Benzylprotected aromatic phosphonic acids for anchoring peptides on titanium

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 2, 2006, Pages 271-273

  Auernheimer, Jörg ^a   Kessler, Horst ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Benzyl protected phosphonic acids; Cell adhesion; Cyclic RGD peptide; Integrin v 3 binding to surfaces; Multimeric phosphonic acids for coating titanium surfaces; Phosphonic acids for coating titanium surfaces; Titanium surface coating

Indexed keywords

BENZYL DERIVATIVE; PEPTIDE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; TITANIUM;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DEPROTECTION REACTION; DRUG SYNTHESIS; MOUSE; NONHUMAN;

ANIMALS; BENZOIC ACIDS; CELL ADHESION; HYDROCARBONS, AROMATIC; MICE; MOLECULAR STRUCTURE; OLIGOPEPTIDES; OSTEOBLASTS; PHOSPHONIC ACIDS; SILANES; TITANIUM; TRIFLUOROACETIC ACID;

ANIMALIA;

EID: 27944450677     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.10.018     Document Type: Article

References (21)

1. T. Albrektsson J. Prosthet. Dent. 50 1983 255
2. P.I. Branemark J. Prosthet. Dent. 50 1983 399
3. M. Rocca, M. Fini, G. Giavaresi, N. Nicoli Aldini, and R. Giardin Int. J. Artif. Organs 24 2001 649
4. R. Haubner, R. Gratias, B. Diefenbach, S.L. Goodman, A. Jonczyk, and H. Kessler J. Am. Chem. Soc. 118 1996 7461
5. M. Kantlehner, P. Schaffner, D. Finsinger, J. Meyer, A. Jonczyk, B. Diefenbach, B. Nies, G. Holzemann, S.L. Goodman, and H. Kessler ChemBioChem 1 2 2000 107
6. M. Pfaff, K. Tangemann, B. Müller, M. Gurrath, G. Müller, H. Kessler, R. Timpl, and J. Engel J. Biol. Chem. 269 1994 20233
7. E.A. Wayner, R.A. Orlando, and D.A. Cheresh J. Cell Biol. 113 1991 919
8. D.I. Leavesley, G.D. Ferguson, E.A. Wayner, and D.A. Cheresh J. Cell Biol. 117 5 1992 1101
9. H. Schliephake, D. Scharnweber, M. Dard, S. Rößler, A. Sewing, J. Meyer, and D. Hoogestraat Clin. Oral Implants Res. 13 2002 312
10. B. Elmengaard, J.E. Bechtold, and K. Søballe Biomaterials 26 2005 3521
11. E. Steinhauser, A. Liebendörfer, A. Enderle, R. Bader, S. Kerschbaumer, T. Brill, R. Busch, and R. Gradinger MP Materialprüfung 47 4 2005 197
12. Auernheimer, J.; Zukowski, D.; Dahmen, C.; Kantlehner, M.; Enderle, A.; Goodman, S.L.; Kessler, H. ChemBioChem 2005, in press.
13. S. Rensing, M. Arendt, A. Springer, T. Grawe, and T. Schrader J. Org. Chem. 66 2001 5814
14. M. Saady, L. Lebeau, and C. Mioskowski Helv. Chim. Acta 78 1995 670
15. 1H NMR (DMSO, 500 MHz): δ (ppm) = 7.80 (2H, s), 7.26 (1H, s), 7.31-7.27 (20H, m), 4.94 (8H, m), 3.37 (4H, dd, J = 5.6, 21.6 Hz).
16. K. Barlos, D. Gatos, J. Kallitsis, G. Papaphotiu, P. Sotiriu, Y. Weqing, and W. Schäffer Tetrahedron Lett. 30 1989 3943
17. G.B. Fields, and R.L. Noble Int. J. Pept. Protein Res. 35 3 1990 161
18. 1 equiv anchor, 1.1 equiv HOAt, 0.97 equiv HATU, and 10 equiv collidine in 2 mL DMF activation for 2 h followed by addition of 1 equiv cyclo(-R(Pbf)GD(OtBu)fK-). Precipitation in water after 24 h.
19. 2O in 30 min. Both with 0.1% TFA.
20. These cells express the αvβ3 and αvβ5 integrins; this was proven by FACS analysis and real-time-PCR. Schaffner, P. Ph.D. thesis, TU Darmstadt, 2003.
21. U. Landegren J. Immunol. Methods 67 1984 379