Substitutes for N-phenylglycine in adhesive bonding to dentin

Using bond strength measurements, we investigated a number of related compounds in order to elucidate the role of the surface-active ingredient, N-phenylglycine (NPG), in experimental two-step and three-step bonding protocols resulting in adhesive bonding to dentin. All active compounds identified for the two-step or the three-step protocol were N-aryl-alpha-amino acids, and the results delineate some of the key features of the NPG molecule for bonding. For the three-step protocol, there was a requirement for a secondary or tertiary aromatic amino group, a carboxylic acid group, and a single (secondary or tertiary) methylene unit between those two functional groups of the amino acid. For the two-step protocol, additional substitutions at the para position of the phenyl ring on the amine improved the bond strength. In both protocols, para-methyl- and para-chloro-substituted NPG analogues ranked higher than NPG. A "catalytic" effect of the aromatic tertiary amino group on the polymerization of the adhering resin in both procedures could not be ruled out.