Designing 2-aminoimidazole alkaloids analogs with anti-biofilm activities: Structure-activities relationships of polysubstituted triazoles

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 22, 2011, Pages 6751-6755

  Linares, D ^a   Bottzeck, O ^a   Pereira, O ^a   Praud Tabaris, A ^a   Blache, Y ^a  

^a UNIVERSITÉ DE TOULON   (France)

Author keywords

1,2,3 Triazole; Biofilm; Click chemistry; Isonaamine A; Naamine A

Indexed keywords

ALKALOID DERIVATIVE; ANTIBIOTIC AGENT; IMIDAZOLE DERIVATIVE; ISONAAMINE A DERIVATIVE; NAAMINE A DERIVATIVE; NORFLOXACIN; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIBIOFILM ACTIVITY; ARTICLE; BACTERIAL GROWTH; BIOFILM; CLICK CHEMISTRY; DRUG DESIGN; DRUG SCREENING; GROWTH INHIBITION; NONHUMAN; PARACOCCUS; PSEUDOALTEROMONAS; PSEUDOMONAS AERUGINOSA; STRUCTURE ACTIVITY RELATION;

ALKALOIDS; ANTI-BACTERIAL AGENTS; BIOFILMS; DRUG DESIGN; GRAM-NEGATIVE BACTERIA; IMIDAZOLES; MODELS, MOLECULAR; PARACOCCUS; PSEUDOALTEROMONAS; SMALL MOLECULE LIBRARIES; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

BACTERIA (MICROORGANISMS); NEGIBACTERIA;

EID: 80054755092     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.09.050     Document Type: Article

References (25)

1. L. Hall-Stoodley, J.W. Costerton, and P. Stoodley Nat. Rev. Microbiol. 2 2004 95
2. S. Saint, and C.E. Chenoweth Infect. Dis. Clin. North Am. 17 2003 411
3. I. Omae Chem. Rev. 103 2003 3431
4. D. Haras Mater. Technol. 93 2005 27
5. P.Y. Qian, S.C.K. Lau, H.U. Dahms, S. Dobretsov, and T. Harder Mar. Biotechnol. 9 2007 399
6. For a general review of the synthesis and activity of 2-aminoimidazole alkaloids, see: M.S. Weinreb Nat. Prod. Rep. 24 2007 931
7. H. Hoffmann, and T. Lindel Synthesis 2003 1753
8. T.L. Harris, R.J. Worthington, and C. Melander Bioorg. Med. Chem. 21 2011 4516
9. R.W. Huigens, J.J. Richards, G. Parise, E. Ballard, W. Zeng, R. Deora, and C. Melander J. Am. Chem. Soc. 129 2007 6966
10. S. Carmely, and Y. Kashman Tetrahedron Lett. 28 1987 3003
11. S. Carmelya, M. Ilanb, and Y. Kashmana Tetrahedron 45 1989 2193
12. D.S. Ermolat, J.B. Bariwal, H.P.L. Steenackers, S.C.J. De Keersmaecker, and E.V. Van der Eycken Angew. Chem., Int. Ed. 49 2010 9465
13. N. Aberle, J. Catimel, E.C. Nicec, and K.G. Watson Bioorg. Med. Chem. Lett. 17 2007 3741
14. A. Praud-Tabaris, L. Dombrowsky, O. Bottzek, J.F. Briand, and Y. Blache Tetrahedron Lett. 50 2009 1645
15. C. Sall, L. Dombrowsky, O. Bottzeck, A. Praud-Tabaries, and Y. Blache Bioorg. Med. Chem. Lett. 21 2011 1493
16. Y. Ikeda, S. Kawahara, M. Taki, A. Kuno, T. Hasegawa, and K. Taira Protein Eng. 16 2003 699
17. R.J. Bochis, J.C. Chabala, E. Harris, L.H. Peterson, L. Barash, T. Beattie, J.E. Brown, D.W. Graham, F.S. Waksmunski, M. Tischler, H. Joshua, J. Smith, L.F. Colwell, M.J. Wyvratt, and M.H. Fisher J. Med. Chem. 34 1991 2843
18. L. Zhang, X. Chen, P. Xue, H.H.Y. Sun, I.D. Williams, K.B. Sharpless, V.V. Fokin, and G. Jia J. Am. Chem. Soc. 127 2005 15998
19. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2596
20. R. Huisgen 1,3-Dipolar Cycloaddition Chemistry 1984 Wiley New York pp 1-176
21. 4 and evaporated to give the corresponding triazoles, which were purified by flash chromatography on silica.
22. H. Nulwala, K. Takizawa, A. Odukale, A. Khan, R.J. Thibault, B.R. Taft, B.H. Lipshutz, and C.J. Hawker Macromolecules 42 2009 6068
23. M. Camps, J.F. Briand, L. Guentas-Dombrowsky, G. Culioli, A. Bazire, and Y. Blache Mar. Pollut. Bull. 62 2011 1032
24. C. Leroy, C. Delbarre-Ladrat, F. Ghillebaert, M.J. Rochet, C. Compre, and D. Combes Lett. Appl. Microbiol. 44 2007 372
25. Antibacterial assays. Bacterial strains were grown on VNSS at 20 °C under shaking conditions (120 rpm) and collected during the exponential phase. After centrifugation, cells were suspended in sterile VNSS (OD600 nm = 0.1). 180 μL at different concentrations for each tested compounds (standard biocides, natural or natural-derived products) were added in four wells of the microtiter plates (sterile transparent PS; Nunc, Fisher Scientific). All the concentrations were tested in triplicate and the fourth well was filled for control. The maximum percentage of solvent used for the dilution of biocides was also tested in triplicate as additional control. For the growth inhibition control, 180 μL of VNSS was added in six wells. Then 20 μL of the bacterial suspension was inoculated on all the wells except the border-row wells and all the wells were filled out to 200 μL with VNSS. Turbidity (OD600 nm) was measured every hour during 6 h.