Synthetic homoserine lactone-derived sulfonylureas as inhibitors of Vibrio fischeri quorum sensing regulator

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 7, 2008, Pages 3550-3556

  Frezza, Marine ^a   Soulère, Laurent ^a   Reverchon, Sylvie ^b   Guiliani, Nicolas ^c   Jerez, Carlos ^c   Queneau, Yves ^a   Doutheau, Alain ^a  

^a UNIVERSITÉ LYON 1   (France)

^b UNIVERSITÉ DE LYON   (France)

^c Laboratorio de Microbiología Molecular y Biotecnología   (Chile)

Author keywords

AHLs; Analogues; Antagonist; Molecular modelling; QS; V. fischeri

Indexed keywords

1 (3 PHENYL PROPYL) 3 (2 OXO TETRAHYDRO FURAN 3 YL)SULFONYLUREA; 1 (4 PHENYL BUTYL) 3 (2 OXO TETRAHYDRO FURAN 3 YL)SULFONYLUREA; 1 BENZYL 3 (2 OXO TETRAHYDRO FURAN 3 YL)SULFONYLUREA; 1 BUTYL 3 (2 OXO TETRAHYDRO FURAN 3 YL)SULFONYLUREA; 1 DECYL 3 (2 OXO TETRAHYDRO FURAN 3 YL)SULFONYLUREA; 1 HEXYL 3 (2 OXO TETRAHYDRO FURAN 3 YL)SULFONYLUREA; 1 OCTYL 3 (2 OXO TETRAHYDRO FURAN 3 YL)SULFONYLUREA; 1 PENTYL 3 (2 OXO TETRAHYDRO FURAN 3 YL)SULFONYLUREA; 1 PHENETHYL 3 (2 OXO TETRAHYDRO FURAN 3 YL)SULFONYLUREA; ALIPHATIC COMPOUND; HOMOSERINE; HYDROGEN; LACTONE; LACTONE DERIVATIVE; LIGAND; PHENYL GROUP; PROTEIN DERIVATIVE; SULFONYLUREA; SULFONYLUREA DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOLUMINESCENCE; DRUG ACTIVITY; DRUG INHIBITION; DRUG MECHANISM; HYDROGEN BOND; MOLECULAR MODEL; NONHUMAN; QUORUM SENSING; VIBRIO FISCHERI;

BACTERIA (MICROORGANISMS); VIBRIO FISCHERI;

EID: 41849085566     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.02.023     Document Type: Article

References (42)

