Tyrosine modified analogues of the α4β7 integrin inhibitor biotin-R 8ERY prepared via Click Chemistry: Synthesis and biological evaluation

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 8, 2012, Pages 2638-2644

  Papst, Stefanie ^a   Noisier, Anaïs ^a   Brimble, Margaret A ^a   Yang, Yi ^a   Krissansen, Geoffrey W ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

Integrin inhibitors; Peptidomimetics

Indexed keywords

ALPHA4BETA7 INTEGRIN; BIOTIN; INTEGRIN; MANGANESE; PROTEIN INHIBITOR; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL ACTIVATION; CELL ADHESION; CLICK CHEMISTRY; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; MOUSE; NONHUMAN; T LYMPHOCYTE;

ANIMALS; BIOTIN; CELL LINE; CLICK CHEMISTRY; DOSE-RESPONSE RELATIONSHIP, DRUG; INTEGRINS; MICE; MODELS, BIOLOGICAL; MOLECULAR STRUCTURE; OLIGOPEPTIDES; STRUCTURE-ACTIVITY RELATIONSHIP; TYROSINE;

EID: 84862821407     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.02.035     Document Type: Article

References (44)

1. R.O. Hynes Cell 69 1992 11
2. J. Boer, D. Gottschling, A. Schuster, M. Semmrich, B. Holzmann, and H. Kessler J. Med. Chem. 44 2001 2586
3. D. Gottschling, J. Boer, A. Schuster, B. Holzmann, and H. Kessler Bioorg. Med. Chem. Lett. 11 2001 2997
4. M.E. Hemler Annu. Rev. Immunol. 8 1990 365
5. A.A. Postigo, P. Sanchez-Mateos, A.I. Lazarovits, F. Sanchez-Madrid, and M.O. de Landazuri J. Immunol. 151 1993 2471
6. I. Sircar, K.S. Gudmundsson, R. Martin, J. Liang, S. Nomura, H. Jayakumar, B.R. Teegarden, D.M. Nowlin, P.M. Cardarelli, J.R. Mah, S. Connell, R.C. Griffith, and E. Lazarides Bioorg. Med. Chem. 10 2002 2051
7. C. Berlin, E.L. Berg, M.J. Briskin, D.P. Andrew, P.J. Kilshaw, B. Holzmann, I.L. Weissman, A. Hamann, and E.C. Butcher Cell 74 1993 185
8. G. Kilger, and B. Holzmann J. Mol. Med. 73 1995 347
9. A.-C. Uhlemann, B. Brenner, E. Gulbins, O. Linderkamp, and F. Lang Biochem. Biophys. Res. Commun. 239 1997 68
10. G. Gorfu, J. Rivera-Nieves, and K. Ley Curr. Mol. Med. 9 2009 836
11. M.P. Schön, A. Arya, E.A. Murphy, C.M. Adams, U.G. Strauch, W.W. Agace, J. Marsal, J.P. Donohue, H. Her, D.R. Beier, S. Olson, L. Lefrancois, M.B. Brenner, M.J. Grusby, and C.M. Parker J. Immunol. 162 1999 6641
12. B.C. Sydora, N. Wagner, J. Lohler, G. Yakoub, M. Kronenberg, W. Müller, and R. Aranda Clin. Exp. Immunol. 129 2002 35
13. D. Picarella, P. Hurlbut, J. Rottman, X. Shi, E. Butcher, and D.J. Ringler J. Immunol. 158 1997 2099
14. B.G. Feagan, G.R. Greenberg, G. Wild, R.N. Fedorak, P. Pare, J.W. McDonald, R. Dube, A. Cohen, A.H. Steinhart, S. Landau, R.A. Aguzzi, I.H. Fox, and M.K.N. Vandervoort Engl. J. Med. 352 2005 2499
15. S. Ueha, M. Murai, H. Yoneyama, M. Kitabatake, T. Imai, T. Shimaoka, S. Yonehara, S. Ishikawa, and K. Matsushima J. Leukoc. Biol. 81 2007 176
