Hexahelicene DNA-binding: Minor groove selectivity, semi-intercalation and chiral recognition

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/68081707:_____/23:00576802 RIV/60076658:12310/23:43907310 RIV/61989592:15110/23:73621015 RIV/61989100:27740/23:10253165

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Hexahelicene DNA-binding: Minor groove selectivity, semi-intercalation and chiral recognition

Popis výsledku v původním jazyce

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

Název v anglickém jazyce

Hexahelicene DNA-binding: Minor groove selectivity, semi-intercalation and chiral recognition

Popis výsledku anglicky

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

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2023

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

International Journal of Biological Macromolecules

ISSN

0141-8130

e-ISSN

1879-0003

Svazek periodika

250

Číslo periodika v rámci svazku

1 October 2023

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

16

Strana od-do

125905

Kód UT WoS článku

001148391800001

EID výsledku v databázi Scopus

2-s2.0-85167435418