1. For recent reviews, see:. Miller M.B., and Bassler B.L. Annu. Rev. Microbiol. 55 (2001) 165-199
2. Whitead N.A., Barnard A.M.L., Slater H., Simpson N.J.L., and Salmond G.P.C. FEMS Microbiol. Rev. 25 (2001) 365-404
3. Lyon G.J., and Muir T.W. Chem. Biol. 10 (2003) 1007
4. Waters C.M., and Bassler B.L. Annu. Rev. Cell Dev. Biol. 21 (2005) 319-346
5. Gonzalez J.E., and Keshavan N.D. Microbiol. Mol. Biol. Rev. 70 (2006) 859-875
6. Rasmussen T.B., and Givskov M. Microbiology 152 (2006) 895-904
7. Reading N.C., and Sperandio V. FEMS Microbiol. Lett. 254 (2006) 1-11
8. Suga H., and Smith K.M. Curr. Opin. Chem. Biol. 7 (2003) 586-591
9. Hentzer M., and Givskov M. J. Clin. Invest. 112 (2003) 1300-1307
10. Hentzer M., Eberl L., Nielsen J., and Givskov M. BioDrugs 17 (2003) 241-250
11. Persson T., Givskov M.M., and Nielsen J. Curr. Med. Chem. 12 (2005) 3103-3115
12. Raffa R.B., Iannuzzo J.R., Levine D.R., Saeid K.K., Schwartz R.C., Sucic N.T., Terleckyj O.D., and Young J.M. J. Pharmacol. Exp. Ther. 312 (2005) 417-423
13. Rice S.A., McDougald D., Kumar N., and Kjelleberg S. Curr. Opin. Investig. Drugs 6 (2005) 168-184
14. Rasmussen T.B., and Givskov M. Int. J. Med. Microbiol. 296 (2006) 149-161
15. Abraham W.-R.A. Curr. Med. Chem. 13 (2006) 1509-1524
16. Sperandio V. Expert Rev. Anti Infect. Ther. 5 (2007) 271-276
17. Eberhard A., Burlingame A.L., Eberhard C., Kenyon G.L., Nealson K.H., and Oppenheimer N.J. Biochemistry 20 (1981) 2444-2449
18. Smith D., Wang J.-H., Swatton J.E., Davenport P., Price B., Mikkelsen H., Stickland H., Nishikawa K., Gardiol N., Spring D.R., and Welch M. Sci. Prog. 89 (2006) 167-211
19. Nasser W., and Reverchon S. Anal. Bioanal. Chem. 387 (2007) 381-390
20. Eberhard A., Widrig C.A., McBath P., and Schineller J.B. Arch. Microbiol. 146 (1986) 35-40
21. Chaabra S.R., Stead P., Bainton N.J., Salmond G.P.C., Stewart G.S.A.B., Williams P., and Bycroft B.W. J. Antibiot. 46 (1993) 441-454
22. Passador L., Tucker K.D., Guertin K.R., Journet M.P., Kende A.S., and Iglewski B.H. J. Bacteriol. (1996) 5995-6000
23. Schaefer A.L., Hanzelka B.L., Eberhard A., and Greenberg E.P. J. Bacteriol. (1996) 2897-2901
24. Zhu J., Beaber J.W., More M.I., Fuqua C., Eberhard A., and Winans S.C. J. Bacteriol. 180 (1998) 5398-5405
25. Kline T., Bowman J., Iglewski B.H., de Kievit T., Kakai Y., and Passador L. Biorg. Med. Chem. Lett. 9 (1999) 3447-3452
26. Smith K.M., Bu Y., and Suga H. Chem. Biol. 10 (2003) 81-89
27. Smith K.M., Bu Y., and Suga H.. Chem. Biol. 10 (2003) 563-571
28. Welch M., Dutton J.M., Glansdorp F.G., Thomas G.L., Smith D.S., Coulthurst S.J., Barnard A.M.L., Salmond G.P.C., and Spring D.R. Biorg. Med. Chem. Lett. 15 (2005) 4235-4238
29. Persson T., Hansen T.H., Rasmussen T.B., Skinderso M.E., Givskov M., and Nielsen J. Org. Biomol. Chem. 3 (2005) 253-262
30. Geske G.D., Wezeman R.J., Siegel A.P., and Blackwell H.E. J. Am. Chem. Soc. 127 (2005) 12762-12763
31. Geske G.D., O'Neill J.C., and Blackwell H.E. ACS Chem. Biol. 2 (2007) 315-319
32. Ishida T., Ikeda T., Takiguchi N., Kuroda A., Ohtake H., and Kato J. Appl. Environ. Microbiol. 73 (2007) 3183-3188
33. Janssens J.C.A., Metzger K., Daniels R., Ptacek D., Verhoeven T., Habel L.W., Vanderleyden J., De Vos D.E., and De Keersmaecker S.C. Appl. Environ. Microbiol. 73 (2007) 535-544
34. Castang S., Chantegrel B., Deshayes C., Dolmazon R., Gouet P., Haser R., Reverchon S., Nasser W., Hugouvieux-Cotte-Pattat N., and Doutheau A. Bioorg. Med. Chem. Lett. 14 (2004) 5145-5149
35. Frezza M., Castang S., Estephane J., Soulere L., Deshayes C., Chantegrel B., Nasser W., Queneau Y., Reverchon S., and Doutheau A. Bioorg. Med. Chem. 14 (2006) 4781-4791
36. Soulère L., Frezza M., Queneau Y., and Doutheau A. J. Mol. Graphics Modell. 26 (2007) 581-590
37. Tickner A.M., Liu C., Hild E., and Mendelson W. Synth. Commun. 24 (1994) 1631-1637
38. DuBois G.E., and Stephenson R.A. J. Org. Chem. 45 (1980) 5371-5373
39. Reverchon S., Chantegrel B., Deshayes C., Doutheau A., and Cotte-Pattat N. Bioorg. Med. Chem. Lett. 12 (2002) 1153-1157
40. SYBYL, Molecular Modeling System, Tripos Associates Inc., S. Hanley Road, St. Louis, MO 63144-62913, USA, 1699.
41. Thompson, M. A. ArgusLaB 4.01, Seattle, WA, Planetaria Software LLC, 2004.
42. Krieger E., Koraimann G., and Vriend G. Proteins 47 (2002) 393-402