Hexahelicene DNA-binding: Minor groove selectivity, semi-intercalation and chiral recognition
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F23%3A00576802" target="_blank" >RIV/67985858:_____/23:00576802 - isvavai.cz</a>
Alternative codes found
RIV/68081707:_____/23:00576802 RIV/60076658:12310/23:43907310 RIV/61989592:15110/23:73621015 RIV/61989100:27740/23:10253165
Result on the web
<a href="https://www.sciencedirect.com/science/article/pii/S0141813023028003?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0141813023028003?via%3Dihub</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.ijbiomac.2023.125905" target="_blank" >10.1016/j.ijbiomac.2023.125905</a>
Alternative languages
Result language
angličtina
Original language name
Hexahelicene DNA-binding: Minor groove selectivity, semi-intercalation and chiral recognition
Original language description
In this contribution, we focused on a fundamental study targeting the interaction of water-soluble [6]helicenenderivative 1 (1-butyl-3-(2-methyl[6]helicenyl)-imidazolium bromide) with double-stranded (ds) DNA. A syn-nthetic 30-base pair duplex, plasmid, chromosomal calf thymus and salmon DNA were investigated using elec-ntrochemistry, electrophoresis and spectroscopic tools supported by molecular dynamics (MD) and quantumnmechanical approaches. Both experimental and theoretical work revealed the minor groove binding of 1 to thendsDNA. Both the positively charged imidazole ring and hydrophobic part of the side chain contributed to thenaccommodation of 1 into the dsDNA structure. Neither intercalation into the duplex DNA nor the stable bindingnof 1 to single-stranded DNA were found in topoisomerase relaxation experiments with structural components ofn1, i.e. [6]helicene (2) and 1-butyl-3-methylimidazolium bromide (3), nor by theoretical calculations. Finally, thenbinding of optically pure enantiomers (P)-1 and (M)-1 was studied using circular dichroism spectroscopy,nisothermal titration calorimetry and UV Resonance Raman (UVRR) methods. Using MD and quantum mechanicalnmethods, minor groove and semi-intercalation were proposed for compound 1 as the predominant bindingnmodes. From the UVRR findings, we also can conclude that 1 tends to preferentially interact with adenine andnguanine residues in the structure of dsDNA
Czech name
—
Czech description
—
Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
International Journal of Biological Macromolecules
ISSN
0141-8130
e-ISSN
1879-0003
Volume of the periodical
250
Issue of the periodical within the volume
1 October 2023
Country of publishing house
NL - THE KINGDOM OF THE NETHERLANDS
Number of pages
16
Pages from-to
125905
UT code for WoS article
001148391800001
EID of the result in the Scopus database
2-s2.0-85167435418