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2-O-Acyl-3-O-(1-acyloxyalkyl) Prodrugs of 5,6-Isopropylidene-L-Ascorbic Acid and L-Ascorbic Acid: Antioxidant Activity and Ability to Permeate Silicone Membranes.
- Source :
-
Pharmaceutics . Sep2016, Vol. 8 Issue 3, p22. 12p. - Publication Year :
- 2016
-
Abstract
- 2-O-Acyl-3-O-(1-acyloxyalkyl) prodrug derivatives, 15, of 5,6-isopropylidene-L-ascorbic acid, VCA, and L-ascorbic acid, VC, have been characterized by measuring (1) their solubilities in water (SAQ) and in 1-octanol (SOCT); (2) the ability of one member of the homologous series, 15a, to diffuse through a silicone membrane from its application in propylene glycol:water (PG:AQ), 30:70; (3) the ability of another member of the series, 15e, to express cellular antioxidant activity (CAA) in HaCaT cells; and (4) the ability of 15e to support cell viability in HaCaT cells. All of the prodrugs were more soluble in 1-octanol than VC or VCA were. 15a, which exhibited a good balance between SOCT and SAQ, was found to deliver approximately 15 times more 15a than VCA delivered VCA through a silicone membrane from PG:AQ, 30:70. Under those conditions, no VC permeated the membrane. 15e, which hydrolyzed to release acetaldehyde as a byproduct instead of the toxin formaldehyde, exhibited approximately 30 times the antioxidant activity of VC in CaHaT cells and supported cell viability up to 900 μM in HaCaT cells. [ABSTRACT FROM AUTHOR]
- Subjects :
- *CHEMICAL derivatives
*VITAMIN C
*PROPYLENE glycols
*ANTIOXIDANTS
*FORMALDEHYDE
Subjects
Details
- Language :
- English
- ISSN :
- 19994923
- Volume :
- 8
- Issue :
- 3
- Database :
- Academic Search Index
- Journal :
- Pharmaceutics
- Publication Type :
- Academic Journal
- Accession number :
- 118331168
- Full Text :
- https://doi.org/10.3390/pharmaceutics8030022