A short, rigid linker between pyrene and guanidiniocarbonyl-pyrrole induced a new set of spectroscopic responses to the ds-DNA secondary structure

Org Biomol Chem. 2015 Feb 14;13(6):1629-33. doi: 10.1039/c4ob02169j.

Abstract

A novel pyrene-guanidiniocarbonyl-pyrrole dye, characterised by a short, rigid linker between the two chromophores, interacts strongly with ds-DNA but only negligibly with ds-RNA. Under neutral conditions the dye shows strong selectivity toward AT-DNA (with respect to GC-DNA). Binding is accompanied by a specific ICD band at 350 nm and fluorescence quenching for all DNAs/RNAs studied. At pH 5 the affinity of the dye is reversed, now favouring GC-DNA over AT-DNA. A strong emission increase for AT-DNA is observed but with quenching for GC-DNA.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • DNA / chemistry*
  • Fluorometry
  • Guanidines / chemistry*
  • Molecular Structure
  • Pyrenes / chemistry*
  • Pyrroles / chemistry*
  • Spectrophotometry, Ultraviolet

Substances

  • Guanidines
  • Pyrenes
  • Pyrroles
  • DNA
  • pyrene