Biocompatibility of alkyl and perfluoroalkyl telomeric surfactants derived from THAM

A preliminary, comparative biological evaluation of two new families of non-ionic telomeric surfactants derived from Tris(hydroxymethyl)acrylaminomethane (THAM) is reported. These trisacryl conjugates, or TAC, were designed with the purpose of improving the stability and biocompatibility of fluorocarbon emulsions to be used in injectable oxygen-delivering systems. Their amphiphilic character arises from the simultaneous presence in the same molecule of several hydrophilic THAM residues and of a hydrophobic tail consisting in either a hydrocarbon (H-TAC family) or a fluorocarbon (F-TAC family) chain. The acute toxicity in mice after intravenous injection is low (LD50 in the 625 to 1250 mg/kg body weight range for the H-TAC compared to 630 to 4500 mg/kg body weight range for F-TAC) and increases with the length of the hydrophobic chain. No hemolytic activity was detected for the F-TAC at concentrations up to 200 g/l, while hemolysis is found for the H-TAC at a concentration of 5 g/l or less and increases with the alkyl chain length. The impact of the new surfactants on the growth and viability of Namalva cell cultures also increases with the length of the hydrophobic chain, with again a better tolerance for the F-TAC. Altogether the fluorinated amphiphiles display better tolerance than their hydrocarbon analogs in spite of their significantly increased surface activity. Both families of compounds appear to have potential as strongly hydrophilic surfactants for biomedical applications.