Synthesis and biochemical evaluation of a cyclic RGD oxorhenium complex as new ligand of αVβ3 integrin

European Journal of Medicinal Chemistry

Volumn 44, Issue 9, 2009, Pages 3394-3401

  Aufort, Marie ^a   Gonera, Marta ^a   Chaignon, Nicolas ^a   Le Clainche, Loïc ^a   Dugave, Christophe ^a  

^a CEA SACLAY   (France)

Author keywords

Angiogenesis; Cyclopeptide; Integrin; RGD; Rhenium; Technetium

Indexed keywords

ARGINYLGLYCYLASPARTIC ACID; GLUTATHIONE; RHENIUM COMPLEX; VITRONECTIN RECEPTOR;

AMINO TERMINAL SEQUENCE; ANGIOGENESIS; ARTICLE; CARBOXY TERMINAL SEQUENCE; DRUG STABILITY; DRUG SYNTHESIS; ISOMERISM; MOLECULAR IMAGING; PEPTIDE SYNTHESIS; TUMOR VASCULARIZATION;

ANIMALS; GLUTATHIONE; INTEGRIN ALPHAVBETA3; LIGANDS; MICE; PEPTIDES, CYCLIC; PLASMA; PROTEIN BINDING; PROTEIN STABILITY; RHENIUM;

EID: 67650427440     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.02.022     Document Type: Article

References (57)

