Recognition of chelerythrine to human telomeric DNA and RNA G-quadruplexes

Sci Rep. 2014 Oct 24:4:6767. doi: 10.1038/srep06767.

Abstract

A study on binding of antitumor chelerythrine to human telomeric DNA/RNA G-quadruplexes was performed by using DNA polymerase stop assay, UV-melting, ESI-TOF-MS, UV-Vis absorption spectrophotometry and fluorescent triazole orange displacement assay. Chelerythrine selectively binds to and stabilizes the K(+)-form hybrid-type human telomeric DNA G-quadruplex of biological significance, compared with the Na(+)-form antiparallel-type DNA G-quadruplex. ESI-TOF-MS study showed that chelerythrine possesses a binding strength for DNA G-quadruplex comparable to that of TMPyP4 tetrachloride. Both 1:1 and 2:1 stoichiometries were observed for chelerythrine's binding with DNA and RNA G-quadruplexes. The binding strength of chelerythrine with RNA G-quadruplex is stronger than that with DNA G-quadruplex. Fluorescent triazole orange displacement assay revealed that chelerythrine interacts with human telomeric RNA/DNA G-quadruplexes by the mode of end- stacking. The relative binding strength of chelerythrine for human telomeric RNA and DNA G-quadruplexes obtained from ESI-TOF-MS experiments are respectively 6.0- and 2.5-fold tighter than that with human telomeric double-stranded hairpin DNA. The binding selectivity of chelerythrine for the biologically significant K(+)-form human telomeric DNA G-quadruplex over the Na(+)-form analogue, and binding specificity for human telomeric RNA G-quadruplex established it as a promising candidate in the structure-based design and development of G-quadruplex specific ligands.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzophenanthridines / chemistry*
  • Benzophenanthridines / metabolism
  • DNA / chemistry*
  • DNA / metabolism
  • DNA Replication
  • G-Quadruplexes*
  • Humans
  • Molecular Structure
  • Nucleic Acid Conformation
  • Oligodeoxyribonucleotides
  • Potassium / chemistry
  • RNA / chemistry*
  • RNA / metabolism
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Telomere / chemistry*
  • Telomere / genetics*
  • Telomere / metabolism

Substances

  • Benzophenanthridines
  • Oligodeoxyribonucleotides
  • RNA
  • DNA
  • chelerythrine
  • Potassium