16. X. Yang, H.-K. Sytwn, H.O. McDevitt, and S.A. Michie Diabetes 46 1997 1542
17. J.R. Kanwar, J.E.B. Harrison, D. Wang, E. Leung, N. Wagner, W. Müller, and G.W. Krissansen J. Neuroimmunol. 103 2000 146
18. L.S. Lin, T. Lanza Jr., E. McCauley, G. Van Riper, U. Kidambi, J. Cao, L.A. Egger, R.A. Mumford, J.A. Schmidt, M. MacCoss, and W.K. Hagmann Bioorg. Med. Chem. Lett. 12 2002 133
19. L.L. Chang, Q. Truong, R.A. Mumford, L.A. Egger, U. Kidmbi, K. Lyons, E. McCauley, G. Van Riper, S. Vincent, J.A. Schmidt, M. MacCoss, and W.K. Hagmann Bioorg. Med. Chem. Lett. 12 2002 159
20. O. Saku, K. Ohta, E. Arai, Y. Nomoto, H. Miura, H. Nakamura, E. Fuse, and Y. Nakasato Bioorg. Med. Chem. Lett. 18 2008 1053
21. D.J. Mitchell, D.T. Kim, L. Steinman, C.G. Fathman, and J.B. Rothbard J. Peptide Res. 56 2000 318
22. R. Sawant, and V. Torchilin Mol. BioSyst. 6 2010 628
23. K.M. Stewart, K.L. Horton, and S.O. Kelley Org. Biomol. Chem. 6 2008 2242
24. G.W. Krissansen, J. Singh, R.K. Kanwar, Y.-C. Chan, E. Leung, K.B. Lehnert, J.R. Kanwar, and Y. Yang Eur. J. Immunol. 36 2006 2203
25. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem. Int. Ed. 40 2001 2004
26. C.W. Tornoe, C. Christensen, and M. Meldal J. Org. Chem. 67 2002 3057
27. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2596
28. N. Miller, G.M. Williams, and M.A. Brimble Int. J. Pept. Res. Ther. 16 2010 125
29. E. Saxon, and C.R. Bertozzi Science 287 2000 2007
30. K.L. Kiieck, E. Saxon, D.A. Tirrel, and C.R. Bertozzi Proc. Natl. Acad. Sci. U.S.A. 99 2002 19
31. W.G. Lewis, L.G. Green, F. Grynszpan, Z. Radic, P.R. Carlier, P. Taylor, M.G. Finn, and K.B. Sharpless Angew. Chem. 114 2002 1095 Angew. Chem. Int. Ed. 2002, 41, 1053
32. A. Deiters, T.A. Cropp, M. Mukherji, J.W. Chin, J.C. Anderson, and P.G. Schultz J. Am. Chem. Soc. 125 2003 11782 11783
33. S. Reitz, M. Cebi, P. Reiß, G. Studnik, U. Linne, U. Koert, and L.-O. Essen Angew. Chem., Int. Ed. 48 2009 4853
34. D.J. Lee, K. Mandal, P.W.R. Harris, M.A. Brimble, and S.B.H. Kent Org. Lett. 11 22 2009 5270
35. M.A. Maier, C.G. Yannopoulos, N. Mohamed, A. Roland, H. Fritz, V. Mohan, G. Just, and M. Manoharan Bioconjugate Chem. 14 2003 18
36. D.J. Lee, P.W.R. Harris, and M.A. Brimble Org. Biomol. Chem. 9 2011 1621
37. H. Yu, H.A. Chokhawala, A. Varki, and X. Chen Org. Biomol. Chem. 5 2007 2458
38. E.D. Goddard-Borger, and R.V. Stick Org. Lett. 9 19 2007 3797
39. S.G. Gouin, and J. Kovensky Tetrahedron Lett. 48 2007 2875
40. K. Asano, and S. Matsubara Org. Lett. 12 21 2010 4988
41. S. Figaroli, and A. Madder Tetrahedron 66 2010 6912
42. J.T. Lundquist, and J.C. Pelletier Org. Lett. 3 5 2001 781
43. N. Miller, G.M. Williams, and M.A. Brimble Org. Lett. 11 11 2009 2409
44. L.A. Alexandrova, A.Y. Skoblov, M.V. Jasko, L.S. Victotova, and A.A. Krayevsky Nucleic Acids Research 26 3 1998 778