Multivalent calixarene-based C-fucosyl derivative: A new Pseudomonas aeruginosa biofilm inhibitor

Tetrahedron Letters

Volumn 52, Issue 44, 2011, Pages 5831-5834

  Consoli, Grazia M L ^a   Granata, Giuseppe ^a   Cafiso, Viviana ^b   Stefani, Stefania ^b   Geraci, Corrada ^a  

^a CNR   (Italy)

^b UNIVERSITY OF CATANIA   (Italy)

Author keywords

C Fucosyl derivative; Calixarene; Inhibition biofilm assay; Multivalency; Pseudomonas aeruginosa

Indexed keywords

ALPHA LEVO FUCOSYL CALIXARENE; ANTIBIOTIC AGENT; CALIXARENE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BIOFILM; CARBOHYDRATE ANALYSIS; CARBON NUCLEAR MAGNETIC RESONANCE; DOSE RESPONSE; ELECTROSPRAY MASS SPECTROMETRY; INHIBITION KINETICS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA;

PSEUDOMONAS AERUGINOSA;

EID: 80054973442     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.08.142     Document Type: Article

References (42)

1. Ernst, B., Hart, G. W., Sinay, P., Eds.Carbohydrates in Chemistry and Biology; Wiley-VCH: Weinheim, 2000.
2. (a) Ling, R.; Yoshida, M.; Mariano, P. S. J. Org. Chem. 1996, 61, 4439-4449;
3. (b) Mortell, K. H.; Weatherman, R. V.; Kiessling, L. L. J. Am. Soc. Chem. 1996, 118, 2297-2298;
4. (c) Mammen, M.; Choi, S.-K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2754-2794;
5. (d) Horan, N.; Yan, L.; Isobe, H.; Whitesides, G. M.; Kahne, D. Proc. Nat. Acad. Soc. 1999, 96, 11782-11786.
6. Goering, B. K. Ph.D. Dissertation, Cornell University, 1995.
7. Wu, H.-C.; Chang, D.-K.; Huang, C.-T. J. Cancer Mol. 2006, 2, 57-66.
8. Roussel, P.; Lamblin, G. Adv. Exp. Med. Biol. 2003, 535, 17-32.
9. Gilboa-Garber, N. Methods Enzymol. 1982, 83, 378-385.
10. (a) Tielker, D.; Hacker, R.; Loris, R.; Strathamann, M.; Wingender, J.; Wilhelm, S.; Roseneau, F.; Jaeger, K.-E. Microbiology 2005, 151, 1313-1323;
11. (b) Chemani, C.; Imberty, A.; de Bentzmann, S.; Pierre, M.; Wimmerova, M.; Guery, B. P.; Faure, K. Infect. Immun. 2009, 77, 2065-2075.
12. Mitchell, E. P.; Sabin, C.; Šnajdrova, L.; Pokorna, M.; Perret, S.; Gautier, C.; Hofr, C.; Gilboa-Garber, N.; Koča, J.; Wimmerova, M.; Imberty, A. Proteins: Struct. Funct. Bioinform. 2005, 58, 735-746.
13. (a) Perret, S.; Sabin, C.; Dumon, C.; Pokorna, M.; Gautier, M.; Galanina, O.; Ilia, S.; Bovin, N.; Nicaise, M.; Desmadril, M.; Gilboa-Garber, N.; Wimmerova, M.; Mitchell, E.; Imberty, A. Biochem. J. 2005, 389, 325-332;
14. (b) Marotte, K.; Sabin, C.; Preville, C.; Moume-Pymbock, M.; Wimmerova, M.; Mitchell, E. P.; Imberty, A.; Roy, R. Chem. Med. Chem. 2007, 2, 1328-1338;
15. (c) Marotte, K.; Preville, C.; Sabin, C.; Moume-Pymbock, M.; Imberty, A.; Roy, R. Org. Biomol. Chem. 2007, 5, 2953-2961.
16. (a) Beha, S.; Giguere, D.; Patnam, R.; Roy, R. Synlett 2006, 1739-1743;
17. (b) Deguise, I.; Lagnoux, D.; Roy, R. New J. Chem. 2007, 31, 1321-1331;
18. (c) Morvan, F.; Meyer, A.; Jochum, A.; Sabin, C.; Chevolot, Y.; Imberty, A.; Praly, J.-P.; Vasseur, J.-J.; Souteyrand, E.; Vidal, S. Bioconjugate Chem. 2007, 18, 1637-1643.
19. (a) Johansson, E. M. V.; Kolomiets, E.; Rosenau, F.; Jaeger, K.-E.; Darbre, T.; Reymond, J.-L. New J. Chem. 2007, 31, 1291-1299;
