An important parameter for successful integration of artificial implants into the body is the cell adhesion at the implant surface. In the past, proteins such as fibronectin, collagen or small peptides like the RGD motif have been immobilized on implants to enhance cell adhesion.
[1] The glyco-conjugates in the extracellular matrix affect cell adhesion as well. Investigating the influence of carbohydrates on cell adhesion is a promising field because it was already shown that HaCaT cells show an enhanced adherence on a galactose-modified poly(d,l)lactic acid surface.
[2]
The aim of this study is the improvement of cell adhesion to surfaces by immobilized carbohydrates. We synthesized a library of monosaccharides α- and β-O-glycosidically attached to an oligo(ethylene glycol) linker. This linker ensures high water solubility and reduces non-specific binding of proteins. Effective 1,2-trans-glycosylation was achieved with the trichloroacetimidate method. The 1,2-cis-glycosides were synthesized by using benzyl protecting groups and an apple-type glycosylation reaction. The glycosides were covalently attached to a succinimidyl-activated glass surface by amide coupling and the efficiency of the coupling was tested with fluorescently labeled lectins. With this library in hand we can investigate the effect of carbohydrate-modified surfaces on cell adhesion.
[1] S. R. Meyers and M. W. Grinstaff, Chem. Rev. 2012, 112, 1615-1632
[2] F. Renò, V. Traina, S. Gatti, E. Battistella, M. Cannas, Biotechnol. Bioeng. 2008, 100, 195-202
Acknowledgement: This work was supported by contract research ‘Glykobiologie/Glykomik’ of the Baden-Württemberg Stiftung.
