Search for New Synthetic Immunosuppressants. Antamanide Analogues Containing the Tetrazole Ring as a cis-Peptide Bond Mimetic

• Autorzy: Zubrzak P. , Kaczmarek K. , Kowalski M. L. , Szkudlińska B. , Zabrocki J.
• Języki publikacji: EN

Abstrakty

EN

Linear and cyclic antamanide (ANT) analogues with dipeptide segments Pro2-Pro3, Pro7-Pro8 and both of them replaced by their tetrazole analogue Pro-psi[CN4]-Ala, respectively, have been synthesized by SPPS method and cyclization with TBTU reagent. The peptides were examined for their immunosuppressive activity in a lymphocyte proliferation test (LPT).

Słowa kluczowe

EN

antamanide; cis-peptide bond; 1,5-disubstituted tetrazole ring; immunosuppression

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2001
• Tom: Vol. 75, nr 12
• Strony: 1869--1876
• Opis fizyczny: Bibliogr. 21 poz., rys.

Twórcy

autor

Zubrzak P.

• Institute of Organic Chemistry, Technical University, 90-924 Łódź, Żeromskiego 116, Poland

autor

Kaczmarek K.

• Institute of Organic Chemistry, Technical University, 90-924 Łódź, Żeromskiego 116, Poland

autor

Kowalski M. L.

• Department of Immunology, Medical Academy of Łódź, 92-215 Łódź, Mazowiecka 11, Poland

autor

Szkudlińska B.

• Department of Immunology, Medical Academy of Łódź, 92-215 Łódź, Mazowiecka 11, Poland

autor

Zabrocki J.

• Institute of Organic Chemistry, Technical University, 90-924 Łódź, Żeromskiego 116, Poland

Bibliografia

• 1. Ellis G. and West G.B., Prog. Med. Chem., 25, 1 (1988).
• 2. Sigal N.H. and Dumont F.J., Ann. Rev. Immunol., 10, 519 (1992).
• 3. Wieland T., Lüben G., Ottenheym H., Faesel J., de Vries J.X., Konz W., Prox A. and Schmid J., Angew. Chem.. Int. Ed. Engl., 7, 204 (1968).
• 4. Wieland T., Lüben G., Ottenheym H. and Schiefer H., Liebigs Ann. Chem., 722, 173 (1969).
• 5. Prox A., Schmid J. and Ottenheym H., Liebigs Ann. Chem., 722, 179 (1969).
• 6. Karle I.L., Karle J., Wieland T., Bürgermeister W., Faulstich H. and Witkop B., Proc. Natl. Acad. Sci. USA, 70, 1836 (1973).
• 7. Karle I.L., Biochem., 13, 2155 (1974).
• 8. Karle I.L., J. Am. Chem. Soc., 96,4000 (1974).
• 9. Kessler H., Müller A. and Pook K.-H., Liebigs Ann. Chem., 903 (1989).
• 10. Kessler H., Bats J.W., Lautz J. and Müller A., Liebigs Ann. Chem., 913 (1989).
• 11. Siemion I.Z., Pędyczak A., Trojnar J., Zimecki M. and Wieczorek Z., Peptides, 13, 1233 (1992).
• 12. Marshall G.R., Humblet C., Van Opdenbosch N. and Zabrocki J., In: Peptides: Synthesis, Structure and Function, Proc.7th Am. Pept. Symp., D. Rich and E. Gross, Eds. Pierce Chemical Co., Rockford IL, 669, (1981).
• 13. Yu K-L. and Johnson R.L., J. Org. Chem., 52, 2051 (1987).
• 14. Zabrocki J., Smith G.D., Dunbar J.B., Jr., Iijima H. and Marshall G.R., J. Am. Chem.Soc., 110, 5875 (1988).
• 15. Zabrocki J., Dunbar J.B., Jr., Marshall K.W., Toth M.V. and Marshall G.R., J. Org. Chem., 57, 202 (1992).
• 16. Smith G.D., Zabrocki J., Flak T.A. and Marshall G.R., Int. J. Peptide Protein Res., 37, 191 (1991).
• 17. Beusen D.D., Zabrocki J., Słomczyńska U., Head R.D., Kao J.L-F. and Marshall G.R., Biopolymers, 36, 181 (1995).
• 18. Dumont F.J., Struch M.J., Koprak S.L., Siekierka J.J., Lin C.S., Harrison R., Sewell T., Kindt V.M., Beattie T.R., Wyvratt M. and Sigal N.H., J. Exp. Med., 176, 751 (1992).
• 19. Kaczmarek K, Jankowski S., Siemion I.Z., Wieczorek Z., Benedetti E., Di Lello P., Isemia C., Saviano M. and Zabrocki J., Biopolymers, (2001) submitted.
• 20. Kalisch R.S., Morimoto C. and Schlossman S.F., Cell. Immunol., Ill, 379 (1988).
• 21. König H., Baerf M.R.M. and de Groot R., Med. Inflam., 4, 194 (1995).