Calix[4]arene decorated with four Tn antigen glycomimetic units and P 3CS immunoadjuvant: Synthesis, characterization, and anticancer immunological evaluation

Bioconjugate Chemistry

Volumn 19, Issue 3, 2008, Pages 751-758

  Geraci, Corrada ^a   Consoli, Grazia M L ^a   Galante, Eva ^a   Bousquet, Ennio ^b   Pappalardo, Maria ^b   Spadaro, Angelo ^b  

^a CNR Consiglio Nazionale delle Ricerche   (Italy)

^b UNIVERSITY OF CATANIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

SCAFFOLDS; VACCINES;

CALIX[4]ARENES; CLUSTER EFFECTS; ELISA ASSAY; GLYCOMIMETICS; IMMUNOADJUVANTS; IMMUNOGENICITY; IN-VIVO; SYNTHESISED;

ANTIGENS;

CALIXARENE; CALIX[4]ARENE; CANCER VACCINE; CYTOKINE; IMMUNOGLOBULIN G ANTIBODY; IMMUNOLOGICAL ADJUVANT; TN ANTIGEN; TRIPALMITOYL S GLYCERYLCYTEINYLSERINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIBODY PRODUCTION; ANTIGEN BINDING; ANTINEOPLASTIC ACTIVITY; ARTICLE; COMPLEX FORMATION; CONTROLLED STUDY; CYTOKINE PRODUCTION; DRUG DESIGN; DRUG SYNTHESIS; ENZYME LINKED IMMUNOSORBENT ASSAY; FEMALE; HELPER CELL; IMMUNE RESPONSE; IMMUNOGENICITY; MOUSE; NONHUMAN; PROTEIN MOTIF; STRUCTURE ACTIVITY RELATION;

MUS;

EID: 41149159638     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc700411w     Document Type: Article

References (59)

