Synthesis and structural properties of oligonucleotides covalently linked to acridine and quindoline derivatives through a threoninol linker

Bioorg Med Chem. 2010 Nov 1;18(21):7348-56. doi: 10.1016/j.bmc.2010.09.023. Epub 2010 Sep 16.

Abstract

Oligonucleotide conjugates containing acridine and quindoline derivatives linked through a threoninol molecule were synthesized. We showed that these conjugates formed duplexes and quadruplexes with higher thermal stability than the corresponding unmodified oligonucleotides. When acridine is located in the middle of the sequence, DNA duplexes have a similar stability independently of the natural base present in front of acridine. Self-complementary oligonucleotides and thrombin binding aptamers (TBA) carrying the acridine and quindoline molecules are studied by NMR.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acridines / chemistry*
  • Alkaloids / chemistry*
  • Amino Alcohols / chemistry*
  • Aptamers, Nucleotide / chemistry
  • Butylene Glycols / chemistry*
  • Circular Dichroism
  • Indoles / chemistry*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Nucleic Acid Conformation
  • Nucleic Acid Denaturation
  • Oligonucleotides / chemical synthesis
  • Oligonucleotides / chemistry*
  • Quinolines / chemistry*

Substances

  • Acridines
  • Alkaloids
  • Amino Alcohols
  • Aptamers, Nucleotide
  • Butylene Glycols
  • Indoles
  • Oligonucleotides
  • Quinolines
  • threoninol
  • thrombin aptamer
  • quindoline