DOUBLE-TAILED PERFLUOROALKYL TELOMERIC SURFACTANTS DERIVED FROM TRIS(HYDROXYMETHYL)ACRYLAMIDOMETHANE FOR MEDICAL APPLICATIONS

A new family of perfluoroalkyl double-tailed amphiphiles was synthesiz ed in order to develop a new drug carrying and delivery system. They w ere obtained by telomerization of tris(hydroxymethyl)acrylamidomethane (THAM) in the presence of various double-tailed primary and secondary thiols as chain-transfer agents, and with AIBN as the initiator. With secondary thiols, telomerization occurred in low yields (25-35% with respect to the thiol), because of the competitive formation of a disul fide by-product, but proceeded in higher yields (45-90%, depending on the stoichiometry of the reagents) with primary thiols, thus allowing the preparation of a new family of perfluoroalkyl telomeric THAM doubl e-tailed amphiphiles. Preliminary biological tests showed no detectabl e hemolytic activity on human red blood cells at concentrations up to 20 mmol/L (50-65 g/L), whereas the hydrocarbon analogs proved to be he molytic at 0,002 mmol/L. The LD50 was found to be higher than 2500 mg/ kg of animal.