Rational design and synthesis of peptide ligands for an anti-carbohydrate antibody and their immunochemical characterization

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 5, 2003, Pages 781-788

  Johnson, Margaret A ^a   Eniade, Adewale A ^a   Pinto, B Mario ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODY; CARBOHYDRATE; CARBOHYDRATE ANTIBODY; LIGAND; PEPTIDE; UNCLASSIFIED DRUG;

ANTIGEN ANTIBODY COMPLEX; ANTIGEN BINDING; ARTICLE; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG SYNTHESIS; IMMUNOCHEMISTRY; IMMUNOGENICITY; MOLECULAR MIMICRY; MOLECULAR MODEL; MOLECULAR RECOGNITION; PEPTIDE SYNTHESIS; PROTEIN INTERACTION; SHIGELLA FLEXNERI; SOLID;

AMINO ACID SEQUENCE; ANTIBODIES; CARBOHYDRATE SEQUENCE; CARBOHYDRATES; DRUG DESIGN; ENZYME-LINKED IMMUNOSORBENT ASSAY; IMMUNOCHEMISTRY; IMMUNOHISTOCHEMISTRY; LIPOPOLYSACCHARIDES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR SEQUENCE DATA; PEPTIDES; SHIGELLA FLEXNERI; THERMODYNAMICS;

SHIGELLA; SHIGELLA FLEXNERI;

EID: 0037353258     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(02)00449-2     Document Type: Article

References (40)

