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Hexahelicene DNA-binding: Minor groove selectivity, semi-intercalation and chiral recognition
- 1.
SYSNO ASEP 0576802 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Hexahelicene DNA-binding: Minor groove selectivity, semi-intercalation and chiral recognition Author(s) Vacek, J. (CZ)
Zatloukalová, M. (CZ)
Bartheldyová, E. (CZ)
Řeha, D. (CZ)
Minofar, B. (CZ)
Bednářová, Klára (BFU-R) ORCID
Renčiuk, Daniel (BFU-R) RID, ORCID
Coufal, Jan (BFU-R) ORCID
Fojta, Miroslav (BFU-R) RID, ORCID
Žádný, Jaroslav (UCHP-M) RID, SAI, ORCID
Gessini, A. (IT)
Rossi, B. (IT)
Storch, Jan (UCHP-M) RID, ORCID, SAI
Kabeláč, M. (CZ)Number of authors 14 Article number 125905 Source Title International Journal of Biological Macromolecules. - : Elsevier - ISSN 0141-8130
Roč. 250, 1 October 2023 (2023)Number of pages 16 s. Language eng - English Country NL - Netherlands Keywords Chirality ; Nucleic acids ; B-DNA double helix ; Semi-intercalation ; [6]helicene ; Imidazolium Subject RIV CC - Organic Chemistry OECD category Organic chemistry Subject RIV - cooperation Institute of Chemical Process Fundamentals - Organic Chemistry R&D Projects TA04010082 GA TA ČR - Technology Agency of the Czech Republic (TA ČR) EF15_003/0000477 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Limited access Institutional support BFU-R - RVO:68081707 ; UCHP-M - RVO:67985858 UT WOS 001148391800001 EID SCOPUS 85167435418 DOI 10.1016/j.ijbiomac.2023.125905 Annotation 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 dsDNAWorkplace Institute of Biophysics Contact Jana Poláková, polakova@ibp.cz, Tel.: 541 517 244 Year of Publishing 2024 Electronic address https://www.sciencedirect.com/science/article/pii/S0141813023028003?via%3Dihub
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