Synthetic and immunological studies of 5′-N-phenylacetyl sTN to develop carbohydrate-based cancer vaccines and to explore the impacts of linkage between carbohydrate antigens and carrier proteins

Bioconjugate Chemistry

Volumn 19, Issue 10, 2008, Pages 2060-2067

  Wang, Qianli ^a   Ekanayaka, Sandamali Amarasingha ^a   Wu, Jian ^a   Zhang, Junping ^a   Guo, Zhongwu ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIGENS; DISEASES; PROTEINS; T-CELLS; VACCINES;

ANTIGEN PROTEINS; CANCER VACCINE; CARRIER PROTEINS; GLYCOCONJUGATE VACCINES; GLYCOCONJUGATES; PARTIAL STRUCTURES; PROTEIN CONJUGATES; REDUCING ENDS; REGIOISOMERS;

CARBOHYDRATES;

ACETIC ACID DERIVATIVE; ANTISERUM; BENZENE DERIVATIVE; CANCER VACCINE; CARBOHYDRATE ANTIGEN; CARRIER PROTEIN; GLYCOCONJUGATE; KEYHOLE LIMPET HEMOCYANIN; TUMOR ANTIGEN;

ANIMAL EXPERIMENT; ANTIBODY RESPONSE; ANTIGEN EXPRESSION; ARTICLE; CELLULAR IMMUNITY; CONJUGATE; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; IMMUNE RESPONSE; INOCULATION; MOUSE; NONHUMAN; REACTION ANALYSIS; STEREOISOMERISM; T LYMPHOCYTE;

MUS;

EID: 55249113651     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc800243f     Document Type: Article

References (30)

