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Pharmaceutics 2016, 8(3), 22; doi:10.3390/pharmaceutics8030022

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

Department of Medicinal Chemistry, University of Florida, P.O. Box 100485, Gainesville, FL 32610, USA
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Academic Editor: Yvonne Perrie
Received: 25 April 2016 / Revised: 21 June 2016 / Accepted: 7 July 2016 / Published: 18 July 2016
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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. View Full-Text
Keywords: vitamin C; l-ascorbic acid; prodrugs; topical delivery; solubilities; cellular antioxidant activity; cytotoxicity; soft alkyl vitamin C; l-ascorbic acid; prodrugs; topical delivery; solubilities; cellular antioxidant activity; cytotoxicity; soft alkyl
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MDPI and ACS Style

Thiele, N.A.; McGowan, J.; Sloan, K.B. 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. Pharmaceutics 2016, 8, 22.

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