Evidence for two populated conformations for the dimeric LeX and LeALeX tumor-associated carbohydrate antigens

Journal of Medicinal Chemistry

Volumn 57, Issue 3, 2014, Pages 817-827

  Jackson, Trudy A ^a,b   Robertson, Valerie ^a   Auzanneau, France Isabelle ^a  

^a UNIVERSITY OF GUELPH   (Canada)

^b Skerrit's Pasture (Gov't Works)   (Antigua and Barbuda)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIGENS, CD15; ANTIGENS, TUMOR-ASSOCIATED, CARBOHYDRATE; DIMERIZATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; MOLECULAR DYNAMICS SIMULATION; OLIGOSACCHARIDES;

EID: 84894059622     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm401576x     Document Type: Article

References (62)

1. Hakomori, S.; Jeanloz, R. W. Isolation of a glycolipid containing fucose, galactose, glucose, and glucosamine from human cancerous tissue J. Biol. Chem. 1964, 239, 3606-3607
2. Hakomori, S. I.; Koscielak, J.; Bloch, K. J.; Jeanloz, R. W. Immunologic relationship between blood group substances and a fucose-containing glycolipid of human adenocarcinoma J. Immunol. 1967, 98, 31-38
3. Buskas, T.; Thompson, P.; Boons, G. J. Immunotherapy for cancer: synthetic carbohydrate-based vaccines Chem. Commun. 2009, 5335-5349
4. Astronomo, R. D.; Burton, D. R. Carbohydrate vaccines: developing sweet solutions to sticky situations? Nat. Rev. Drug Discovery 2010, 9, 308-324
5. Morelli, L.; Poletti, L.; Lay, L. Carbohydrates and immunology: Synthetic oligosaccharide antigens for vaccine formulation Eur. J. Org. Chem. 2011, 5723-5777
6. Hevey, R.; Ling, C. C. Recent advances in developing synthetic carbohydrate-based vaccines for cancer immunotherapies Future Med. Chem. 2012, 4, 545-584
7. Liu, C.-C.; Ye, X.-S. Carbohydrate-based cancer vaccines: Target cancer with sugar bullets Glycoconjugate J. 2012, 29, 259-271
8. Hakomori, S. Aberrant glycosylation in tumors and tumor-associated carbohydrate antigens Adv. Cancer Res. 1989, 52, 257-331
9. Brockhaus, M.; Magnani, J. L.; Herlyn, M.; Blaszczyk, M.; Steplewski, Z.; Koprowski, H.; Ginsburg, V. Monoclonal antibodies directed against the sugar sequence of lacto-N-fucopentaose III are obtained from mice immunized with human tumors Arch. Biochem. Biophys. 1982, 217, 647-651
10. Huang, L. C.; Brockhaus, M.; Magnani, J. L.; Cuttitta, F.; Rosen, S.; Minna, J. D.; Ginsburg, V. Many monoclonal antibodies with an apparent specificity for certain lung cancers are directed against a sugar sequence found in lacto-N-fucopentaose III Arch. Biochem. Biophys. 1983, 220, 318-320
11. MaÌŠrtensson, S.; Due, C.; Pahlsson, P.; Nilsson, B.; Eriksson, H.; Zopf, D.; Olsson, L.; Lundblad, A. A carbohydrate epitope associated with human squamous lung-cancer Cancer Res. 1988, 48, 2125-2131
12. Fox, N.; Damjanov, I.; Knowles, B. B.; Solter, D. Immunohistochemical localization of the mouse stage-specific embryonic antigen 1 in human tissues and tumors Cancer Res. 1983, 43, 669-678
13. Shi, Z. R.; McIntyre, L. J.; Knowles, B. B.; Solter, D.; Kim, Y. S. Expression of a carbohydrate differentiation antigen, stage-specific embryonic antigen 1, in human colonic adenocarcinoma Cancer Res. 1984, 44, 1142-1147
