S.F. Porcella, L.D. Parkins, D.S. Campbell, T.M. Smith, J.K. McCormick, D.Y.M. Leung, P.M. Schlievert, and J.M. Musser PNAS 99 2002 10078
15. B.J. Leslie, and P.J. Hergenrother Chem. Soc. Rev. 37 2008 1347
16. M.W. Harding, A. Galat, D.E. Uehling, and S.L. Schreiber Nature 341 1989 758
17. G.C. Adam, C.D. Vanderwal, E.J. Sorensen, and B.F. Cravatt Angew. Chem., Int. Ed. 42 2003 5480
18. S. Bach, M. Knockaert, J. Reinhardt, O. Lozach, S. Schmitt, B. Baratte, M. Koken, S.P. Coburn, L. Tang, T. Jiang, D.C. Liang, H. Galons, J.F. Dierick, L.A. Pinna, F. Meggio, F. Totzke, C. Schachtele, A.S. Lerman, A. Carnero, Y.Q. Wan, N. Gray, and L. Meijer J. Biol. Chem. 280 2005 31208
19. A.L. MacKinnon, J.L. Garrison, R.S. Hegde, and J. Taunton J. Am. Chem. Soc. 129 2007 14560
20. T. Mayer, and M.E. Maier Eur. J. Org. Chem. 28 2007 4711
21. D.J. Lapinsky Bioorg. Med. Chem. 20 2012 6237
22. T. Fujii, Y. Manabe, T. Sugimoto, and M. Ueda Tetrahedron 61 2005 7874
23. C.M. Salisbury, and B.F. Cravatt QSAR Comb. Sci. 26 2007 1229
24. S.A. Fleming Tetrahedron 51 1995 12479
25. K. Kobayashi, T. Uneda, K. Takada, H. Tanaka, T. Kitamura, O. Morikawa, and H. Konishi J. Org. Chem. 62 1997 664
26. P. Carato, Z. Moussavi, A. Sabaouni, N. Lebegue, P. Berthelot, and S. Yous Tetrahedron 62 2006 9054
27. A.S. Moriello, L. Balas, A. Ligresti, M.G. Cascio, T. Durand, E. Morera, G. Ortar, and V. Di Marzo J. Med. Chem. 49 2006 2320
28. M.R. Bond, H.C. Zhang, P.D. Vu, and J.J. Kohler Nat. Protoc. 4 2009 1044
29. R.F.R. Church, and M.J. Weiss J. Org. Chem. 35 1970 2465
30. J.Y. Chae, and S.L. Buchwald J. Org. Chem. 69 2004 3336
31. J. Andersen, U. Madsen, F. Bjorkling, and X.F. Liang Synlett 2005 2209
32. A.I. Markosyan, R.A. Kuroyan, S.V. Dilanyan, M.S. Aleksanyan, A.A. Karapetyan, and Y.T. Struchkov Khim. Geterotsikl. Soedin. 5 2000 658
33. A. Nickon Acc. Chem. Res. 26 1993 84
34. C.-S. Kuhn, J. Lehmann, and J. Steck Tetrahedron 46 1990 3129
35. J.R. Colca, W.G. McDonald, D.J. Waldon, L.M. Thomasco, R.C. Gadwood, E.T. Lund, G.S. Cavey, W.R. Mathews, L.D. Adams, E.T. Cecil, J.D. Pearson, J.H. Bock, J.E. Mott, D.L. Shinabarger, L.Q. Xiong, and A.S. Mankin J. Biol. Chem. 278 2003 21972
36. S.E. Ong, M. Schenone, A.A. Margolin, X.Y. Li, K. Do, M.K. Doud, D.R. Mani, L. Kuai, X. Wang, J.L. Wood, N.J. Tolliday, A.N. Koehler, L.A. Marcaurelle, T.R. Golub, R.J. Gould, S.L. Schreiber, and S.A. Carr PNAS 106 2009 4617
37. S. Ghaemmaghami, W. Huh, K. Bower, R.W. Howson, A. Belle, N. Dephoure, E.K. O'Shea, and J.S. Weissman Nature 425 2003 737
38. P.P. Sche, K.M. McKenzie, J.D. White, and D.J. Austin Chem. Biol. 6 1999 707