Cyclopeptides of Linum usitatissimum

Journal of Peptide Science

Volumn 12, Issue 9, 2006, Pages 569-574

  Picur, Bolesłiaw ^a   Cebrat, Marek ^a   Zabrocki, Janusz ^b   Siemion, Ignacy Z ^a  

^a UNIVERSITY OF WROC AW   (Poland)

^b LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Cyclolinopeptide; Cyclosporin; Edge to face; Immunomodulation; Immunosuppression

Indexed keywords

CALCINEURIN; CHOLIC ACID; CYCLOLINOPEPTIDE A; CYCLOLINOPEPTIDE X; CYCLOPEPTIDE; CYCLOPHILIN A; LINSEED OIL; PHENYLALANINE; PROLINE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANTIMALARIAL ACTIVITY; CHEMICAL BOND; DRUG STRUCTURE; IMMUNOMODULATION; LIVER CELL; NONHUMAN; PRIORITY JOURNAL; REVIEW; SEQUENCE ANALYSIS; SOLID STATE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

AMINO ACID SEQUENCE; FLAX; IMMUNOSUPPRESSIVE AGENTS; MOLECULAR SEQUENCE DATA; PEPTIDES, CYCLIC; PHENYLALANINE; PROLINE; SEEDS; STRUCTURE-ACTIVITY RELATIONSHIP;

LINUM USITATISSIMUM;

EID: 33748743292     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.779     Document Type: Review

References (62)

