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Int. J. Mol. Sci. 2013, 14(1), 1443-1454; doi:10.3390/ijms14011443
Article

Quantitative Structure-Activity Relationships Predicting the Antioxidant Potency of 17β-Estradiol-Related Polycyclic Phenols to Inhibit Lipid Peroxidation

1,* , 1,†
 and 2
Received: 13 December 2012; in revised form: 3 January 2013 / Accepted: 5 January 2013 / Published: 11 January 2013
(This article belongs to the Special Issue Neuroprotective Strategies 2012)
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Abstract: The antioxidant potency of 17β-estradiol and related polycyclic phenols has been well established. This property is an important component of the complex events by which these types of agents are capable to protect neurons against the detrimental consequences of oxidative stress. In order to relate their molecular structure and properties with their capacity to inhibit lipid peroxidation, a marker of oxidative stress, quantitative structure-activity relationship (QSAR) studies were conducted. The inhibition of Fe3+-induced lipid peroxidation in rat brain homogenate, measured through an assay detecting thiobarbituric acid reactive substances for about seventy compounds were correlated with various molecular descriptors. We found that lipophilicity (modeled by the logarithm of the n-octanol/water partition coefficient, logP) was the property that influenced most profoundly the potency of these compounds to inhibit lipid peroxidation in the biological medium studied. Additionally, the important contribution of the bond dissociation enthalpy of the phenolic O-H group, a shape index, the solvent-accessible surface area and the energy required to remove an electron from the highest occupied molecular orbital were also confirmed. Several QSAR equations were validated as potentially useful exploratory tools for identifying or designing novel phenolic antioxidants incorporating the structural backbone of 17β-estradiol to assist therapy development against oxidative stress-associated neurodegeneration.
Keywords: 17β-estradiol; estrogens; lipid peroxidation; phenolic antioxidant; oxidative stress; QSAR; TBARS 17β-estradiol; estrogens; lipid peroxidation; phenolic antioxidant; oxidative stress; QSAR; TBARS
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Prokai, L.; Rivera-Portalatin, N.M.; Prokai-Tatrai, K. Quantitative Structure-Activity Relationships Predicting the Antioxidant Potency of 17β-Estradiol-Related Polycyclic Phenols to Inhibit Lipid Peroxidation. Int. J. Mol. Sci. 2013, 14, 1443-1454.

AMA Style

Prokai L, Rivera-Portalatin NM, Prokai-Tatrai K. Quantitative Structure-Activity Relationships Predicting the Antioxidant Potency of 17β-Estradiol-Related Polycyclic Phenols to Inhibit Lipid Peroxidation. International Journal of Molecular Sciences. 2013; 14(1):1443-1454.

Chicago/Turabian Style

Prokai, Laszlo; Rivera-Portalatin, Nilka M.; Prokai-Tatrai, Katalin. 2013. "Quantitative Structure-Activity Relationships Predicting the Antioxidant Potency of 17β-Estradiol-Related Polycyclic Phenols to Inhibit Lipid Peroxidation." Int. J. Mol. Sci. 14, no. 1: 1443-1454.



Int. J. Mol. Sci. EISSN 1422-0067 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert