Selectivity among two lectins: Probing the effect of topology, multivalency and flexibility of "clicked" multivalent glycoclusters

Chemistry - A European Journal

Volumn 17, Issue 7, 2011, Pages 2146-2159

  Cecioni, Samy ^a,b   Faure, Sophie ^c,d   Darbost, Ulrich ^e   Bonnamour, Isabelle ^e   Parrot Lopez, Hélène ^e   Roy, Olivier ^c,d   Taillefumier, Claude ^c,d   Wimmerová, Michaela ^f   Praly, Jean Pierre ^a   Imberty, Anne ^b   Vidal, Sébastien ^a  

^a UNIVERSITÉ LYON 1   (France)

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

^c UNIVERSITÉ CLERMONT AUVERGNE   (France)

^d CNRS   (France)

^e UNIVERSITÉ LYON 1   (France)

^f MASARYK UNIVERSITY   (Czech Republic)

Author keywords

calixarenes; carbohydrates; glycoclusters; lectins; multivalency

Indexed keywords

ANTIGEN-ANTIBODY REACTIONS; BINDING ENERGY; CARBOHYDRATES; COPPER COMPOUNDS; LIGANDS; SCAFFOLDS; SURFACE PLASMON RESONANCE;

AZIDE-ALKYNE CYCLOADDITION; CALIXARENES; CARBOHYDRATE DERIVATIVES; GLYCOCLUSTERS; ISOTHERMAL TITRATION MICROCALORIMETRY; LECTINS; MULTIVALENCY; PSEUDOMONAS AERUGINOSA;

PROTEINS;

EID: 79551702852     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201002635     Document Type: Article

References (79)

