High affinity glycodendrimers for the lectin LecB from Pseudomonas aeruginosa

Bioconjugate Chemistry

Volumn 24, Issue 9, 2013, Pages 1598-1611

  Berthet, Nathalie ^a   Thomas, Baptiste ^a   Bossu, Isabelle ^a   Dufour, Emilie ^a   Gillon, Emilie ^b   Garcia, Julian ^a   Spinelli, Nicolas ^a   Imberty, Anne ^b   Dumy, Pascal ^a,c   Renaudet, Olivier ^a,d  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

^b CENTRE DE RECHERCHES SUR LES MACROMOLÉCULES VÉGÉTALES CERMAV CNRS   (France)

^c INSTITUT CHARLES GERHARDT   (France)

^d INSTITUT UNIVERSITAIRE DE FRANCE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BACTERIA; DISSOCIATION; LIGANDS; SCAFFOLDS;

ANOMERS; CYCLOPEPTIDES; DENDRONS; FUNCTIONALIZED; GLYCODENDRIMERS; GLYCOSYLATED; HIGH AFFINITY; ISOTHERMAL TITRATION; PSEUDOMONAS AERUGINOSA; VALENCIES;

PROTEINS;

CHELATE; CYCLOPEPTIDE; FUCOSE; LECTIN; LECTIN LECB; LIGAND; LYSINE; SUGAR; UNCLASSIFIED DRUG;

ARTICLE; BINDING KINETICS; CHEMICAL STRUCTURE; DISSOCIATION CONSTANT; ISOTHERMAL TITRATION CALORIMETRY; MOLECULAR MODEL; PSEUDOMONAS AERUGINOSA;

PSEUDOMONAS AERUGINOSA; TETRA;

DENDRIMERS; GLYCOPEPTIDES; HUMANS; LECTINS; MODELS, MOLECULAR; PROTEIN BINDING; PSEUDOMONAS AERUGINOSA; PSEUDOMONAS INFECTIONS;

EID: 84884362649     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc400239m     Document Type: Article

References (52)

