Fluorogenic 7-azidocoumarin and 3/4-azidophthalimide derivatives as indicators of reductase activity in microorganisms

Bioorg Med Chem Lett. 2019 Aug 15;29(16):2354-2357. doi: 10.1016/j.bmcl.2019.06.010. Epub 2019 Jun 7.

Abstract

A series of fluorogenic heterocyclic azides were prepared and assessed as reductase substrates across a selection of Gram-negative and Gram-positive microorganisms. The majority of these azides showed similar activity profiles to nitroreductase substrates. Microorganisms that do not produce hydrogen sulfide reduced the azides, indicating reductase activity was not linked to hydrogen sulfide production.

Keywords: Fluorogenic azides; Fluorogenic substrates; Microorganism detection; Nitroreductase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Coumarins / chemical synthesis
  • Coumarins / chemistry*
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Gram-Negative Bacteria / enzymology*
  • Gram-Positive Bacteria / enzymology*
  • Molecular Structure
  • Nitroreductases / metabolism*
  • Phthalimides / chemical synthesis
  • Phthalimides / chemistry*
  • Substrate Specificity

Substances

  • Coumarins
  • Fluorescent Dyes
  • Phthalimides
  • coumarin
  • Nitroreductases