Nitroreductase-triggered activation of a novel caged fluorescent probe obtained from methylene blue

Chem Commun (Camb). 2015 Aug 18;51(64):12787-90. doi: 10.1039/c5cc03824c.

Abstract

A near-infrared fluorescent probe based on methylene blue (p-NBMB) was developed for the detection of nitroreductase. Conjugating methylene blue with a p-nitrobenzyl moiety enables it to be activated by nitroreductase-catalyzed 1,6-elimination, resulting in the release of an active methylene blue fluorophore.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Drug Design
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / metabolism
  • Methylene Blue / analogs & derivatives*
  • Methylene Blue / chemistry*
  • Methylene Blue / metabolism
  • Models, Molecular
  • Nitroreductases / chemistry
  • Nitroreductases / metabolism*
  • Protein Conformation

Substances

  • Fluorescent Dyes
  • p-nitrobenzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate
  • Nitroreductases
  • Methylene Blue