A latent green fluorescent styrylcoumarin probe for the selective growth and detection of Gram negative bacteria

Bioorg Med Chem. 2018 Sep 1;26(16):4745-4750. doi: 10.1016/j.bmc.2018.08.015. Epub 2018 Aug 12.

Abstract

A novel, green fluorescent β-alanylstyrylcoumarin derivative was synthesized and evaluated for its performance as a fluorogenic enzyme substrate on a range of clinically relevant microorganisms. The substrate was selectively hydrolysed by β-alanyl aminopeptidase producing P. aeruginosa resulting in an on-to-off fluorescent signal. Growth inhibitory effect of the substrate was observed on Gram positive bacteria and yeasts. Meanwhile, Gram negative species, despite their extremely protective cell envelope, showed ready uptake and accumulation of the substrate within their healthy growing colonies displaying intense green fluorescence.

Keywords: Fluorescent enzyme substrate; Gram negative detection; Selective growth inhibitor; Styrylcoumarin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / metabolism
  • Anti-Infective Agents / pharmacology
  • CD13 Antigens / metabolism*
  • Coumarins / chemistry*
  • Coumarins / metabolism
  • Coumarins / pharmacology
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / metabolism
  • Gram-Negative Bacteria / drug effects
  • Gram-Negative Bacteria / growth & development
  • Gram-Positive Bacteria / drug effects
  • Gram-Positive Bacteria / growth & development
  • Pseudomonas aeruginosa / enzymology
  • Substrate Specificity
  • Yeasts / drug effects
  • Yeasts / growth & development

Substances

  • Anti-Infective Agents
  • Coumarins
  • Fluorescent Dyes
  • coumarin
  • CD13 Antigens