1. Rosenberg, S. A. (2001) Progress in human tumor immunology and immunotherapy. Nature 411, 380-384.
2. Le Poole, I. C., Gerberi, M. A. T., and Kast, W. M. (2002) Emerging strategies in tumor vaccines. Therapeutic modalities. Curr. Opin. Oncol. 14, 641-648.
3. Rosenberg, S. A., Yang, J. C., and Restifo, N. P. (2004) Cancer immunotherapy: moving beyond current vaccines. Nat. Med. 10, 909-915.
4. Hougthon, A. N., Gold, J. S., and Blachere, N. E. (2001) Immunity against cancer: lessons learned from melanoma. Curr. Opin. Immunol. 13, 134-140.
5. Springer, G. F. (1997) Immunoreactive T and Tn epitopes in cancer diagnosis, prognosis, and immunotherapy. J. Mol. Med. 75, 594-602.
6. Hakomori, S. (1989) Aberrant glycosylation in tumor and tumor-associated carbohydrate antigens. Adv. Cancer Res. 52, 257-331.
7. Kuberan, B., and Linhardt, R. J. (2000) Carbohydrate based vaccines. Curr. Org. Chem. 4, 653-677.
8. Freire, T., Lo-Man, R., Piller, F., Piller, V., Leclerc, C., and Bay, S. (2006) Enzymatic large-scale synthesis of MUC6-Tn glyconjugates for antitumor vaccination. Glycobiology 16, 390-401.
9. Kim, Y. J., and Varki, A. (1997) Perspectives on the significance of altered glycosylation of glycoproteins in cancer. Glyconjugate J. 14, 569-576.
10. Svarovsky, S. A., and Barchi, J. J. (2003) Higly efficient preparation of tumor antigen-containing glycopeptide building blocks from novel pentenyl glycosides. Carbohydr. Res. 338, 1925-1935 and references therein.
11. Springer, G. F. (1984) T and Tn, general carcinoma autoantigens. Science 224, 1198-1206.
12. Toyokuni, T., Dean, B., Cai, S., Boivin, D., Hakomori, S.-I., and Singhal, A. K. (1994) Synthetic vaccines: synthesis of a dimeric Tn antigen-lipopeptide conjugate that elicits immune responses against Tn-expressing glycoproteins. J. Am. Chem. Soc. 116, 395-396.
13. Dziadek, S., Kowalczyk, D., and Kunz, H. (2005) Synthetic vaccines consisting of tumor-associated MUC1 glycopeptide antigens and bovine serum albumin. Angew. Chem., Int. Ed. 44, 7624-7630.
14. Kim, J. M., and Roy, R. (1997) Oligomeric glycopeptidomimetics bearing the cancer related TN-antigen. Tetrahedron Lett. 38, 3487-3490.
15. Buskas, T., Ingale, S., and Boons, G.-J. (2005) Towards a fully synthetic carbohydrate-based anticancer vaccine: synthesis and immunological evaluation of a lipidated glycopeptide containing the tumor-associated Tn antigen. Angew. Chem., Int. Ed. 44, 5985-5988.
16. Cipolla, L., Rescigno, M., Leone, A., Peri, F., La Ferla, B., and Nicotra, F. (2002) Novel Tn antigen-containing neoglycopeptides: synthesis and evaluation a anti tumor vaccines. Bioorg. Med. Chem. 10, 1639-1646.
17. Ouerfelli, O., Warren, J. D., Wilson, R. M., and Danishefsky, S. J. (2005) Synthetic carboydrate-based antitumor vaccines: challenges and opportunities. Expert Rev. Vaccines 4, 677-685.
18. Ragupathi, G., Koide, F., Livingston, P. O., Cho, Y. S., Endo, A., Wan, Q., Spassova, M. K., Keding, S. J., Allen, J., Ouerfelli, O., Wilson, R. M., and Danishefsky, S. J. (2006) Preparation and evaluation of unimolecular pentavalent and hexavalent antigenic constructs targeting prostate and breast cancer: a synthetic route to anticancer vaccine candidates. J. Am. Chem. Soc. 128, 2715-2725.
19. Nakada, H., Numata, Y., Inoue, M., Tanaka, N., Kitagawa, H., Funakoshi, I., Fukui, S., and Yamashima, I. (1991) Elucidation of an essential structure recognized by an anti-GalNac-Ser(Thr) monoclonal antibody (MLS 128). J. Biol. Chem. 266, 12402-12405.
20. Nakada, H., Inoue, M., Numata, Y., Tanaka, N., Funakoshi, I., Fukui, S., Mellors, A., and Yamashina, I. (1993) Epitopic structure of Tn glycophorin A for an anti-Tn antibody (MLS 128). Proc. Natl. Acad. Sci. U.S.A. 90, 2495-2499.
21. Reddish, M. A., Jackson, L., Koganty, R. R., Qiu, D. X., Hong, W., and Longenecker, B. M. (1997) Specificities of anti-sialyl-Tn and anti-Tn monoclonal antibodies generated using novel clustered synthetic glycopeptide epitopes. Glycoconjugate J. 14, 549-560.
