Amide-to-ester substitution allows fine-tuning of the cyclopeptide conformational ensemble

Angewandte Chemie - International Edition

Volumn 49, Issue 15, 2010, Pages 2732-2737

  Cupido, Tommaso ^a   Spengler, Jan ^a   Ruiz Rodriguez, Javier ^a   Adan, Jaume ^b   Mitjans, Francesc ^b   Piulats, Jaume ^b   Albericio, Fernando ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b LEITAT TECHNOLOGICAL CENTER   (Spain)

Author keywords

Bioorganic chemistry; Conformation analysis; Depsipeptides; Molecular dynamicsNMR spectroscopy

Indexed keywords

3D STRUCTURE; BIOLOGICAL ACTIVITIES; BIOORGANIC CHEMISTRY; CONFORMATION ANALYSIS; CONFORMATIONAL ENSEMBLE; CONFORMATIONAL EQUILIBRIUM; CYCLOPEPTIDES; DEPSIPEPTIDES; INTEGRINS;

AMIDES; BIOCHEMISTRY; ESTERIFICATION; ESTERS; THREE DIMENSIONAL;

CONFORMATIONS;

AMIDE; ARGINYL-GLYCYL-ASPARTIC ACID; ARGINYLGLYCYLASPARTIC ACID; CYCLOPEPTIDE; ESTER; INTEGRIN; OLIGOPEPTIDE;

ARTICLE; CELL ADHESION; CELL LINE; CHEMISTRY; DRUG ANTAGONISM; HUMAN; METABOLISM; MOLECULAR DYNAMICS; PROTEIN TERTIARY STRUCTURE;

AMIDES; CELL ADHESION; CELL LINE; ESTERS; HUMANS; INTEGRINS; MOLECULAR DYNAMICS SIMULATION; OLIGOPEPTIDES; PEPTIDES, CYCLIC; PROTEIN STRUCTURE, TERTIARY;

EID: 77950473237     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200907274     Document Type: Article

References (37)

