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Abstract
AbstractA new family of perfluoroalkyl double‐tailed amphiphiles was synthesized in order to develop a new drug carrying and delivery system. They were 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 disulfide 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 double‐tailed amphiphiles. Preliminary biological tests showed no detectable 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 hemolytic at 0,002 mmol/L. The LD50 was found to be higher than 2500 mg/kg of animal.
Published Version
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