New analogue of cyclolinopeptide B modified by amphiphilic residue of alpha-hydroxymethylmethionine

• Autorzy: Witkowska R. , Donigiewicz A. , Zimecki M. , Zabrocki J.
• Języki publikacji: EN

Abstrakty

EN

In order to evaluate the role and influence of the methionine residue on the biologi­cal activity of cyclolinopeptide B, an analogue with methionine residue in position 7 replaced by the amphiphilic (S)-a-hydroxymethylmethionine residue was synthe­sized. This peptide exhibits high immunosuppressive activity in the cellular, and to a lesser degree in the humoral immune response, comparable to that of CsA. In addi­tion, the peptide was devoid of toxicity, even at high doses.

Słowa kluczowe

EN

biological activity; alpha-hydroksymethylamino acid; transplantology; methionine residue; cyclosporin A; alpha-hydroksymethylmethionine; cyclolinopeptide B

• Wydawca: -
• Czasopismo: Acta Biochimica Polonica
• Rocznik: 2004
• Tom: 51
• Numer: 1
• Opis fizyczny: p.67-72,fig.,ref.

Twórcy

autor

Witkowska R.

• Technical University of Lodz, 90-924 Lodz, Poland

autor

Donigiewicz A.

autor

Zimecki M.

autor

Zabrocki J.

Bibliografia

• Hojo M, Morimoto T, Maluccio M, Asano T, Morimoto K, Lagman M, Shimbo T, Suthanthiran M. (1999) Cyclosporine induces cancer progression by a cell autonomous mechanism. Nature.; 397: 530-4.
• Kaiser E, Colescott RL, Bossinger CD, Cook PI. (1970) Color test for detection of free terminal amino group in the solid­phase synthesis of peptides. Anal Biochem.; 34: 595-8.
• Kaufman HP, Tobschirbel A. (1959) Uber ein Oligopeptid aus Leinsamen. Chem Ber.; 92: 2805-9.
• Khalil EM, Subasinghe NL, Johnson RL. (1996) An efficient and high yield method for the N-tert-butoxycarbonyl protection of sterically hindered amino acids. Tetrahedron Lett.; 37: 3441-4.
• Matsumoto T, Shishido AT, Morita H, Itokawa H, Takeya K. (2002) Conformational analysis of cyclolinopeptides A and B. Tetrahedron.; 58: 5135-40.
• Mishell RI, Dutton RW. (1967) Immunization of dissociated spleen cell cultures from normal mice. J Exp Med.; 126: 423-42.
• Morita H, Shishido A, Takeya K, Itokawa H, Hirano T, Oka K, Shirota O. (1997) A new immunosuppressive cyclic nonapeptide cyclolinopeptide B from Linum usitatissimum. BioorgMed Chem Lett.; 7: 1269-72.
• Morita H, Shishido A, Matsumoto T, Itokawa H, Takeya K. (1999) Cyclolinopeptides B-E, new cyclic peptides from Linum usitatissimum. Tetrahedron.; 55: 967-76.
• Picur B, Brzezicka A, Chliszcz P, Cebrat M, Lisowski M, Olejarnik M, Ruchala P, Spiewak K, Siemion IZ. (2002) Cyclic peptides from different flaxes. In Peptides 2002, Proc. 27th Eur. Peptide Symposium, Bennedetti E, Pedone C, eds, pp 396-7, Edizioni Ziino, Napoli.
• Prox A, Weygand F. (1967) Sequenzanalyse von Peptiden durch Kombination von Gaschromatographie und Massenspektrometrie. In Peptides 1966, Proc. 8th Eur. Peptide Symposium, Bayerman HC van den Linde A, Massen van den Bring W, eds, pp 158-72. North-Holland Publishing Co, Amsterdam.
• Soy D, Campistol JM, Brunet M, Roca M, Carreras E, Andreu H, Codina C, Ribas J. (1995) Role of cyclosporine metabolites and chemical toxicity in organ transplantation. Transplant Proc.; 27: 2415-6.
• Weygand F. (1968) Entwicklunglinien Biochemischer Analytik. ZAnal Chem.; 243: 2-17.
• Witkowska R, Kaczmarek K, Crisma M, Toniolo C, Zabrocki J. (2001) Calpha-Hydroxymethyl methionine: synthesis, optical resolution and crystal structure of its (+)-Nalpha-benzoyl derivative. JPept Sci.; 7: 619-25.