Comparative genotoxic evaluation of 2-furylethylenes and 5-nitrofurans by using the comet assay in TK6 cells

Mutagenesis. 2005 May;20(3):193-7. doi: 10.1093/mutage/gei026. Epub 2005 Apr 7.

Abstract

The genotoxicity of three 2-furylethylene derivatives and four 5-nitrofurans was evaluated by using the comet assay in human lymphoblastoid cultured TK6 cells. The 2-furylethylene derivatives were 2-furyl-1-nitroethene, 1-(5-bromofur-2-yl)-2-nitroethene and 1-(5-bromofur-2-yl)-2-bromo-2-nitroethene, while the 5-nitrofurans were nitrofurantoin, nitrofurazone, furazolidone and 5-nitro-2-furanacrolein. The treatments lasted for 3 h in the absence of metabolic activation. No genotoxic effects were observed for two of the 2-furylethylene compounds, while the derivative 1-(5-bromofur-2-yl)-2-nitroethene showed a statistically significant response mainly at the highest concentration tested; this effect was considered biologically relevant and the compound was classified as slightly genotoxic. On the other hand, for the classical 5-nitrofurans tested there is a tendency towards a dose-related increase of the DNA damage in the comet assay and the observed increases for the parameters analysed (Olive tail moment, tail % DNA and tail length) were significant for all compounds. Then, the four 5-nitrofurans tested were considered genotoxic. These results show that the position of the nitro group influences the genotoxicity of the assayed compounds. Thus, in this comet assay, the 2-furylethylene derivatives having the nitro group attached outside the furan ring appear to be much less genotoxic than the 5-nitrofurans.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line, Tumor
  • Comet Assay
  • DNA / drug effects
  • DNA Damage*
  • Dose-Response Relationship, Drug
  • Furans / chemistry
  • Furans / toxicity*
  • Humans
  • Molecular Structure
  • Mutagens / chemistry
  • Mutagens / toxicity*
  • Nitro Compounds / chemistry
  • Nitro Compounds / toxicity*
  • Nitrofurans / chemistry
  • Nitrofurans / toxicity*
  • Structure-Activity Relationship

Substances

  • 1-(5-bromofuran-2-yl)-2-nitroethene
  • 2-furyl-1-nitroethene
  • Furans
  • Mutagens
  • Nitro Compounds
  • Nitrofurans
  • DNA