Synthesis and evaluation of thiazolidinedione and dioxazaborocane analogues as inhibitors of AI-2 quorum sensing in Vibrio harveyi

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 3, 2013, Pages 660-667

  Brackman, Gilles ^a   Al Quntar, Abed Al Aziz ^b,c   Enk, Claes D ^d   Karalic, Izet ^a   Nelis, Hans J ^a   Van Calenbergh, Serge ^a   Srebnik, Morris ^b   Coenye, Tom ^a  

^a GHENT UNIVERSITY   (Belgium)

^b HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^c AL QUDS UNIVERSITY   (Palestine)

^d HEBREW UNIVERSITY   (Israel)

Author keywords

AI 2; Dioxazaborocane; Quorum sensing; Thiazolidinedione; Vibrio harveyi

Indexed keywords

1 (4,8 DIMETHYL 2 PHENYL 1,3,6,2 DIOXAZABOROCAN 6 YL)PROPAN 2 OL; 2 (2 PHENYL 1,3,6,2 DIOXAZABOROCAN 6 YL)ETHANOL; 2 (4 BROMOPHENYL) 6 METHYL 1,3,6,2 DIOXAZABOROCANE; 2,4 THIAZOLIDINEDIONE DERIVATIVE; 3 (6 METHYL 1,3,6,2 DIOXAZABOROCAN 2 YL)ANILINE; 3 (6 METHYL 1,3,6,2 DIOXAZABOROCAN 2 YL)BENZOIC ACID; 4 (6 METHYL 1,3,6,2 DIOXAZABOROCAN 2 YL)BENZALDEHYDE; 4 (6 METHYL 1,3,6,2 DIOXAZABOROCAN 2 YL)BENZOIC ACID; 4 (6 METHYL 1,3,6,2 DIOXAZABOROCAN 2 YL)PHENOL; 4 [(6 METHYL 1,3,6,2 DIOXAZABOROCAN 2 YL)PHENYL]METHANOL; 5 DECYLIDENETHIAZOLIDINE 2,4 DIONE; 5 DECYLTHIAZOLIDINE 2,4 DIONE; 5 DODECYLIDENETHIAZOLIDINE 2,4 DIONE; 5 OCTYLIDENETHIAZOLIDINE 2,4 DIONE; 5 UNDECYLIDENETHIAZOLIDINE 2,4 DIONE; DIOXAZABOROCANE DERIVATIVE; OXAZABOROLIDINE DERIVATIVE; TRANSCRIPTION FACTOR LUXR; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GROWTH; BACTERIAL STRAIN; BACTERIUM CULTURE; BIOLUMINESCENCE; CONCENTRATION (PARAMETERS); DNA BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; INHIBITION KINETICS; MINIMUM INHIBITORY CONCENTRATION; MUTANT; NONHUMAN; PHARMACOLOGICAL BLOCKING; QUORUM SENSING; VIBRIO HARVEYI;

ANTI-BACTERIAL AGENTS; BORON COMPOUNDS; DOSE-RESPONSE RELATIONSHIP, DRUG; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; QUORUM SENSING; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLIDINEDIONES; VIBRIO;

VIBRIO HARVEYI;

EID: 84872322143     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.11.055     Document Type: Article

References (32)

