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Influence of Thermodynamic Parameters on the Genotoxicity of Bioactive Phenolic Compounds Present in Food
Published: 31 October 2013 by MDPI in The 17th International Electronic Conference on Synthetic Organic Chemistry session Computational Chemistry
Abstract: The effects in health of food rich in phenols require currently studies related to safety. It has been shown that these compounds can present dual activity (antioxidant/pro-oxidant effects). In this sense, this work it is focused on an in silico study to determine the relationships of various thermodynamic parameters to genotoxicity (GT) of phenolic compounds: flavonoids, cinnamic acids and coumarins. The fundamental basis of the extra-thermodynamic methodology establishes that the structure of the bioactive molecule is a function of certain local and global properties. It was modeled the influence of local and global parameters that characterize the structure (hydrophobic, steric, electronic, and log P properties) relative to the clastogenic capacity (chromosome aberration generated by DNA damage due to its pro-oxidant activity). To achieve these objectives they were used ChemDraw, MODESLAB and STATISTIC software. They were identified properties influencing the genetic damage caused by the studied compounds with pro-oxidant activity, expressed through different Multivariate Linear Regression (MLR) statistical models. It was shown that steric (Sterimol, L) and hydrophobic (Π) properties presented greater influence than the electronic properties (Hammett constant, Σ*). Regarding the global property analysed, it was found that a decrease in the log P is associated with increased DNA damage by clastogenicity. The results allow us to produce an analysis of structure-toxicity relationship in designing strategies for nutraceuticals, functional foods and novel drug with such phenolic compounds on their structure.
Keywords: phenolic compounds, thermodynamic parameters; genotoxicity, pro-oxidant activity.