1. Hakomori, S. (2001) Tumor-associated carbohydrate antigens defining tumor malignancy: Basis for development of anti-cancer vaccines. Adv. Exp. Med. Biol. 491, 369-402.
2. Danishefsky, S. J., and Allen, J. R. (2000) From the laboratory to the clinic: A retrospective on fully synthetic carbohydrate-based anticancer vaccines. Angew. Chem., Int. Ed. 39, 837-863.
3. Ragupathi, G. (1998) Carbohydrate antigens as targets for active specific immunotherapy. Cancer Immunol. Immunother. 46, 82-87.
4. Jennings, H. J., and Sood, R. K. (1994) Synthetic glycoconjugates as human vaccines, in Neoglycoconjugates: Preparation and Applications (Lee, Y. C., and Lee, R. T., Eds.) pp 325-371, Academic Press, San Diego.
5. Lee, Y. C., and Lee, R. T. (1994) Neoglycoconjugates: preparation and applications, Academic Press, San Diego.
6. Xue, J., Pan, Y., and Guo, Z. (2002) Neoglycoprotein cancer vaccines: Synthesis of an azido derivative of GM3 and its efficient coupling to proteins through a new linker. Tetrahedron Lett. 43, 1599-1602.
7. Wu, J., and Guo, Z. (2006) Improving the antigenicity of sTn antigen by modification of its sialic acid residue for development of glycoconjugate cancer vaccines. Bioconjugate Chem. 17, 1537-1544.
8. Pan, Y. B., Chefalo, P., Nagy, N., Harding, C. V., and Guo, Z. (2005) Synthesis and immunological properties of N-modified GM3 antigens as therapeutic cancer vaccines. J. Med. Chem. 48, 875-883.
9. Buskas, T., Li, Y., and Boons, G. J. (2004) The immunogenicity of the tumor-associated antigen Lewis (y) may be suppressed by a bi-functional cross-linker required for coupling to a carrier protein. Chem. Eur. J. 10, 3517-3524.
10. Ni, J., Song, H., Wang, Y., Stamatos, N. M., and Wang, L. X. (2006) Toward a carbohydrate-based HIV-1 vaccine: synthesis and immunological studies of oligomannose-containing glycoconjugates. Bioconjugate Chem. 17, 493-500.
11. Mawas, F., Niggemann, J., Jones, C., Corbel, M. J., Kamerling, J. P., and Vliegenthart, J. F. G. (2002) Immunogenicity in a mouse model of a conjugate vaccine made with a synthetic single repeating unit of type 14 pneumococcal polysaccharide coupled to CRM197. Infect. Immun. 70, 5107-5114.
12. Yonezawa, S., Tachikawa, T., and Sato, E. (1992) Sialosyl-Tn antigens. Its distribution in normal human tissues and expression in adenocarcinoma. Am. J. Clin. Pathol. 98, 167-174.
13. Itzkowitz, S. H., Bloom, E. J., and Kim, Y. S. (1990) Sialosyl-Tn. A novel mucin antigen associated with prognosis in colorectal cancer patients. Cancer (Phila) 66, 1960-1966.
14. Kobayashi, H., Terao, T., and Kawashima, Y. (1992) Serum sialyl Tn as an independent predictor of poor prognosis in patients with epithelial ovraian cancer. J. Clin. Oncol. 10, 95-101.
15. Leivonen, M., Nordling, S., Lundin, J., and Haglund, C. (2001) sTn and prognosis in breast cancer. Oncology 61, 299-305.
16. Bresalier, R. S., Niv, Y., Byrd, J. C., Duh, Q. Y., Toribara, N. W., Rockwell, R. W., Dahiya, Y., and Kim, Y. S. (1991) Mucin production by human colonic carcinoma cells correlates with their metastatic potential in animal models of colon cancer metastasis. J. Clin. Invest. 87, 1037-1045.
17. Adluri, S., Helling, F., Ogata, S., and Livingston, P. O. (1995) Immunogenicity of synthetic TF-KLH and sTn-KLH conjugates in colorectal carcinoma patients. Cancer Immunol. Immunother. 41, 185-192.
18. Livingston, P. O., Zhang, S., and Lloyd, K. O. (1997) Carbohydrate vaccines that induce antibodies against cancer. 1. Rationale. Cancer Immunol. Immunother. 45, 1-9.
19. Ragupathi, G., Koganty, R. R., Qiu, D., Lloyd, K. O., and Livingston, P. O. (1998) A novel and efficient method for synthetic carbohydrate conjugate vaccine preparation: synthesis of sialyl Tn-KLH conjugate using a 4-(4-N-maleimidomethyl)cyclohexane-1-carboxyl hydrazide (MMCCH) linker arm. Glycoconjugate J. 15, 217-221.
20. Ragupathi, G., Howard, L., Cappello, S., Koganty, R., and Livingston, P. O. (1999) Vaccines prepared with sialyl-Tn and sialyl-Tn trimers using the 4-(4-maleimidomethyl)cyclohexane-1-carboxyl hydrazide linker group result in optimal antibody titers against ovine submaxillary mucin and sialyl-Tn-positive tumor cells. Cancer Immunol. Immunother. 48, 1-8.
21. MacLean, G. D., Reddish, M., Koganty, R. R., Wong, T., and Longenecker, B. M. (1993) Immunization of breast cancer patients using a synthetic sialyl-Tn glycoconjugate plus Detox adjuvant. Cancer Immunol. Immunother. 36, 215-222.
22. Miles, D. W., Towlson, K. E., Graham, R., Reddish, M., Longenecker, B. M., and Rubens, R. D. (1996) A randomized phase II study of sialyl-Tn and DETOX-B adjuvant with or without cyclophosphamide pretreatment for the active specific immunotherapy of breast cancer. Br. J. Cancer 74, 1292-1296.
23. Kayser, H., Zeitler, R., Kannicht, C., Grunow, D., Nuck, R., and Reutter, W. (1992) Biosynthesis of a nonphysiological sialic acid in different rat organs, using N-propanoyl-D-hexosamines as precursors. J. Biol. Chem. 267, 16934-16938.
24. Mahal, K. L., Yarema, K. J., and Bertozzi, C. R. (1997) Engineering chemical reactivity on cell surfaces through oligosaccharide biosynthesis. Science 276, 1125-1128.
25. Liu, T., Guo, Z., Yang, Q., Sad, S., and Jennings, H. J. (2000) Biochemical engineering of surface α(2-8)polysialic acid for immunotargeting cancer cells. J. Biol. Chem. 275, 32832-32836.
26. Wang, Q., Zhang, J., and Guo, Z. (2007) Efficient glycoengineering of GM3 on melanoma cell and monoclonal antibody-mediated selective killing of the glycoengineered cancer cell. Bioorg. Med. Chem. 15, 7561-7567.
27. Chefalo, P., Pan, Y., Nagy, N., Harding, C., and Guo, Z. (2006) Effective metabolic engineering of GM3 on tumor cells by N-phenylacetyl-D- mannosamine. Biochemistry 45, 3733-3739.
28. Sanki, A., and Mahal, L. K. (2006) A one-step synthesis of azide-tagged carbohydrates: Versatile intermediates for glycotechnology. Synlett 455-459.
29. De Meo, C., Demchenko, A. V., and Boons, G.-J. (2001) A stereoselective approach for the synthesis of α-sialosides. J. Org. Chem. 66, 5490-5497.
30. Travis, B. R., Narayan, R. S., and Borhan, B. (2002) Osmium tetroxide-promoted catalytic oxidative cleavage of olefins: an organometallic ozonolysis. J. Am. Chem. Soc. 124, 3824-3825.