Synthetic, crystallographic, computational, and biological studies of 1,4-difluorobenzo[c]phenanthrene and its metabolites

The synthesis and characterization of 1,4-difluorobenzo[c]phenanthrene (1,4-DFBcPh) was carried to understand its extent of DNA binding by the metabolities of dihydrodiol and diol epoxides. The findings showed that increased molecular distortion decreased metabolic activation to the terminal metabolities and the formation of diol epoxide metabolites was the DNA-damaging species.