1. Kaufmann HP, Tobschirbel A. Ueber ein oligopeptid aus leinsamen. Chem. Ber. 1959; 92: 2805-2809.
2. Prox A, Weygand F. Sequenzanalyse von peptiden durch kombination von gas chromatographic and massen spectrometrie. In Peptides Proceedings 8th European Peptide Symposium, Beyerman HC, van de Linde A, Maasen van den Brink W (eds). North-Holland: Amsterdam, 1967; 158-172.
3. Weygand F. Entwicklunglinien biochemischer analytik. Z. Anal. Chem. Freseniu. 1968; 243: 2-17.
4. Obermeier R. Massenspektrometrische Identifizierung substituierter Phenylthiodantoine des Edmanabbaus mit Anwendungen in der Peptidchemie. PhD Thesis, Munich Technical University, Munich, 1969.
5. Morita H, Shishido A, Matsumoto T, Takeya K, Itokawa H, Hirano T, Oka K. Cyclic peptides from higher plants. 42. A new immunosuppressive cyclic nonapeptide B from Linum usitatissium. Bioorg. Med. Chem. Lett. 1997; 7: 1269-1272.
6. Morita H, Shishido A, Matsumoto T, Itokawa H, Takeya K. Cyclic peptides from higher plants. 45. Cyclolinopeptides B-E, new cyclic peptides from Linum usitatissium. Tetrahedron 1999; 55: 967-976.
7. Matsumoto T, Shishido A, Morita H, Itokawa H, Takeya K. Cyclolinopeptides F-I, cyclic peptides from linseed. Phytochemistry 2001; 57: 251-260.
8. Picur B, Lisowski M, Siemion IZ. A new cyclolinopeptide containing nonproteinaceous amino acid N-methyl-4-aminoproline. Lett. Pept. Sci. 1998; 5: 183-187.
9. Ruchala P, Picur B, Lisowski M, Cierpicki T, Wieczorek Z, Siemion IZ. Synthesis, conformation, and immunosuppressive activity of CLX and its analogues. Biopolymers 2003; 70: 497-511.
10. Naider F, Benedetti E, Goodman M. Conformation of cyclolinopeptide A by circular dichroism. Proc. Natl. Acad. Sct. U.S.A. 1971; 68: 1195-1198.
11. Brewster AI, Bovey FA. Conformation of cyclolinopeptide A observed by nuclear magnetic resonance spectroscopy. Proc. Natl. Acad. Sci. U.S.A. 1971; 68: 1199-1202.
12. Tonelli AE. Approximate treatment of the conformational characteristics of a cyclic nonapeptide, cyclolinopeptide A. Proc. Natl. Acad. Sci. U.S.A. 1971; 68: 1203-1207.
13. Siemion IZ, Klis WA, Sucharda-Sobczyk A, Obermeler R. Conformation of cyclolinopeptide A in solution. Rocz. Chem. 1976; 51: 1489-1498.
14. Di Blasio B, Rossi F, Benedetti E, Pavone V, Pedone C, Temussi PA, Zanotti G, Tancredi T. Bioactive peptide: solid-state and solution conformation of cyclolinopeptide A. J. Am. Chem. Soc. 1989; 111: 9089-9098.
15. Benedetti E, Pedone C. Cyclolinopeptide A: inhibitor, immunosuppressor or other? J. Pept. Sci. 2005; 11: 268-272.
16. Tancredi T, Zanotti G, Rossi F, Benedetti E, Pedone C, Temussi PA. Comparison of the conformations of cyclolinopeptide A in the solid state and in solution. Biopolymers 1989; 28: 513-523.
17. Neela BS, Manjula MV, Ramakumar S, Balasubramanian D, Viswamitra MA. Conformation of cyclolinopeptide dihydrate: an antamanide analogue. Biopolymers 1990; 29: 1499-1501.
18. Raghothama S, Ramakrishnan C, Balasubramanian D, Balaram P. Conformational analysis of cyclolinopeptide A, a cyclic nonapeptide: nuclear Overhauser effect and energy minimization studies. Biopolymers 1989; 28: 573-588.
19. Di Blasio B, Rossi F, Benedetti E, Pavone V, Saviano M, Pedone C, Zanotti G, Tancredi T. Bioactive peptides: X-ray and NMR conformational study of [Aib5,6-D-Ala8]cyclolinopeotide A. J. Am. Chem. Soc. 1992; 114: 8277-8283.
20. Saviano M, Rossi F, Filizola M, Isernia C, Di Blasio B, Benedetti E, Pedone C, Siemion IZ, Pedyczak A. Bioactive peptides: conformational studies of [Tyr4]cyclolinopeptide A. Biopolymers 1995; 36: 453-460.
21. Castiglione-Morelli MA, Pastore A, Pedone C, Temussi PA, Zanotti G, Tancredi T. Conformational study of cyclolinopeptide A. A distance geometry and molecular dynamics approach. Int. J. Pept. Protein Res. 1991; 37: 81-89.
22. Saviano M, Aida M, Corongiu G. Molecular dynamics simulation in vacuo and in solution of cyclolinopeptide A: a conformational study. Biopolymers 1991; 31: 1017-1024.
23. Mazzeo M, Isernia C, Rossi F, Saviano M, Pedone C, Paolillo L, Benedetti E, Pavone V. Conformational behaviour of a cyclolinopeptide A analogue: two-dimensional NMR study of cyclo(Pro1-Pro-Phe-Phe-Ac6c-Ile-ala-Val8). J. Pept. Sci. 1995; 1: 330-340.
