Inhibitory potential of chemical substitutions at bioinspired sites of β-d-galactopyranose on neoglycoprotein/cell surface binding of two classes of medically relevant lectins

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 10, 2011, Pages 3280-3287

  Gigure, Denis ^a   André, Sabine ^b   Bonin, Marc André ^a   Bellefleur, Marc André ^a   Provencal, Alexandre ^a   Cloutier, Philipe ^a   Pucci, Bernard ^c   Roy, René ^a   Gabius, Hans Joachim ^b  

^a UNIVERSITÉ DU QUÉBEC À MONTRÉAL   (Canada)

^b UNIVERSITY OF MUNICH   (Germany)

^c UNIVERSITY OF AVIGNON   (France)

Author keywords

Agglutinin; Blood group; Glycocluster; Malignancy; Multivalency; Neoglycoconjugate

Indexed keywords

BETA DEXTRO GALACTOPYRANOSE; GALACTOSIDE; GALECTIN; LECTIN; NEOGLYCOPROTEIN; PHYTOHEMAGGLUTININ; PLANT TOXIN; THIOGLYCOSIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BIOCOMPATIBILITY; BIOLOGICAL ACTIVITY; CANCER CELL CULTURE; CANCER INHIBITION; CELL PROTECTION; CELL SURFACE; CONCENTRATION RESPONSE; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; CYTOTOXICITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; HUMAN; HUMAN CELL; IC 50; LIGAND BINDING; PROTEIN BINDING; PROTEIN CARBOHYDRATE INTERACTION; SUBSTITUTION REACTION; TOXIN ANALYSIS;

CELL LINE, TUMOR; CELL PROLIFERATION; GALACTOSE; GALECTINS; GLYCOPROTEINS; HUMANS; JURKAT CELLS; LECTINS; MISTLETOE; MODELS, MOLECULAR; PROTEIN BINDING; SMALL MOLECULE LIBRARIES;

EID: 79956187792     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.03.022     Document Type: Article

References (67)

