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dc.contributor.authorMartin-Benlloch, Xavier
dc.contributor.authorHaid, Sybille
dc.contributor.authorNovodomska, Alexandra
dc.contributor.authorRominger, Frank
dc.contributor.authorPietschmann, Thomas
dc.contributor.authorDavioud-Charvet, Elisabeth
dc.contributor.authorElhabiri, Mourad
dc.date.accessioned2019-04-18T13:16:05Z
dc.date.available2019-04-18T13:16:05Z
dc.date.issued2019-03-05
dc.identifier.citationACS Omega 2019 Mar 5;4(3):4871. doi: 10.1021/acsomega.8b03332.en_US
dc.identifier.issn2470-1343
dc.identifier.pmid31459671EN
dc.identifier.doi10.1021/acsomega.8b03332
dc.identifier.urihttp://hdl.handle.net/10033/621755
dc.description.abstractLadanein (i.e., 5,6,7-trihydroxylated flavone) was demonstrated to act as a powerful virucidal agent toward a broad range of enveloped virus particles. Fe(III) coordination and pH are indeed among the key parameters that might favor both bioactivation of the flavone and consequent host cell entry inhibition. In this present work, the impact of fluorinated groups on the physicochemical and antiviral properties of the flavone was investigated, thus allowing a deeper understanding of the antiviral mode of action. The improved synthesis of ladanein allowed accessing a broad range of analogues, some of them being significantly more active than the former ladanein lead compound. We first determined the acido-basic properties of this homogenous series of compounds and then investigated their electrochemical behavior. Fe(III) coordination properties (stability, spectral behavior, and kinetics) of ladanein and its analogues were then examined (quasiphysiological conditions) and provided key information of their stability and reactivity. Using the determined physicochemical parameters, the critical impact of the iron complexation and medium acidity was confirmed on hepatitis C virus (HCV) particles (pre)treated with ladanein. Finally, a preliminary structure–HCV entry inhibition relationship study evidenced the superior antiviral activity of the ladanein analogues bearing an electron-withdrawing group in para position (FCF3 > FOCF3 > FFCF3 > FF > FOMe) on the B cycle in comparison with the parent ladanein itself.en_US
dc.language.isoenen_US
dc.publisherAmerican Chemical Societyen_US
dc.rightsAttribution-NonCommercial-ShareAlike 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/4.0/*
dc.titlePhysicochemical Properties Govern the Activity of Potent Antiviral Flavonesen_US
dc.typeArticleen_US
dc.contributor.departmentTWINCORE, Zentrum für experimentelle und klinische Infektionsforschung GmbH, Feodor-Lynen-Str.7,30625 Hannover, Germany.en_US
dc.identifier.journalACS Omegaen_US


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