Antitumour polycyclic acridines. Part 4. Physico-chemical studies on the interactions between DNA and novel tetracyclic acridine derivatives

Anticancer Drug Des. 1998 Jul;13(5):431-51.

Abstract

The non-covalent interactions between a series of new tetracyclic acridine derivatives (5-11) and DNA have been studied by spectrophotometric analysis, fluorescences quenching, thermal denaturation, and circular and linear dichroism. In order to compare the extent of the DNA binding by compounds 5-11 in their neutral and cationic forms, all experiments were conducted at pH 7.4 (physiological pH) and 5.0. The results indicated that compounds 5-11 are strong DNA-binding ligands with DNA affinities comparable to that of m-AMSA (1) or even higher. They showed a stronger DNA binding activity at pH 5.0 as a result of the N-protonation of the pyridoacridine aromatic chromophore. Ethidium-DNA fluorescence assays showed an A-T base pair preference of the binding distinguishing these novel compounds from simple acridines which show a slight G-C base pair preference. Circular and linear dichroism studies indicated that the drugs bind to DNA by undergoing intercalation inside the duplex macromolecule at high DNA:drug ratios and revealed alternative binding modes at low DNA:drug ratios.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acridines / chemistry*
  • Acridines / pharmacology*
  • Algorithms
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Buffers
  • Chemical Phenomena
  • Chemistry, Physical
  • Circular Dichroism
  • DNA / chemistry*
  • DNA / drug effects*
  • Ethidium / chemistry
  • Hot Temperature
  • Kinetics
  • Nucleic Acid Denaturation
  • Spectrometry, Fluorescence
  • Spectrophotometry, Ultraviolet

Substances

  • Acridines
  • Antineoplastic Agents
  • Buffers
  • DNA
  • Ethidium