Fluorinated amphiphilic amino acid derivatives as antioxidant carriers: a new class of protective agents

Journal of Medicinal Chemistry
Stéphanie OrtialB Pucci

Abstract

The use of classical antioxidants is limited by their low bioavailabilities, and therefore, high doses are usually required to display significant protective activity. In a recent article (J. Med. Chem. 2003, 46, 5230) we showed that the ability of the alpha-phenyl-N-tert-butylnitrone (PBN) to restore the viability of ATPase-deficient human skin fibroblasts was greatly enhanced by grafting it on a fluorinated amphiphilic carrier. With the aim of extending this concept to other antioxidants, we present here the design, the synthesis, and the physicochemical measurements of a new series of fluorinated amphiphilic antioxidant derivatives. The hydroxyl radical scavenging activity and the radical reducing potency of these newly designed compounds were respectively demonstrated in an ABTS competition and an ABTS(*+) reduction assay. We also showed that the protective effects of amphiphilic antioxidants derived from PBN, Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid) or lipoic acid (5-[1,2]-dithiolan-3-ylpentanoic acid) in primary cortical mixed cell cultures exposed to oxidotoxins are greatly improved compared to their parent compounds in the following rank-order: (1) PBN, (2) Trolox, and (3) lipoic acid. In contrast...Continue Reading

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Citations

Oct 15, 2013·Colloids and Surfaces. B, Biointerfaces·Stéphanie OrtialGrégory Durand
Aug 15, 2009·Chemical Research in Toxicology·Grégory DurandFrederick A Villamena
Oct 29, 2008·Evidence-based Complementary and Alternative Medicine : ECAM·Erica Weinstein TeixeiraPaulo César Stringheta
May 9, 2013·Biotechnology Advances·Saúl AlonsoMario Díaz
Dec 25, 2009·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Rüdiger Hardeland
Apr 19, 2007·Chemistry, an Asian Journal·Kenzo YamatsuguMasakatsu Shibasaki
Mar 28, 2008·The Journal of Physical Chemistry. B·Dmitriy N PolovyanenkoElena G Bagryanskaya
Oct 28, 2008·Journal of the American Chemical Society·Cristina GentiliniLucia Pasquato
Nov 13, 2008·The Journal of Physical Chemistry. a·Grégory DurandFrederick A Villamena
Jun 10, 2010·Journal of Medicinal Chemistry·Grégory DurandBernard Pucci
Sep 14, 2010·Journal of Combinatorial Chemistry·Florence S Gaucher-WieczorekPhilippe Durand
Dec 23, 2011·The Journal of Organic Chemistry·Fanny ChoteauGrégory Durand
Jun 27, 2014·The Journal of Organic Chemistry·Marie RosselinGrégory Durand
Oct 13, 2012·Journal of Colloid and Interface Science·Thi Huong Viet NgoRobert Coudert

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