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In vitro evaluation of quercetin-3-O-acyl esters as topical prodrugs. 2007

Lucia Montenegro, and Claudia Carbone, and Claudio Maniscalco, and Daniela Lambusta, and Giovanni Nicolosi, and Cinzia A Ventura, and Giovanni Puglisi
Department of Pharmaceutical Sciences, University of Catania, V.le A.Doria 6, Catania I-95125, Italy. lmontene@unict.it

Quercetin-3-O-acyl esters (I-VI) were synthesized and their usefulness as quercetin topical prodrugs was evaluated. Quercetin esters were assayed to determine their water stability and solubility, their susceptibility to undergoing enzymatic hydrolysis and their permeation through excised human skin. Quercetin ethyl (I) and hexyl (IV) esters proved poorly stable in aqueous media and they were not assayed further. Among the derivatives tested, quercetin propyl (II) and butyl (III) esters were more water-soluble than the parent drug. Esters II, III and V were readily hydrolyzed by human plasma and esters II and III penetrated excised human skin better than quercetin from aqueous saturated solutions. On the basis of the results obtained, esters II and III could be regarded as promising quercetin topical prodrugs.

UI MeSH Term Description Entries
D010539 Permeability Property of membranes and other structures to permit passage of light, heat, gases, liquids, metabolites, and mineral ions. Permeabilities
D011355 Prodrugs A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug. Drug Precursor,Drug Precursors,Pro-Drug,Prodrug,Pro-Drugs,Precursor, Drug,Precursors, Drug,Pro Drug,Pro Drugs
D011794 Quercetin A flavonol widely distributed in plants. It is an antioxidant, like many other phenolic heterocyclic compounds. Glycosylated forms include RUTIN and quercetrin. 3,3',4',5,7-Pentahydroxyflavone,Dikvertin
D002851 Chromatography, High Pressure Liquid Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed. Chromatography, High Performance Liquid,Chromatography, High Speed Liquid,Chromatography, Liquid, High Pressure,HPLC,High Performance Liquid Chromatography,High-Performance Liquid Chromatography,UPLC,Ultra Performance Liquid Chromatography,Chromatography, High-Performance Liquid,High-Performance Liquid Chromatographies,Liquid Chromatography, High-Performance
D004355 Drug Stability The chemical and physical integrity of a pharmaceutical product. Drug Shelf Life,Drugs Shelf Lives,Shelf Life, Drugs,Drug Stabilities,Drugs Shelf Life,Drugs Shelf Live,Life, Drugs Shelf,Shelf Life, Drug,Shelf Live, Drugs,Shelf Lives, Drugs
D004952 Esters Compounds derived from organic or inorganic acids in which at least one hydroxyl group is replaced by an –O-alkyl or another organic group. They can be represented by the structure formula RCOOR’ and are usually formed by the reaction between an acid and an alcohol with elimination of water. Ester
D005419 Flavonoids A group of phenyl benzopyrans named for having structures like FLAVONES. 2-Phenyl-Benzopyran,2-Phenyl-Chromene,Bioflavonoid,Bioflavonoids,Flavonoid,2-Phenyl-Benzopyrans,2-Phenyl-Chromenes,2 Phenyl Benzopyran,2 Phenyl Benzopyrans,2 Phenyl Chromene,2 Phenyl Chromenes
D006207 Half-Life The time it takes for a substance (drug, radioactive nuclide, or other) to lose half of its pharmacologic, physiologic, or radiologic activity. Halflife,Half Life,Half-Lifes,Halflifes
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D006868 Hydrolysis The process of cleaving a chemical compound by the addition of a molecule of water.

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