14. Croce, M. V.; Isla-Larrain, M.; Rabassa, M. E.; Demichelis, S.; Colussi, A. G.; Crespo, M.; Lacunza, E.; Segal-Eiras, A. Lewis x is highly expressed in normal tissues: A comparative immunohistochemical study and literature revision Pathol. Oncol. Res. 2007, 13, 130-138
15. Lemieux, R. U.; Baker, D. A.; Weinstein, W. M.; Switzer, C. M. Artificial antigens. Antibody preparations for the localization of Lewis determinants in tissues Biochemistry 1981, 20, 199-205
16. Pettijohn, D. E.; Stranahan, P. L.; Due, C.; Rønne, E.; Sørensen, H. R.; Olsson, L. Glycoproteins distinguishing non-small cell from small cell human lung carcinoma recognized by monoclonal antibody 43-9F Cancer Res. 1987, 47, 1161-1169
17. Fukushi, Y.; Hakomori, S.; Nudelman, E.; Cochran, N. Novel fucolipids accumulating in human adenocarcinoma. II. Selective isolation of hybridoma antibodies that differentially recognize mono-, di-, and trifucosylated type 2 chain J. Biol. Chem. 1984, 259, 4681-4685
18. Fukushi, Y.; Hakomori, S.; Shepard, T. Localization and alteration of mono-, di-, and trifucosyl alpha 1→3 type 2 chain structures during human embryogenesis and in human cancer J. Exp. Med. 1984, 160, 506-520
19. Fukushi, Y.; Kannagi, R.; Hakomori, S.; Shepard, T.; Kulander, B. G.; Singer, J. W. Location and distribution of difucoganglioside (VI3NeuAcV3III3Fuc2nlc6) in normal and tumor-tissues defined by its monoclonal-antibody FH6 Cancer Res. 1985, 45, 3711-3717
20. x-related antigen expression in human-malignant and nonmalignant colonic tissues Cancer Res. 1986, 46, 2627-2632
21. Nakasaki, H.; Mitomi, T.; Noto, T.; Ogoshi, K.; Hanaue, H.; Tanaka, Y.; Makuuchi, H.; Clausen, H.; Hakomori, S. Mosaicism in the expression of tumor-associated carbohydrate antigens in human colonic and gastric cancers Cancer Res. 1989, 49, 3662-3669
22. x-containing glycoproteins and glycolipids in sera of patients with adenocarcinoma Cancer Res. 1990, 50, 1375-1380
23. Pettijohn, D. E.; Pfenninger, O.; Brown, J.; Duke, R.; Olsson, L. Tumorigenic human squamous lung-cancer cells have defined cell-surface carbohydrates that are absent from nontumorigenic cells Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 802-806
24. Battifora, H.; Sorensen, H. R.; Mehta, P.; Ahn, C.; Niland, J.; Hage, E.; Pettijohn, D. E.; Olsson, L. Tumor-associated antigen 43-9F is of prognostic value in squamous cell carcinoma of the lung. A retrospective immunohistochemical study Cancer 1992, 70, 1867-1872
25. Stranahan, P. L.; Howard, R. B.; Pfenninger, O.; Cowen, M. E.; Johnston, M. R.; Pettijohn, D. E. Mucin gel formed by tumorigenic squamous lung-carcinoma cells has Le(a)-X oligosaccharides and excludes antibodies from underlying cells Cancer Res. 1992, 52, 2923-2930
26. Stranahan, P. L.; Laroe, J.; McCombs, R.; Goldsmith, A.; Rahim, I.; Overland, M.; Pettijohn, D. E. Cell-cell interactions influence oligosaccharide modifications on mucins and other large glycoproteins Glycoconjugate J. 1996, 13, 741-747
