Water-soluble tetraphenylethene derivatives as fluorescent "light-up" probes for nucleic acid detection and their applications in cell imaging

Chem Asian J. 2013 Aug;8(8):1806-12. doi: 10.1002/asia.201300065. Epub 2013 Apr 17.

Abstract

The detection of nucleic acids, such as DNA and RNA, plays a significant role in genetic engineering, forensics, and bioinformatics. Traditional nucleic acid probes are mainly intercalators, which are potential mutagens, or groove binders that show high preference only for double-stranded DNA. We herein present two versatile fluorescent probes for nucleic acid detection and visualization. The nonemissive tetraphenylethene derivatives (TTAPE) are induced by DNA/RNA to emit, thereby showing a novel phenomenon of aggregation-induced emission (AIE). This kind of "light-up" property enables the quantitation and visualization of nucleic acids in aqueous solution and electrophoretic gels, respectively. The cationic TTAPE can penetrate cells with a compromised plasma membrane easily but cannot enter live cells with an intact membrane, thus making them useful for the differentiation between dead and live cells. On account of the high binding affinity to DNA, TTAPE can selectively label the chromosomes and nuclei in fixed cells, which provides a simple and fast method for the observation of cell mitosis. Owing to their AIE characteristics, the dye molecules aggregate in DNA-rich regions and exert appreciable quantum efficiency as well as superior photostability.

Keywords: aggregation; electrostatic interactions; fluorescent probes; nucleic acids; phenylethene.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Chromosomes / chemistry
  • DNA / analysis*
  • Drosophila / genetics
  • Fluorescent Dyes / chemistry*
  • HeLa Cells
  • Humans
  • Microscopy, Fluorescence
  • Quaternary Ammonium Compounds / chemistry*
  • Spectrometry, Fluorescence
  • Static Electricity
  • Stilbenes / chemistry*
  • Water / chemistry

Substances

  • 1,1,2,2-tetrakis(4-(2-triethylammonioethoxy)phenyl)ethene tetrabromide
  • Fluorescent Dyes
  • Quaternary Ammonium Compounds
  • Stilbenes
  • Water
  • DNA