1. H.-J. Gabius The Sugar Code. Fundamentals of glycosciences 2009 Wiley-VCH Weinheim Germany
2. A. Imberty, Y.M. Chabre, and R. Roy Chem. Eur. J. 14 2008 7490
3. Y.M. Chabre, and R. Roy Curr. Top. Med. Chem. 14 2008 1237
4. S. Rorive, N. Belot, C. Decaestecker, F. Lefranc, L. Gordower, S. Micik, C.-A. Maurage, H. Kaltner, M.-M. Ruchoux, A. Danguy, H.-J. Gabius, I. Salmon, R. Kiss, and I. Camby Glia 33 2001 241
5. Y.-H. Liu, M. D'Ambrosio, T.-D. Liao, H. Peng, N.E. Rhaleb, U.C. Sharma, S. André, H.-J. Gabius, and O.A. Carretero Am. J. Physiol. Heart Circ. Physiol. 296 2009 H404
6. H.M.I. Osborn, and A. Turkson H.-J. Gabius, The Sugar Code. Fundamentals of glycosciences 2009 Wiley-VCH Weinheim, Germany pp. 469-483
7. O. Roda, E. Ortiz-Zapater, N. Martínez-Bosch, R. Gutiérrez-Gallego, M. Vila-Perelló, C. Ampurdanés, H.-J. Gabius, S. André, D. Andreu, F.X. Real, and P. Navarro Gastroenterology 136 2009 1379
8. M. Jiménez, J.L. Sáiz, S. André, H.-J. Gabius, and D. Solís Glycobiology 15 2005 1386
9. A. Villalobo, A. Nogales-González, and H.-J. Gabius Trends Glycosci. Glycotechnol. 18 2006 1
10. R. Schwartz-Albiez H.-J. Gabius, The Sugar Code. Fundamentals of glycosciences 2009 Wiley-VCH Weinheim Germany pp. 447-467
11. C.P. Sparrow, H. Leffler, and S.H. Barondes J. Biol. Chem. 262 1987 7383
12. O.E. Galanina, H. Kaltner, L.S. Khraltsova, N.V. Bovin, and H.-J. Gabius J. Mol. Recognit. 10 1997 139
13. N. Ahmad, H.-J. Gabius, H. Kaltner, S. André, I. Kuwabara, F.-T. Liu, S. Oscarson, T. Norberg, and C.F. Brewer Can. J. Chem. 80 2002 1096
14. J. Hirabayashi, T. Hashidate, Y. Arata, N. Nishi, T. Nakamura, M. Hirashima, T. Urashima, T. Oka, M. Futai, W.E.G. Müller, F. Yagi, and K.I. Kasai Biochim. Biophys. Acta 1572 2002 232
15. T.K. Dam, H.-J. Gabius, S. André, H. Kaltner, M. Lensch, and C.F. Brewer Biochemistry 44 2005 12564
16. L. He, S. André, H.-C. Siebert, H. Helmholz, B. Niemeyer, and H.-J. Gabius Biophys. J. 85 2003 511
17. M. Jiménez, S. André, C. Barillari, A. Romero, D. Rognan, H.-J. Gabius, and D. Solís FEBS Lett. 582 2008 2309
18. L. He, S. André, V.M. Garamus, H.-C. Siebert, C. Chi, B. Niemeyer, and H.-J. Gabius Glycoconjug. J. 26 2009 111
19. A. Göhler, S. André, H. Kaltner, M. Sauer, H.-J. Gabius, and S. Doose Biophys. J. 98 2010 3044
20. J.M. Rini Annu. Rev. Biophys. Biomol. Struct. 24 1995 551
21. R. Roy Trends Glycosci. Glycotechnol. 15 2003 289
22. J. Kopitz, M. Bergmann, and H.-J. Gabius IUBMB Life 62 2010 624
23. Y.C. Lee Trends Glycosci. Glycotechnol. 22 2010 95
24. S. André, D. Gigure, T.K. Dam, C.F. Brewer, H.-J. Gabius, and R. Roy New J. Chem. 34 2010 2229
25. R.T. Lee, H.-J. Gabius, and Y.C. Lee J. Biol. Chem. 267 1992 23722
26. H. Ahmed, H.J. Allen, A. Sharma, and K.L. Matta Biochemistry 29 1990 5315
27. R.T. Lee, Y. Ichikawa, H.J. Allen, and Y.C. Lee J. Biol. Chem. 265 1990 7864
28. D. Gigure, S. Sato, C. St-Pierre, S. Sirois, and R. Roy Bioorg. Med. Chem. Lett. 16 2006 1668
29. D. Gigure, R. Patnam, M.-A. Bellefleur, C. St-Pierre, S. Sato, and R. Roy Chem. Commun. 2006 2379
30. S. Sirois, D. Gigure, and R. Roy Med. Chem. 2 2006 481
31. T.L. Lowary, and O. Hindsgaul Carbohydr. Res. 251 1994 33
32. S. Béha, D. Gigure, R. Patnam, and R. Roy Synlett 2006 1739
33. R. Patnam, J.M. Juárez-Ruiz, and R. Roy Org. Lett. 8 2006 2691
34. Giguère, D. M. Sc. Thesis, Université du Québec à Montréal, 2006.
35. Bellefleur, M.-A. M. Sc. Thesis, Université du Québec Montréal, 2007.
36. D. Gigure, M.-A. Bonin, P. Cloutier, R. Patnam, C. St-Pierre, S. Sato, and R. Roy Bioorg. Med. Chem. 16 2008 7811
37. D. Gigure, R. Patnam, J.M. Juárez-Ruiz, M. Neault, and R. Roy Tetrahedron Lett. 50 2009 4254
