Synthesis, in vitro screening and in vivo evaluation of cyclic RGD analogs cyclized through oxorhenium and oxotechnetium coordination

European Journal of Medicinal Chemistry

Volumn 46, Issue 5, 2011, Pages 1779-1788

  Aufort, Marie ^a   Gonera, Marta ^a   Lelait, Marie Anne ^a   Czarny, Bertrand ^a   Le Clainche, Loïc ^a   Thaï, Robert ^a   Landra, Amandine ^a   Ruinart De Brimont, Mathias ^a   Dugave, Christophe ^a  

^a SERVICE DE CHIMIE BIOORGANIQUE ET DE MARQUAGE   (France)

Author keywords

Angiogenesis; Cyclopeptide; Integrin; RGD; Rhenium; Technetium

Indexed keywords

ALPHA2BETA3 INTEGRIN; ALPHAVBETA5 INTEGRIN; INTEGRIN; OXORHENIUM; OXOTECHNETIUM; RHENIUM 16; RHENIUM 17; RHENIUM 18; RHENIUM 19; RHENIUM 20; RHENIUM 21; RHENIUM 22; RHENIUM 23; RHENIUM 33; RHENIUM 50; RHENIUM 54; RHENIUM 66; RHENIUM COMPLEX; TECHNETIUM 14; TECHNETIUM 16; TECHNETIUM 33; TECHNETIUM 50; TECHNETIUM 54; TECHNETIUM 66; TECHNETIUM 99M; TECHNETIUM COMPLEX; TRIPEPTIDE; UNCLASSIFIED DRUG; VITRONECTIN RECEPTOR;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CYCLIZATION; DRUG DISTRIBUTION; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; IC 50; MOUSE; NONHUMAN; RADIOACTIVITY; TUMOR XENOGRAFT;

ANIMALS; CYCLIZATION; HUMANS; MICE; MICE, NUDE; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; PEPTIDES, CYCLIC; RHENIUM; STEREOISOMERISM; TECHNETIUM; TISSUE DISTRIBUTION; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 79953205891     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.02.032     Document Type: Article

References (64)

