Parallel synthesis and anti-inflammatory activity of cyclic peptides cyclosquamosin D and Met-cherimolacyclopeptide B and their analogs

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 19, 2010, Pages 5653-5657

  Dellai, Afef ^a   Maricic, Igor ^b   Kumar, Vipin ^b   Arutyunyan, Sergey ^b   Bouraoui, Abderrahman ^a   Nefzi, Adel ^b  

^a UNIVERSITY OF MONASTIR   (Tunisia)

^b TORREY PINES INSTITUTE FOR MOLECULAR STUDIES   (United States)

Author keywords

Anti inflammatory activity; Natural cyclopeptides; Parallel synthesis; Solid phase synthesis

Indexed keywords

ANTIINFLAMMATORY AGENT; CYCLOSQUAMMOSIN D; INTERLEUKIN 6; LIPOPOLYSACCHARIDE; MET CHERIMOLACYCLOPEPTIDE B; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANIMAL CELL; ANNONA; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CELL STIMULATION; CONTROLLED STUDY; CYTOKINE PRODUCTION; CYTOKINE RELEASE; DRUG ISOLATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; MACROPHAGE; MOUSE; NONHUMAN; PLANT SEED;

ANIMALS; ANNONA; ANTI-INFLAMMATORY AGENTS; CELL LINE; INTERLEUKIN-6; MICE; PEPTIDES, CYCLIC; SEEDS; TUMOR NECROSIS FACTOR-ALPHA;

ANNONA SQUAMOSA;

EID: 77957556782     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.08.033     Document Type: Article

References (26)

1. S. Tamai, M. Kaneda, and S. Nakamura J. Antibiot. 35 1982 1130
2. C.T. Walsh Science 261 1993 308
3. R. Kannan, C.M. Harris, T.M. Harris, G.P. Waltho, N.J. Skelton, and D.H. Williams J. Am. Chem. Soc. 110 1988 2946
4. P. Wipf Chem. Rev. 95 1995 2115
5. Y. Hamada, and T. Shioiri Chem. Rev. 105 2005 4441
6. A.B. Pomilio, M.E. Battista, and A.A. Vitale Curr. Org. Chem. 10 2006 2075
7. E.R. Blout Biopolymers 20 1981 1901
8. W. Mongkolvisut, S. Sutthivaiyakit, H. Leutbecher, S. Mika, I. Klaiber, W. Moller, H. Rosner, U. Beifuss, and J. Conrad J. Nat. Prod. 69 2006 14355
9. R. Dahiya, and K. Kaur Arch. Pharm. Res. 30 2007 1380
10. H. Morita, A. Shishido, T. Matsumoto, H. Itokawa, and K. Takeya Tetrahedron 55 1999 967
11. C. Baraguey, A. Blond, I. Correia, J.-L. Pousset, B. Bodo, J.-L. Auvin-Guette, and A. Mahafacyclin Tetrahedron Lett. 41 2000 325
12. H. Morita, T. Lizuka, C.Y. Choo, K.L. Chan, H. Itokawa, and K. Takeya J. Nat. Prod. 68 2005 1686
13. H. Morita, A. Shishido, T. Kayashita, K. Takeya, and H. Itokawa J. Nat. Prod. 60 1997 404
14. S. Yahara, C. Shigeyama, T. Nohara, H. Okuda, K. Wakamatsu, and T. Yasuhara Tetrahedron Lett. 30 1989 6041
15. Y.L. Yang, K.F. Hua, P.H. Chuang, S.H. Wu, K.Y. Wu, F.R. Chang, and Y.C. Wu J. Agric. Food Chem. 56 2008 386
16. R.B. Merrifield J. Am. Chem. Soc. 85 1963 2149
17. R.B. Merrifield Science 232 1986 341
18. A.R. Mitchell Biopolymers 90 2008 3175
19. G.B. Fields, and R.L. Noble Int. J. Pept. Protein Res. 35 1990 161
20. R.A. Houghton Proc. Natl. Acad. Sci. U.S.A. 82 1985 5131
21. C. Cabrele, M. Langer, and A.G. Beck-Sickinger J. Org. Chem. 64 1999 4353
22. S. Ficht, R.J. Payne, R.T. Guy, and C.-H. Wong Chem.-A Eur. J. 14 2008 3620
23. M.J. Dixon, A. Nathubhai, O.A. Andersen, D.M.F. van Aalten, and I.M. Eggleston Org. Biomol. Chem. 7 2009 259
24. X. Tang, I. Maricic, N. Purohit, B. Bakamjian, L.M. Reed-Loisel, T. Beeston, P. Jensen, and V. Kumar J. Immunol. 177 2006 7645
25. T.R. Smith, X. Tang, I. Maricic, Z. Garcia, S. Fanchiang, and V. Kumar J. Immunol. 182 2009 6959
26. - 10 mg of linear crude peptide was dissolved in 600 μL of DMF anhydrous. PyBOP (3 equiv) and HOBt (3 equiv) were added to the reaction vessel in the presence of DIEA (3 equiv). The clear solution was stirred overnight at room temperature. The completion of the cyclization was monitored by LC-MS. The DMF was evaporated and the crude product was purified using reversed-phase high-performance liquid chromatography (RP HPLC). All the compounds were obtained in good yield ranging from 50 to 60%.