22. Reis, C. A., Sorensen, T., Mandel, U., David, L., Mirgorodskaya, E., Roepstorff, P., Kihlberg, J., Hansen, J. E., and Clausen, H. (1998) Development and characterization of an antibody directed to an α-N-acetyl-D- galactosamine glycosylated MUC2 peptide. Glycoconjugate J. 15, 51-62.
23. Osinaga, E., Bay, S., Tello, D., Babino, A., Pritsch, O., Assemat, K., Cantacuzène, D., Nakada, H., and Alzari, P. (2000) Analysis of the fine specificity of Tn-binding proteins using synthetic glycopeptide epitopes and a biosensor based on surface plasmon resonance spectroscopy. FEBS Lett. 469, 24-28.
24. Tam, J. P. (1988) Synthetic peptide vaccine design: synthesis and properties of a high-density multiple antigenic peptide system. Proc. Nat. Acad. Sci. U.S.A. 85, 5409-5413.
25. Lo-Man, R., Vichier-Guerre, S., Bay, S., Dériaud, E., Huteau, V., Cantacuzène, D., and Leclerc, C. (2001) Antitumor immunity provided by a synthetic multiple antigenic glycopeptides (MAG) displaying tri-Tn glycotope. J. Immunol. 166, 2849-2854.
26. Grigalevicius, S., Chierici, S, Renaudet, O., Lo-Man, R., Dériaud, E., Leclerc, C., and Dumy, P. (2005) Chemoselectivity assembly and immulogical evaluation of multiepitopic glyconjugates bearing clustered Tn antigen as synthetic anticancer vaccines. Bioconjugate Chem. 16, 1149-1159.
27. Lo-Man, R., Vichier-Guerre, S., Perraut, R., Dériaud, E., Huteau, V., BenMohamed, L., Diop, O. M., Livingston, P. O., Bay, S., and Leclerc, C. (2004) A fully synthetic therapeutic vaccine candidate targeting carcinoma-associated Tn carbohydrate antigen induces tumor-specific antibodies in nonhuman primates. Cancer Res. 64, 4987-4994.
28. Iwamoto, K., Araki, K., and Shinkai, S. (1991) Conformation and structures of Tetra-O-alkyl-p-tert-butylcalix[4]arenes. How is the conformation of calix[4]arenes immobilized? J. Org. Chem. 56, 4955-4962.
29. Bousquet, E., Spadaro, A., Pappalardo, M. S., Bernardini, R., Romeo, R., Panza, L., and Ronsisvalle, G. (2000) Synthesis and immunostimulating activity of a thioglycopeptide glycomimetic as a potential anticancer vaccine derived from Tn antigens. J. Carbohydr. Chem. 19, 527-541.
30. Davis, H. L., Mancini, M., Michel, M. L., and Whalen, R. G. (1996) DNA-mediated immunization to hepatitis B surface antigen: longevity of primary response and effect of boost. Vaccine 14, 910-915.
31. Iida, S., Yamamoto, K., and Irimura, T. (1999) Interaction of human macrophage C-type lectin with O-linked and N-acetylgalactosamine residues on mucin glycopeptides. J. Biol. Chem. 274, 10697-10705.
32. Gutsche, C. D. (1989) Calixarenes. In Monographs in Supramolecular Chemistry (Stoddart, J. F., Ed.) Royal Society of Chemistry, Cambridge, UK.
33. Gutsche, C. D. (1998) Calixarenes Revisited. In Monographs in Supramolecular Chemistry (Stoddart, J. F., Ed.) Royal Society of Chemistry, Cambridge, UK.
34. (2001) Calixarenes 2001 (Asfari, Z., Böhmer, V., Harrowfield, J., and Vicens, J., Eds.) Kluwer, Dordrecht, NL.
35. Da Silva, E., Shahgaldian, P., and Coleman, A. W. (2004) Haemolytic properties of some water-soluble para-sulphonatocalix[n]-arenes. Int. J. Pharm. 273, 57-62.
36. Grote Gansey, M. H. B., de Haan, A. S., Bos, E. S., Verboom, W., and Reinhoudt, D. N. (1999) Conjugation, immunoreactivity, and immunogenicity of calix[4]arene; model study to potential calix[4]arene-based Ac3+ chelators. Bioconjugate Chem. 10, 613-623.
37. Da Silva, E., Lazar, A. N., and Coleman, A. W. (2004) Biopharmaceutical application of calixarenes. J. Drug Del. Sci. Tech. 14, 3-20.
38. Paquet, V., Zumbuehl, A., and Carreira, E. M. (2006) Biologically active amphotericin B-calix[4]arene conjugates. Bioconjugate Chem. 17, 1460-1463.
