Synthesis and kinetics of cyclization of MHC class II-derived cyclic peptide vaccine for diabetes

Journal of Peptide Research

Volumn 54, Issue 2, 1999, Pages 112-119

  Berezhkovskiy, L ^a   Pham, S ^a,b   Reich, E P ^a   Deshpande, Shrikant ^a  

^a GLAXOSMITHKLINE   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Cyclic peptide; Diabetes; Kinetic model of cyclization; NOD mouse; Peptide synthesis; Temperature and pH dependence of cyclization

Indexed keywords

DIABETES VACCINE; MAJOR HISTOCOMPATIBILITY ANTIGEN CLASS 2; MONOCLONAL ANTIBODY; PEPTIDE VACCINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANTIGEN PRESENTING CELL; ARTICLE; AUTOIMMUNE DISEASE; CYCLIZATION; DIABETES MELLITUS; DISULFIDE BOND; HYPOTHESIS; IMMUNE RESPONSE; IMMUNOLOGICAL TOLERANCE; INSULITIS; MAJOR HISTOCOMPATIBILITY COMPLEX RESTRICTION; MASS SPECTROMETRY; MOUSE; NONHUMAN; OXIDATION; PEPTIDE SYNTHESIS; PH; PRIORITY JOURNAL; PROTEIN STRUCTURE; VACCINATION;

AMINO ACID SEQUENCE; ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIABETES MELLITUS, TYPE 1; HISTOCOMPATIBILITY ANTIGENS CLASS II; MASS SPECTROMETRY; MICE; MICE, INBRED NOD; MOLECULAR SEQUENCE DATA; OXIDATION-REDUCTION; PEPTIDES, CYCLIC; VACCINES;

ANIMALIA;

EID: 0032783155     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.1999.00084.x     Document Type: Article

References (23)

1. Roep, B.O. (1996) T cell responses to autoantigens in IDDM, the search for the holy grail. Diabetes 45, 1147-1156.
2. Wraith, D.C., Smilek, D.E., Mitchell, D.J., Steinman, L. & McDevitt, H.O. (1989) Antigen recognition in autoimmune encephalomyclitis and potential for peptide mediated immunotherapy. Cell 59, 257-255.
3. Hurtenbach, U., Lier, E., Adorini, L. & Nagy, Z.A. (1993) Prevention of autoimmune diabetes in non-obese diabetic mice by treatment with a class II major histocompatibility complex-blocking peptide. J. Exp. Med. 117, 1499-1504.
4. Tian, J., Clare-Salzler, M., Hershenfeld, A., Middleton, B., Newman, D., Mueller, R., Arita, S., Evans, C., Atkinson, M.A., Mullen, Y., Sarvetnick, N., Tobin, A.J., Lehmann, P.V. & Kaufman, D.L. (1996) Modulating autoimmune responses to GAD inhibits disease progression and prolongs islet graft survival in diabetes-prone mice. Nature Med. 2, 1348-1353.
5. Lepage, V., Lamm, L.U. & Charron, D. (1993) Molecular aspects of class II and some autoimmune diseases. Eur. J. Immunogenetics 20, 153-164.
6. Nepom, G.T. & Erlich, H. (1991) MHC class II molecules and autoimmunity. Annu. Rev. Immunol. 9, 493-425.
7. Bright, J.J., Topham, D.J., Nag, B., Lodge, P.A. & Sriram, S. (1996) Vaccination with peptides from MHC class II beta chain hypervariable region causes allele specific suppression of EAE. J. Neuroimmunol. 67, 119-124.
8. Sriram, S. & Steinman, L.S. (1983) Anti-IA antibody suppresses active EAE: treatment model for disease linked IR genes. J. Exp. Med. 158, 1362-1368.
9. Dunsavage, M.B., Stewart, M.A., Islar, J., Berezbkovskiy, L., Winkelhake, J., Deshpande, S. & Reich, E.-P. (1997) A novel therapeutic vaccine prevents IDDM in NOD mice. Diabetes 46 (Suppl. 1), 613Ao.
10. Leonetti, M., Cotton, J., Leroy, S., Mourier, G. & Menez, A. (1995) Immunogenecity of T epitope containing cyclic peptides. J. Immunol. 155, 210-218.
11. Gilbert, H.F. (1990) Molecular and cellular aspects of thiol-disulfide exchange. Adv. Enzymol 63, 69-172.
12. Moroder, L., Basse, D., Musiol, H.J., Rudolf- Bohner, S. & Siedler, F. (1996) Oxidative folding of cysteine-rich peptides versus regioselective cysteine pairing strategies. Biopolymers 40, 207-234.
13. Luu, T., Pham, S. & Deshpande, S. (1996) Automated multiple peptide synthesis: improvements in obtaining quality peptides. Int. J. Peptide Protein Res. 47, 91-97.
14. King, D., Fields, C.G. & Fields, G.B. (1990) A cleavage method which minimizes reactions following Fmoc solid. Int. J. Peptide Protein Res. 36, 255-266.
15. Albericio, F., Kneib-Cordonier, N., Biancalana, S., Gera, L., Masada, R.I., Hudson, D. & Barany, G. (1990) Preparation and application of the 5-(4- (9-fluorenylmethyloxycarbonyl) aminoethyl- 3,5-dimethoxyphenoxy)-valeric acid (PAL) handle for solid-phase synthesis of C- terminal peptide amides under mild conditions. J. Org. Chem. 55, 3730-3743.
16. Riddles, P.W., Blakeley, R.L. & Zerner, B. (1979) Ellman's reagent: 5,5′-dithiobis (2-nitrobenzoic acid) - a reexamination. Analyt. Biochem. 94, 75-81.
17. Dick, F. (1994) Acid cleavage/deprotection in Fmoc/tBu solid-phase peptide synthesis. In Peptide Synthesis Protocols (Pennington, M.W. & Dunn, B.M., eds.), Methods in Molecular Biology series, Vol. 35, pp. 63-72, Humana Press, Totowa, NJ.
18. Annis, I., Chen, L. & Barany, G. (1998) Novel solid phase reagents for facile formation of intramolecular disultide bridges in peptides under mild conditions. J. Am. Chem. Soc. 120, 7226-7238.
19. Kudryavtseva, E.V., Sidorova, M.V., Ovchinnikov, M.V., Bespalova, Zh.D. & Bushuev, V.N. (1997) Comparative evaluation of different methods for disulfide bond formation in synthesis of the HIV-2 antigenic determinant. Peptide Res. 49, 52-58.
20. Andreu, D., Albericio, F., Sole, N.A., Munson, M.C., Ferrer, M. & Barany, G. (1994) Formation of disulfide bonds in synthetic peptides and proteins. In Peptide Synthesis Protocols (Pennington, M.W. & Dunn, B.M., eds.). Methods in Molecular Biology series, Vol. 35, Humana Press, Totowa, NJ, pp. 91- 169.
21. Budanszky, M. (1988) Peptide Chemistry. A Practical Textbook. Springer-Verlag, Berlin, pp. 111-112.
22. Albericio, F., Hammer, R.P., Garcia-Echevarria, C., Molins, M.A., Chang, J.L., Munson, M.C., Pons, M., Giralt, E. & Barany, G. (1991) Cyclization of disulfide containing peptides in solid phase synthesis. Int. J. Peptide Protein Res. 37, 402-413.
23. K7 derived peptide protects NOD mice from the development of diabetes. J. Autoimmunity, in press