1. Varki, A. (1993) Biological roles of oligosaccharides: all of the theories are correct Glycobiology 3, 97-130 (Pubitemid 23132602)
2. Dwek, R. A. (1996) Glycobiology: toward understanding the function of sugars Chem. Rev. 96, 683-720 (Pubitemid 126649163)
3. Lis, H. and Sharon, N. (1998) Lectins: carbohydrate-specific proteins that mediate cellular recognition Chem. Rev. 98, 637-674 (Pubitemid 128631438)
4. Bertozzi, C. R. and Kiessling, L. L. (2001) Chemical glycobiology Science 291, 2357-2364 (Pubitemid 32231790)
5. Sharon, N. (1996) Carbohydrate-lectin interactions in infectious disease Adv. Exp. Med. Biol. 408, 1-8 (Pubitemid 26331047)
6. Imberty, A. and Varrot, A. (2008) Microbial recognition of human cell surface glycoconjugates Curr. Opin. Struct. Biol. 18, 567-576
7. Pieters, R. J. (2011) Carbohydrate mediated bacterial adhesion Adv. Exp. Med. Biol. 715, 227-240
8. Gilboa-Garber, N. (1982) Pseudomonas aeruginosa lectins Methods Enzymol. 83, 378-385
9. Imberty, A., Wimmerova, M., Mitchell, E. P., and Gilboa-Garber, N. (2004) Structures of the lectins from Pseudomonas aeruginosa: insights into the molecular basis for host glycan recognition Microb. Infect. 6, 221-228 (Pubitemid 38293301)
10. Bernardi, A., Jiménez-Barbero, J., Casnati, A., De Castro, C., Darbre, T., Fieschi, F., Finne, J., Funken, H., Jaeger, K.-E., Lahmann, M., Lindhorst, T. K., Marradi, M., Messner, P., Molinaro, A., Murphy, P. V., Nativi, C., Oscarson, S., Penadés, S., Peri, F., Pieters, R. J., Renaudet, O., Reymond, J.-L., Richichi, B., Rojo, J., Sansone, F., Schäffer, C., Turnbull, W. B., Velasco-Torrijos, T., Vidal, S., Vincent, S., Wennekes, T., Zuilhof, H., and Imberty, A. (2013) Multivalent glycoconjugates as anti-pathogenic agents Chem. Soc. Rev. 42, 4709-4727
11. Imberty, A., Chabre, Y. M., and Roy, R. (2008) Glycomimetics and glycodendrimers as high affinity microbial anti-adhesins Chem.-Eur. J. 14, 7490-7499
12. Branson, T. R. and Turnbull, W. B. (2013) Bacterial toxin inhibitors based on multivalent scaffolds Chem. Soc. Rev. 42, 4613-4622
13. Chemani, C., Imberty, A., de Bentzmann, S., Pierre, M., Wimmerova, M., Guery, B. P., and Faure, K. (2009) Role of LecA and LecB lectins in Pseudomonas aeruginosa -induced lung injury and effect of carbohydrate ligands Infect. Immun. 77, 2065-2075
14. Hauber, H. P., Schulz, M., Pforte, A., Mack, D., Zabel, P., and Schumacher, U. (2008) Inhalation with fucose and galactose for treatment of Pseudomonas aeruginosa in cystic fibrosis patients Int. J. Med. Sci. 5, 371-376
15. Lee, Y. C. and Lee, R. T. (1995) Carbohydrate-protein interactions: basis of glycobiology Acc. Chem. Res. 28, 321-327
16. Mammen, M., Choi, S. K., and Whitesides, G. M. (1998) Polyvalent interactions in biological systems: implications for design and use of multivalent ligands and inhibitors Angew. Chem., Int. Ed. 37, 2755-2794
17. Lundquist, J. J. and Toone, E. J. (2002) The cluster glycoside effect Chem. Rev. 102, 555-578 (Pubitemid 35377623)
18. Mitchell, E., Houles, C., Sudakevitz, D., Wimmerova, M., Gautier, C., Pérez, S., Wu, A. M., Gilboa-Garber, N., and Imberty, A. (2002) Structural basis for oligosaccharide-mediated adhesion of Pseudomonas aeruginosa in the lungs of cystic fibrosis patients Nat. Struct. Biol. 9, 918-921 (Pubitemid 35417060)
19. Perret, S., Sabin, C., Dumon, C., Pokorna, M., Gautier, C., Galanina, O., Ilia, S., Bovin, N., Nicaise, M., Desmadril, M., Gilboa-Garber, N., Wimmerova, M., Mitchell, E. P., and Imberty, A. (2005) Structural basis for the interaction between human milk oligosaccharides and the bacterial lectin PA-IIL of Pseudomonas aeruginosa Biochem. J. 389, 325-332 (Pubitemid 41021135)