24. Saviano M, Isernia C, Rossi F, Di Blasio B, Iacovino R, Mazzeo M, Pedone C, Benedetti E. Solid state structural analysis of the cyclooctapeptide cyclo-(Pro1- Pro-Phe-Phe-Ac6c-Ile-D-Ala-Val8). Biopolymers 2000; 53: 189-199.
25. Siemion IZ. A new example of edge-to-face interaction of aromatic rings in oligopeptides: cyclolinopeptide A. Z. Naturforsch. 1990; 456: 1324-1326.
26. Siemion IZ, Cebrat M, Jankowski A, Lisowski M, Pedyczak A, Wyslouch A. Does the edge-to-face interaction between aromatic rings occur in cyclolinopeptide A analogues? Int. J. Pept. Protein Res. 1994; 44: 61-69.
27. Karle IL, Flippen-Anderson JL, Wieland T. Conformational stability of antamanide and analogs. Crystal structure of perhydrosymmetric antamanide, cyclic (-Val-Pro-Pro-Cha-Cha-Val-Pro-Pro-Cha-Cha-). Int. J. Pept. Protein Res. 1989; 33: 422-427.
28. Balasubramanian D, Chopra P, Ardeshir F. Cyclolinopeptide: an antamanide analog. FEBS Lett. 1976; 65: 69-72.
29. Klis WA, Obermeier R, Siemion IZ, Sucharda-Sobczyk A, Gatner K. Complexing ability of cyclolinopeptide A. Rocz. Chem. 1977; 51: 1499-1509.
30. Tancredi T, Benedetti E, Grimaldi M, Pedone C, Rossi F, Saviano M, Temussi PA, Zanotti G. Ion binding of cyclolinopeptide A: an NMR and CD conformational study. Biopolymers 1991; 31: 761-767.
31. Zanotti G, Maione A, Rossi F, Saviano M, Pedone C, Tancredi T. Bioactive peptides: conformational study of a cystinyl cycloheptapeptide in its free and calcium complexed forms. Biopolymers 1993; 33: 1083-1091.
32. Saviano G, Rossi F, Benedetti E, Pedone C, Mierke DF, Maione A, Zanotti G, Tancredi T, Saviano M. Structural consequences of metal complexation of cyclo[Pro-Phe-Phe-Ala-Xaa]2 decapeptides. Chem. -Eur. J. 2001; 7: 1176-1183.
33. Kessler H, Klein M, Miller A, Wagner K, Bats JW, Ziegler K, Frimmer M. Conformational prerequisites for the in vitro inhibition of cholate uptake in hepatocytes by cyclic analogues of antamanide and somatostatin. Angew. Chem., Int. Ed. Engl. 1986; 25: 997-999.
34. Rossi F, Saviano M, Di Talia P, Di Blasio B, Pedone C, Zanotti G, Mosca M, Saviano G, Tancredi T, Ziegler K, Benedetti E. Solution and solid state structure of an aib-containing cyclodecapeptide inhibiting the cholate uptake in hepatocytes. Biopolymers 1996; 40: 465-478.
35. Siemion IZ, Bengtsson B, Trojnar J, Wieczorek Z. New peptide immunosuppressors. In Peptides 1990 Proceedings 21st European Peptide Symposium, Giralt E, Andreu D (eds). ESCOM: Leiden, 1991; 882-884.
36. Wieczorek Z, Bengtsson B, Trojnar J, Siemion IZ. Immunosuppressive activity of cyclolinopeptide A. Pept. Res. 1991; 4: 275-283.
37. Gaymes TJ, Cebrat M, Siemion IZ, Kay JE. Cyclolinopeptide A (CLA) mediates its immunosuppressive activity through cyclophilin-dependent calcineurin inactivation. FEBS Lett. 1997; 418: 224-227.
38. Gaymes TJ, Carrett NJ, Patel N, Kay JE, Siemion IZ. Effects of cyclolinopeptide A on T lymphocyte activation and peptidyl prolyl isomerase activity. Biochem. Soc. Trans. 1996; 24: 90S.
39. Gallo P, Saviano M, Rossi F, Pavone V, Pedone C, Ragone R, Stiuso P, Colonna G. Specific interaction between cyclophilin and cyclic peptides. Biopolymers 1995; 36: 273-281.
40. Kemmer H, Tripier D, Jouvenal K, Scriba D, Zanotti G, Maione AM, Ziegler K. Binding proteins for cyclic and linear oligopeptides in plasma membranes and the cytosol of rat hepatocytes. Biochem. Pharmacol. 1997; 54: 481-490.
41. Bell A, McSteen PM, Cebrat M, Picur B, Siemion IZ. Antimalarial activity of cyclolinopeptide A and its analogues. Acta Pol. Pharm. 2000; 57(Suppl.): 134-136.
42. Siemion IZ, Cebrat M, Wieczorek Z. Cyclolinopeptides and their analogs - a new family of peptide immunosuppressants affecting the calcineurin system. Arch. Immunol. Ther. Exp. 1999; 47: 143-153.
43. Siemion IZ, Bengtsson B, Trojnar J, Pedyczak A, Cebrat M, Zimecki M, Wieczorek Z. Immunosuppressive activity of cyclolinopeptide A analogs. In Peptides Chemistry and Biology, Proceedings 12th American Peptide Symposium, Smith JA, Rivier JE (eds). ESCOM: Leiden, 1992; 871-872.
