Synthesis of tailor-made glycoconjugate mimetics of heparan sulfate that bind IFN-γ in the nanomolar range

Chemistry - A European Journal

Volumn 10, Issue 17, 2004, Pages 4265-4282

  Lubineau, André ^a   Lortat Jacob, Hugues ^a   Gavard, Ollivier ^a,b   Sarrazin, Stéphane ^a   Bonnaffé, David ^a  

^a CNRS   (France)

^b Cerise Chemtech   (Belgium)

Author keywords

Combinatorial chemistry; Cytokines; Glycosylation; Heparin; Oligosaccharides

Indexed keywords

DEMODULATION; POLYETHYLENE GLYCOLS; POLYSACCHARIDES; SURFACE PLASMON RESONANCE; SYNTHESIS (CHEMICAL);

GLYCOCONJUCATE MIMETICS; HEPARAN SULFATE (HS); OCTASACCHARIDES;

SULFUR COMPOUNDS;

ALLYL COMPOUND; DISACCHARIDE; GAMMA INTERFERON; GLYCOCONJUGATE; HEPARAN SULFATE; MACROGOL; OLIGOSACCHARIDE;

ARTICLE; BINDING SITE; CHEMICAL INTERACTION; COMBINATORIAL CHEMISTRY; COMBINATORIAL LIBRARY; CONJUGATION; DEPROTECTION REACTION; GLYCOSYLATION; IC 50; QUANTUM YIELD; STEREOCHEMISTRY; SURFACE PLASMON RESONANCE; SYNTHESIS; ULTRAVIOLET IRRADIATION;

AMINO ACID SEQUENCE; BIOMIMETICS; CARBOHYDRATE SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMATOGRAPHY, THIN LAYER; ELECTROPHORESIS, POLYACRYLAMIDE GEL; GLYCOPROTEINS; HEPARITIN SULFATE; INDICATORS AND REAGENTS; INTERFERON TYPE II; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PROTEIN CONFORMATION; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 4644266139     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200306063     Document Type: Article

References (77)