20. Sabin, C., Mitchell, E. P., Pokorna, M., Gautier, C., Utille, J.-P., Wimmerova, M., and Imberty, A. (2006) Binding of different monosaccharides by lectin PA-IIL from Pseudomonas aeruginosa: thermodynamics data correlated with X-ray structures FEBS Lett. 580, 982-987 (Pubitemid 43152323)
21. Marotte, K., Preville, C., Sabin, C., Moume-Pymbock, M., Imberty, A., and Roy, R. (2007) Synthesis and binding properties of divalent and trivalent clusters of the Lewis a disaccharide moiety to Pseudomonas aeruginosa lectin PA-IIL Org. Biomol. Chem. 5, 2953-2961 (Pubitemid 47340685)
22. Andreini, M., Anderluh, M., Audfray, A., Bernardi, A., and Imberty, A. (2010) Monovalent and bivalent N -fucosyl amides as high affinity ligands for Pseudomonas aeruginosa PA-IIL lectin Carbohydr. Res. 345, 1400-1407
23. Deguise, I., Lagnoux, D., and Roy, R. (2007) Synthesis of glycodendrimers containing both fucoside and galactoside residues and their binding properties to PA-IL and PA-IIL lectins from Pseudomonas aeruginosa New J. Chem. 31, 1321-1331 (Pubitemid 47036640)
24. Marotte, K., Sabin, C., Préville, C., Moumé-Pymbock, M., Wimmerova, M., Mitchell, E. P., Imberty, A., and Roy, R. (2007) X-ray structures and thermodynamics of the interaction of PA-IIL from Pseudomonas aeruginosa with disaccharide derivatives ChemMedChem 2, 1328-1338
25. Morvan, F., Meyer, A., Jochum, A., Sabin, C., Chevolot, Y., Imberty, A., Praly, J.-P., Vasseur, J.-J., Souteyrand, E., and Vidal, S. (2007) Fucosylated pentaerythrityl phosphodiester oligomers (PePOs): automated synthesis of DNA-based glycoclusters and binding to Pseudomonas aeruginosa lectin (PA-IIL) Bioconjugate Chem. 18, 1637-1643 (Pubitemid 47464074)
26. Reymond, J.-L., Bergmann, M., and Dabre, T. (2013) Glycopeptide dendrimers as Pseudomonas aeruginosa biofilm inhibitors Chem. Soc. Rev. 42, 4814-4822
27. Kolomiets, E., Johansson, E. M., Renaudet, O., Darbre, T., and Reymond, J.-L. (2007) Neoglycopeptide dendrimer libraries as a source of lectin binding ligands Org. Lett. 9, 1465-1468
28. Johansson, E. M. V., Crusz, S. A., Kolomiets, E., Buts, L., Kadam, R. U., Cacciarini, M., Bartels, K.-M., Diggle, S. P., Cámara, M., Williams, P., Loris, R., Nativi, C., Rosenau, F., Jaeger, K.-E., Darbre, T., and Reymond, J.-L. (2008) Inhibition and dispersion of Pseudomonas aeruginosa biofilms by glycopeptide dendrimers targeting the fucose-specific lectin LecB Chem. Biol. 15, 1249-1257 (Pubitemid 352841467)
29. Kolomiets, E., Swiderska, M. A., Kadam, R. U., Johansson, E. M. V, Jaeger, K.-E., Darbre, T., and Reymond, J.-L. (2009) Glycopeptide dendrimers with high affinity for the fucose-binding lectin LecB from Pseudomonas aeruginosa ChemMedChem 4, 562-469
30. 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., and Reymond, J.-L. (2011) Inhibition of Pseudomonas aeruginosa biofilms with a glycopeptide dendrimer containing D-amino acids MedChemComm 2, 418-420
31. Galan, M. C., Dumy, P., and Renaudet, O. (2013) Multivalent glycol(cyclo)peptides Chem. Soc. Rev. 42, 4599-4612
32. Renaudet, O., BenMohamed, L., Dasgupta, G., Bettahi, I., and Dumy, P. (2008) Towards self-adjuvanting multivalent B and T-cell epitopes synthetic glyco-lipopeptide cancer vaccine ChemMedChem 3, 737-741
33. Renaudet, O., Dasgupta, G., Bettahi, I., Shi, A., Nesburn, A. B., Dumy, P., and BenMohamed, L. (2010) Linear and branched glyco-lipopeptides vaccines follow distinct cross-presentation pathways and generate different magnitudes of antitumor immunity Plos ONE 5, e11216
34. Pujol, A. M., Cuillel, M., Renaudet, O., Lebrun, C., Charbonnier, P., Cassio, D., Gateau, C., Dumy, P., Mintz, E., and Delangle, P. (2011) Hepatocyte targeting and intracellular copper chelation by a thiol-containing glycocyclopeptide J. Am. Chem. Soc. 133, 286-296
