Spectra, stability and labeling of 1-(5-carboxypentyl)-4-(2-(N-ethyl-carbazole-3-yl) vinyl) pyridinium bromide with a large Stokes shift

Luminescence. 2016 Mar;31(2):380-387. doi: 10.1002/bio.2970. Epub 2015 Aug 6.

Abstract

Carbazole and its derivatives have been widely utilized as a functional building block in the fabrication of the organic medicine, pesticides, materials, etc., because of their excellent solubility, stability and biological activity. In this paper, 1-(5-carboxypentyl)-4-(2-(N-ethyl-carbazole-3-yl) vinyl) pyridinium bromide with a large Stokes shift was synthesized and characterized by (1)H NMR and MS. The UV/vis absorption and fluorescence spectra in different solvents and at different pH values were investigated preliminarily. The photostability and thermostability were also studied and the results showed that the compound was stable. The compound was also used to label bovine serum albumin (BSA) and calf thymus (ct)DNA. The results showed that the fluorescence intensity is enhanced when labeling with BSA and the binding ability is stronger than ctDNA, making it may be used as a biological probe.

Keywords: carbazole; labeling; large Stokes shift; spectra; stability.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Carbazoles / chemical synthesis
  • Carbazoles / chemistry*
  • Cattle
  • DNA / chemistry*
  • Hydrogen-Ion Concentration
  • Mass Spectrometry
  • Molecular Structure
  • Proton Magnetic Resonance Spectroscopy
  • Pyridinium Compounds / chemical synthesis
  • Pyridinium Compounds / chemistry*
  • Serum Albumin, Bovine / chemistry*
  • Spectrometry, Fluorescence
  • Spectrophotometry, Ultraviolet

Substances

  • 1-(5-carboxypentyl)-4-(2-(N-ethyl-carbazole-3-yl)vinyl)pyridinium bromide
  • Carbazoles
  • Pyridinium Compounds
  • Serum Albumin, Bovine
  • DNA
  • calf thymus DNA