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J. Funct. Biomater. 2014, 5(3), 99-110; doi:10.3390/jfb5030099

A New Pro-Prodrug Aminoacid-Based for Trans-Ferulic Acid and Silybin Intestinal Release

Department of Pharmacy and Health and Nutrition Sciences, University of Calabria, 87036 Arcavacata di Rende Cosenza, Italy
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Received: 23 May 2014 / Revised: 23 June 2014 / Accepted: 9 July 2014 / Published: 24 July 2014
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Abstract

The aim of this work was the preparation and characterization of a pro-prodrug able to simultaneously transport silybin, a drug possessing various pharmacological effects, and trans-ferulic acid, a known antioxidant. More specifically, l-phenylalanine-N-(4-hydroxy-3-methoxy-phenyl) prop-2-en-O-(2R,3R)-3,5,7-trihydroxy-2-((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-benzo-(1,4)-dioxin-6-yl)croman-4-one was synthesized by using the aminoacid l-phenylalanine (l-Phe) as carrier. Indeed, l-Phe is characterized by an intrinsic chemical reactivity due to the presence of an amino group, placed on the chiral center, and of a carboxylic group. The synthesis has been characterized first by adding silybin by means of carboxylic group and then, with the aim to confer antioxidant properties to this new carrier, by linking trans-ferulic acid to l-Phe via amino group. The so obtained derivative was then characterized by FT-IR, and 1H-NMR spectroscopies. Furthermore, its ability to inhibit lipid peroxidation induced by tert-butyl hydroperoxide in rat liver microsomes, was evaluated. The 1,1-diphenyl-2-picrylhydrazyl radical-scavenging effect, was also assessed. The release of silybin and trans-ferulic acid was determined in simulated gastric and intestinal fluids over the time. The results showed that the covalent bond between both (i) silybin; or (ii) trans-ferulic acid and the amino acid was degraded by enzymatic reactions. In addition, the pro-prodrug, showed strong antioxidant and scavenger activities. Due to these properties, this new pro-prodrug could be applied for the treatment of intestinal pathologies and it might improve the therapeutic potential of silybin which is strongly limited by its low solubility. View Full-Text
Keywords: l-phenylalanine; silybin; trans-ferulic acid; lipid peroxidation; simulated gastric fluid and intestinal fluid l-phenylalanine; silybin; trans-ferulic acid; lipid peroxidation; simulated gastric fluid and intestinal fluid
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MDPI and ACS Style

Trombino, S.; Ferrarelli, T.; Cassano, R. A New Pro-Prodrug Aminoacid-Based for Trans-Ferulic Acid and Silybin Intestinal Release. J. Funct. Biomater. 2014, 5, 99-110.

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J. Funct. Biomater. EISSN 2079-4983 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
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