Xanthamide fluorescent dyes

Anal Chem. 2002 Dec 15;74(24):6397-401. doi: 10.1021/ac020368+.

Abstract

Two derivatives of fluorescein, termed "xanthamides," were prepared from fluorescein, an inexpensive dye. Relative to fluorescein, which contains a 6-phenolic OH and a 2'-carboxyl, the first derivative (5) contains a carboxymethyl ether at the 6-position and a secondary amide of dimethylamine at the 2'-position. The second derivative (8) contains a corresponding 6-methyl ether and a secondary amide of isonipecotic acid at the 2'-position. Thus, both derivatives contain a single carboxyl group, making them monofunctional. Especially 8 is much more photostable (about 10 times) than either fluorescein or BODIPY FL dye when exposed to ordinary light (tungsten light bulb). When tested for relative response in a capillary electrophoresis instrument fitted with an argon ion laser detector (488 nm) and a broad band emission filter, 8 was found to be 4-fold less bright than fluorescein. Both xanthamides, consistent with prior literature on 6-O-alkylated fluorescein, exhibit relatively pH-independent fluorescence (pH 4-10 was tested here). Because they possess two absorbance maximums, the xanthamides can be excited over a broader wavelength range than fluorescein or BODIPY. These collective properties of the xanthamides will make them advantageous over fluorescein and BODIPY dyes for some applications.

Publication types

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

MeSH terms

  • Boron Compounds / chemistry
  • Electrophoresis, Capillary
  • Fluoresceins / chemical synthesis*
  • Fluoresceins / chemistry*
  • Hydrogen-Ion Concentration
  • Molecular Structure
  • Spectrometry, Fluorescence

Substances

  • BODIPY FL hydrazide
  • Boron Compounds
  • Fluoresceins