Flavonolignan Conjugates as DNA-binding Ligands and Topoisomerase I Inhibitors: Electrochemical and Electrophoretic Approaches

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68081707%3A_____%2F16%3A00467830" target="_blank" >RIV/68081707:_____/16:00467830 - isvavai.cz</a>

Alternative codes found

RIV/61388971:_____/16:00467830 RIV/61989592:15110/16:33160665

Result on the web

<a href="http://dx.doi.org/10.1002/elan.201600146" target="_blank" >http://dx.doi.org/10.1002/elan.201600146</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/elan.201600146" target="_blank" >10.1002/elan.201600146</a>

Result language

angličtina

Original language name

Flavonolignan Conjugates as DNA-binding Ligands and Topoisomerase I Inhibitors: Electrochemical and Electrophoretic Approaches

Original language description

In this work, the electrochemical behavior of flavonolignan silybin (SB) and 2,3-dehydrosilybin (DHSB) and their respective conjugates SB-SB and DHSB-DHSB were studied using voltammetric techniques at a glassy carbon electrode. The redox mechanism of SB and its conjugate occurs in two oxidation steps where the hydroxy groups of the guaiacyl and resorcinol moiety are involved. DHSB and its conjugate are oxidized in three subsequent steps. The enol group in DHSB and DHSB-DHSB is involved in the additional oxidation step, due to the enhanced electron-donor capacity and reactivity of the 2,3-dehydroderivatives compared to the parent flavonolignan molecule. The developed voltammetric methods were subsequently used for the analysis of flavonolignan-DNA interactions. Comparative experiments revealed a remarkable binding affinity between the flavonolignan homoconjugates and double-helical calf thymus DNA, compared to the corresponding monomeric compounds. In addition, biochemical and electrophoretic experiments revealed the flavonolignan-dsDNA binding not to involve intercalation as the major interaction mode. The same experiments have also shown that both flavonolignan conjugates inhibit the activity of type I topoisomerase, which is a DNA topology (superhelicity) modulating enzyme. We suppose that our results could be used in further studies focused on DNA flavonolignan binding and DNA processing protein inhibition by flavonolignan 2,3-dehydroderivatives.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CG - Electrochemistry

OECD FORD branch

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Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2016

Confidentiality

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

Name of the periodical

Electroanalysis

ISSN

1040-0397

e-ISSN

—

Volume of the periodical

28

Issue of the periodical within the volume

11

Country of publishing house

DE - GERMANY

Number of pages

9

Pages from-to

2866-2874

UT code for WoS article

000387891400032

EID of the result in the Scopus database

2-s2.0-84981328394