1. E. Perola, S. P. Charifson, J. Med. Chem. 2004, 47, 2499.
2. G. H. Loew, S. K. Burt, Proc. Natl. Acad. Sci. USA 1978, 75, 7-11.
3. a) J. D. Tyndall. B. Pfeiffer, G. Abbenante, D. P. Fairlie, Chem. Rev. 2005, 105, 793:
4. b) R. M. Freidinger, D. F. Veber. D. S. Perlow, J. R. Brooks, R. Sapestein, Science 1980, 210, 4470;
5. c) R. M. Freidinger, et al., J. Med. Chem. 1990, 33, 1843 (see the Supporting Information for full citation).
6. a) S. Home, C. A. Olsen, J. M. Beierle, A. Montero, M. R. Ghadiri, Angew. Chem. 2009. 121. 4812;
7. Angew. Chem. Int. Ed. 2009, 48, 4718;
8. b) J. Jiménez-Barbero, A. Canales, P. T. Northcote, R. M. Buey, J. M. Andreu, J. F. Diaz, J. Am. Chem. Soc. 2006, 128, 8757.
9. R. Haubner, R. Gratias, B. Diefenbach, S. L. Goodman, A. Jonczyk, H. Kessler, J. Am. Chem. Soc. 1996, 118, 7461.
10. a) E. T. Powers, S. Deechongkit, J. W. Kelly, Adv. Protein Chem. 2005, 72, 39:
11. b) J. A. Scheike, C. Baldauf, J. Spengler, F. Albericio, M. T. Pisabarro, B. Koksch, Angew. Chem. 2007, 119, 7912;
12. Angew. Chem. Int. Ed. 2007, 46, 7766.
13. M. A. Dechantsreiter, E. Planker, B. Matha, E. Lohof, G. Holzemann, A. Jonczyk, S. L. Goodman, H. Kessler. J. Med. Chem. 1999, 42, 3033.
14. a) G. C. Alghisi, L. Ponsonnet, C. Ruegg, PLoS One 2009, 4, e4449;
15. b) S. M. Weis, D. G. Stupack, D. A. Cheresh, Cancer Cell 2009, 15, 359;
16. c) Recent results shown that low nM concentrations of cilengitide can promote tumour angiogenesis by agonizing instead of antagonizing the αvβ3 integrin. A. R. Reynolds, et al., Nat. Med. 2009, 15, 392. (see the Supporting Information for full citation).
17. a) A. Geyer, G. Müller, H. Kessler, J. Am. Chem. Soc. 1994, 116, 7735;
18. b) G. Müller, M. Gurrath, H. Kessler, R. Timpl, Angew. Chem. 1992, 104, 341;
19. Angew. Chem. Int. Ed. Engl. 1992, 31, 326.
20. a) F. Albericio, K. Burger. J. Ruiz-Rodriguez, J. Spengler, Org. Lett. 2005, 7, 597:
21. b) Typically, this coupling step requires 4 hours in THF, whereas the coupling of HFA-(D)OPhe to the Nterminal NMeVal required 48 hours and a higher number of molar equivalente Glycolic acid (OGly), phenylacetic acid [(D)OPhe], and hydroxyvalerianic acid (OVa1) used for the substitution of the Gly, (D)Phe. and NMeVal are commercially available. Appropriately protected malic (OAsp) and argininic acid (OArg) were obtained as described; for OAsp, see: K. Pumpor, E. Windeisen, J. Spengler, F. Albericio, K. Burger, Monatsh. Chem. 2004, 135, 1427;
22. for OArg, see: T. Cupido, J. Spengler, K. Burger, F. Albericio, Tetrahedron Lett. 2005, 46, 6733.
23. O. Kuisle. E. Quǐoà, R. J. Riguera, Org. Chem. 1999, 64, 8063.
24. F. Albericio. J. M. Bofill. A. El-Faham. S. A. Kates. J. Org. Chem. 1998, 63, 9678.
25. a) B. F. Gisin, R. B. Merrifield, J. Am. Chem. Soc. 1972, 94, 3102;
26. b) S. Capasso, A. Vergara L. Mazzarella, J. Am. Chem. Soc. 1998, 120, 1990.
27. a) Phosphonium salts are preferred ahead of the uronium/ aminium salts, because they do not provoke capping of the N terminal function as the latter do, see: F. Albericio, M. Cases, J. Alsina, S. A. Triolo, L. A. Carpino, S. A. Kates, Tetrahedron Lett. 1997, 38, 4853.3
28. a) D. G. Stupack, X. S. Puente, S. Boutsaboualoy. C.M. Storgard, D. A. Cheresh. J. Cell Biol. 2001, 155, 459:
29. b) S. Maubant, D. Saint-Dizier, M. Boutillon, F. Perron-Sierra, P. J. Casara, J. A. Hickman, G. C. Tucker, E. Van Obberghen-Schilling, Blood 2006, 108, 3035.
30. C. Li, J. B. McCarthy, L. T. Furcht, G. B. Fields, Biochemistry 1997, 36, 15404.
31. D. G. Stupack, D. A. Cheresh, Oncogene 2003, 22, 9022.
32. F. Mitjans, D. Sander, J. Adan, A. Sutter, J. M. Martinez, C. S. Jaggle, J. M. Moyano. H. G. Kreysch, J. Piulats. S. L. Goodman, J. Cell Sci. 1995, 108, 2825.
33. J. Xiong. T. Stehle, R. Zhang, A. Joachimiak, M. Frech. S. L. Goodman, M. A. Arnaout, Science 2002, 296,151.
34. a) R. W. Dixon, P. A. Kollman, J. Comput. Chem. 1997, 18, 1632;
35. b) V. Babin, J. Baucom,T. A. Darden. C. Sagui, J. Phys. Chem. B 2006, 110, 11571.
36. C. M. Wilmot, J. M. Thornton Protein Engineering, Design and Selection 1990, 3, 479.
37. L. Marinelli, A. Lavecchia. K. E. Gottschalk, E. Novellino. H. Kessler, J. Med. Chem. 2003, 46, 4393.