39. Francese, S., Cozzolino, A., Caputo, I., Esposito, C., Martino, M., Gaeta, C., Troisi, F., and Neri, P. (2005) Transglutaminase surface recognition by peptidocalix[4]arene diversomers. Tetrahedron Lett. 46, 1611-1615.
40. Mecca, T., Consoli, G. M. L., Geraci, C., and Cunsolo, F. (2004) Designed calix[8]arene-based ligands for selective tryptase surface recognition. Bioorg. Med. Chem. 12, 5057-5062.
41. Consoli, G. M. L., Granata, G., Galante, E., Di Silvestro, I., Salafia, L., and Geraci, C. (2007) Synthesis of water-soluble nucleotide-calixarene conjugates and preliminary investigation of their in vitro DNA replication inhibitory activity. Tetrahedron 63, 10758-10763.
42. Hwang, K. M., Qi, Y. M., Liu, S. Y., Lee, T. C., Choy, W., and Chen, J. (1996) U.S. Patent 5,409,959, 1995. Chem. Abstr. 123, 959c.
43. Blaskovich, M. A., Lin, Q., Delarue, F. L., Sun, J., Park, H. S., Coppola, D., Hamilton, A. D., and Sebti, S. M. (2000) Design of GFB-111, a platelet-derived growth factor binding molecule with antiagiogenic and anticancer activity against human tumors in mice. Nat. Biotechnol. 18, 1065-1070.
44. Hwang, K. M., Qi, Y. M., Liu, S. Y., Lee, T. C., Choy, W., and Chen, J. (1996) U.S. Patent 5,441,983, 1995. Chem. Abstr. 123, 275992d.
45. Tanaka, M., and Kikuchi, A. (1996) Jpn. Patent 7,187,930, 1995. Chem. Abstr. 123, 220827y.
46. Aliprantis, A. O., Yang, R.-B., Mark, M. R., Sugett, S., Devaux, B., Radolf, J. D., Klimpel, G, R., Godowsky, P., and Zychlinsky, A. (1999) Cell activation and apoptosis by bacterial lipoproteins through toll-like receptor-2. Science 285, 736-739.
47. Wiesmüller, K. H., Bessler, W., and Jung, G. (1983) Synthesis of the mitogenic S-[2,3-bis. (palmitoyloxy)propyl]-N-palmitoyl-pentapeptide from Escherichia coli lipoprotein. Hoppe-Seyler's Z. Physiol. Chem. 364, 593-596.
48. See: Bulletin No. 6 from "Bulletins and Tech Notes" at www.nuncbrand.com.
49. Toyokuni, T., Hakomori, S., and Singhal, A. K. (1994) Synthetic carbohydrate vaccines: synthesis and immunogenicity of Tn antigen conjugates. Bioorg. Med. Chem. 2, 1119-1132.
50. See: Tech Note, Vol. 1, No. 9, from "Bulletins and Tech Notes" at www.nuncbrand.com.
51. Wallner, F. K., Norberg, H. A., Johansson, A. I., Mogemark, M., and Elofsson, M. (2005) Solid-phase synthesis of serine-based glycosphingolipid analogues for preparation of glycoconjugate arrays. Org. Biomol. Chem. 3, 309-315.
52. Consoli, G. M. L., Cunsolo, F., Geraci, C., and Sgarlata, V. (2004) Synthesis and lectin binding ability of glycosamino acid-calixarenes exposing GlcNAc clusters. Org. Lett. 6, 4163-4166.
53. Mammen, M., Choi, S.-K., and Whitesides, G. M. (1998) Polyvalent interactions in biological systems: implications for design and use of multivalent ligands and inhibitors. Angew. Chem., Int. Ed. Engl. 37, 2754-2794.
54. Dam, T. K., Roy, R., Das, S. K., Oscarson, S., and Brewer, C. F. (2000) Binding of multivalent carbohydrates to concanavalin A and Dioclea grandiflora lectin. Thermodynamic analysis of the multivalency effect. J. Biol. Chem. 275, 14223-14230.
55. Gupta, D., Kaltner, H., Dong, X., Gabius, H. J., and Brewer, C. F. (1996) Comparative cross-linking activities oflactose-specific plant and animal lectins and a natural lactose-binding immunoglobulin G fraction from human serum with asialofetuin. Glycobiology 6, 843-849.
56. Hughes, R. C. (2001) Galectins as modulators of cell adhesion. Biochimie 83, 667-676.
57. Bundle, D. R., and Young, N. M. (1992) Carbohydrate-protein interactions in antibodies and lectins. Curr. Opin. Struct. Biol. 2, 666-673.
58. Kiessling, L. L., and Pohl, N. L. (1996) Strength in numbers: Non-natural polyvalent carbohydrate derivatives. Chem. Biol. 3, 71-77.
59. Roy, R., Park, W. K. C., Srivastava, O. P., and Foxall, C. (1996) Combined glycomimetic and multivalent strategies for the design of potent selectin antagonists. Bioorg. Med. Chem. Lett. 6, 1399-1402.