20. (b) Kolomiets, E.; Johansson, E. M. V.; Renaudet, O.; Darbre, T.; Reymond, J.-L. Org. Lett. 2007, 9, 1465-1468;
21. (c) Johansson, E. M. V.; Crusz, S. A.; Kolomiets, E.; Buts, L.; Kadam, R. U.; Cacciarini, M.; Bartels, K.-M.; Diggle, S. P.; Camara, M.; Williams, P.; Loris, R.; Nativi, C.; Rosenau, F.; Jaeger, K.-E.; Darbre, T.; Reymond, J.-L. Chem. Bio. 2008, 15, 1249-1257;
22. (d) Johansson, E. M. V.; Kadam, R. U.; Rispoli, G.; Crusz, S. A.; Bartels, K.-M.; Diggle, S. P.; Camara, M.; Williams, P.; Jaeger, K. E.; Darbre, T.; Reymond, J.-L. Med. Chem. Commun. 2011, 2, 418-420.
23. To the best of our knowledge are not known previous examples of calixarenes fucosyl derivatives designed in order to inhibit Pseudomonas aeruginosa biofilm, whereas only two works on calixarene-based galactoside clusters with the ability to recognize PA-IL lectin are reported in the literature: (a) Moni, L.; Pourceau, G.; Zhang, J.; Meyer, A.; Vidal, S.; Souteyrand, E.; Dondoni, A.; Morvan, F.; Chevolot, Y.; Vasseur, J.-J.; Marra, A. Chem. Bio. Chem 2009, 10, 1369-1378;
24. (b) Cecioni, S.; Lalor, R.; Blanchard, B.; Praly, J.-P.; Imberty, A.; Matthews, S. E.; Vidal, S. Chem Eur. J. 2009, 15, 13232-13240.
25. (a) (a)Calixarene 2001; Asfari, Z., Bohmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer: Dordrecht, 2001;
26. (b) Gutsche, C. D. Calixarenes: An Introduction; Royal Society of Chemistry: Cambridge, 2008;
27. (c) Da Silva, E.; Lazar, A. N.; Coleman, A. W. J. Drug Del. Sci. Tech. 2004, 14, 3-20;
28. (d) Mecca, T.; Consoli, G. M. L.; Geraci, C.; La Spina, R.; Cunsolo, F. Org. Biomol. Chem. 2006, 4, 3763-3768;
29. (e) Consoli, G. M. L.; Granata, G.; Galante, E.; Di Silvestro, I.; Salafia, L.; Geraci, C. Tetrahedron 2007, 63, 10758-10763;
30. (f) Lalor, R.; Baillie-Johnson, H.; Redshaw, C.; Matthews, S. E.; Mueller, A. J. Am. Chem. Soc. 2008, 130, 2892-2893;
31. (g) Geraci, C.; Consoli, G. M. L.; Galante, E.; Bousquet, E.; Pappalardo, M.; Spadaro, A. Bioconjugate Chem. 2008, 19, 751-758;
32. (h) Mutihac, L. Curr. Drug Discovery Technol. 2008, 5, 98-104;
33. (i) de Fatima, A.; Fernandes, S. A.; Sabino, A. A. Curr. Drug Discovery Technol. 2009, 6, 151-170;
34. (l) Rodik, R. V.; Boyko, V. I.; Kalchenko, V. I. Curr. Med. Chem. 2009, 16, 1630-1655;
35. (m) Dondoni, A.; Marra, A. Chem. Rev. 2010, 110, 4949;
36. (n) Pourabdollah, K.; Dalali, N. J. Incl. Phenom. Macrocycl. Chem. 2011, 69, 1-55.
37. Consoli, G. M. L.; Cunsolo, F.; Geraci, C.; Sgarlata, V. Org. Lett. 2004, 6, 4163-4166.
38. (a) Prihar, H. S.; Behrman, E. J. Biochemistry 1973, 12, 997-1009;
39. (b) Luengo, J. I.; Gleason, J. G. Tetrahedron Lett. 1992, 33, 6911-6914;
40. (c) Uchiyama, T.; Woltering, T. J.; Wong, W.; Lin, C.-C.; Kajimoto, T.; Takebayashi, M.; Weitz-Schmidt, G.; Asakura, T.; Noda, M.; Wong, C.-H. Biorg. Med. Chem. 1996, 4, 1149-1165.
41. Adam, J.; Pokorna, M.; Sabin, C.; Mitchell, E. P.; Imberty, A.; Wimmerova, M. BMC Struct. Biol. 2007, 7, 36.
42. Nick, J. A; Parks, Q. M. U.S. Patent 200801599509, 2008.