1. H. Lis, N. Sharon, Chem. Rev. 1998, 98, 637-674.
2. R. T. Lee, Y. Ichikawa, T. Kawasaki, K. Drickamer, Y. C. Lee, Arch. Biochem. Biophys. 1992, 299, 129-136.
3. Y. C. Lee, R. T. Lee, Acc. Chem. Res. 1995, 28, 321-327.
4. J. J. Lundquist, E. J. Toone, Chem. Rev. 2002, 102, 555-578.
5. Y. M. Chabre, R. Roy, Adv. Carbohydr. Chem. Biochem. 2010, 63, 165-393.
6. C. Carpenter, S. A. Nepogodiev, Eur. J. Org. Chem. 2005, 3286-3296.
7. S. Dedola, S. A. Nepogodiev, R. A. Field, Org. Biomol. Chem. 2007, 5, 1006-1017.
8. M. Dubber, O. Sperling, T. K. Lindhorst, Org. Biomol. Chem. 2006, 4, 3901-3912.
9. D. A. Fulton, J. F. Stoddart, J. Org. Chem. 2001, 66, 8309-8319.
10. A. Nelson, J. M. Belitsky, S. Vidal, C. S. Joiner, L. G. Baum, J. F. Stoddart, J. Am. Chem. Soc. 2004, 126, 11914-11922.
11. V. Wittmann, S. Seeberger, Angew. Chem. 2004, 116, 918-921
12. Angew. Chem. Int. Ed. 2004, 43, 900-903.
13. M. J. Cloninger, Curr. Opin. Chem. Biol. 2002, 6, 742-748.
14. S. A. Nepogodiev, J. F. Stoddart, Adv. Macromol. Carbohydr. Res. 2003, 2, 191-239.
15. R. Roy, Trends Glycosci. Glycotechnol. 2003, 15, 291-310.
16. S. L. Flitsch, Current Opinion in Chemical Biology 2000, 4, 619-625.
17. S.-I. Nishimura, Y. C. Lee, in Polysaccharides: Structural Diversity and Functional Versatility (Ed.:, S. Dimitriu,), Marcel Dekker, New York, 1998, pp. 523-537.
18. R. Roy, in Carbohydrate Chemistry (Ed.:, G.-J. Boons,), Blackie, London, 1998, pp. 243-321.
19. J. M. deaLaaFuente, S. Penadés, Biochim. Biophys. Acta Gen. Subj. 2006, 1760, 636-651.
20. A. CarvalhoadeaSouza, J. F. G. Vliegenthart, J. P. Kamerling, Org. Biomol. Chem. 2008, 6, 2095-2102.
21. R. Narain, A. Housni, G. Gody, P. Boullanger, M.-T. Charreyre, T. Delair, Langmuir 2007, 23, 12835-12841.
22. C. L. Schofield, A. H. Haines, R. A. Field, D. A. Russell, Langmuir 2006, 22, 6707-6711.
23. M. Marradi, M. Martín-Lomas, S. Penadés, H. Derek, Adv. Carbohydr. Chem. Biochem. 2010, 64, 211-290.
24. S. André, F. Sansone, H. Kaltner, A. Casnati, J. Kopitz, H. J. Gabius, R. Ungaro, ChemBioChem 2008, 9, 1649-1661.
25. S. Cecioni, R. Lalor, B. Blanchard, J.-P. Praly, A. Imberty, S. E. Matthews, S. Vidal, Chem. Eur. J. 2009, 15, 13232-13240.
26. T. K. Dam, S. Oscarson, R. Roy, S. K. Das, D. Pagé, F. Macaluso, C. F. Brewer, J. Biol. Chem. 2004, 280, 8640-8646.
27. J. E. Gestwicki, C. W. Cairo, L. E. Strong, K. A. Oetjen, L. L. Kiessling, J. Am. Chem. Soc. 2002, 124, 14922-14933.
28. M. Lahmann, Top. Curr. Chem. 2009, 288, 17-65.
29. B. Blanchard, A. Nurisso, E. Hollville, C. Tétaud, J. Wiels, M. Pokorná, M. Wimmerová, A. Varrot, A. Imberty, J. Mol. Biol. 2008, 383, 837-853.
30. A. Nurisso, B. Blanchard, A. Audfray, L. Rydner, S. Oscarson, A. Varrot, A. Imberty, J. Biol. Chem. 2010, 285, 20316-20327.
31. G. Cioci, E. P. Mitchell, C. Gautier, M. Wimmerova, D. Sudakevitz, S. Perez, N. Gilboa-Garber, A. Imberty, FEBS Lett. 2003, 555, 297-301.
32. C. Svensson, S. Teneberg, C. L. Nilsson, A. Kjellberg, F. P. Schwarz, N. Sharon, U. Krengel, J. Mol. Biol. 2002, 321, 69-83.
33. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075
34. Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
35. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711
36. Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
37. Q. Wang, T. R. Chan, R. Hilgraf, V. V. Fokin, K. B. Sharpless, M. G. Finn, J. Am. Chem. Soc. 2003, 125, 3192-3193.
38. P. Wu, M. Malkoch, J. N. Hunt, R. Vestberg, E. Kaltgrad, M. G. Finn, V. V. Fokin, K. B. Sharpless, C. J. Hawker, Chem. Commun. 2005, 5775-5777.
39. M. Meldal, C. W. Tornoe, Chem. Rev. 2008, 108, 2952-3015.
40. C. W. Tornoe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064.
41. C. Bouillon, A. Meyer, S. Vidal, A. Jochum, Y. Chevolot, J. P. Cloarec, J. P. Praly, J. J. Vasseur, F. Morvan, J. Org. Chem. 2006, 71, 4700-4702.
42. F. Morvan, A. Meyer, A. Jochum, C. Sabin, Y. Chevolot, A. Imberty, J.-P. Praly, J.-J. Vasseur, E. Souteyrand, S. Vidal, Bioconjugate Chem. 2007, 18, 1637-1643.