1. M.B. Miller, and B.L. Bassler Annu. Rev. Microbiol. 55 2001 165
2. P.A. Sokol, R.J. Malott, K. Riedel, and L. Eberl Future Microbiol. 2 2007 555
3. T.B. Rasmussen, and M. Givskov Microbiology 152 2006 895
4. R.B. Raffa, J.R. Iannuzzo, D.R. Levine, K.K. Saeid, R.C. Schwartz, N.T. Sucic, O.D. Terleckyj, and J.M. Young J. Pharmacol. Exp. Ther. 312 2005 417
5. M. Kleerebezem, L.E. Quadri, O.P. Kuipers, and W.M. de Vos Mol. Microbiol. 24 1997 895
6. M.E. Taga ACS Chem. Biol. 2 2007 89
7. S. Schauder, K. Shokat, M.G. Surette, and B.L. Bassler Mol. Microbiol. 41 2001 463
8. X. Chen, S. Schauder, N. Potier, A. Van Dorsselaer, I. Pelczer, B.L. Bassler, and F.M. Hughson Nature 415 2002 545
9. D.L. Milton Int. J. Med. Microbiol. 296 2006 61
10. D.A. Higgins, M.E. Pomianek, C.M. Kraml, R.K. Taylor, M.F. Semmelhack, and B.L. Bassler Nature 450 2007 883
11. J.A. Freeman, and B.L. Bassler J. Bacteriol. 181 1999 899
12. B.L. Bassler, M. Wright, and M.R. Silverman Mol. Microbiol. 13 1994 273
13. J.A. Freeman, and B.L. Bassler Mol. Microbiol. 31 1999 665
14. A. Vendeville, K. Winzer, K. Heurlier, C.M. Tang, and K.R. Hardie Nat. Rev. Microbiol. 3 2005 383
15. R. Aharoni, M. Bronstheyn, A. Jabbour, B. Zaks, M. Srebnik, and D. Steinberg Bioorg. Med. Chem. 16 2008 1596
16. N. Ni, M. Li, J. Wang, and B. Wang Med. Res. Rev. 29 2009 65
17. G. Brackman, T. Defoirdt, C. Miyamoto, P. Bossier, S. Van Calenbergh, H.J. Nelis, and T. Coenye BMC Microbiol. 8 2008 149
18. G. Brackman, S. Celen, K. Baruah, P. Bossier, S. Van Calenbergh, H.J. Nelis, and T. Coenye Microbiology 155 2009 4114
19. J. Estephane, J. Dauvergne, L. Soulère, S. Reverchon, Y. Queneau, and A. Doutheau Bioorg. Med. Chem. Lett. 18 2008 4321
20. A.M. Stevens, Y. Queneau, L. Soulère, S. von Bodman, and A. Doutheau Chem. Rev. 111 2011 4
21. W.R. Galloway, J.T. Hodgkinson, S.D. Bowden, M. Welch, and D.R. Spring Chem. Rev. 111 2011 28
22. N. Ni, H.T. Chou, J. Wang, M. Li, C.D. Lu, P.C. Tai, and B. Wang Biochem. Biophys. Res. Commun. 369 2008 590
23. N. Ni, G. Choudhary, M. Li, and B. Wang Bioorg. Med. Chem. Lett. 18 2008 1567
24. M. Li, N. Ni, H.T. Chou, C.D. Lu, P.C. Tai, and B. Wang ChemMedChem 3 2008 1242
25. G. Brackman, S. Celen, U. Hillaert, S. Van Calenbergh, P. Cos, L. Maes, H.J. Nelis, and T. Coenye PLoS One 6 2011 e16084
26. A.J. Pompeani, J.J. Irgon, M.F. Berger, M.L. Bulyk, N.S. Wingreen, and B.L. Bassler Mol. Microbiol. 70 2008 76
27. B.L. Bassler, E.P. Greenberg, and A.M. Stevens J. Bacteriol. 179 1997 4043
28. M.G. Surette, M.B. Miller, and B.L. Bassler Proc. Natl. Acad. Sci. U.S.A. 96 1999 1639
29. B.L. Bassler, M. Wright, R.E. Showalter, and M.R. Silverman Mol. Microbiol. 9 1993 773
30. T. Defoirdt, R. Crab, T.K. Wood, P. Sorgeloos, W. Verstraete, and P. Bossier Appl. Environ. Microbiol. 72 2006 6419
31. D.H. Lenz, K.C. Mok, B.N. Lilley, R.V. Kulkami, N.S. Wingreen, and B.L. Bassler Cell 118 2004 69
32. D. Ren, L.A. Bedzyk, R.W. Ye, S.M. Thomas, and T.K. Wood Biotech. Bioeng. 88 2004 630