Leila Zarif

Perfluoroalkylated monoesters of 1,4-D-sorbitan, isosorbide and isomannide: new surfactants for biomedical applications

Abstract A one step selective synthesis of pure 1,4-D-Sorbitan monoesters 4 was achieved by treating 1,4-D-Sorbitan 1 with RF(CH2)nCOCI (RF=C4F9, C5F11, C8F17; n = 2, 10) in pyridine at room temperature. 13C NMR establishes that esterification occurred on carbon 6 only. While isomannide, 3, gives only one monoester, 8, the less symmetrical isosorbide 2 leads to two monoesters displaying significantly different physical properties. These compounds display moderate surface activities and do not perturb the growth and viability of Namalva lymphoblastoid cell cultures.

New fluorinated biocompatible non-ionic telomeric amphiphiles bearing trishydroxymethyl groups

Abstract New perfluoroalkylated telomeric surfactants derived from tris(hydroxymethyl)aminomethane were synthesized in two steps and 50% overall yield. These surfactants display significantly better surface activity and enhanced capacity to emulsify fluorocarbons compared to Pluronic F-68®. Preliminary in vitro and in vivo evaluation (cell cultures, hemolysis, LD50 i.v. in mice) indicates that this type of compounds is remarkably non-toxic, and could find applications in preparations for biomedical uses including injectable fluorocarbon emulsions. New perfluoroalkylated telomeric surfactants derived from tris(hydroxymethyl)aminomethane were synthesized in 50% overall yield. These surfactants display significantly better surface activity, enhanced capacity to emulsify fluorocarbons compared to Pluronic F-68®, and are not hemolytic.