Morpholine-based RGD-cyclopentapeptides as αvβ3/αvβ5 integrin ligands: Role of configuration towards receptor binding affinity

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 4, 2009, Pages 1542-1549

  Cini, Nicoletta ^a   Trabocchi, Andrea ^a   Menchi, Gloria ^a   Bottoncetti, Anna ^a   Raspanti, Silvia ^a   Pupi, Alberto ^a   Guarna, Antonio ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Conformational analysis; NMR; Peptide; Peptidomimetic

Indexed keywords

ALPHAVBETA5 INTEGRIN; ARGINYLGLYCYLASPARTIC ACID; CILENGITIDE; CYCLOPEPTIDE; ECHISTATIN; MORPHOLINE DERIVATIVE; PENTAPEPTIDE; ST 1646; UNCLASSIFIED DRUG; VITRONECTIN RECEPTOR;

ARTICLE; DRUG CONFORMATION; DRUG RECEPTOR BINDING; LIGAND BINDING; PEPTIDE ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

BINDING SITES; HUMANS; INTEGRIN ALPHAVBETA3; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MORPHOLINES; OLIGOPEPTIDES; PEPTIDES, CYCLIC; PROTEIN BINDING; PROTEIN CONFORMATION; RECEPTORS, VITRONECTIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 60049090431     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.01.006     Document Type: Article

References (45)