35. Renaudet, O. and Dumy, P. (2003) Chemoselectively template-assembled glycoconjugates as mimics for multivalent presentation of carbohydrates Org. Lett. 5, 243-245
36. Bossu, I., Šulc, M., Křenek, K., Dufour, E., Garcia, J., Berthet, N., Dumy, P., Křen, V., and Renaudet, O. (2011) Dendri-RAFTs: a second generation of cyclopeptide-based glycoclusters Org. Biomol. Chem. 9, 1948-1959
37. André, S., Renaudet, O., Bossu, I., Dumy, P., and Gabius, H.-J. (2011) Cyclic glycodecapeptides: how to increase their inhibitory activity and selectivity on lectin/toxin binding to a glycoprotein and cells J. Pept. Sci. 17, 427-437
38. Mitchell, E. P., Sabin, C., Snajdrova, L., Budova, M., Perret, S., Gautier, C., Hofr, C., Gilboa-Garber, N., Koča, J., Wimmerová, M., and Imberty, A. (2005) High affinity fucose binding of Pseudomonas aeruginosa lectin PA-IIL: 1.0 Å resolution crystal structure of the complex combined with thermodynamics and computational chemistry approaches Proteins: Struct. Funct. Bioinf. 58, 735-746 (Pubitemid 40176045)
39. Braunschweiler, L. and Ernst, R. R. (1983) Heteronuclear correlation spectroscopy in rotating solids J. Magn. Reson. 53, 521-528
40. Piantini, U., Sørensen, O. W., and Ernst, R. R. (1982) Multiple quantum filters for elucidating NMR coupling networks J. Am. Chem. Soc. 104, 6800-6801
41. Jeener, J., Meier, B. H., Bachmann, P., and Ernst, R. R. (1979) Investigation of exchange processes by 2-dimensional NMR-spectroscopy J. Chem. Phys. 71, 4546-4553
42. Shaka, A. J., Lee, C. J., and Pines, A. (1988) Iterative schemes for bilinear operators-application to spin decoupling J. Magn. Reson. 77, 274-293
43. Hwang, T. L. and Shaka, A. J. (1995) Water suppression that works-excitation sculpting using arbitrary wave-forms and pulsed-field gradients J. Magn. Reson. 112, 275-279
44. Dayringer, H. E., Tramontano, A., Sprang, S. R., and Fletterick, R. J. (1986) Interactive program for visualization and modeling of proteins, nucleic-acids and small molecules J. Mol. Graph. 6, 82-87
45. Duléry, V., Renaudet, O., Philouze, C., and Dumy, P. (2007) α or β L-fucopyranosyl oxyamines: key intermediates for the preparation of fucose-containing glycoconjugates by oxime ligation Carbohydr. Res. 342, 894-900 (Pubitemid 46385913)
46. Renaudet, O. and Dumy, P. (2001) Expedient synthesis of aminooxylated-carbohydrates for chemoselective access of glycoconjugates Tetrahedron Lett. 42, 7575-7578 (Pubitemid 32946959)
47. Bossu, I., Berthet, N., Dumy, P., and Renaudet, O. (2011) Synthesis of glycocyclopeptides by click chemistry and inhibition assays with lectins J. Carbohydr. Chem. 30, 458-468
48. Grigalevicius, S., Chierici, S., Renaudet, O., Lo-Man, R., Dériaud, E., Leclerc, C., and Dumy, P. (2005) Chemoselective assembly and immunological evaluation of multiepitopic glycoconjugates bearing clustered Tn antigen as synthetic anticancer vaccine Bioconjugate Chem. 5, 1149-1159 (Pubitemid 41368116)
49. Duléry, V., Renaudet, O., and Dumy, P. (2007) Ethoxyethylidene protecting group prevents N -overacylation in aminooxy peptide synthesis Tetrahedron 63, 11952-11958 (Pubitemid 47575619)
50. Dam, T. K., Roy, R., Pagé, D., and Brewer, C. F. (2002) Thermodynamic binding parameters of individual epitopes of multivalent carbohydrates to Concanavalin A as determined by "reverse" Isothermal Titration Microcalorimetry Biochemistry 41, 1359-1363 (Pubitemid 34083791)
51. Wüthrich, K. (1986) NMR of Proteins and Nucleic Acids, John Wiley and Sons, New York.
52. Nardin, E. H., Calvo-Calle, J. M., Oliveira, G. A., Clavijo, P., Nussenzweig, R., Simon, R., Zeng, W., and Rose., K. (1998) Plasmodium falciparum polyoximes: highly immunogenic synthetic vaccines constructed by chemoselective ligation of repeat B-cell epitopes and a universal T-cell epitope of CS protein Vaccine 16, 590-600 (Pubitemid 28112556)