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DNA sequence-specific ligands: XV. Synthesis and spectral characteristics of a new series of dimeric bisbenzimidazoles DB(1, 2, 6, 8, 9, 10, 12)

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Abstract

Seven fluorescent symmetric dimeric bisbenzimidazoles DB(n) capable of occupying up to one turn of the double-stranded B-form DNA have been designed and synthesized with the aim to develop DNAdependent enzyme inhibitors. The DB(n) compounds contain four 2,6-substituted benzimidazole fragments and differ by the length of the oligomethylene linker (n = 1, 2, 6, 8, 9, 10, 12) between the bisbenzimidazole blocks. The formation of DB(n)–double-stranded DNA complexes and the localization of the ligands in the DNA minor groove have been confirmed by a number of physicochemical methods.

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Abbreviations

BOP:

(benzotriazol-1-yloxy)tris(dimethylamino)phoshonium hexafluorophosphate

DB(n):

dimeric bisbenzimidazoles

DIPEA:

N,N-diisopropylethylamine

MB:

monomeric bisbenzimidazole

dsDNA:

double-stranded DNA

PEG:

polyethylene glycol

CLCD:

cholesteric liquid crystalline dispersion

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Authors and Affiliations

  1. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, ul. Vavilova 32, Moscow, 119334, Russia

    V. I. Salyanov & A. L. Zhuze

  2. Research Institute of Carcinogenesis, Blokhin Russian Oncological Research Center, Russian Academy of Medical Sciences, Kashirskoe sh. 24, Moscow, 115478, Russia

    A. A. Ivanov

Authors
  1. A. A. Ivanov
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  2. V. I. Salyanov
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  3. A. L. Zhuze
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Correspondence to A. L. Zhuze.

Additional information

For XIV, see [1].

Original Russian Text © A.A. Ivanov, V.I. Salyanov, A.L. Zhuze, 2016, published in Bioorganicheskaya Khimiya, 2016, Vol. 42, No. 2, pp. 205–213.

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Ivanov, A.A., Salyanov, V.I. & Zhuze, A.L. DNA sequence-specific ligands: XV. Synthesis and spectral characteristics of a new series of dimeric bisbenzimidazoles DB(1, 2, 6, 8, 9, 10, 12). Russ J Bioorg Chem 42, 183–190 (2016). https://doi.org/10.1134/S1068162016020059

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  • DOI: https://doi.org/10.1134/S1068162016020059

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