1. I. Capila, R. J. Linhardt, Angew. Chem. 2002, 114, 426-450; Angew. Chem. Int. Ed. 2002, 41, 390-412.
2. I. Capila, R. J. Linhardt, Angew. Chem. 2002, 114, 426-450; Angew. Chem. Int. Ed. 2002, 41, 390-412.
3. H. Lortat Jacob, A. Grosdidier, A. Imberty, Proc. Natl. Acad. Sci. USA 2002, 99, 1229-1234.
4. J. D. Esko, U. Lindhal, J. Clin. Invest. 2001, 108, 169-173.
5. U. Lindhal, M. Kusche-Gullherg, L. J. Kjellen, J. Biol. Chem. 1998, 273, 24979-24982.
6. J. T. Gallagher, Biochem. Soc. Trans. 1997, 25, 1206-1209.
7. M. A. B. A. Dennissen, G. J. Jenniskens, M. Pieffers, E. M. M. Versteeg, M. Petitou, J. H. Veerkamp, T. van Kuppevelt, J. Biol. Chem. 2002, 277, 10982-10986.
8. K. Sugahara, H. Kitagawa, Curr. Opin. Struct. Biol. 2000, 10, 518-527.
9. U. Lindahl, G. Bäckström, L. Thunberg, I. G. Leder, Proc. Natl. Acad. Sci. USA 1980, 77, 6551-6555.
10. B. Casu, P. Oreste, G. Torri, G. Zoppetti, J. Choay, J. C. Lormeau, M. Petitou, P. Sinaÿ, Biohem. J. 1981, 197, 599-609.
11. C. A. A. van Boeckel, M. Petitou, Angew. Chem. 1993, 105, 1741-1761; Angew. Chem. Int. Ed. Engl. 1993, 32, 1671-1818.
12. C. A. A. van Boeckel, M. Petitou, Angew. Chem. 1993, 105, 1741-1761; Angew. Chem. Int. Ed. Engl. 1993, 32, 1671-1818.
13. J. Kovenzky, J. M. Mallet, J. Esnault, P. A. Driguez, P. Sizun, J. P. Hérault, J. M. Herbert, M. Petitou, P. Sinaÿ, Eur. J. Org. Chem. 2002, 3595-3603.
14. J. L. de Paz, J. Angulo, J. M. Lassaletta, P. M. Nieto, M. Redondo-Horcajo, R. M. Lozano, G. Giménez-Gallego, M. Martin-Lomas, ChemBioChem 2001, 2, 673-685.
15. R. Ojeda, J. Angulo, P. M. Nieto, M. Martin-Lomas, Can. J. Chem. 2002, 80, 917-936.
16. J. D. C. Codée. G. A. van der Marel, C. A. A. van Boeckel, J. H. van Boom, Eur. J. Org. Chem. 2002, 3954-3965.
17. L. Poleti, M. Fleischer, C. Vogel, M. Guerrini, G. Torri, L. Lay, Eur. J. Org. Chem. 2001, 2727-2734.
18. H. A. Orgueira, A. Bartolozzi, P. Schell, R. E. J. N. Litjens, E. R. Palmacci, P. H. Seeberger, Chem. Eur. J. 2003, 143-169.
19. L. Poletti, L. Lay, Eur. J. Org. Chem. 2003, 2999-3124.
20. N. A. Karst, R. J. Linhardt, Curr. Med. Chem. 2003, 10, 1993-2031.
21. J.-L. de Paz, R. Ojeda, N. Reichardt, M. Martin-Lomas, Eur. J. Org. Chem. 2003, 3308-3324.
22. A. Prabhu, A. Venot, G.-J. Boons, Org. Lett. 2003, 5, 4975-4978.
23. A. Lubineau, D. Bonnaffé, Eur. J. Org. Chem. 1999, 2523-2532.
24. O. Gavard, Y. Hersant, J. Alais, V. Duverger, A. Dilhas, A. Bascou, D. Bonnaffé, Eur. J. Org. Chem. 2003, 3603-3620.
25. A. Dilhas, D. Bonnaffé, Tetrahedron Lett. 2004, 45, 3643-3645.
26. R. Lucas, D. Hamza, A. Lubineau, D. Bonnaffé, Eur. J. Org. Chem. 2004, in press.
27. J. E. Turnbull, J. T. Gallagher, Biochem. J. 1991, 273, 553-559.
28. R. Sadir, F. Baleux, A. Grosdidier, A. Imberty, H. Lortat-Jacob, J. Biol. Chem. 2001, 276, 8288-8296.
29. H. Lortat-Jacob, J. E. Turnbull, J. A. Grimaud, Biochem. J. 1995, 310, 497-505.
30. S. E. Stringer, J. T. Gallagher, J. Biol. Chem. 1997, 272, 20 508-20 514.
