Michael-type addition as a tool for surface functionalization

Bioconjugate Chemistry

Volumn 14, Issue 5, 2003, Pages 967-973

  Heggli, Martin ^c   Tirelli, Nicola ^a,b   Zisch, Andreas ^a   Hubbell, Jeffrey A ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

^c ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

COLLOIDAL CARRIERS; CONJUGATE ADDITION REACTIONS; GROUP BOUND; MICHAEL-TYPE ADDITIONS; REACTION PARTNERS; SURFACE FUNCTIONALIZATION;

ADDITION REACTIONS;

ACRYLIC ACID DERIVATIVE; ALKENE DERIVATIVE; MACROGOL; THIOL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; ELECTRON; MICHAEL ADDITION; PEPTIDE SYNTHESIS; SURFACE PROPERTY;

EID: 0141569715     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc0340621     Document Type: Article

References (36)

1. Kasemo, B., and Gold, J. (1999) Implant surfaces and interface processes. Adv. Dent. Res. 13, 8.
2. Jones, F. H. (2001) Teeth and bones: applications of surface science to dental materials and related biomaterials. Surf. Sci. Rep. 42, 79.
3. Klee, D., and Hocker, H. (1999) Polymers for biomedical applications: Improvement of the interface compatibility. Biomedical Applications: Polymer Blends. Adv. Polym. Sci. 149, 1.
4. Cai, K. Y., Lin, S. B., and Yao, K. D. (2001) Advances in research on surface engineering of biomaterials for tissue engineering. Prog. Chem. 13, 56.
5. Folch, A., and Toner, M. (2000) Microengineering of cellular interactions. Annu. Rev. Biomed. Eng. 2, 227.
6. Heibel, C., Maus, S., Knoll, W., and Ruhe, J. (1998) Polymer-supported biomembrane models. Organic Thin Films (ACS Symposium Series 695) p 104, American Chemical Society, Washington.
7. Kasemo, B. (1998) Biological surface science. Curr. Opin. Solid State Mater. Sci. 3, 451.
8. Massia, S. P., and Hubbell, J. A. (1990) Covalently attached GRGD on polymer surfaces promotes biospecific adhesion of mammalian cells. Ann. N.Y. Acad. Sci. 589, 261.
9. Marchand-Brynaert, J., Detrait, E., Noiset, O., Boxus, T., Schneider, Y. J., and Remacle, C. (1999) Biological evaluation of RGD peptidomimetics, designed for the covalent derivatization of cell culture substrata, as potential promoters of cellular adhesion. Biomaterials 20, 1773.
10. Noiset, O., Schneider, Y. J., and Marchand-Brynaert, J. (1999) Fibronectin adsorption or and covalent grafting on chemically modified PEEK film surfaces. J. Biomat. Sci.-Polym. E. 10, 657.
11. Liu, J., Zhang, Q., Remsen, E. E., and Wooley, K. L. (2001) Nanostructured materials designed for cell binding and transduction. Biomacromolecules 2, 362.
12. Merrett, K., Griffith, C. M., Deslandes, Y., Pleizier, G., and Sheardown, H. (2001) Adhesion of corneal epithelial cells to cell adhesion peptide modified pHEMA surfaces. J. Biomater. Sci. Polym. Ed. 12, 647.
13. Chevolot, Y., Bucher, O., Leonard, D., Mathieu, H. J., and Sigrist, H. (1999) Synthesis and characterization of a photoactivatable glycoaryldiazirine for surface glycoengineering. Bioconjugate Chem. 10, 169.
14. Gao, H., Sanger, M., Luginbuhl, R., and Sigrist, H. (1995) Immunosensing with photoimmobilized immunoreagents on planar optical wave guides. Biosens. Bioelectron. 10, 317.
15. Mann, B. K., Tsai, A. T., Scott-Burden, T., and West, J. L. (1999) Modification of surfaces with cell adhesion peptides alters extracellular matrix deposition. Biomaterials 20, 2281.
16. Irvine, D. J., Ruzette, A. V., Mayes, A. M., and Griffith, L. G. (2001) Nanoscale Clustering of RGD Peptides at Surfaces Using Comb Polymers. 2. Surface Segregation of Comb Polymers in Polylactide. Biomacromolecules 2, 545.
17. McMillan, R., Meeks, B., Bensebaa, F., Deslandes, Y., and Sheardown, H. (2001) Cell adhesion peptide modification of gold-coated polyurethanes for vascular endothelial cell adhesion. J. Biomed. Mater. Res. 54, 272.
