Russian Journal of Bioorganic Chemistry

, Volume 43, Issue 2, pp 143–149 | Cite as

DNA sequence-specific ligands: XVI. Series of the DBP(n) fluorescent dimeric bisbenzimidazoles with 1,4-piperazine-containing linkers

  • V. S. Koval
  • A. A. Ivanov
  • V. I. Salyanov
  • A. A. Stomakhin
  • V. A. Oleinikov
  • A. L. Zhuze
Article

Abstract

A novel series of the DBP(n) fluorescent symmetric dimeric bisbenzimidazoles in which the bisbenzimidazole fragments were attached to an oligomeric linker with the 1,4-piperazine residue in its center were prepared. The DBP(n) molecules were distinguished by the number of methylene groups n (where n = 1, 2, 3, 4) in the linker. The DBP(n) synthesis was based on a condensation of the monomeric bisbenzimidazole (MB) with 1,4-piperazinedialkylcarbonic acids. The ability of the DBP(n) dimeric bisbenzimidazoles to form complexes with the double-stranded DNA was demonstrated by a complex of physicochemical methods, including spectroscopy in the visual UV-area, circular dichroism (CD), and fluorescence. The DBP(1–4) molecules were localized in the DNA minor groove by the CD method with the use of cholesteric liquid-crystalline dispersions (CLCD) of the double-stranded DNA. The DBP(n) dimeric bisbenzimidazoles were easily soluble in water, penetrated through cellular and nuclear membranes, and stained DNA in living cells distinct from the previously synthesized DB(n) series.

Keywords

dimeric bisbenzimidazole DBP(ncomplexes with the double-stranded DNA DNA minorgroove binder fluorescence circular dichroism 

Abbreviations

dsDNA

the double-stranded DNA

X-ray

X-ray structural analysis

CD

circular dichroism

CLCD

the cholesteric liquid-crystalline dispersion

BOP

benzotriazolyl-1-oxy)tris(dimethylamino)-phosphonium hexafluorophosphate

DIPEA

N,N-diisopropylamine

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Copyright information

© Pleiades Publishing, Ltd. 2017

Authors and Affiliations

  • V. S. Koval
    • 1
  • A. A. Ivanov
    • 2
  • V. I. Salyanov
    • 1
  • A. A. Stomakhin
    • 1
  • V. A. Oleinikov
    • 3
  • A. L. Zhuze
    • 1
  1. 1.Engelhardt Institute of Molecular BiologyRussian Academy of SciencesMoscowRussia
  2. 2.Blokhin Russian Cancer Research CenterMinistry of Health of the Russian FederationMoscowRussia
  3. 3.Shemyakin–Ovchinnikov Institute of Bioorganic ChemistryRussian Academy of SciencesMoscowRussia

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