1. F.M. Watt EMBO J. 21 2002 3919 3926
2. B. Wehrle-Haller, and B.A. Imhof J. Pathol. 200 2003 481 487
3. S.A. Mousa Mol. Biotechnol. 38 2008 33 40
4. W. Guo, and F.G. Giancotti Nat. Rev. Mol. Cell Biol. 5 2004 816 826
5. G. Bergers, and D. Hanahan Nat. Rev. Cancer 8 2008 592 603
6. E. K-Gottschalk, and H. Kessler Angew. Chem. Int. Ed. 41 2002 3767 3774
7. J.D. Humphries, A. Byron, and M.J. Humphries J. Cell Sci. 119 2006 3901 3903
8. D. Heckmann, B. Laufer, L. Marinelli, V. Limongelli, E. Novellino, G. Zahn, R. Stragies, and H. Kessler Angew. Chem. Int. Ed. 48 2009 4436 4440
9. B. Cacciari, and G. Spalluto Curr. Med. Chem. 12 2005 51 70
10. J. Chatterjee, O. Ovadia, G. Zahn, L. Marinelli, A. Hoffman, C. Gilon, and H. Kessler J. Med. Chem. 50 2007 5878 5881
11. M. Schotellius, B. Laufer, H. Kessler, and H.-J. Wester Acc. Chem. Res. 42 2009 969 980
12. S. Liu Bioconjugate Chem. 20 2009 2199 2213
13. S. Liu Mol. Pharm. 3 2006 472 487
14. W. Cai, S.S. Gambhir, and X. Chen BioTechniques 6 2005 6 17
15. M.R. Lewis J. Nucl. Med. 46 2005 2 4
16. R. Haubner, H.-J. Wester, U. Reuning, R. Senekowitsch-Schmidtke, B. Diefenbach, H. Kessler, G. Stöcklin, and M.J. Schwaiger Nucl. Med 40 1999 1061 1071
17. X. Zhang, Z. Xiong, Y. Wu, W. Cai, J.R. Tseng, S.S. Gambhir, and X. Chen J. Nucl. Med. 47 2006 113 121
18. R. Haubner, W.A. Weber, A.J. Beer, E. Valbuliene, D. Reim, M. Sarbia, K.-F. Becker, M. Goebel, R. Hein, H.-J. Wester, H. Kessler, and M. Schwaiger PLOS Med. 2 2005 244 252
19. R. Haubner, B. Kuhnast, C. Mang, W.A. Weber, H. Kessler, H.-J. Wester, and M. Schwaiger Bioconjugate Chem. 15 2004 61 69
20. X. Chen, R. Park, M. Thome, A.H. Shahinian, J.R. Bading, and P.S. Conti Bioconjugate Chem. 15 2004 41 49
21. X. Chen, R. Park, Y. Hou, V. Khankaldyyan, I. Gonzales-Gomez, M. Thome, J.R. Bading, W.E. Laug, and P.S. Conti Eur. J. Nucl. Med. Mol. Imaging 31 2004 1081 1089
22. X. Chen, R. Park, A.H. Shahinian, M. Thome, V. Khankaldyyan, M.H. Bozorgzahed, J.R. Bading, R. Moats, W.E. Laug, and P.S. Conti Nucl. Med. Biol. 31 2004 179 189
23. Y. Wu, X. Zhang, Z. Xiong, Z. Cheng, D.R. Fischer, S. Liu, S.S. Gambhir, and X. Chen J. Nucl. Med. 46 2005 1707 1718
24. X. Chen, Y. Hou, M. Thome, R. Park, V. Khankaldyyan, I. Gonzales-Gomez, J.R. Bading, W.E. Laug, and P.S. Conti J. Nucl. Med. 45 2004 1776 1783
25. S. Alves, J.D.G. Correia, L. Gano, T.L. Rold, A. Prasanphanich, R. Haubner, M. Rupprich, R. Alberto, C. Dechristoforo, I. Santos, and C.J. Smith Bioconjugate Chem. 18 2007 530 537
26. R. Haubner, F. Bruchertseifer, M. Bock, H. Kessler, M. Schwaiger, and H.-J. Wester Nuklearmedizin 43 2004 26 32
27. S. Liu, D.S. Edwards, and A.R. Harris Bioconjugate Chem. 9 1998 583 595
28. F. Z-Su, G. Liu, S. Gupta, Z. Zhu, M. Rusckowski, and D.J. Hnatowich Bioconjugate Chem. 13 2002 561 570
29. F. Z-Su, J. He, M. Rusckowski, and D.J. Hnatowitch Nucl. Med. Biol. 30 2003 141 149
30. B. Jia, J. Shi, Z. Yang, B. Xu, Z. Liu, H. Zhao, S. Liu, and F. Wang Bioconjugate Chem. 17 2006 1069 1076
31. S. Liu, W.-Y. Hsieh, Y. Jiang, Y.-S. Kim, S.G. Sreerama, X. Chen, B. Jia, and F. Wang Bioconjugate Chem. 18 2007 438 446
32. M.L. Janssen, W.J. Oyen, I. Dijkgraaf, L.F. Massuger, C. Frielink, D.S. Edwards, M. Rajopadhye, H. Boonstra, F.H. Corstens, and O.C. Boerman Cancer Res. 62 2002 6146 6151
