Recurrent caries (tooth decay) is the most frequent cause for the failure of dental restorations. Fluoride-releasing restorative materials reduce recurrent caries at the restoration margins. Composite resin filling materials have been widely used in restorative dentistry because they have high strength and good esthetics, but they have low fluoride release and recharge capabilities and require bonding agents to bond to tooth structure. Current dental bonding agents have little fluoride-releasing and recharging capabilities and form a barrier hindering the transport of fluoride from the restorative materials into the tooth structures. Sealants, which are resins with or without fillers, have been used to fill the pits and fissures in posterior teeth, but many dentists are reluctant to use sealants because they fear that caries in sealed carious pits or fissures may progress. The goal of this project is to develop a series of new adhesive chelating monomers that have high fluoride release and recharge capability. These new monomers will have potential applications in many resin-based dental materials. In this in-vitro study, the applications of the new monomers in dental bonding agents and sealants will be explored. The hypotheses are (1) the new monomers will have adhesive and self-etching capabilities; (2) the fluoride-releasing bonding agents based on these new monomers will release fluoride directly into the tooth structure; (3) the new bonding agents will facilitate the transport of fluoride from fluoride-releasing compomers and composites to the tooth structure; and (4) the sealant containing the new monomers will have better adhesion to enamel and fluoride-releasing and recharging capabilities and thus inhibit the potential carious process beneath the sealant. The fluoride-releasing bonding agents and sealants will be formulated and fabricated. The bonding strength, fluoride release and recharge capability will be tested and optimized. Artificial caries and microleakage studies will be conducted. If this project is successful, the fluoride-releasing materials based on these new monomers will significantly reduce the recurrent caries around the restoration, and therefore, they will have significant oral health benefits and economic impact.