DNA sequence-specific ligands: XVI. Series of the DBP(<Emphasis Type="Italic">n</Emphasis>) fluorescent dimeric bisbenzimidazoles with 1,4-piperazine-containing linkers |
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Authors: | V S Koval A A Ivanov V I Salyanov A A Stomakhin V A Oleinikov A L Zhuze |
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Institution: | 1.Engelhardt Institute of Molecular Biology,Russian Academy of Sciences,Moscow,Russia;2.Blokhin Russian Cancer Research Center,Ministry of Health of the Russian Federation,Moscow,Russia;3.Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry,Russian Academy of Sciences,Moscow,Russia |
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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. |
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