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Related Experiment Videos

DNA interstrand cross-linking by epichlorohydrin.

Keith P Romano1, Adam G Newman, Rami W Zahran

  • 1Department of Chemistry, Colby College, Waterville Maine 04901, USA.

Chemical Research in Toxicology
|April 20, 2007
PubMed
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Epichlorohydrin and epibromohydrin form DNA cross-links, primarily at guanine sites. Epibromohydrin is a more potent cross-linker than epichlorohydrin, and R-epichlorohydrin is more cytotoxic than S-epichlorohydrin.

Area of Science:

  • Chemical carcinogenesis
  • DNA damage and repair
  • Toxicology

Background:

  • Epichlorohydrin (ECH) is an industrial chemical and a suspect carcinogen.
  • ECH is a bifunctional alkylating agent known to react with DNA.
  • Occupational exposure to ECH can cause chromosomal aberrations.

Purpose of the Study:

  • To investigate the formation of DNA interstrand cross-links by ECH and epibromohydrin (EBH).
  • To compare the cross-linking efficiency of ECH and EBH.
  • To examine the influence of pH and DNA sequence on cross-linking.
  • To correlate the cross-linking activity of ECH isomers with their cytotoxicity.

Main Methods:

  • Denaturing polyacrylamide gel electrophoresis (dPAGE) was used to detect DNA cross-links.

Related Experiment Videos

  • DNA oligomers were treated with ECH and EBH under varying pH conditions.
  • The efficiency of cross-linking at specific DNA sequences (5'-GGC and 5'GC) was assessed.
  • Cytotoxicity of R-ECH and S-ECH isomers was compared.

    • Main Results:

    • Both ECH and EBH formed interstrand cross-links between deoxyguanosine residues.
    • EBH was a more efficient cross-linker than ECH.
    • ECH showed optimal cross-linking at pH 5.0, while EBH was more efficient at pH 7.0.
    • Both agents exhibited flexibility in targeting DNA sequences.
    • R-ECH demonstrated approximately twice the potency of S-ECH in interstrand cross-linking and cytotoxicity.

    Conclusions:

    • ECH and EBH are capable of forming DNA interstrand cross-links, primarily at guanine residues.
    • EBH is a more effective DNA cross-linking agent than ECH.
    • The stereochemistry of ECH isomers influences their DNA cross-linking ability and cytotoxicity.