27. x: A cell surface marker for carcinomas derived from embryonic endoderm Oncol. Rep. 1998, 5, 235-239
28. Imberty, A.; Mikros, E.; Koca, J.; Mollicone, R.; Oriol, R.; Pérez, S. Computer simulation of histo-blood group oligosaccharides: energy maps of all constituting disaccharides and potential energy surfaces of 14 ABH and Lewis carbohydrate antigens Glycoconjugate J. 1995, 12, 331-349
29. Perez, S.; Mouhous-Riou, N.; Nifant'ev, N. E.; Tsvetkov, Y. E.; Bachet, B.; Imberty, A. Crystal and molecular structure of a histo-blood group antigen involved in cell adhesion: The Lewis x trisaccharide Glycobiology 1996, 6, 537-542
30. Reynolds, M.; Fuchs, A.; Lindhorst, T. K.; Perez, S. The hydration features of carbohydrate determinants of Lewis antigens Mol. Simul. 2008, 34, 447-460
31. Miller, K. E.; Mukhopadhyay, C.; Cagas, P.; Bush, C. A. Solution structure of the Lewis x oligosaccharide determined by NMR spectroscopy and molecular dynamics simulations Biochemistry 1992, 31, 6703-6709
32. x and related saccharides by two lectins J. Am. Chem. Soc. 2001, 123, 10705-10714
33. x monoclonal antibody SH1: The identification of a non-cross reactive analogue Bioorg. Med. Chem. 2010, 18, 7174-7185
34. Lemieux, R. U.; Bock, K.; Delbaere, L. T. J.; Koto, S.; Rao, V. S. The conformations of oligosaccharides related to the ABH and Lewis human-blood group determinants Can. J. Chem. 1980, 58, 631-653
35. Biswas, M.; Rao, V. S. R. Conformational studies on the ABH and Lewis blood group oligosaccharides Carbohydr. Polym. 1982, 2, 205-222
36. b, and SSEA-1 Carbohydr. Res. 1988, 178, 67-78
37. Mukhopadhyay, C.; Bush, C. A. Molecular dynamics simulation of Lewis blood groups and related oligosaccharides Biopolymers 1991, 31, 1737-1746
38. Sawen, E.; Hinterholzinger, F.; Landersjo, C.; Widmalm, G. Conformational flexibility of the pentasaccharide LNF-2 deduced from NMR spectroscopy and molecular dynamics simulations Org. Biomol. Chem. 2012, 10, 4577-4585
39. Martin-Pastor, M.; Bush, C. A. The use of NMR residual dipolar couplings in aqueous dilute liquid crystalline medium for conformational studies of complex oligosaccharides Carbohydr. Res. 2000, 323, 147-155
40. Cagas, P.; Bush, C. A. Determination of the conformation of Lewis blood group oligosaccharides by simulation of two-dimensional nuclear Overhauser data Biopolymers 1990, 30, 1123-1138
41. a blood group antigen component as related to the specificity of monoclonal antibody CO 19-9 J. Biol. Chem. 1990, 265, 2028-2037
42. a using NMR spectroscopy and molecular dynamics simulations Glycobiology 1994, 4, 49-57
43. Martin-Pastor, M.; Bush, C. A. Conformational studies of human milk oligosaccharides using H-1-C-13 one-bond NMR residual dipolar couplings Biochemistry 2000, 39, 4674-4683
44. Auzanneau, F.-I.; Jackson, T. A.; Liao, L. Stochastic searches and NMR experiments on four Lewis A analogues: NMR experiments support some flexibility around the fucosidic bond Bioorg. Med. Chem. 2012, 20, 5085-5093
45. IUPAC-IUBMB Joint Commission on Biochemical Nomenclature (JCBN) Nomenclature of Carbohydrates. Recommendations 1996. In European Journal of Biochemistry; Blackwell Science Ltd: Oxford, 1997; Vol. 243, p 9.
