Amphiphilic sugar phosphates with single or double perfluoroalkylated hydrophobic chains for use in oxygen and drug delivery systems.
New anionic amphiphiles with a phosphate ester junction between the fluorophilic-lipophilic tail and the sugar-based hydrophilic head were synthesized and evaluated. The single hydrophobic chain surfactants 1 a, b and 2a allowed the preparation of stable and fine highly concentrated emulsions of perfluorodecalin or perfluoroocytl bromide, either when used alone or in conjunction with egg yolk phospholipids (EYP). Surfactants 3d, 5d, 6d and 6e, with two hydrophobic chains, one fluorinated the other not, gave liposomal structures, and displayed encapsulation properties for carboxyfluorescein. The phosphodiesters tested cause no significant inhibition of the growth and viability of Namalva cell cultures (0.1-1 g/L range). Single chain phosphodiesters manifest no detectable hemolytic activity (at 100 g/L for 1a) whereas double chain compounds do moderately (ca 20% hemolysis at 20 g/L). The maximum tolerated dose compatible with the survival of all of a series of 10 intravenously injected mice is in 130 mg/kg body weight range.
Guillod
F
F
Université de Nice-Sophia Antipolis, Laboratoire de Chimie Moléculaire, Unité Associée au CNRS 426, Parc Valrose, France.
Greiner
J
J
Milius
A
A
Riess
J G
JG
D000478:Alkylation; D001802:Blood Substitutes / Q000737:chemistry*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004337:Drug Carriers; D016503:Drug Delivery Systems; D004355:Drug Stability; D004655:Emulsions; D005069:Evaluation Studies as Topic; D005466:Fluorocarbons / Q000737:chemistry*; D006842:Hydrocarbons, Brominated; D008081:Liposomes; D008422:Materials Testing; D015394:Molecular Structure; D010100:Oxygen / Q000008:administration & dosage*; D012995:Solubility; D013403:Sugar Phosphates / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D001802:Blood Substitutes; D004337:Drug Carriers; D004655:Emulsions; D005466:Fluorocarbons; D006842:Hydrocarbons, Brominated; D008081:Liposomes; D013403:Sugar Phosphates; D014867:Water; C008805:perfluorodecalin; C003072:perflubron; D010100:Oxygen