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Carcinogenesis of urethane: simulation versus experiment.

Andrej Lajovic1, Leslie D Nagy2, F Peter Guengerich2

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Urethane, a food byproduct, can cause cancer. This study used experiments and calculations to show how urethane

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Area of Science:

  • Chemical carcinogenesis
  • Computational chemistry
  • Molecular toxicology

Background:

  • Urethane (ethyl carbamate) is a fermentation byproduct found in foods.
  • Urethane is a known carcinogen, and its mechanism of action involves DNA adduct formation.

Purpose of the Study:

  • To investigate the carcinogenesis of urethane using kinetic experiments and quantum chemical calculations.
  • To determine the activation free energy (ΔG(⧧)) for the SN2 reaction between urethane's ultimate carcinogen, vinyl carbamate epoxide (VCE), and DNA nucleobases.

Main Methods:

  • Experimental determination of second-order reaction rate constants for adduct formation.
  • Ab initio, DFT, and semiempirical MO calculations of activation barriers for VCE reactions with nucleobases.
  • Incorporation of hydration effects using solvent reaction field and Langevin dipoles models.

Main Results:

  • Computational results for the main adduct formation agreed well with experimental data, supporting an SN2 mechanism.
  • Calculations predicted activation barriers for side product formation, identifying preferential formation of the 7-(2-oxoethyl)deoxyguanosine adduct.
  • The study elucidated factors influencing adduct formation, including activation barriers and DNA geometry requirements.

Conclusions:

  • The proposed SN2 mechanism for urethane-induced DNA adduct formation is validated by combined experimental and computational approaches.
  • The preferential formation of the 7-(2-oxoethyl)deoxyguanosine adduct is explained by higher activation barriers for other adducts or unfavorable reaction geometries.
  • This study provides insights into urethane's carcinogenic pathway and aids in predicting other potential DNA adducts.