Full-text resources of PSJD and other databases are now available in the new Library of Science.
Visit https://bibliotekanauki.pl

PL EN


Preferences help
enabled [disable] Abstract
Number of results
2004 | 51 | 1 | 67-72

Article title

New analogue of cyclolinopeptide B modified by amphiphilic residue of α-hydroxymethylmethionine.

Content

Title variants

Languages of publication

EN

Abstracts

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.

Year

Volume

51

Issue

1

Pages

67-72

Physical description

Dates

published
2004
received
2003-10-31
revised
2004-01-27
accepted
2004-02-08

Contributors

  • Institute of Organic Chemistry, Technical University of Łódź, Łódź, Poland
  • Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wrocław, Poland
  • Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wrocław, Poland
  • Institute of Organic Chemistry, Technical University of Łódź, Łódź, Poland

References

  • 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 solid-phase synthesis of peptides. Anal Biochem.; 34: 595-8.
  • Kaufman HP, Tobschirbel A. (1959) Über 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. Bioorg Med 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, Ruchała P, Śpiewak 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. Z Anal Chem.; 243: 2-17.
  • Witkowska R, Kaczmarek K, Crisma M, Toniolo C, Zabrocki J. (2001) Cα-Hydroxymethyl methionine: synthesis, optical resolution and crystal structure of its (+)-Nα-benzoyl derivative. J Pept Sci.; 7: 619-25.

Document Type

Publication order reference

Identifiers

YADDA identifier

bwmeta1.element.bwnjournal-article-abpv51i1p67kz
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.