38. I. Vrasidas, J. Kemmink, R.M.J. Liskamp, and R.J. Pieters Org. Lett. 4 2002 1807
39. S. André, R.J. Pieters, I. Vrasidas, H. Kaltner, I. Kuwabara, F.-T. Liu, R.M.J. Liskamp, and H.-J. Gabius ChemBioChem 2 2001 822
40. I. Vrasidas, S. André, P. Valentini, C. Böck, M. Lensch, H. Kaltner, R.M.J. Liskamp, H.-J. Gabius, and R.J. Pieters Org. Biomol. Chem. 1 2003 803
41. F. Lebaupain, A.G. Salvay, B. Olivier, G. Durand, A.-S. Fabiano, N. Michel, J.-L. Popot, C. Ebel, C. Breyton, and B. Pucci Langmuir 22 2006 8881
42. A. Polidori, B. Pucci, J.C. Maurizis, and A.A. Pavia New. J. Chem. 18 1994 839
43. J. Kopitz, C. von Reitzenstein, S. André, H. Kaltner, J. Uhl, V. Ehemann, M. Cantz, and H.-J. Gabius J. Biol. Chem. 276 2001 35917
44. H. Sanchez-Ruderisch, C. Fischer, K.M. Detjen, M. Welzel, A. Wimmel, J.C. Manning, S. André, and H.-J. Gabius J. FEBS 277 2010 3552
45. J.P. Ribeiro, S. André, F.J. Cañada, H.-J. Gabius, A.P. Butera, R.J. Alves, and J. Jiménez-Barbero ChemMedChem 5 2010 415
46. F.J. Muñoz, J.I. Santos, A. Ardá, S. André, H.-J. Gabius, J.V. Sinisterra, J. Jiménez-Barbero, and M.J. Hernáiz Org. Biomol. Chem. 8 2010 2986
47. D. Solís, A. Romero, H. Kaltner, H.-J. Gabius, and T. Díaz-Mauriño J. Biol. Chem. 271 1996 12744
48. P. Sörme, P. Arnoux, B. Kahl-Knutsson, H. Leffler, J.M. Rini, and U.J. Nilsson J. Am. Chem. Soc. 127 2005 1737
49. S. André, D. Specker, N.V. Bovin, M. Lensch, H. Kaltner, H.-J. Gabius, and V. Wittmann Bioconjug. Chem. 20 2009 1716
50. D. Solís, M.J. Maté, M. Lohr, J.P. Ribeiro, L. López-Merino, S. André, E. Buzamet, F.J. Cañada, H. Kaltner, M. Lensch, F.M. Ruiz, G. Haroske, U. Wollina, M. Kloor, J. Kopitz, J.L. Sáiz, M. Menéndez, J. Jiménez-Barbero, A. Romero, and H.-J. Gabius Int. J. Biochem. Cell Biol. 42 2010 1019
51. S. André, C.E.P. Maljaars, K.M. Halkes, H.-J. Gabius, and J.P. Kamerling Bioorg. Med. Chem. Lett. 17 2007 793
52. J. Jiménez-Barbero, E. Dragoni, C. Venturi, F. Nannucci, A. Ardá, M. Fontanella, S. André, F.J. Cañada, H.-J. Gabius, and C. Nativi Chem. Eur. J. 15 2009 10423
53. S. André, T. Kožár, S. Kojima, C. Unverzagt, and H.-J. Gabius Biol. Chem. 390 2009 557
54. S. Oscarson H.-J. Gabius, The Sugar Code. Fundamentals of glycosciences 2009 Wiley-VCH Weinheim Germany pp. 31-51
55. S. André, P.J. Ortega, M.A. Perez, R. Roy, and H.-J. Gabius Glycobiology 9 1999 1253
56. S. André, B. Liu, H.-J. Gabius, and R. Roy Org. Biomol. Chem. 1 2003 3909
57. S. André, F. Sansone, H. Kaltner, A. Casnati, J. Kopitz, H.-J. Gabius, and R. Ungaro ChemBioChem 9 2008 1649
58. R. Leyden, T. Velasco-Torrijos, S. André, S. Gouin, H.-J. Gabius, and P. Murphy J. Org. Chem. 74 2009 9010
59. S. André, M. Lahmann, H.-J. Gabius, and S. Oscarson Mol. Pharmaceut. 7 2010 2270
60. M. Krzeminski, T. Singh, S. André, M. Lensch, A.M. Wu, A.M.J.J. Bonvin, and H.-J. Gabius Biochim. Biophys. Acta 1810 2011 150
61. Y.M. Chabre, and R. Roy H.-J. Gabius, The Sugar Code. Fundamentals of glycosciences 2009 Wiley-VCH Weinheim Germany pp. 53-70
62. Y.M. Chabre, and R. Roy Adv. Carbohydr. Chem. Biochem. 63 2010 265
63. H.-J. Gabius, R. Engelhardt, F. Cramer, R. Bätge, and G.A. Nagel Cancer Res. 45 1985 253
64. H.-J. Gabius, H. Walzel, S.S. Joshi, J. Kruip, S. Kojima, V. Gerke, H. Kratzin, and S. Gabius Anticancer Res. 12 1992 669
65. H.-J. Gabius, S. Bodanowitz, and A. Schauer Cancer 61 1988 1125
66. S. André, Z. Pei, H.-C. Siebert, O. Ramström, and H.-J. Gabius Bioorg. Med. Chem. 14 2006 6314
67. H.-J. Gabius, F. Darro, M. Remmelink, S. André, J. Kopitz, A. Danguy, S. Gabius, I. Salmon, and R. Kiss Cancer Invest. 19 2001 114