A biotinylated piperazine-rhodol derivative: a 'turn-on' probe for nitroreductase triggered hypoxia imaging

Analyst. 2017 Jan 16;142(2):345-350. doi: 10.1039/c6an02107g.

Abstract

We developed a nitroreductase responsive theranostic probe 1; it comprises biotinylated rhodol in conjunction with p-nitrobenzyl functionality. The probe 1 showed a remarkable fluorescence 'turn-on' signal in the presence of nitroreductase under physiological conditions. The probe is considerably stable within a wide biological pH range (6-8) and also is very sensitive toward a reducing micro-environment e.g. liver microsome. Further, it enables providing cellular and in vivo nematode images in a reducing microenvironment.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biotin / analogs & derivatives*
  • Biotin / chemical synthesis
  • Biotin / pharmacology*
  • Biotin / toxicity
  • Caenorhabditis elegans
  • Cell Line, Tumor
  • Fluorescence
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacology*
  • Fluorescent Dyes / toxicity
  • Humans
  • Hypoxia / diagnostic imaging*
  • Lepidoptera
  • Limit of Detection
  • Microsomes, Liver / metabolism
  • Nitroreductases / metabolism*
  • Piperazines / chemical synthesis
  • Piperazines / chemistry
  • Piperazines / pharmacology
  • Piperazines / toxicity
  • Rats
  • Theranostic Nanomedicine
  • Xanthones / chemical synthesis
  • Xanthones / chemistry
  • Xanthones / pharmacology*
  • Xanthones / toxicity

Substances

  • Fluorescent Dyes
  • Piperazines
  • Xanthones
  • rhodol
  • Biotin
  • Nitroreductases