46. Pachler, K. G. R. Investigation of a dimeric Lewis X octasaccharide derivative by H-1 and C-13 NMR spectroscopy Magn. Reson. Chem. 1996, 34, 711-714
47. x tumor associated antigen studied by NMR spectroscopy and molecular dynamics simulations Eur. J. Org. Chem. 2012, 4705-4715
48. Maaheimo, H.; Kosma, P.; Brade, L.; Brade, H.; Peters, T. Mapping the binding of synthetic disaccharides representing epitopes of Chlamydial lipopolysaccharide to antibodies with NMR Biochemistry 2000, 39, 12778-12788
49. x monoclonal antibodies J. Med. Chem. 2013, 56, 8183-8190
50. Jackson, T. A.; Robertson, V.; Imberty, A.; Auzanneau, F.-I. The flexibility of the Le(a)Le(x) tumor associated antigen central fragment studied by systematic and stochastic searches as well as dynamic simulations Bioorg. Med. Chem. 2009, 17, 1514-1526
51. Case, D. A.; Cheatham, T. E., III; Simmerling, C. L.; Wang, J.; Duke, R. E.; Luo, R.; Crowley, M.; Walker, R. C.; Zhang, W.; Merz, K. M.; Wang, B.; Hayik, S.; Roitberg, A.; Seabra, G.; Kolossváry, I.; Wong, K. F.; Paesani, F.; Vanicek, J.; Wu, X.; Brozell, S. R.; Steinbrecher, T.; Gohlke, H.; Yang, L.; Tan, C.; Mongan, J.; Hornak, V.; Cui, G.; Mathews, D. H.; Seetin, M. G.; Sagui, C.; Babin, V.;; Kollman, P. A. AMBER 10; University of California, San Francisco, 2008.
52. Kirschner, K. N.; Yongye, A. B.; Tschampel, S. M.; Gonzalez-Outeirino, J.; Daniels, C. R.; Foley, B. L.; Woods, R. J. GLYCAM06: a generalizable biomolecular force field. Carbohydrates J. Comput. Chem. 2007, 29, 622-655
53. Chang, G.; Guida, W. C.; Still, W. C. An internal-coordinate Monte Carlo method for searching conformational space J. Am. Chem. Soc. 1989, 111, 4379-4386
54. Xia, J. C.; Daly, R. P.; Chuang, F. C.; Parker, L.; Jensen, J. H.; Margulis, C. J. Sugar folding: A novel structural prediction tool for oligosaccharides and polysaccharides J. Chem. Theory Comput. 2007, 3, 1629-1643
55. Xia, J. C.; Margulis, C. A tool for the prediction of structures of complex sugars J. Biomol. NMR 2008, 42, 241-256
56. Sawen, E.; Stevensson, B.; Ostervall, J.; Maliniak, A.; Widmalm, G. Molecular conformations in the pentasaccharide LNF-1 derived from NMR spectroscopy and molecular dynamics simulations J. Phys. Chem. B 2011, 115, 7109-7121
57. Lemieux, R. U. How water provides the impetus for molecular recognition in aqueous solution Acc. Chem. Res. 1996, 29, 373-380
58. Asensio, J. L.; Arda, A.; Canada, F. J.; Jimenez-Barbero, J. Carbohydrate-aromatic interactions Acc. Chem. Res. 2013, 46, 946-954
59. McGavin, R. S.; Gagne, R. A.; Chervenak, M. C.; Bundle, D. R. The design, synthesis and evaluation of high affinity macrocyclic carbohydrate inhibitors Org. Biomol. Chem. 2005, 3, 2723-2732
60. Johnson, M. A.; Bundle, D. R. Designing a new antifungal glycoconjugate vaccine Chem. Soc. Rev. 2013, 42, 4327-4344
61. Wang, L.-X. Synthetic carbohydrate antigens for HIV vaccine design Curr. Opin. Chem. Biol. 2013, 17, 997-1005
62. x oligosaccharide fragments and efficient one-step deprotection Carbohydr. Res. 2010, 345, 1216-1221