18. Quirk, R. A., Chan, W. C., Davies, M. C., Tendler, S. J., and Shakesheff, K. M. (2001) Poly(L-lysine)-GRGDS as a biomimetic surface modifier for poly(lactic acid). Biomaterials 22, 865.
19. Neff, J. A., Caldwell, K. D., and Tresco, P. A. (1998) A novel method for surface modification to promote cell attachment to hydrophobic substrates. J. Biomed. Mater. Res. 40, 511.
20. Neff, J. A., Tresco, P. A., and Caldwell, K. D. (1999) Surface modification for controlled studies of cell-ligand interactions. Biomaterials 20, 2377.
21. Romanowska, A., Meunier, S. J., Tropper, F. D., Laferrière, C. A., and Roy, R. (1994) Michael Additions for Syntheses of Neoglycoproteins. Methods Enzymol. 242, 90.
22. Lutolf, M. P., Tirelli, N., Cerritelli, S., Cavalli, L., and Hubbell, J. A. (2001) Systematic Modulation of Michael-Type Reactivity of Thiols through the Use of Charged Amino Acids. Bioconjugate Chem. 12, 1051.
23. Elbert, D. L., Pratt, A. B., Lutolf, M. P., Halstenberg, S., and Hubbell, J. A. (2001) Protein delivery from materials formed by self-selective conjugate addition reactions. J. Controlled Release 76, 11.
24. Bontempo, D., Tirelli, N., Masci, G., Crescenzi, V., and Hubbell, J. A. (2002) Thick coating and functionalization of organic surfaces via ATRP in water. Macromol. Rapid Commun. 23, 418.
25. Napoli, A., Tirelli, N., Wehrli, E., and Hubbell, J. A. (2002) Lyotropic behavior in water of amphiphilic ABA triblock copolymers based on poly(propylene sulfide) and poly(ethylene glycol). Langmuir 18, 8324.
26. Rehor, A., Tirelli, N., and Hubbell, J. A. (2002) A new living emulsion polymerization mechanism: Episulfide anionic polymerization. Macromolecules 35, 8688.
27. Ramires, P. A., Mirenghi, L., Romano, A. R., Palumbo, F., and Nicolardi, G. (2000) Plasma-treated PET surfaces improve the biocompatibility of human endothelial cells. J. Biomed. Mater. Res. 51, 535.
28. Griesser, H. J., Chatelier, R. C., Gengenbach, T. R., Johnson, G., and Steele, J. G. (1994) Growth of Human-Cells on Plasma Polymers - Putative Role of Amine and Amide Groups. J. Biomater. Sci.-Polym. Ed. 5, 531.
29. Look, G. C., Holmes, C. P., Chinn, J. P., and Gallop, M. A. (1994) Methods for Combinatorial Synthesis: The Use of Fast 13C NMR Analysis for Gel Phase Reaction Monitoring. J. Org. Chem. 59, 7588.
30. Takahashi, N., and Creighton, T. E. (1996) On the reactivity and ionization of the active site cysteine residues of escherichia coli thioredoxin. Biochemistry 35, 8342.
31. Stolnik, S., Illum, L., and DAVIS, S. S. (1995) Long Circulating Microparticulate Drug Carriers. Adv. Drug Delivery Rev. 16, 215.
32. Peracchia, M. T., Fattal, E., Desmaele, D., Besnard, M., Noel, J. P., Gomis, J. M., M., A., D'Angelo, J., and Couvreur, P. (1999) Stealth (R) PEGylated polycyanoacrylate nanoparticles for intravenous administration and splenic targeting. J. Controlled Release 60, 121.
33. Gref, R., Luck, M., Quellec, P., Marchand, M., Dellacherie, E., Harnisch, S., Blunk, T., and Muller, R. H. (2000) 'Stealth' corona-core nanoparticles surface modified by poly(ethylene glycol) (PEG): influences of the corona (PEG chain length and surface density) and of the core composition on phagocytic uptake and plasma protein adsorption. Colloids Surf. B 18, 301.
34. Kingshott, P., and Griesser, H. J. (1999) Surfaces that resist bioadhesion. Curr. Opin. Solid State Mater. Sci. 4, 403.
35. Hansell, P., Maione, T. E., and Borgstrom, P. (1995) Selective binding of platelet factor 4 to regions of active angiogenesis in vivo. Am. J. Physiol. 269, H829.
36. Maione, T. E., Gray, G. S., Petro, J., Hunt, A. J., Donner, A. L., Bauer, S. I., Carson, H. F., and Sharpe, R. J. (1990) Inhibition of angiogenesis by recombinant human platelet factor-4 and related peptides. Science 247, 77.