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A novel bis(intercalating) agent for DNA based on the bis(benzoquinolizinium) derivative

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Abstract

The derivative of bis(styrylisoquinoline) E,E-1 was synthesized for the first time. When irradiated for a short time with the nonfiltered light of a high-pressure mercury lamp, E,E-1 can experience consecutive transformations including photoisomerization to isomer Z,Z-1, photoinduced intramolecular cyclization via the electrocyclic reaction mechanism, and the formation of bis(benzoquinolizinium) derivative due to the oxidation of the electrocyclic reaction product with air oxygen. The study of the bis(polyheteroaromatic) derivative revealed its high affinity with respect to calf thymus DNA. This compound is able to form complexes with DNA due to the intercalation of one or both polyheteroaromatic fragments.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelements Compounds, Russian Academy of Sciences, Build. 1, 28 ul. Vavilova, 119334, Moscow, Russian Federation

    A. E. Saifutiarova, E. N. Gulakova, Yu. V. Fedorov & O. A. Fedorova

Authors
  1. A. E. Saifutiarova
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  2. E. N. Gulakova
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  3. Yu. V. Fedorov
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  4. O. A. Fedorova
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Corresponding author

Correspondence to A. E. Saifutiarova.

Additional information

The spectral studies were carried out using the scientific equipment of the Center of Molecule Structure Investigation at the A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences.

This work was financially supported by the Russian Science Foundation (Project No. 21-73-20158).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 7, pp. 1701–1710, July, 2023.

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Saifutiarova, A.E., Gulakova, E.N., Fedorov, Y.V. et al. A novel bis(intercalating) agent for DNA based on the bis(benzoquinolizinium) derivative. Russ Chem Bull 72, 1701–1710 (2023). https://doi.org/10.1007/s11172-023-3950-7

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  • DOI: https://doi.org/10.1007/s11172-023-3950-7

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