1. Hale, T. L. In Topley and Wilson's Microbiology and Microbial Infections; Hansler, W. J., Shuman, M., Eds.; Arnold: London, 1998; Vol. 3, pp 479-493.
2. Kenne L., Lindberg B., Petersson K., Romanowska E. Carbohydr. Res. 1977, 56, 363. Kenne L., Lindberg B., Petersson K., Katzenellenbogen E., Romanowska E. Eur. J. Biochem. 1977, 76, 327. Kenne L., Lindberg B., Petersson K., Katzenellenbogen E., Romanowska E. Eur. J. Biochem. 1978, 91, 279.
3. Kenne L., Lindberg B., Petersson K., Romanowska E. Carbohydr. Res. 1977, 56, 363. Kenne L., Lindberg B., Petersson K., Katzenellenbogen E., Romanowska E. Eur. J. Biochem. 1977, 76, 327. Kenne L., Lindberg B., Petersson K., Katzenellenbogen E., Romanowska E. Eur. J. Biochem. 1978, 91, 279.
4. Kenne L., Lindberg B., Petersson K., Romanowska E. Carbohydr. Res. 1977, 56, 363. Kenne L., Lindberg B., Petersson K., Katzenellenbogen E., Romanowska E. Eur. J. Biochem. 1977, 76, 327. Kenne L., Lindberg B., Petersson K., Katzenellenbogen E., Romanowska E. Eur. J. Biochem. 1978, 91, 279.
5. Bundle, D. R.; Gidney, M. A. J.; Josephson, S.; Wessel, H.-P. Synthesis of Shigella flexneri O-Antigenic Repeating Units. Conformational Probes and Aids to Monoclonal Antibody Production. In ACS Symp. Ser. 231; Anderson, L., Unger, F. M., Eds.; American Chemical Society: Washington, 1983; pp 49-63. Carlin, N. I. A.; Gidney, M. A. J.; Lindberg, A. A.; Bundle, D. R. J. Immunol. 1986, 137, 2361.
6. Bundle, D. R.; Gidney, M. A. J.; Josephson, S.; Wessel, H.-P. Synthesis of Shigella flexneri O-Antigenic Repeating Units. Conformational Probes and Aids to Monoclonal Antibody Production. In ACS Symp. Ser. 231; Anderson, L., Unger, F. M., Eds.; American Chemical Society: Washington, 1983; pp 49-63. Carlin, N. I. A.; Gidney, M. A. J.; Lindberg, A. A.; Bundle, D. R. J. Immunol. 1986, 137, 2361.
7. Bundle, D. R.; Gidney, M. A. J.; Josephson, S.; Wessel, H.-P. Synthesis of Shigella flexneri O-Antigenic Repeating Units. Conformational Probes and Aids to Monoclonal Antibody Production. In ACS Symp. Ser. 231; Anderson, L., Unger, F. M., Eds.; American Chemical Society: Washington, 1983; pp 49-63. Carlin, N. I. A.; Gidney, M. A. J.; Lindberg, A. A.; Bundle, D. R. J. Immunol. 1986, 137, 2361.
8. Lindberg A.A. Vaccine. 1999, 17(Suppl. 2), S28. Robbins J.B., Schneerson R., Szu S.C., Pozsgay V. Pure Appl. Chem. 1999, 71, 745. Jennings H.J. Curr. Top. Microbiol. Immunol. C. 1990, 125, 373. Jennings H.J. Adv. Exp. Med. Biol. 1988, 228, 495. Lee C. J. Mol. Immunol. 1987, 24, 1005. Jennings H.J. Adv. Carbohydr. Chem. Biochem. 1983, 41, 155.
9. Lindberg A.A. Vaccine. 1999, 17(Suppl. 2), S28. Robbins J.B., Schneerson R., Szu S.C., Pozsgay V. Pure Appl. Chem. 1999, 71, 745. Jennings H.J. Curr. Top. Microbiol. Immunol. C. 1990, 125, 373. Jennings H.J. Adv. Exp. Med. Biol. 1988, 228, 495. Lee C. J. Mol. Immunol. 1987, 24, 1005. Jennings H.J. Adv. Carbohydr. Chem. Biochem. 1983, 41, 155.
10. Lindberg A.A. Vaccine. 1999, 17(Suppl. 2), S28. Robbins J.B., Schneerson R., Szu S.C., Pozsgay V. Pure Appl. Chem. 1999, 71, 745. Jennings H.J. Curr. Top. Microbiol. Immunol. C. 1990, 125, 373. Jennings H.J. Adv. Exp. Med. Biol. 1988, 228, 495. Lee C. J. Mol. Immunol. 1987, 24, 1005. Jennings H.J. Adv. Carbohydr. Chem. Biochem. 1983, 41, 155.
11. Lindberg A.A. Vaccine. 1999, 17(Suppl. 2), S28. Robbins J.B., Schneerson R., Szu S.C., Pozsgay V. Pure Appl. Chem. 1999, 71, 745. Jennings H.J. Curr. Top. Microbiol. Immunol. C. 1990, 125, 373. Jennings H.J. Adv. Exp. Med. Biol. 1988, 228, 495. Lee C. J. Mol. Immunol. 1987, 24, 1005. Jennings H.J. Adv. Carbohydr. Chem. Biochem. 1983, 41, 155.
12. Lindberg A.A. Vaccine. 1999, 17(Suppl. 2), S28. Robbins J.B., Schneerson R., Szu S.C., Pozsgay V. Pure Appl. Chem. 1999, 71, 745. Jennings H.J. Curr. Top. Microbiol. Immunol. C. 1990, 125, 373. Jennings H.J. Adv. Exp. Med. Biol. 1988, 228, 495. Lee C. J. Mol. Immunol. 1987, 24, 1005. Jennings H.J. Adv. Carbohydr. Chem. Biochem. 1983, 41, 155.