1. Arnaout M.A., Goodman S.L., and Xiong J.P. Curr. Opin. Cell Biol. 14 (2002) 641
2. Hynes R.O. Cell 110 (2002) 673
3. Plow E.F., Haas T.A., Zhang L., Loftus J., and Smith J.W. J. Biol. Chem. 275 (2000) 21785
4. Humphries M.J. Biochem. Soc. Trans. 28 (2000) 311
5. Ruoslathi E., and Pierschbacher M.D. Science 238 (1987) 491
6. 3, see:. Eliceiri B.P., and Cheresh D.A. Cancer J. 13 (2000) 245
7. Burke P.A., De Nardo S.J., Miers L.A., Lamborn K.L., Matzku S., and De Nardo G.L. Cancer Res. 62 (2002) 4263
8. Haubner R., Finsinger D., and Kessler H. Angew. Chem., Int. Ed. 36 (1997) 1374
9. 5, see:. Marinelli L., Gottschalk K.E., Meyer A., Novellino E., and Kessler H. J. Med. Chem. 47 (2004) 4166
10. Friedlander M., Theesfeld C.L., Sugita M., Fruttiger M., Thomas M.A., Chang S., and Cheresh D.A. Proc. Natl. Acad. Sci. 93 (1996) 9764
11. Friedlander M., Brooks P.C., Shaffer R.W., Kincaid C.M., Varner J.A., and Cheresh D.A. Science 270 (1995) 1500
12. Brooks P.C., Stromblad S., Klemke R., Visscher D., Sarkar F.H., and Cheresh D.A. J. Clin. Invest. 96 (1995) 1815
13. Kumar C.C., Malkowski M., Yin Z., Tanghetti E., Yaremko B., Nechuta T., Varner J., Liu M., Smith E.M., Neustadt B., Presta M., and Armstrong L. Cancer Res. 61 (2001) 2232
14. Mitjans F., Meyer T., Fittschen C., Goodman S., Jonczyk A., Marshall J.F., Reyes G., and Piulats J. Int. J. Cancer 87 (2000) 716
15. MacDonald T.J., Taga T., Shimada H., Tabrizi P., Zlokovic B.V., Cheresh D.A., and Laug W.E. Neurosurgery 48 (2001) 151
16. Wermuth J., Goodman S.L., Jonczyk A., and Kessler H. J. Am. Chem. Soc. 119 (1997) 1328
17. Bach II A.C., Espina J.R., Jackson S.A., Stouten P.F.W., Duke J.L., Mousa S.A., and DeGrado W.F. J. Am. Chem. Soc. 118 (1996) 293
18. Dechantsreiter M., Plnaker E., Mathä B., Lohof E., Hölzemann G., Jonczyk A., Goodman S.L., and Kessler H. J. Med. Chem. 42 (1999) 3033
19. Lohof E., Plnaker E., Mang C., Burkhart F., Dechantsreiter M.A., Haubner R., Wester H.J., Schwaiger M., Hölzemann G., Goodman S.L., and Kessler H. Angew. Chem. Int. Ed. 39 (2000) 2761
20. Belvisi L., Bernardi A., Checchia A., Manzoni L., Potenza D., Scolastico C., Castorina M., Capelli A., Giannini G., Carminati P., and Pisano C. Org. Lett. 3 (2001) 1001
21. Casiraghi G., Rassu G., Auzzas L., Bureddu P., Gaetani E., Battistini L., Zanardi F., Curti C., Nicastro G., Belvisi L., Motto I., Castorina M., Giannini G., and Pisano C. J. Med. Chem. 48 (2005) 7675
22. Belvisi L., Bernardi A., Colombo M., Manzoni L., Potenza D., Scolastico C., Giannini G., Marcellini M., Riccioni T., Castorina M., LoGiudice P., Carminati P., and Pisano C. Bioorg. Med. Chem. 14 (2006) 169
23. Trabocchi A., Menchi G., Guarna F., Machetti F., Scarpi D., and Guarna A. Synlett (2006) 331
24. Trabocchi A., Potenza D., and Guarna A. Eur. J. Org. Chem. (2004) 4621
25. Trabocchi A., Occhiato E.G., Potenza D., and Guarna A. J. Org. Chem 67 (2002) 7483
26. Sladojevich F., Trabocchi A., and Guarna A. J. Org. Chem. 72 (2007) 4254
27. Krchnák V., Vágner J., Sáfar P., and Lebl M. Collect. Czech. Chem.Commun. 53 (1988) 2542
28. Belkin V.M., Belkin A.M., and Koteliansky V.E. J. Cell Biol. 111 (1990) 2159
29. Pytela R., Pierschbacher M.D., Argraves S., Suzuki S., and Ruoslahti E. Methods Enzymol. 144 (1987) 475
30. Kumar C.C., Nie H., Rogers C.P., Malkowski M., Maxwell E., Catino J.J., and Armstrong L. J. Pharmacol. Exp. Ther. 283 (1997) 843
31. Dijkgraaf I., Kruijtzer J.A., Frielink C., Soede A.C., Hilbers H.W., Oyen W.J., Corstens F.H., Liskamp R.M., and Boerman O.C. Nucl. Med. Biol. 33 (2006) 953
32. Zanardi F., Burreddu P., Rassu G., Auzzas L., Battistini L., Curti C., Sartori A., Nicastro G., Menchi G., Cini N., Bottoncetti A., Raspanti S., and Casiraghi G. J. Med. Chem 51 (2008) 1771
33. Takagi J., Petre B.M., Walz T., and Springer T.A. Cell 110 (2002) 599
34. Humphries M.J., McEwan P.A., Barton S.J., Buckley P.A., Bella J., and Mould A.P. Trends Biochem. Sci. 28 (2003) 313
35. Shimaoka M., and Springer T.A. Nat. Rev. Drug Discov. 2 (2003) 703
36. Xiong J.P., Stehle T., Zhang R., Joachimiak A., Frech M., Goodman S.L., and Arnaout M.A. Science 296 (2002) 151
37. Bednar R.A., Gaul S.L., Hamill T.G., Egbertson M.S., Shafer J.A., Hartman G.D., Gould R.J., and Bednar B. J. Pharmacol. Exp. Ther. 285 (1998) 1317
38. Mohamadi F., Richards N.G.J., Guida W.C., Liskamp R., Lipton M., Caufield C., Chang G., Hendrickson T., and Still W.C. J. Comput. Chem. 11 (1990) 440
39. Weiner S.J., Kollman P.A., Nguyen D.T., and Case D.A. J. Comput. Chem. 7 (1986) 230
40. Still W.C., Tempczyk A., Hawley R.C., and Hendrickson T. J. Am. Chem. Soc. 112 (1990) 6127
41. Chang G., Guida W.C., and Still W.C. J. Am. Chem. Soc 111 (1989) 4379
42. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., and Olson A.J. J. Comput. Chem. 19 (1998) 1639
43. Kumar C.C., Nie H., Armstrong L., Zhang R., Vijay-Kumar S., and Tsarbopoulos A. FEBS Lett. 429 (1998) 239
44. Gillet A., Sanner M., Stoffler D., and Olson D. Structure 13 (2005) 483
45. DeLano, W.L. The PyMOL Molecular Graphics System, DeLano Scientific LLC: San Carlos, CA, USA. http://www.pymol.org.