Comparative QSAR evidence for a free-radical mechanism of phenol-induced toxicity.

@article{Hansch2000ComparativeQE,
  title={Comparative QSAR evidence for a free-radical mechanism of phenol-induced toxicity.},
  author={Corwin Hansch and Susan C. McKarns and C J Smith and David J. Doolittle},
  journal={Chemico-biological interactions},
  year={2000},
  volume={127 1},
  pages={
          61-72
        }
}
Understanding the toxicity of phenols: using quantitative structure-activity relationship and enthalpy changes to discriminate between possible mechanisms.
TLDR
The study of net enthalpy changes of reactions reveals that once the phenoxyl radical is present, the corresponding quinone is rapidly formed, so that quin one formation may be ultimately responsible for toxicity of EDG-phenols.
Quantitative structure toxicity relationships for phenols in isolated rat hepatocytes.
TLDR
It is shown that a collapse of hepatocyte mitochondrial membrane potential preceded the cytotoxicity of most phenols, and that phenols with higher lipophilicity, BDE, or sigma+ values or with lower pK(a) and redox potential were more toxic towards hepatocytes.
Computational modeling of substituent effects on phenol toxicity.
TLDR
The rate constant for production of phenoxyl radical is focused on, giving rate constants as a function of DeltaBDE values for both EDG and EWG sets and it is argued that competing parallel mechanisms of toxicity are likely to be dominant for EWG-substituted phenols.
The importance of hydrophobicity and electrophilicity descriptors in mechanistically-based QSARs for toxicological endpoints
TLDR
Quantitative structure-activity relationship (QSAR) analysis of four toxicological data sets is described, demonstrating that mechanistically based QSARs can be developed for these diverse endpoints which are as good as, if not better, than QSars based on less mechanistically interpretable descriptors.
Comparative QSAR Studies on Toxicity of Phenol Derivatives Using Quantum Topological Molecular Similarity Indices
TLDR
It was found that toxicities of phenols to all strains, except with L1210 Leukemia, are significantly affected by electronic features of the phenolic hydroxyl group (C‐O‐H).
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