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Halogenated hydrocarbon epoxides: some predictive methods for carcinogenic activity based on electronic mechanisms
1Department of Chemistry, University of New Orleans, Louisiana 70148.
Molecular Toxicology
|January 1, 1987
Summary
Computational studies reveal that halogenated hydrocarbon epoxides' carcinogenicity is linked to oxygen protonation and intermediate reactivity. Negative electrostatic potentials identify suspect carcinogens, while C-O bond orders may rank their activity.
Area of Science:
- Computational chemistry
- Toxicology
- Organic chemistry
Background:
- Halogenated olefins and their epoxide metabolites are potential carcinogens.
- Carcinogenicity is influenced by epoxide properties like protonation tendency and reactivity.
Purpose of the Study:
- To computationally study the reactive properties of halogenated hydrocarbon epoxides.
- To identify factors determining their carcinogenicity.
- To explore methods for identifying and ranking potential carcinogens.
Main Methods:
- Utilizing ab initio self-consistent-field molecular orbital procedures.
- Analyzing electrostatic potentials near epoxide oxygens.
- Calculating C-O bond orders as reactivity indicators.
Main Results:
- Epoxide carcinogenicity correlates with strong negative electrostatic potentials at oxygen protonation sites.
- Optimal carcinogenicity requires intermediate epoxide reactivity.
- Calculated C-O bond orders show promise for measuring reactivity.
Conclusions:
- Negative electrostatic potentials can help identify suspect carcinogenic epoxides.
- C-O bond orders may provide a quantitative method for ranking epoxide carcinogen activity.