Synthetic vaccines consisting of tumor-associated MUC1 glycopeptide antigens and bovine serum albumin

Angewandte Chemie - International Edition

Volumn 44, Issue 46, 2005, Pages 7624-7630

  Dziadek, Sebastian ^a   Kowalczyk, Danuta ^a   Kunz, Horst ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Antigens; Antitumor agents; Carbohydrates; Glycopeptides; Synthetic vaccines

Indexed keywords

ANTIGEN-ANTIBODY REACTIONS; ANTIGENS; CARBOHYDRATES; MEDICINE; MICROTRONS; ONCOGENIC VIRUSES;

ANTITUMOR AGENTS; GLYCOPEPTIDES; SYNTHETIC VACCINES;

VACCINES;

BOVINE SERUM ALBUMIN; CA 15-3 ANTIGEN; CANCER VACCINE; GLYCOPEPTIDE; RECOMBINANT VACCINE;

ANIMAL; ARTICLE; CARBOHYDRATE ANALYSIS; CATTLE; CHEMISTRY; CONFORMATION; HUMAN; MOLECULAR GENETICS; STEREOISOMERISM; SYNTHESIS;

ANIMALS; CA-15-3 ANTIGEN; CANCER VACCINES; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; CATTLE; GLYCOPEPTIDES; HUMANS; MOLECULAR SEQUENCE DATA; SERUM ALBUMIN, BOVINE; STEREOISOMERISM; VACCINES, SYNTHETIC;

EID: 28244475915     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200501593     Document Type: Article

References (67)

