A nucleic acid probe labeled with desmethyl thiazole orange: a new type of hybridization-sensitive fluorescent oligonucleotide for live-cell RNA imaging

Org Biomol Chem. 2013 Jan 14;11(2):362-71. doi: 10.1039/c2ob26707a. Epub 2012 Nov 22.

Abstract

A new fluorescent nucleotide with desmethyl thiazole orange dyes, D'(505), has been developed for expansion of the function of fluorescent probes for live-cell RNA imaging. The nucleoside unit of D'(505) for DNA autosynthesis was soluble in organic solvents, which made the preparation of nucleoside units and the reactions in the cycles of DNA synthesis more efficient. The dyes of D'(505)-containing oligodeoxynucleotide were protonated below pH 7 and the oligodeoxynucleotide exhibited hybridization-sensitive fluorescence emission through the control of excitonic interactions of the dyes of D'(505). The simplified procedure and effective hybridization-sensitive fluorescence emission produced multicolored hybridization-sensitive fluorescent probes, which were useful for live-cell RNA imaging. The acceptor-bleaching method gave us information on RNA in a specific cell among many living cells.

MeSH terms

  • Benzothiazoles / chemistry
  • Benzothiazoles / metabolism*
  • Cell Survival
  • Circular Dichroism
  • Fluorescence Resonance Energy Transfer
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / metabolism*
  • HeLa Cells
  • Humans
  • Intracellular Space / metabolism
  • Molecular Imaging / methods*
  • Nucleic Acid Hybridization / methods*
  • Nucleic Acid Probes / chemistry
  • Nucleic Acid Probes / metabolism*
  • Oligonucleotides / chemical synthesis
  • Oligonucleotides / chemistry
  • Oligonucleotides / metabolism*
  • Photobleaching
  • Protons
  • Quinolines / chemistry
  • Quinolines / metabolism*
  • RNA / metabolism*
  • Staining and Labeling
  • Thymine Nucleotides / chemistry
  • Thymine Nucleotides / metabolism*

Substances

  • Benzothiazoles
  • D'(505) nucleotide
  • Fluorescent Dyes
  • Nucleic Acid Probes
  • Oligonucleotides
  • Protons
  • Quinolines
  • Thymine Nucleotides
  • thiazole orange
  • RNA