44. Siemion IZ, Pedyczak A, Strug I, Wieczorek Z. Synthesis and biological studies on analogs of cyclolinopeptide A with a shortened peptide chain. Arch Immunol. Ther. Exp. 1994; 42: 459-465.
45. Siemion IZ, Cebrat M, Pedyczak A, Zimecki M, Wieczorek Z. Synthesis and immunosuppressive activity of glycine containing linear analogs of cyclolinopeptide A. Arch. Immunol. Ther. Exp. 1993; 41: 285-289.
46. Wieczorek Z, Zimecki M, Pedyczak A, Lisowski M, Siemion IZ. Immunosuppressive activity of alanine analogs of cyclolinopeptide A. Arch. Immunol. Ther. Exp. 1993; 41: 291-296.
47. Wieczorek Z, Pedyczak A, Bodalski T, Lisowski M, Trojnar J, Zimecki M, Siemion IZ. Immunosuppressive activity of tyrosine analogues of cyclolinopeptide A. Arch. Immunol. Ther. Exp. 1992; 40: 213-216.
48. Cebrat M, Lisowski M, Siemion IZ, Wieczorek Z. The cyclolinopeptide A analogues with D-Phe, D-Tyr, and L- and D-Trp residues. Pol. J. Chem. 1997; 71: 1401-1412.
49. Siemion IZ, Lisowski M, Cebrat M, Pedyczak A, Wyslouch A. Chirooptical properties of aromatic residues in cyclolinopeptide A and its analogues. Pol. J. Chem. 1994; 68: 963-968.
50. Siemion IZ, Cebrat M, Lisowski M. Further investigations on the optical activity of aromatic residues in cyclolinopeptide A analogues. Pol. J. Chem. 2000; 74: 955-964.
51. Siemion IZ, Cebrat M, Lisowski M, Zimecki M, Wieczorek Z. Immunosuppressive activity of threonine-containing analogues of cyclolinopeptide A. Arch. Immunol. Ther. Exp. 1992; 40: 257-261.
52. Cebrat M, Lisowski M, Siemion IZ, Zimecki M, Wieczorek Z. Sulfonated analogues of cyclolinopeptide A: synthesis, immunosuppressive activity and CD studies. J. Pept. Res. 1997; 49: 415-420.
53. Cebrat M, Ruchala P, Micewicz E, Woznica I, Picur B, Szewczuk Z. Analogues of cyclolinopeptides conjugated to the cell-permeable sequences. In 18th Polish Peptide Symposium, Wroc3aw, 4-8 September 2005; 98-99.
54. Zubrzak P, Banas A, Kaczmarek K, Leplawy MT, Sochacki M, Kowalski ML, Szkudlinska B, Zabrocki J, Di Lello P, Isernia C, Saviano M, Pedone C, Benedetti E. Analogues of cyclolinopeptide A containing alpha-hydroxymethyl amino acid residues. Biopolymers 2005; 80: 347-356.
55. Witkowska R, Donigiewicz A, Zimecki M, Zabrocki J. New analogue of cyclolinopeptide B modified by amphiphilic residue of alpha-hydroxymethylmethionine. Acta Biochim. Pol. 2004; 51: 67-72.
56. Kaczmarek K, Jankowski S, Siemion IZ, Wieczorek Z, Benedetti E, Di Lello P, Isernia C, Saviano M, Zabrocki J. Tetrazole analogues of cyclolinopeptide A: synthesis, conformation, and biology. Biopolymers 2002; 63: 343-357.
57. Zubrzak P, Kociolek K, Smoluch M, Silberring J, Kowalski ML, Szkudlinska B, Zabrocki J. Search for new synthetic immunosuppressants II. Tetrazole analogues of hymenistatin I. Acta Biochim. Pol. 2001; 48: 1151-1154.
58. Zubrzak P, Kaczmarek K, Kowalski ML, Szkudlin'ska B, Zabrocki J. Search for new synthetic immunosuppressants. Antamanide analogues containing the tetrazole ring as a cis-peptide bond mimetic. Pol. J. Chem. 2001; 75: 1869-1876.
59. Kaczmarek K, Silberring J, Smoluch M, Kowalski ML, Grochulska E, Szkudlin'ska B, Zabrocki J. Cyclolinopeptide A analogue containing (2S,4R)-4-aminopyroglutamic acid (4tAPy) residue as a cis-peptide bond motif. In Peptides 2000 Proceedings 26th European Peptide Symposium, Martinez J, Fehrene JA (eds). EDK: Paris, 2001; 821-822.
60. Leplawy MT, Zubrzak P, Olejniczak B, Paneth P, Smoluch M, Silberring J, Kowalski ML, Szkudlin'ska B, Grochulska E, Zabrocki J. Cyclolinopeptide A analogues containing N-benzoylglycine as a peptoid building block. In Peptides 2000 Proceedings 26th European Peptide Symposium, Martinez J, Fehrene JA (eds). EDK: Paris, 2001; 859-860.
61. Zubrzak P, Leplawy MT, Kowalski ML, Szkudlin'ska B, Paneth P, Silberring J, Suder P, Zabrocki J. Correlating biological activity with calculated geometric motifs in cyclolinopeptide A analogs. J. Phys. Org. Chem. 2004; 17: 625-630.
62. Katarzynska J, Bilska M, Adamek E, Zimecki M, Zabrocki J. Analogues of cyclolinopeptide A containing conformationally constrained dipeptide fragments. In 18th Polish Peptide Symposium, Wroc3aw, 4-8 September 2005; 130-131.