33. B.H. Kujipers, S. Groothuys, A.C. Soede, P. Laverman, O.C. Boerman, F.L. van Delft, and F.P.J.T. Rutjes Bioconjugate Chem. 18 2007 1847 1854
34. X. Chen, R. Park, A.H. Shahinian, J.R. Bading, and P.S. Conti Nucl. Med. Biol. 31 2004 11 19
35. R. Haubner, H.-J. Wester, F. Burkhart, R. Senekowitsch-Schmidtke, W. Weber, S.L. Goodman, H. Kessler, and M. Schwaiger J. Nucl. Med. 42 2001 326 336
36. J. Zeng, W.-H. Xie, S.-L. Hu, and M.-X. Jin Chinese Med. J. 119 2006 1435 1443
37. Y. Shi, and S. Sharma Bioorg. Med. Chem. Lett. 9 1999 1469 1474
38. M. Aufort, M. Gonera, N. Chaignon, L. Le Clainche, and C. Dugave Eur. J. Med. Chem. 44 2009 3394 3401
39. M.F. Giblin, N. Wang, T.J. Hoffman, S.S. Jurisson, and T.P. Quinn Proc. Natl. Acad. Sci. U. S. A. 95 1998 12814 12818
40. M.F. Giblin, S.S. Jurisson, and T.P. Quinn Bioconjugate Chem. 8 1997 347 353
41. Z. Cheng, J. Chen, Y. Miao, N.K. Owen, T.P. Quinn, and S.S. Jurisson J. Med. Chem. 45 2002 3048 3056
42. Y. Barda, N. Cohen, V. Lev, N. Ben-Aroya, Y. Koch, E. Mishani, M. Fridkin, and C. Gilon Nucl. Med. Biol. 31 2004 921 933
43. H.M. Bigott-Hennkens, S. Junnotula, L. Ma, F. Gallazzi, M.R. Lewis, and S.S. Jurisson J. Med. Chem. 51 2008 1223 1230
44. G. Fridkin, T.A. Bonasera, P. Litman, and C. Gilon Nucl. Med. Biol. 32 2005 39 50
45. Y. Fu, M. Létourneau, Q.T. Nguyen, D. Chatenet, J. Dupuis, and A. Fournier Eur. J. Pharmacol. 617 2009 118 123
46. B. Costopoulos, D. Benaki, M. Pelecanou, E. Mikros, C.I. Stassinopoulou, A.D. Varvarigou, and S.C. Archimandritis Inorg. Chem. 43 2004 5598 5602
47. C. Clavaud, M. Heckenroth, C. Stricane, A. Menez, and C. Dugave Bioconjugate Chem. 17 2006 807 814
48. Z. Su, and Y. Xu J. Label Compd. Radiopharm. 51 2008 93 100
49. C. Clavaud, J. Le Gal, R. Thai, M. Moutiez, and C. Dugave ChemBioChem 9 2008 1823 1829
50. J.E. Cyr, D.A. Pearson, C.A. Nelson, B.A. Lyons, Y. Zheng, J. Bartis, J. He, M.V. Cantorias, and R.C. Howell J. Med. Chem. 50 2007 4295 4303
51. C. Clavaud, M. Heckenroth, C. Stricane, M.-A. Lelait, A. Menez, and C. Dugave ChemBioChem 7 2006 1352 1355
52. R. Dayam, F. Aiello, J. Deng, Y. Wu, A. Garofalo, X. Chen, and N. Neamati J. Med. Chem. 49 2006 4526 4534
53. L. Marinelli, A. Lavecchia, E. K-Gottschalk, E. Novellino, and H. Kessler J. Med. Chem. 46 2003 4393 4404
54. R. Haubner, D. Finsinger, and H. Kessler Angew. Chem. Int. Ed. Engl. 36 1997 1374 1379
55. W. Chan, and P. White Fmoc Solid Phase Peptide Synthesis 2000 Oxford University Press New York
56. Y. Yang, W.S. Sweeney, K. Schneider, S. Thörnqvist, B.T. Chait, and J.P. Tam Tetrahedron Lett. 35 1994 9689 9692
57. E. Nicolas, E. Pedroso, and E. Giralt Tetrahedron Lett. 30 1989 497 500
58. J. Zhu, and R.E. Marchant J. Pept. Sci. 14 2007 690 696
59. R.S. Feinberg, and R.B. Merrifiel J. Am. Chem. Soc. 97 1975 3485 3496
60. K. Schwochau Technetium: Chemistry and Radiopharmaceutical Applications 2000 Wiley-VCH
61. X. Wang, and Z. Guo Anti-cancer Agents Med. Chem. 7 2007 19 34
62. D.M. Townsend, K.D. Tew, and H. Tapiero Biomed. Pharmacother. 47 2003 145 155
63. P.J. Sadler, and Z. Guo Pure Appl. Chem. 70 1998 863 871
64. J.S. Lazo, S.M. Kuo, E.S. Woo, and B.R. Pitt Chem.Biol. Interact. 111-112 1998 255 262