Does hydrophobicity always enhance antioxidant drugs? A cut-off effect of the chain length of functionalized chlorogenate esters on ROS-overexpressing fibroblasts

Abstract

The understanding of this sudden collapse of the antioxidant capacity through the cut-off theory will be discussed in this article, and may contribute towards development of a rational approach to design novel amphiphilic antioxidant drugs, especially phenolipids with medium fatty chain.

Biology-oriented development of novel lipophilic antioxidants with neuroprotective activity

“…Cu and Fe), 9 (c) induction of cytoprotective signalling pathways (e.g. 26 The inability to successfully diffuse through biological barriers, in particular the blood-brain barrier (BBB), hinders their activity at the target sites within the central nervous system (CNS). 12 Dietary HCAs have demonstrated a signicant impact on human health, with potential benets for several disorders associated with oxidative stress.…”

Mass Transport Phenomena in Lipid Oxidation and Antioxidation

“…In this context, a mass transfer-based approach to account for lipid oxidation describes a school of thought implying that the oxidation rate can be primarily affected by the mass transport of reactants (i.e., free radicals, lipid substrates, LOOHs, and transition metals). By the same line of reasoning, such an approach has been theoretically developed to account for the antioxidant activity in multiphase systems (Laguerre et al 2013b) and has been experimentally demonstrated by Niki (1997), Ingold et al (1993), and Castle & Perkins (1986).…”

“…Using a broad range of homologous series of antioxidants in dispersed lipid models and cultured cells, it has been demonstrated that the antioxidant activity increases progressively with increasing chain length up to a critical point, beyond which the activity of the compounds decreases (Figure 4). Since its first mention (Laguerre et al 2009), this cut-off effect for antioxidants has been the subject of extensive research in lipid dispersions (Alemán et al 2015;Costa et al 2015;Laguerre et al 2010;Lee et al 2013;Losada-Barreiro et al 2013;Medina et al 2009;Panya et al 2012;Sørensen et al 2012Sørensen et al , 2014Sørensen et al , 2015 and cellular models , Laguerre et al 2011, Munoz-Marin et al 2013) as well as of review articles (Laguerre et al 2013a(Laguerre et al ,b, 2015Shahidi & Zhong 2011;Zhao et al 2015). Table 1 gives some examples of the experimental confirmations of the occurrence of a cut-off effect.…”

Oxidative Stability in Oil‐in‐Water Emulsions with Quercetin or Rutin Under Iron Catalysis or Riboflavin Photosensitization

“…According to recent studies on the interfacial phenomenon between water and oil, compounds located near the oil–water interface have efficient antioxidant activity (Laguree and others ). An appropriate length alkyl chain esterified rosmarinate or chlorogenate had higher antioxidant properties in O/W emulsion than phytochemicals with shorter or longer alkyl chains, which is called a “cut‐off” phenomena (Laguerre and others ; Panya and others ; Lee and others ). Quercetin may be positioned more properly than rutin at the oil–water interface due to the polarity difference or smaller size.…”