Solubilization of hydrophobic drugs in octanoyl-6-O-ascorbic acid micellar dispersions.
Alkanoyl-6-O-ascorbic acid esters are easily obtained from vitamin C, and produce self-assembled aggregates in water solutions, with an inner hydrophobic pool surrounded by an external hydrophilic shell. Compared to ascorbic acid, their solubility in oils and fats is greatly enhanced, while the peculiar antioxidant activity is retained in the polar head groups of such surfactants. In virtue of their amphiphilic nature, ascorbic acid-based supramolecular systems can dissolve relevant amounts of hydrophobic, poorly water soluble chemicals such as drugs, vitamins, and so on, and at the same time they provide a suitable shield against oxidative deterioration of valuable materials. In this article we report our study on the self-assembling properties of octanoyl-6-O-ascorbic acid in water, and on the solubilization of some lipophilic molecules in its dispersions.
Departamento de Farmacia, Fac. de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, 5000, Argentina.
Santiago
S
Palma
Ruben Hilario
RH
Manzo
Daniel
D
Allemandi
Laura
L
Fratoni
Pierandrea
P
Lo Nostro
D000975:Antioxidants / Q000737:chemistry; D001205:Ascorbic Acid / Q000031:analogs & derivatives / Q000737:chemistry; D001713:Biphenyl Compounds; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004553:Electric Conductivity; D008027:Light; D008823:Micelles; D016877:Oxidants / Q000737:chemistry; D004364:Pharmaceutical Preparations / Q000737:chemistry*; D010851:Picrates / Q000737:chemistry; D012031:Refractometry; D012542:Scattering, Radiation; D012995:Solubility; D012997:Solvents; D013056:Spectrophotometry, Ultraviolet; D013500:Surface Tension; D014783:Viscosity
D000975:Antioxidants; D001713:Biphenyl Compounds; D008823:Micelles; D016877:Oxidants; D004364:Pharmaceutical Preparations; D010851:Picrates; D012997:Solvents; C470083:octanoyl-6-O-ascorbic acid; C004931:1,1-diphenyl-2-picrylhydrazyl; D001205:Ascorbic Acid