Synthesis of Polymerizable Cyclodextrin Derivatives for Use in Adhesion-Promoting Monomer Formulations

Area of Science:

• Polymer Chemistry
• Biomaterials Science
• Dental Materials

Background:

• Beta-cyclodextrin (a cyclic oligosaccharide) possesses numerous hydroxyl groups available for chemical modification.
• Current dental resins and composites primarily utilize methacrylate monomers, limiting adhesion to hydrated biological tissues.
• Hydrolytically stable ether linkages are desirable for durable biomaterial applications.

Purpose of the Study:

• To synthesize novel cyclodextrin derivatives with polymerizable groups for enhanced dental adhesion.
• To explore the potential of these derivatives in copolymerization with existing dental resin systems.
• To investigate the interaction of these derivatives with dentin and enamel components.

Main Methods:

• Literature research and three-dimensional molecular modeling guided the synthesis strategy.
• Derivatization of beta-cyclodextrin hydroxyl groups with vinylbenzylether and hexanoate moieties.
• Analysis of reaction products to determine the combination and number of functional groups per molecule.

Main Results:

• A family of cyclodextrin derivatives with varying vinylbenzyl and hexanoate groups was synthesized.
• The derivatives contain polymerizable vinylbenzylether groups capable of homopolymerization and copolymerization with methacrylates.
• Hydrophilic ligands and residual hydroxyl groups facilitate penetration into hydrated dentin and enamel.

Conclusions:

• The synthesized cyclodextrin derivatives support the hypothesis of improved adhesive bonding to dentin.
• These novel materials show promise for creating stronger and more durable attachments to hydrated biological substrates.
• Further synthetic optimization is planned to ensure consistent incorporation of copolymerizable moieties for widespread benefits in dental and biomedical applications.