13. Lindberg A.A. Vaccine. 1999, 17(Suppl. 2), S28. Robbins J.B., Schneerson R., Szu S.C., Pozsgay V. Pure Appl. Chem. 1999, 71, 745. Jennings H.J. Curr. Top. Microbiol. Immunol. C. 1990, 125, 373. Jennings H.J. Adv. Exp. Med. Biol. 1988, 228, 495. Lee C. J. Mol. Immunol. 1987, 24, 1005. Jennings H.J. Adv. Carbohydr. Chem. Biochem. 1983, 41, 155.
14. Johnson M.A., Pinto B.M. Aust. J. Chem. 55:2002;13, and references cited therein.
15. Harris S.L., Craig L., Mehroke J.S., Rashed M., Zwick M.B., Kenar K., Toone E.J., Greenspan N., Auzanneau F.-I., Marino-Albernas J.-R., Pinto B.M., Scott J.K. Proc. Natl. Acad. Sci. U.S.A. 94:1997;2454.
16. Pinto, B. M.; Johnson, M. A.; Bundle, D. R.; Vyas, M. N.; Vyas, N. K.; Quiocho, F. A. XIX International Carbohydrate Symposium, 1998 San Diego, USA, Abstr. CP 132, CO 019. Vyas, N. K.; Vyas, M. N.; Johnson, M. A.; Harris, S. L.; Scott, J. K.; Chervenak, M. C.; Bundle, D. R.; Pinto, B. M.; Quiocho, F. A., Manuscript in preparation.
17. Pinto, B. M.; Johnson, M. A.; Bundle, D. R.; Vyas, M. N.; Vyas, N. K.; Quiocho, F. A. XIX International Carbohydrate Symposium, 1998 San Diego, USA, Abstr. CP 132, CO 019. Vyas, N. K.; Vyas, M. N.; Johnson, M. A.; Harris, S. L.; Scott, J. K.; Chervenak, M. C.; Bundle, D. R.; Pinto, B. M.; Quiocho, F. A., Manuscript in preparation.
18. Dunitz J.D. Science. 264:1994;670.
19. D'Aquino J.A., Freire E., Amzel L.M. Proteins. 2000, 4, 93. and references cited therein. Bundle D.R., Alibés R., Nilar S., Otter A., Warwas M., Zhang P. J. Am. Chem. Soc. 1998, 120, 5317. Carver J.P. Pure Appl. Chem. 1993, 65, 763. Searle M.S., Williams D.H. J. Am. Chem. Soc. 1992, 114, 10690.
20. D'Aquino J.A., Freire E., Amzel L.M. Proteins. 2000, 4, 93. and references cited therein. Bundle D.R., Alibés R., Nilar S., Otter A., Warwas M., Zhang P. J. Am. Chem. Soc. 1998, 120, 5317. Carver J.P. Pure Appl. Chem. 1993, 65, 763. Searle M.S., Williams D.H. J. Am. Chem. Soc. 1992, 114, 10690.
21. D'Aquino J.A., Freire E., Amzel L.M. Proteins. 2000, 4, 93. and references cited therein. Bundle D.R., Alibés R., Nilar S., Otter A., Warwas M., Zhang P. J. Am. Chem. Soc. 1998, 120, 5317. Carver J.P. Pure Appl. Chem. 1993, 65, 763. Searle M.S., Williams D.H. J. Am. Chem. Soc. 1992, 114, 10690.
22. D'Aquino J.A., Freire E., Amzel L.M. Proteins. 2000, 4, 93. and references cited therein. Bundle D.R., Alibés R., Nilar S., Otter A., Warwas M., Zhang P. J. Am. Chem. Soc. 1998, 120, 5317. Carver J.P. Pure Appl. Chem. 1993, 65, 763. Searle M.S., Williams D.H. J. Am. Chem. Soc. 1992, 114, 10690.
23. Richardson, J. S.; Richardson, D. C. In Prediction of Protein Structure and the Principles of Protein Conformation; Fasman, G. D., Ed.; Plenum Press: New York, 1989, pp 2-98.
24. Harris, S. L. PhD thesis, Simon Fraser University, 1997.
25. Geysen H.M., Meloen R.H., Barteling S.J. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 3998. Geysen H.M., Rodda S.J., Mason T.J., Tribbick G., Schoofs P.G. J. Immunol. Meth. 1987, 102, 259. Geysen H.M., Tainer J.A., Rodda S.J., Mason T.J., Alexander H., Getzoff E.D., Lerner R.A. Science. 1987, 235, 1184.
26. Geysen H.M., Meloen R.H., Barteling S.J. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 3998. Geysen H.M., Rodda S.J., Mason T.J., Tribbick G., Schoofs P.G. J. Immunol. Meth. 1987, 102, 259. Geysen H.M., Tainer J.A., Rodda S.J., Mason T.J., Alexander H., Getzoff E.D., Lerner R.A. Science. 1987, 235, 1184.
27. Geysen H.M., Meloen R.H., Barteling S.J. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 3998. Geysen H.M., Rodda S.J., Mason T.J., Tribbick G., Schoofs P.G. J. Immunol. Meth. 1987, 102, 259. Geysen H.M., Tainer J.A., Rodda S.J., Mason T.J., Alexander H., Getzoff E.D., Lerner R.A. Science. 1987, 235, 1184.
