Rate and extent of ion-exchange process: the effect of physico-chemical characteristics of salicylate anions.

Ten salicylate anions were used as model compounds in order to investigate systematically the impact of compound lipophilicity, valence, aqueous solubility and hydrogen bonding on binding into and release from a strong anion-exchange fiber, Smopex DS-218v. The release of salicylates from the fiber was studied at 1/10, 1/1 or 10/1 molar ratios of the external chloride-ions versus the salicylate bound in the fiber. The Donnan potential between the fiber and external solution (electrostatic interaction) appeared to be the main factor affecting the release of salicylates from the strong base anion-exchange fiber--an increase in the molar amount of the external chloride-ions resulted in a more effective release of all the salicylates from the fiber. The highest chloride-ion concentration (10/1) released the monovalent salicylates practically completely, while the lowest concentration (1/10) released only 10-35% of the loaded salicylates. The nature and strength of salicylate binding to the fiber by non-electrostatic interactions affected also the ion-exchange process, especially in dilute Cl- solutions. Hydrophobic interactions decreased the rate and amount of drug release from the fiber with the most lipophilic salicylates. Hydrogen bonding between the fiber and the compound restricted also the rate and extent of ion-exchange process of the hydrophilic 5-aminosalicylic acid and 5-hydroxysalicylic acid. The amount of divalent 5-carboxylsalicylic acid bound into and released from the fiber was clearly smaller as compared to the monovalent salicylates potentially due to cross-linking of the fiber chains.