Postsynthetic modification of oligonucleotides with imidazophenazine dye and its effect on duplex stability

Nucleosides Nucleotides Nucleic Acids. 2011 Jul-Aug;30(7-8):585-96. doi: 10.1080/15257770.2011.598489.

Abstract

Carboxyalkyl derivative of the intercalating agent imidazo[4,5-b]phenazine was used for the postsynthetic oligonucleotide modification. Model pentadecathymidylate-imidazophenazine conjugate was prepared from 5'-aminoalkyl-modified (dT)(15) by using phosphonium coupling reagent BOP in the presence of 1-hydroxybenzotriazole. Spectral-fluorescent properties of the conjugate were studied. The attachment of the dye was found to increase the thermal stability of (dT)(15) duplex with poly(dA) by more than 4°C, probably by the intercalation mechanism.

MeSH terms

  • Coloring Agents / chemistry*
  • Imidazoles / chemistry*
  • Intercalating Agents / chemistry
  • Nucleic Acid Conformation
  • Oligonucleotides / chemical synthesis
  • Oligonucleotides / chemistry*
  • Phenazines / chemistry*
  • Spectrometry, Fluorescence

Substances

  • Coloring Agents
  • Imidazoles
  • Intercalating Agents
  • Oligonucleotides
  • Phenazines
  • imidazole