A synthetic model glycoprotein was successfully synthesized using gelatin and mono-6-para-toluenesulfonyl-β-cyclodextrin which were reacted under microwave conditions in basic media. The resulting glycoprotein is observed to form intermolecular inclusion complexes through complexation of the aromatic moieties along the polymer chain by the attached cyclodextrins. This phenomenon was analyzed and proven by 2D NMR spectroscopy (ROESY) and dynamic light scattering (DLS). Above the denaturation temperature, a strong increase of the hydrodynamic diameter was found due to enhanced supramolecular agglomeration. Such a novel glycoprotein with supramolecular self-recognition would be promising in biomedical applications serving as a drug-delivery basis polymer.
Hydrolyzed cyclocopolymer prepared from divinyl ether and maleic anhydride, poly[(divinyl ether)-co-(maleic anhydride)] (DIVEMA), was functionalized with aminoadamantane and subsequently compared with the hydrolyzed DIVEMA with respect to physicochemical properties. The complexation behavior of adamantyl modified DIVEMA with cyclodextrin derivatives was examined by dynamic light scattering, nuclear magnetic resonance spectroscopy and zeta potential. The scattering studies indicated the formation of well-defined aggregated structures with an average diameter of 120 nm. These aggregated structures collapsed on addition of randomly methylated β-cyclodextrin to give 4.2 nm in hydrodynamic diameter. Interactions with crosslinked β-cyclodextrins indicated gel formation which was analyzed by means of rheology and temperature-dependent viscosity showing disaggregation of the host-guest system at 42 • C. This novel physical hydrogel is very interesting for medical applications as a drug delivery system with included anti-tumor activity.
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