1. G. F. Springer, Science 1984, 224, 1198.
2. H. Kunz, S. Birnbach, Angew. Chem. 1986, 98, 354;
3. Angew. Chem. Int. Ed. Engl. 1986, 25, 360.
4. a) W. Dippold, A. Steinborn, K.-H. Meyer zum Büschenfelde, Environ. Health Perspect. 1990, 88, 255;
5. W. Dippold, A. Steinborn, S. Birnbach, H. Kunz, unpublished results;
6. A. Steinborn, PhD thesis, Universität Mainz, 1990;
7. b) S. Dziadek, H. Kunz, Chem. Rec. 2004, 4, 308.
8. a) S. Gendler, C. A. Lancaster, J. Taylor-Papadimitriou, T. Duhig, N. Peal, J. Burchell, L. Pemberton, E. N. Lalani, P. Wilson, J. Biol. Chem. 1990, 265, 15286;
9. b) for a short overview, see: J. Taylor-Papadimitriou, J. M. Burchell, D.W. Miles, M. Dalziel, Biochim. Biophys. Acta 1999, 1455, 301.
10. D. M. Swallow, S. J. Gendler, B. Griffith, G. Corney, J. Taylor-Papadimitriou, Nature 1987, 328, 82.
11. a) I. Brockhausen, Biochim. Biophys. Acta 1999, 1473, 67;
12. I. Brockhausen, Biochem. Soc. Trans. 2003, 31, 318;
13. b) K. O. Lloyd, J. Burchell, V. Kundryashov, B. W. Yin, J. Taylor-Papadimitriou, J. Biol. Chem. 1996, 271, 33325;
14. c) J. M. Burchell, A. Mungul, J. Taylor-Papadimitriou, J. Mammary Gland. Biol. Neoplasia 2001, 6, 355.
15. a) J. Burchell, J. Taylor-Papadimitriou, M. Boshell, S. Gendler, T. Duhig, Int. J. Cancer 1989, 44, 691;
16. b) M. R. Price, F. Hudecz, C. O'Sullivan, R. W. Baldwin, P. M. Edwards, S. B. J. Tendler, Mol. Immunol. 1990, 62, 795.
17. a) G. F. Hanisch, S. Müller, Glycobiology 2000, 10, 439;
18. b) S. Müller, F. G. Hanisch, J. Biol. Chem. 2002, 277, 26103;
19. c) U. Karsten, N. Serttas, H. Paulsen, A. Danielczyk, S. Goletz, Glycobiology 2004, 14, 681.
20. S. von Mensdorff-Pouilly, F. G. M. Snijdewint, A.A. Verstraeten, R. H. M. Verheijen, P. Kenemans, Int. J. Biol. Markers 2000, 15, 343.
21. H. Möller, N. Serttas, H. Paulsen, J. M. Burchell, J. Taylor-Papadimitriou, B. Meyer, Eur. J. Biochem. 2002, 269, 1444.
22. a) O. Seitz, H. Kunz, Angew. Chem. 1995, 107, 901;
23. Angew. Chem. Int. Ed. Engl. 1995, 34, 803;
24. b) M. Leuck, H. Kunz, J. Prakt. Chem. 1997, 339, 332;
25. c) P. Braun, G. M. Davies, M. R. Price, P. M. Williams, S. B. J. Tendler, H. Kunz, Bioorg. Med. Chem. 1998, 6, 1531.
26. B. Liebe, H. Kunz, Angew. Chem. 1997, 109, 629;
27. Angew. Chem. Int. Ed. Engl. 1997, 36, 618.
28. Other groups also synthesized mucin glycopeptides with Tn, T, and sialyl-Tn antigen saccharides: a) E. Meinjohanns, M. Meldal, A. Schleyer, H. Paulsen, K. Bock, J. Chem. Soc. Perkin Trans. 1 1996, 985;
29. b) S. D. Kuduk, J. B. Schwarz, X.-T. Chen, P. W. Glunz, D. Sames, G. Ragapunti, P. O. Livingston, S. J. Danishefsky, J. Am. Chem. Soc. 1998, 120, 12474;
30. c) J. B. Schwarz, S. D. Kuduk, X.-T. Chen, D. Sames, P. W. Glunz, S. J. Danishefsky, J. Am. Chem. Soc. 1999, 121, 2662;
31. d) M. A. Reddish, L. Jackson, R. R. Koganti, D. Qui, W. Hong, B. M. Longenecker, Glycoconjugate J. 1997, 14, 549.
32. S. Keil, C. Claus, W. Dippold, H. Kunz, Angew. Chem. 2001, 113, 379;
33. Angew. Chem. Int. Ed. 2001, 40, 366.
34. a) C. Brocke, H. Kunz, Synlett 2003, 2052;
35. b) S. Dziadek, H. Kunz, Synlett 2003, 1623.
36. B. Liebe, H. Kunz, Helv. Chem. Acta. 1997, 80, 1473.
37. a) R. R. Schmidt, J. Michel, Angew. Chem. 1980, 92, 763;
38. Angew. Chem. Int. Ed. Engl. 1980, 19, 731;
39. b) R. R. Schmidt, Angew. Chem. 1986, 98, 213;
40. Angew. Chem. Int. Ed. Engl. 1986, 25, 212.
41. T. Reipen, H. Kunz, Synthesis 2003, 2487.
42. M. Lergenmüller, Y. Ito, T. Ogawa, Tetrahedron 1988, 44, 1381.
43. B. Helferich, F. Wedemeyer, Justus Liebigs Ann. Chem. 1949, 563, 139.
44. F. Dasgupta, P. Garegg, Carbohydr. Res. 1988, 177, C13.
45. N. Mathieux, H. Paulsen, M. Meldal, K. Bock, J. Chem. Soc. Perkin Trans. 1 1997, 2359.
46. eq).
47. +.
48. x glycopeptides (M. Rösch, H. Herzner, W. Dippold, M. Wild, D. Vestweber, H. Kunz, Angew. Chem. 2001, 113, 3954;
49. [15] can be difficult.
50. C. Brocke, H. Kunz, Synthesis 2004, 525.
51. J. M. J. Frechét, K. E. Haque, Tetrahedron Lett. 1975, 16, 3055.
52. E. Bayer, W. Rapp, Chem. Pept. Proteins 1986, 3, 3.
53. L. A. Carpino, G. Y. Han, J. Am. Chem. Soc. 1970, 92, 5748.
54. L. A. Carpino, D. Jonescu, A. El-Falham, J. Org. Chem. 1996, 61, 2460.
55. a) R. Knorr, A. Trzeciak, W. Bannwarth, D. Gillessen, Tetrahedron Lett. 1989, 30, 1927;
56. b) V. Dourtoglou, B. Gross, V. Lambropoulou, C. Ziondrou, Synthesis 1984, 572;
57. c) W. König, R. Geiger, Chem. Ber. 1970, 103, 788.
58. D. A. Pearson, M. Blanchette, M. L. Baker, C. A. Guidon, Tetrahedron Lett. 1989, 30, 2739.
59. 6]DMSO, COSY, TOCSY, HMQC, HMBC): δ = 4.76 (2′-H), 4.21 (4′-H), 4.01 ppm (3′-H).
60. 6]DMSO, HMQC, HMBC): δ = 104.5 (C1′), 98.8 (C1), 98.4 (C2″), 98.1 ppm (C2‴).
61. [14]
62. L. F. Tietze, C. Schröder, S. Gabius, U. Brinck, A. Goerlach-Graw, H.-J. Gabius, Bioconjugate Chem. 1991, 2, 148.
63. eq).
64. A. Bergh, B.-G. Magnusson, J. Ohlsson, U. Wellmar, U. J. Milsson, Glycoconjugate J. 2005, 18, 615.
65. 4, see reference [2].
66. See the following Communication in this issue: S. Dziadek, A. Hobel, E. Schmitt, H. Kunz, Angew. Chem. 2005, 117, 7803;
67. Angew. Chem. Int. Ed. 2005, 44, 7630.