Interactions of cryptolepine and neocryptolepine with unusual DNA structures

Biochimie. 2003 May;85(5):535-47. doi: 10.1016/s0300-9084(03)00035-x.

Abstract

Cryptolepine, the main alkaloid present in the roots of Cryptolepis sanguinolenta, presents a large spectrum of biological properties. It has been reported to behave like a DNA intercalator with a preference for GC-rich sequences. In this study, dialysis competition assay and mass spectrometry experiments were used to determine the affinity of cryptolepine and neocryptolepine for DNA structures among duplexes, triplexes, quadruplexes and single strands. Our data confirm that cryptolepine and neocryptolepine prefer GC over AT-rich duplex sequences, but also recognize triplex and quadruplex structures. These compounds are weak telomerase inhibitors and exhibit a significant preference for triplexes over quadruplexes or duplexes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / metabolism*
  • Alkaloids / pharmacology
  • Animals
  • Cryptolepis / chemistry
  • DNA / chemistry
  • DNA / metabolism*
  • Enzyme Inhibitors / pharmacology
  • Indole Alkaloids
  • Indoles / chemistry
  • Indoles / metabolism*
  • Indoles / pharmacology
  • Mass Spectrometry
  • Nucleic Acid Conformation
  • Protein Binding
  • Quinolines / chemistry
  • Quinolines / metabolism*
  • Quinolines / pharmacology
  • Structure-Activity Relationship
  • Substrate Specificity
  • Telomerase / drug effects

Substances

  • Alkaloids
  • Enzyme Inhibitors
  • Indole Alkaloids
  • Indoles
  • Quinolines
  • neocryptolepine
  • cryptolepine
  • DNA
  • Telomerase