31. R. R. Vivès, R. Sadir, A. Imberty, A. Rencurosi, H. Lortat-Jacob, Biochemistry 2002, 41, 14 779-14 789.
32. S. E. Stringer, M. J. Forster, B. Mulloy, C. R. Bishop, G. J. Graham, J. T. Gallagher, Blood 2002, 100, 1546-1550.
33. J. T. Gallagher, J. Clin. Invest. 2001, 408, 357-361.
34. M. Petiou, P. Duchaussoy, P.-A. Driguez, G. Jaurand, J.-P. Hérault, J.-C. Lormeau, C. A. A. van Boeckel, J.-M. Herbert, Angew. Chem. 1998, 110, 3186-3191; Angew. Chem. Int. Ed. Engl. 1998, 37, 3009-3014.
35. M. Petiou, P. Duchaussoy, P.-A. Driguez, G. Jaurand, J.-P. Hérault, J.-C. Lormeau, C. A. A. van Boeckel, J.-M. Herbert, Angew. Chem. 1998, 110, 3186-3191; Angew. Chem. Int. Ed. Engl. 1998, 37, 3009-3014.
36. M. Petitou, J. P. Héault, A. Bernat, P. A. Driguez, P. Duchaussoy, J. C. Lormeau, J. M. Herbert, Nature 1999, 398, 417-422.
37. M. Petiou, A. Imberty, P. Duchaussoy, P.-A. Driguez, M.-L. Ceccato, F. Gouvenec, P. Sizun, J.-P. Hérault, S. Perez, J.-M. Herbert, Chem. Eur. J. 200, 7, 858-873.
38. P. D. J. Grootenhuis, P. Westerduin, D. Meuleman, M. Petitou, C. A. A. van Boeckel, Nat. Struc. Biol. 1995, 2, 736-739.
39. P. Westerduin, J. E. M. Basten, M. A. Broekhoven, V. de Kimpe, W. H. A. Kuijpers, C. A. A. van Boeckel, Angew. Chem. 1996, 108, 339-342; Angew. Chem. Int. Ed. Engl. 1996, 35, 331-333.
40. P. Westerduin, J. E. M. Basten, M. A. Broekhoven, V. de Kimpe, W. H. A. Kuijpers, C. A. A. van Boeckel, Angew. Chem. 1996, 108, 339-342; Angew. Chem. Int. Ed. Engl. 1996, 35, 331-333.
41. A. Lubineau, S. Escher, J. Alais, D. Bonnaffé, Tetrahedron Lett. 1997, 38, 4087-4090.
42. H. Lortat-Jacob, H. K. Kleinman, J. A. Grimaud, J. Clin. Invest. 1991, 87, 878-883.
43. H. Lortat-Jacob, F. Baltzer, J. A. Grimaud, J. Biol. Chem. 1996, 271, 16 139-16 143.
44. H. Lortat-Jacob, C. Brisson, S. Guerret, G. Morel, Cytokine 1996, 8, 557-566.
45. B. Skurkovitch, S. Surkovitch, Curr. Opin. Mol. Therapeutics, 2003, 5, 52-57.
46. P. Parronchi, P. Romagnani, F. Annunziato, S. Sampognaro, A. Becchio, L. Giannarini, E. Maggi, C. Pupilli, F. Tonelli, S. Romagnani, Am. J. Pathol. 1997, 150, 823-832.
47. H. Lortat-Jacob, J. A. Grimaud, FEBS Lett. 1991, 280, 152-154.
48. This length was calculated for a conformation of the NA domain close to the helical one of heparin; B. Mulloy, M. J. Forster, C. Jones, D. B. Davies, Biochem. J. 1993, 293, 849-858.
49. Competition analysis between synthetic peptides encompassing the KRKR domain or the RGRR domain and full-length IFN-γ suggests that the KRKR sequence is the main contributor in the binding; H. Lortat-Jacob, J. A. Grimaud, FEBS Lett. 1991, 280, 152-154.
50. PDB entry 1HIG: S. E. Ealick, W. J. Cook, S. Vijay-Kumar, M. Carson, T. L. Nagabhushan, P. P. Trotta, C. E. Bugg, Science 1991, 252, 698-702.
51. PDB entry 1F9G: D. J. Thiel, M. L. le Du, R. L. Walter, A. D'Arcy, C. Chene, M. Fountoulakis, G. Garotta, F. K. Winkler, S. E. Ealick, Struct. Fold. Des 2000, 8, 927-936.
