Adhesion to and decalcification of hydroxyapatite by carboxylic acids.

Fundamental to the processes of decalcification of or adhesion to mineralized tissues is the molecular interaction of acids with hydroxyapatite. This study was undertaken to chemically analyze the interaction of 1 mono-, 2 di-, 1 tri-, and 2 polycarboxylic acids with hydroxyapatite in an attempt to elucidate the underlying mechanism. Maleic, citric, and lactic acid decalcified hydroxyapatite, in contrast to oxalic acid and the two polycarboxylic acids that were chemically bonded to hydroxyapatite. Solubility tests showed that the calcium salts of the former were very soluble, whereas those of the latter could hardly be dissolved in the respective acid solutions. Based on these data, an adhesion/decalcification concept was advanced that predicts that carboxylic acids, regardless of concentration/pH, either adhere to or decalcify hydroxyapatite, depending on the dissolution rate of the respective calcium salts in the acid solution. This contrasting behavior of organic acids most likely results from their differential structural conformations.