Fluorescent probe for detection of bacteria:conformational trigger upon bacterial reduction of an azo bridge

Using biomimetic chemical reduction or Clostridium perfringens cell extract containing azoreductase, the dimer-fluorescent probe 2,4-O-bisdansyl-6,7- diazabicyclooct-6-ene, which possesses a conformationally constrained cis-azo bridge, is reduced to the tetra-equatorial 2,4-O-bisdansyl-cyclohexyl-3,5- bisammonium salt which exhibits fluorescence indicative of a dansyl monomer. © 2012 The Royal Society of Chemistry.