Synthesis and structure-DNA binding relationship analysis of DNA triple-helix specific intercalators

J Med Chem. 1996 Sep 27;39(20):3980-3. doi: 10.1021/jm9603734.

Abstract

4-[N-(Aminoalkyl)amino]-2-arylquinolines with conformational freedom around positions 2 and 4 of the quinoline stabilize strongly poly(dT.dA.dT) (triplex DNA) and bind weakly to poly-(dA.dT) (duplex DNA). Basicity of N1 of the quinoline parallels the interaction strength of these compounds with the triple-helical DNA structure suggesting that N1 of the quinoline is protonated in the complex with the DNA triplex. The experimental results support the interaction model suggested previously.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • DNA / chemistry*
  • DNA / metabolism*
  • Intercalating Agents / chemical synthesis*
  • Intercalating Agents / metabolism*
  • Molecular Structure
  • Nucleic Acid Conformation*
  • Poly T / metabolism
  • Poly dA-dT / metabolism
  • Quinolines / chemistry*
  • Quinolines / metabolism
  • Spectrophotometry
  • Structure-Activity Relationship
  • Thermodynamics

Substances

  • Intercalating Agents
  • Quinolines
  • Poly T
  • Poly dA-dT
  • DNA