43. Y. Chevolot, C. Bouillon, S. Vidal, F. Morvan, A. Meyer, J.-P. Cloarec, A. Jochum, J.-P. Praly, J.-J. Vasseur, E. Souteyrand, Angew. Chem. 2007, 119, 2450-2454
44. Angew. Chem. Int. Ed. 2007, 46, 2398-2402.
45. F. Fazio, M. C. Bryan, O. Blixt, J. C. Paulson, C. H. Wong, J. Am. Chem. Soc. 2002, 124, 14397-14402.
46. F. Pérez-Balderas, M. Ortega-Munoz, J. Morales-Sanfrutos, F. Hernandez-Mateo, F. G. Calvo-Flores, J. A. Calvo-Asin, J. Isac-Garcia, F. Santoyo-Gonzalez, Org. Lett. 2003, 5, 1951-1954.
47. B. C. Hamper, S. A. Kolodziej, A. M. Scates, R. G. Smith, E. Cortez, J. Org. Chem. 1998, 63, 708-718.
48. O. Roy, S. Faure, V. Thery, C. Didierjean, C. Taillefumier, Org. Lett. 2008, 10, 921-924.
49. J. M. Holub, K. Kirshenbaum, Chem. Soc. Rev. 2010, 39, 1325-1337.
50. C. Schilling, N. Jung, S. Bräse, in Click Chemistry for Biotechnology and Materials Science (Ed.:, J. Lahann,), Wiley, Chichester, 2009, pp. 9-28.
51. A. Dondoni, Chem. Asian J. 2007, 2, 700-708.
52. Z. Szurmai, L. Szabó, A. Lipták, Acta Chim. Hung. 1989, 126, 259-269.
53. R. Roy, J. M. Kim, Angew. Chem. 1999, 111, 380-384
54. Angew. Chem. Int. Ed. 1999, 38, 369-372.
55. A. Marra, M.-C. Scherrmann, A. Dondoni, R. Ungaro, A. Casnati, P. Minari, Angew. Chem., Int. Ed. Engl. 1995, 33, 2479-2481.
56. A. Dondoni, A. Marra, M.-C. Scherrmann, A. Casnati, F. Sansone, R. Ungaro, Chem. Eur. J. 1997, 3, 1774-1782.
57. A. Dondoni, M. Kleban, X. Hu, A. Marra, H. D. Banks, J. Org. Chem. 2002, 67, 4722-4733.
58. S. P. Bew, R. A. Brimage, N. L′Hermite, S. V. Sharma, Org. Lett. 2007, 9, 3713-3716.
59. A. Dondoni, M. Kleban, A. Marra, Tetrahedron Lett. 1997, 38, 7801-7804.
60. C. Félix, H. Parrot-Lopez, V. Kalchenko, A. W. Coleman, Tetrahedron Lett. 1998, 39, 9171-9174.
61. Z. Asfari, V. Bohmer, J. Harrowfield, J. Vicens, Calixarenes 2001, Kluwer Academic Publishers, Dordrecht, 2001.
62. R. G. Janssen, W. Verboom, D. N. Reinhoudt, A. Casnati, M. Freriks, A. Pochini, F. Ugozzoli, R. Ungaro, P. M. Nieto, M. Carramolino, F. L. Cuevas, P. Prados, J. deaMendoza, Synthesis 1993, 380-386.
63. J. P. M. vanaDuynhoven, R. G. Janssen, W. Verboom, S. M. Franken, A. Casnati, A. Pochini, R. Ungaro, J. deaMendoza, P. M. Nieto, J. Am. Chem. Soc. 1994, 116, 5814-5822.
64. S. Kanamathareddy, C. D. Gutsche, J. Org. Chem. 1994, 59, 3871-3879.
65. C. Kaldapa, J. C. Blais, V. Carré, R. Granet, V. Sol, M. Guilloton, M. Spiro, P. Krausz, Tetrahedron Lett. 2000, 41, 331-335.
66. V. Sol, J. C. Blais, G. Bolbach, V. Carré, R. Granet, M. Guilloton, M. Spiro, P. Krausz, Tetrahedron Lett. 1997, 38, 6391-6394.
67. V. Sol, J. C. Blais, V. Carre, R. Granet, M. Guilloton, M. Spiro, P. Krausz, J. Org. Chem. 1999, 64, 4431-4444.
68. V. Sol, P. Branland, R. Granet, C. Kaldapa, B. Verneuil, P. Krausz, Bioorg. Med. Chem. Lett. 1998, 8, 3007-3010.
69. V. Sol, V. Chaleix, Y. Champavier, R. Granet, Y. M. Huang, P. Krausz, Bioorg. Med. Chem. 2006, 14, 7745-7760.
70. V. Sol, V. Chaleix, R. Granet, P. Krausz, Tetrahedron 2008, 64, 364-371.
71. Y. Liu, C.-F. Ke, H.-Y. Zhang, J. Cui, F. Ding, J. Am. Chem. Soc. 2008, 130, 600-605.
72. M. A. Olson, A. Coskun, R. Klajn, L. Fang, S. K. Dey, K. P. Browne, B. A. Grzybowski, J. F. Stoddart, Nano Lett. 2009, 9, 3185-3190.
73. M. Pal, K. Parasuraman, K. R. Yeleswarapu, Org. Lett. 2003, 5, 349-352.
74. J.-S. Marois, K. Cantin, A. Desmarais, J.-F. Morin, Org. Lett. 2008, 10, 33-36.
75. G. Costa, E. Reisenhofer, L. Stefani, J. Inorg. Nucl. Chem. 1965, 27, 2581-2584.
76. C. Chemani, A. Imberty, S. deaBentzmann, M. Pierre, M. Wimmerova, B. P. Guery, K. Faure, Infect. Immun. 2009, 77, 2065-2075.
77. B. Blanchard, PhD Thesis, Etudes structurales et fonctionnelles deaLectines et adhésines chez Pseudomonas aeruginosa, CERMAV, Université Joseph Fourier Grenoble 2009.
78. T. K. Dam, T. A. Gerken, C. F. Brewer, Biochemistry 2009, 48, 3822-3827.
79. J. B. Corbell, J. J. Lundquist, E. J. Toone, Tetrahedron: Asymmetry 2000, 11, 95-111.