Double-Tailed Perfluoroalkylated Glycolipids as Components for Drug Delivery and Targeting Systems. Preliminary Biocompatibility Results

Abstract

Vesicles are being investigated as drug carriers, especially for enhancing the therapeutic effectiveness of the drug while minimizing its side effects. Drug targeting can be achieved if there is a specific recognition of the vesicle's outer wall by specific cells. With these objectives in mind new glycolipids fitted with fluorinated, hydrogenated or mixed, single and double-tails, containing either a gluco- or a galactopyranose residue in their hydrophilic head, were synthesized and their ability to achieve self-organized supramolecular systems was assessed. Replacement of hydrogen by fluorine in these glycolipids was found to enhance biological tolerance. Thus, a fluorinated single-tailed glycolipid displayed no action on red blood cells at concentrations as high as 50 g/l while its hydrogenated analog was hemolytic at 5 g/l. 100% of survival was obtained one month after intravenous or intraperitoneal injection into mice of isotonic dispersions of single and double-tailed glycolipids at a dose of 500 mg/kg. These glycolipids were innocuous on Namalva cell cultures at a concentration of 0.1 g/l.

Carbohydrate-Derived Surfactants

“…The investigation of carbohydrate derived fluorinated amphiphiles has been expending in the recent years [61]. Several works describing the preparation of fluorinated alkyl amides [66][67][68][69][70][71][72][73], ureas [74,75] or carbamates [76][77][78][79][80] derived from carbohydrates have been published. Several works describing the preparation of fluorinated alkyl amides [66][67][68][69][70][71][72][73], ureas [74,75] or carbamates [76][77][78][79][80] derived from carbohydrates have been published.…”

“…Treatment of 1-amino-1-deoxy-lactitol derivative 56 with the fluorinated acylating reagent 57 gave compound 58 (yield 20%) [72].F-alkyl-D-gluconamides 59[68,72] and F-alkyl-Dlactobionamides 61 and 63[65,[68][69][70][71][72][73] were obtained from Treatment of 1-amino-1-deoxy-lactitol derivative 56 with the fluorinated acylating reagent 57 gave compound 58 (yield 20%) [72].F-alkyl-D-gluconamides 59[68,72] and F-alkyl-Dlactobionamides 61 and 63[65,[68][69][70][71][72][73] were obtained from…”

Perfluorocarbon nanodroplets stabilized by fluorinated surfactants: characterization and potentiality as theranostic agents

“…Even if little is known about their toxicity, several studies have used them in contrast agent formulation. 19,23,24 Another uorinated surfactant, called FTAC, was initially designed in the nineties as an oxygen carrier 25,26 and a drug carrier. 27,28 It was later used for the solubilization of membrane proteins.…”