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Physicochemical Properties Govern the Activity of Potent AntiviralFlavones

機(jī)譯：理化特性控制有效的抗病毒活性黃酮類

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Ladanein (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 ofthe iron complexation and medium acidity was confirmed on hepatitisC virus (HCV) particles (pre)treated with ladanein. Finally, a preliminarystructure–HCV entry inhibition relationship study evidencedthe superior antiviral activity of the ladanein analogues bearingan electron-withdrawing group in para position (>FCF>3 > >FOCF>3 > >FFCF>3 > >FF > >FOMe) on the B cycle in comparison with the parentladanein itself.
機(jī)譯：拉丹寧（即5,6,7-三羥基黃酮）被證明對多種包膜病毒顆粒具有強(qiáng)大的殺病毒作用。 Fe（III）的配位和pH確實(shí)是可能有利于黃酮生物活化和隨之而來的宿主細(xì)胞進(jìn)入抑制的關(guān)鍵參數(shù)。在本工作中，研究了氟化基團(tuán)對黃酮的理化性質(zhì)和抗病毒特性的影響，從而使人們對抗病毒作用方式有更深的了解。拉丹寧合成方法的改進(jìn)使人們可以使用各種各樣的類似物，其中一些比以前的拉丹寧先導(dǎo)化合物活性更高。我們首先確定了該系列同質(zhì)化合物的酸堿性，然后研究了它們的電化學(xué)行為。然后檢查了（化學(xué)生理?xiàng)l件）拉丹寧及其類似物的Fe（III）配位性質(zhì)（穩(wěn)定性，光譜行為和動(dòng)力學(xué)），并提供了其穩(wěn)定性和反應(yīng)性的關(guān)鍵信息。使用確定的理化參數(shù)，證實(shí)肝炎中鐵的絡(luò)合和中等酸度用拉丹寧處理過的C病毒（HCV）顆粒。最后，初步結(jié)構(gòu)-HCV進(jìn)入抑制關(guān)系的研究證明拉丹寧類似物具有優(yōu)異的抗病毒活性處于對位的吸電子基團(tuán)（> FCF > 3 FOCF > 3 FFCF > 3 FF FOMe ）拉丹寧本身。

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