52. C. Tabeur, J. M. Mallet, F. Bono, J. M. Herbert, M. Petitou, P. Sinaÿ, Bioorg. Med. Chem. 1999, 7, 2003-2012.
53. T. Ogawa, S. Nakabayashi, T. Kitajima, Carbohydr. Res. 1983, 114, 225-236.
54. C. Lamberth, M. D. Bednarski, Tetrahedron Lett. 1991, 32, 7369-7372.
55. J. J. Oltvoort, C. A. A. van Boeckel, J. H. Koning, J. H. van Boom, Synthesis 1981, 305-308.
56. 13C chemical shifts (δ = 97.4ppm) for 7 at the anomeric centre of the newly formed glycosidic linkage are consistent with the proposed α stereochemistry.
57. J. Kovensky, P. Duchaussoy, F. Bono, M. Salmivirta, P. Sizun, J.-M. Herbert, M. Petitou, P. Sinaÿ, Bioorg. Med. Chem. 1999, 7, 1567-1580.
58. P. Duchaussoy, G. Jaurand, P.-A. Driguez, I. Lederman, F. Gourvenec, J.-M. Strasel, P. Sizun, M. Petitou, J.-M. Herbert, Carbohydr. Res. 1999, 317, 63-84.
59. 13C chemical shifts to (δ = 97.4 ppm for 10 and δ = 97.4 or 97.8 ppm for 11) at the anomeric centres of the newly formed glycosidic linkages are consistent with the proposed αstereochemistry.
60. W. S. Mungall, G. L. Greene, G. A. Heavner, R. L. Letsinger, J. Org. Chem. 1915, 40, 1659-1662.
61. E. J. Corey, K. C. Nicolaou, R. D. Balanson, Y. Machida, Synthesis, 1975, 590-591.
62. L. Benati, P. C. Montevecchi, D. Nanni, P. Spagnolo, M. Volta, Tetrahedron Lett. 1995, 36, 7313-7314; C. Goulaouic-Dubois, M. Hesse, Tetrahedron Lett. 1995, 36, 7427-7430.
63. L. Benati, P. C. Montevecchi, D. Nanni, P. Spagnolo, M. Volta, Tetrahedron Lett. 1995, 36, 7313-7314; C. Goulaouic-Dubois, M. Hesse, Tetrahedron Lett. 1995, 36, 7427-7430.
64. H. Bayley, D. N. Standring, J. R. Knowles, Tetrahedron Lett. 1978, 79, 3633-7634.
65. M. Nitz, B. W. Purse, D. R. Bundle, Org. Lett. 2000, 2, 1939-2942.
66. The glycoconjugate purity was measured by HPLC with UV detection at 220 nm and by assuming that compounds and impurities had the same absorbance at this wavelength.
67. B. M. Trost, D. P. Curran, Tetrahedron Lett. 1981, 22, 1287-1290.
68. 2/C with an acetonitrile/water (50:50) mixture to recover the debenzylated compounds in good yields.
69. W. Chai, J. Luo, A. M. Lawson. Anal. Chem. 1998, 70, 2060-2066.
70. A. J. Rhomberg, S. Ernst, R. Sasisekharan, K. Biemann, Proc. Natl. Acad. Sci. USA, 1998, 95, 4176-4181.
71. B. Kuberan, M. Lech, L. Zhang, Z. L. Wu, D. L. Beeler, R. D. Rosenberg, J. Am. Chem. Soc. 2002, 124, 8707-8718.
72. C. Thanawiroon, K. G. Rice, T. Toida, R. J. Linhardt, J. Biol. Chem. 2004, 279, 2608-2675.
73. T. Bitter, H. M. Muir, Anal. Biochem. 1962, 4, 330-334.
74. D. D. Perrin, W. L. F. Armarego, Purification of Laboratory Chemicals, 3rd ed., Pergamon Press, Oxford, 1988.
75. T. Feizi, M. S. Stoll, C.-T. Yuen, W. Chai, A. M. Lawson, Methods Enzymol. 1994, 230, 484-519.
76. R. R. Vives, S. Goodger, D. A. Pye, Biochem. J. 2001, 354, 141-147.
77. P. W. Riddles, R. L. Blackley, B. Zerner, Anal. Biochem. 1979, 94, 75-81.