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Hexahelicene DNA-binding: Minor groove selectivity, semi-intercalation and chiral recognition
- 1.0576802 - BFÚ 2024 RIV NL eng J - Journal Article
Vacek, J. - Zatloukalová, M. - Bartheldyová, E. - Řeha, D. - Minofar, B. - Bednářová, Klára - Renčiuk, Daniel - Coufal, Jan - Fojta, Miroslav - Žádný, Jaroslav - Gessini, A. - Rossi, B. - Storch, Jan - Kabeláč, M.
Hexahelicene DNA-binding: Minor groove selectivity, semi-intercalation and chiral recognition.
International Journal of Biological Macromolecules. Roč. 250, 1 October 2023 (2023), č. článku 125905. ISSN 0141-8130. E-ISSN 1879-0003
R&D Projects: GA TA ČR TA04010082; GA MŠMT EF15_003/0000477
Institutional support: RVO:68081707 ; RVO:67985858
Keywords : Chirality * Nucleic acids * B-DNA double helix * Semi-intercalation * [6]helicene * Imidazolium
OECD category: Organic chemistry; Organic chemistry (UCHP-M)
Impact factor: 8.2, year: 2022
Method of publishing: Limited access
https://www.sciencedirect.com/science/article/pii/S0141813023028003?via%3Dihub
In this contribution, we focused on a fundamental study targeting the interaction of water-soluble [6]helicene
derivative 1 (1-butyl-3-(2-methyl[6]helicenyl)-imidazolium bromide) with double-stranded (ds) DNA. A syn-
thetic 30-base pair duplex, plasmid, chromosomal calf thymus and salmon DNA were investigated using elec-
trochemistry, electrophoresis and spectroscopic tools supported by molecular dynamics (MD) and quantum
mechanical approaches. Both experimental and theoretical work revealed the minor groove binding of 1 to the
dsDNA. Both the positively charged imidazole ring and hydrophobic part of the side chain contributed to the
accommodation of 1 into the dsDNA structure. Neither intercalation into the duplex DNA nor the stable binding
of 1 to single-stranded DNA were found in topoisomerase relaxation experiments with structural components of
1, i.e. [6]helicene (2) and 1-butyl-3-methylimidazolium bromide (3), nor by theoretical calculations. Finally, the
binding of optically pure enantiomers (P)-1 and (M)-1 was studied using circular dichroism spectroscopy,
isothermal titration calorimetry and UV Resonance Raman (UVRR) methods. Using MD and quantum mechanical
methods, minor groove and semi-intercalation were proposed for compound 1 as the predominant binding
modes. From the UVRR findings, we also can conclude that 1 tends to preferentially interact with adenine and
guanine residues in the structure of dsDNA
Permanent Link: https://hdl.handle.net/11104/0346205
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