New peptide conjugates with 9-aminoacridine: synthesis and binding to DNA

J Pept Sci. 2006 Jul;12(7):472-80. doi: 10.1002/psc.752.

Abstract

New peptides-9-aminoacridine conjugates with an ethylene diamine linker-have been synthesized (both solution and solid phase methods were used) and their interactions with DNA have been studied. The affinity of H-Phe-Gln-Gly-Ile(2)-NHCH(2)CH(2)NH-Acr conjugate and of its extended analogue containing 6-aminohexanoic acid to DNA were lower than that of a standard H-Gly-NHCH(2)CH(2)NH-Acr conjugate. The results fit well into our concept of peptide conjugates with lowered binding activity to DNA, which could be capable of unlimited extravascular distribution. Moreover, new structures could be potentially useful as the mild tuners of DNA interaction with strong bis-acridine binders.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminacrine / chemistry*
  • Amino Acid Sequence
  • Animals
  • Base Sequence
  • Cattle
  • DNA / metabolism*
  • In Vitro Techniques
  • Kinetics
  • Molecular Structure
  • Oligodeoxyribonucleotides / chemistry
  • Oligodeoxyribonucleotides / metabolism
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / chemistry
  • Oligopeptides / metabolism*
  • Protein Binding

Substances

  • Oligodeoxyribonucleotides
  • Oligopeptides
  • Aminacrine
  • DNA