Development of a fluorescent chemosensor for the detection of kynurenine

Org Lett. 2013 Jan 18;15(2):235-7. doi: 10.1021/ol303025m. Epub 2012 Dec 24.

Abstract

Kynurenine, a metabolite of tryptophan, is known to contribute to cancer progression when overproduced. A method for facile fluorescent sensing of kynurenine using sensor 1 has been developed. When bound at low pH, sensor 1 undergoes a very large bathochromic shift because kynurenine extends the conjugation of the fluorophore. This unusual mechanism of activation provides a 390-fold fluorescence enhancement that is very specific to kynurenine and a wavelength of fluorescence that extends into the red.

Publication types

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

MeSH terms

  • Chromatography, High Pressure Liquid
  • Fluorescence
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Humans
  • Kynurenine / analysis*
  • Kynurenine / chemistry
  • Kynurenine / pharmacology
  • Molecular Structure
  • Tryptophan / metabolism*

Substances

  • Fluorescent Dyes
  • Kynurenine
  • Tryptophan