28. Atherton E., Sheppard R.C. Solid Phase Peptide Synthesis: A Practical Approach. 1989;IRL Press, New York.
29. Rink H. Tetrahedron Lett. 1987, 28, 3787. Bernatowicz M.S., Daniels S.B., Koster H. Tetrahedron Lett. 1989, 30, 4645.
30. Rink H. Tetrahedron Lett. 1987, 28, 3787. Bernatowicz M.S., Daniels S.B., Koster H. Tetrahedron Lett. 1989, 30, 4645.
31. Cammish, L. E.; Kates, S. A. In Fmoc Solid Phase Peptide Synthesis: A Practical Approach; Chan, W. C.; White, P. D., Eds.; Oxford University Press: Oxford, England, 2000.
32. Dourtoglou V., Ziegler J.C., Gross B. Tetrahedron Lett. 1978, 19, 1269. Dourtoglou V., Gross B., Lambropoulou V., Zioudrou C. Synthesis. 1984, 572. Knorr R., Trzeciak A., Bannwarth W., Gillessen D. Tetrahedron Lett. 1989, 30, 1927.
33. Dourtoglou V., Ziegler J.C., Gross B. Tetrahedron Lett. 1978, 19, 1269. Dourtoglou V., Gross B., Lambropoulou V., Zioudrou C. Synthesis. 1984, 572. Knorr R., Trzeciak A., Bannwarth W., Gillessen D. Tetrahedron Lett. 1989, 30, 1927.
34. Dourtoglou V., Ziegler J.C., Gross B. Tetrahedron Lett. 1978, 19, 1269. Dourtoglou V., Gross B., Lambropoulou V., Zioudrou C. Synthesis. 1984, 572. Knorr R., Trzeciak A., Bannwarth W., Gillessen D. Tetrahedron Lett. 1989, 30, 1927.
35. Dauber-Osguthorpe P., Roberts V.A., Osguthorpe D.J., Wolff J., Genest M., Hagler A.T. Proteins: Structure, Function and Genetics. 4:1988;31.
36. For leading references: Structure-Based Ligand Design, Methods and Principles of Medicinal Chemistry; Gubernator, K.; Böhm, H.-J., Eds.; VCH: Weinheim, Germany, 1998, Vol. 6. Ripka A.S., Rich D.H. Curr. Opin. Chem. Biol. 1998, 2, 441. Veerapandian P. Structure-Based Drug Design. Marcel Dekker: New York, 1997. Babine R.E., Bender S.L. Chem. Rev. 1997, 97, 1359. Rami Reddy M., Varney M.D., Kalish V., Viswanadhan V.N., Appelt K. J. Med. Chem. 1994, 37, 1145.
37. For leading references: Structure-Based Ligand Design, Methods and Principles of Medicinal Chemistry; Gubernator, K.; Böhm, H.-J., Eds.; VCH: Weinheim, Germany, 1998, Vol. 6. Ripka A.S., Rich D.H. Curr. Opin. Chem. Biol. 1998, 2, 441. Veerapandian P. Structure-Based Drug Design. Marcel Dekker: New York, 1997. Babine R.E., Bender S.L. Chem. Rev. 1997, 97, 1359. Rami Reddy M., Varney M.D., Kalish V., Viswanadhan V.N., Appelt K. J. Med. Chem. 1994, 37, 1145.
38. For leading references: Structure-Based Ligand Design, Methods and Principles of Medicinal Chemistry; Gubernator, K.; Böhm, H.-J., Eds.; VCH: Weinheim, Germany, 1998, Vol. 6. Ripka A.S., Rich D.H. Curr. Opin. Chem. Biol. 1998, 2, 441. Veerapandian P. Structure-Based Drug Design. Marcel Dekker: New York, 1997. Babine R.E., Bender S.L. Chem. Rev. 1997, 97, 1359. Rami Reddy M., Varney M.D., Kalish V., Viswanadhan V.N., Appelt K. J. Med. Chem. 1994, 37, 1145.
39. For leading references: Structure-Based Ligand Design, Methods and Principles of Medicinal Chemistry; Gubernator, K.; Böhm, H.-J., Eds.; VCH: Weinheim, Germany, 1998, Vol. 6. Ripka A.S., Rich D.H. Curr. Opin. Chem. Biol. 1998, 2, 441. Veerapandian P. Structure-Based Drug Design. Marcel Dekker: New York, 1997. Babine R.E., Bender S.L. Chem. Rev. 1997, 97, 1359. Rami Reddy M., Varney M.D., Kalish V., Viswanadhan V.N., Appelt K. J. Med. Chem. 1994, 37, 1145.
40. For leading references: Structure-Based Ligand Design, Methods and Principles of Medicinal Chemistry; Gubernator, K.; Böhm, H.-J., Eds.; VCH: Weinheim, Germany, 1998, Vol. 6. Ripka A.S., Rich D.H. Curr. Opin. Chem. Biol. 1998, 2, 441. Veerapandian P. Structure-Based Drug Design. Marcel Dekker: New York, 1997. Babine R.E., Bender S.L. Chem. Rev. 1997, 97, 1359. Rami Reddy M., Varney M.D., Kalish V., Viswanadhan V.N., Appelt K. J. Med. Chem. 1994, 37, 1145.