1. Hynes R.O. Cell 110 (2002) 673-687
2. Watt F.M. EMBO. J 21 (2002) 3919-3926
3. Haubner R., Fisinger D., and Kessler H. Angew. Chem. Int. Ed. Engl. 36 (1997) 1374-1389
4. Mizejewski G.J. Proc. Soc. Exp. Biol. Med. 222 (1999) 124-138
5. Wehrle-Haller B., and Imhof B.A. J. Pathol. 200 (2003) 481-487
6. Kumar C.C., Nie H., Prorock Rogers C., Malkowski M., Maxwell E., Catino J., and Armstrong L.J. Pharmacol. Exp. Therapeut. 283 (1997) 843-853
7. Humphries J.D., Byron A., and Humphries M.J. J. Cell Sci. 119 (2006) 3901-3903
8. Dechantsreiter M.A., Planker E., Mathä B., Lohof E., Hölzemann G., Jonczyk A., Goodman S.L., and Kessler H. J. Med. Chem. 42 (1999) 3033-3040
9. Xiong J.-P., Stehle T., Zhang R., Joachimiak A., Frech M., Goodman S.L., and Arnaout M.A. Science 296 (2002) 151-155
10. Smith J.W. Curr. Opin. Investig. Drugs 4 (2003) 741-745
11. Goodman S.L., Hölzemann G., Sulyok G.A., and Kessler H. J. Med. Chem. 45 (2002) 1045-1051
12. Haubner R., Wester H.-J., Reuning U., Senekowitsch-Schmidtke R., Diefenbach B., Kessler H., Stöcklin G., and Schwaiger M. J. Nucl. Med. 40 (1999) 1061-1071
13. Lohof E., Planker 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. Engl. 39 (2000) 2761-2764
14. van Well R.M., Overkleeft H.S., van der marel G.A., Bruss D., Thibault G., de Groot P.G., van Boom J.H., and Overhand M. Biorg. Med. Chem. Lett. 13 (2003) 331-334
15. Belvisi L., Bernardi A., Checchia A., Manzoni L., Potenza D., Scolastico C., Castorina M., Cupelli A., Giannini G., Carminati P., and Pisano C. Org. Lett. 3 (2001) 1001-1004
16. Urman S., Gaus K., Yang Y., Strijowski V., Sewald N., De Pol S., and Reiser O. Angew. Chem. Int. Ed. 46 (2007) 3976-3978
17. Casiraghi G., Rassu G., Auzzas L., Burreddu 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) 7675-7687
18. Zanardi F., Burreddu P., Rassu G., Auzzas L., Battistini L., Curti C., Sartori A., Nicastro G., Menchi G., Cini N., Bottonocetti A., Raspanti S., and Casiraghi G. J. Med. Chem. 51 (2008) 1771-1782
19. Kelleman A., R-Mattern H., Pierschbacher M.D., and Goodman M. Biopolymers 71 (2003) 686-695
20. Cacciari B., and Spalluto G. Curr. Med. Chem. 12 (2005) 51-70
21. Moussa S.A. Mol. Biotechnol. 38 (2008) 33-40
22. Albrecht M., Stortz P., Runsink J., and Weis P. Chem. Eur. J. 10 (2004) 3657-3666
23. Curley G.P., Blum H., and Humphries M.J. Cell Mol. Life Sci. 56 (1999) 427-441
24. Temming K., Schiffelers R.M., Molema G., and Kok R.J. Drug Resist. Updat. 8 (2005) 381-402
25. Haubner R., Wester H.-W., Burkhart F., Senekowitsch-Schmidtke R., Weber W., Goodman S.L., Kessler H., and Schwaiger M. J. Nucl. Med. 42 (2001) 326-336
26. Haubner R., H-Wester W., Weber W.A., Mang C., Ziegler S.I., Goodman S.L., Senekowitsch-Schmidtke R., Kessler H., and Schwaiger M. Cancer Res. 61 (2001) 1781-1785
27. Janssen M.L., Oyen W.J., Dijkgraaf I., Massuger L.F., Frielink C., Edwards D.S., Rajopadhye M., Boonstra H., Korstens F.H., and Boerman O. Cancer Res. 62 (2002) 6146-6151
28. Chen X., Tohme M., Park R., Hou Y., Bading J.R., and Conti P.S. Mol. Imaging 3 (2004) 96-104
29. Chen X., Park R., Shahinian A.H., Bading J.R., and Conti P.S. Nucl. Med. Biol. 31 (2004) 11-19
30. Chen X., Park R., Shahinian A.H., Tohme M., Klankaldyyan V., Bozorgzadeh M.H., Bading J.R., Moats R., laug W.E., and Conti P.S. Nucl. Med. Biol. 31 (2004) 179-189
31. Chen X., Park R., Hou Y., Klankaldyyan V., Gonzales-Gomez I., Tohme M., Bading J.R., Laug W.E., and Conti P.S. Eur. J. Nucl. Med. Mol. Imaging 31 (2004) 1081-1089
32. Chen X., Park R., Hou Y., Klankaldyyan V., Gonzales-Gomez I., Tohme M., Bading J.R., Laug W.E., and Conti P.S. J. Nucl. Med. 45 (2004) 1776-1783
33. Haubner R., Bruchertseifer F., Bock M., Kessler H., Schwaiger M., and Wester H.-J. Nuklearmedizin 1 (2004) 26-32
34. Chen X., Park R., Tohme M., Shahinian A.H., Bading J.R., and Conti P.S. Bioconjug. Chem. 15 (2004) 41-49
35. Haubner R., Kuhnast B., Mang C., Weber W.A., Kessler H., H-Wester W., and Schwaiger M. Bioconjug. Chem. 15 (2004) 61-69
36. Cheng Z., Wu Y., Xiong Z., Gambhir S.S., and Chen X. Bioconjug. Chem. 16 (2005) 1433-1441
37. Wu Y., Zhang X., Xiong Z., Cheng Z., Fischer D.R., Liu S., Gambhir S., and Chen X. J. Nucl. Med. 46 (2005) 1707-1718
38. Zhang X., Xiong Z., Wu Y., Cai W., Tseng J.R., Gambhir S.S., and Chen X. J. Nucl. Med. 47 (2006) 113-121
39. Sancey L., Ardisson V., Riou L.M., Ahmadi M., Martibattle D., Boturyn D., Dumy P., Fagret D., Ghezzi C., and Vuillez J.P. Eur. J. Nucl. Med. Mol. Imaging 34 (2007) 2037-2047
40. Jin Z.-H., Razkin J., Josserand V., Boturyn D., Grichine A., Texier I., Favrot M.-C., Dumy P., and Coll J.-L. Mol. Imaging 6 (2007) 43-55
41. Jin Z.-H., Josserand J., Foillard S., Boturyn D., Dumy P., Favrot M.-C., and Coll J.-L. Mol. Cancer 6 (2007) 41
42. Dimastromatteo J., Pons G., Riou L., Pellegrini E., Gavrilina T., Ahmadi M., Boturyn D., Dumy P., Fagret D., and Ghezzi C. Circulation 116 (2008) 659-660
43. Albrecht M., and Stortz P. Chem. Soc. Rev. 34 (2005) 496-506
44. Barda Y., Cohen N., Lev V., Ben-Aroya N., Koch Y., Mishani E., Fridkin M., and Gilon C. Nucl. Med. Biol. 31 (2004) 921-933
45. Fridkin G., Bonasera T.A., Litman P., and Gilon C. Nucl. Med. Biol. 32 (2005) 39-50
46. Wei L., Butcher C., Miao Y., Gallazzi F., Quinn T.P., Welch M.J., and Lewis J.S. J. Nucl. Med. 48 (2007) 64-72
47. Bigott-Hennkens H.M., Junnotula S., Ma L., Gallazzi F., Lewis M.R., and Jurisson S.S. J. Med. Chem. 51 (2008) 1223-1230
48. Dilworth J.R., and Parrott S.J. Chem. Soc. Rev. 27 (1998) 43-55
49. Liu S., and Edwards S. Chem. Rev. 99 (1999) 2235-2268
50. Clavaud C., Heckenroth M., Stricane C., Ménez A., and Dugave C. Bioconjug. Chem. 17 (2006) 807-814
51. Papadopoulos M.S., Pirmettis I.C., Pelecanou M., Raptopoulou C.P., Terzis A., Stassinopoulou C.I., and Chiotellis E. Inorg. Chem. 35 (1996) 7377-7383
52. Pelecanou M., Chryssou K., and Stassinopoulou C.I. J. Inorg. Biochem. 79 (2000) 347-351
53. Davison A., Orvig C., Trop H.S., Sohn M., and DePamphilis B.V. Inorg. Chem. 19 (1980) 1988-1992
54. Davison A., Trop H., DePamphilis B., and Jones A. Inorg. Synth. 21 (1982) 160-162
55. Friedrich-Bochnitschek S., Waldmann H., and Kunz H. J. Org. Chem. 54 (1989) 751-756
56. Orlando R.A., and Cheresh D.A. J. Biol. Chem. 266 (1991) 19543-19550
57. Clavaud C., Le Gal J., Thai R., and Moutiez M. Chem. Biol. Chem. 9 (2008) 1823-1829