Intramolecular Proton and Charge Transfer of Pyrene‐based        <i >transtrans        ‐Stilbene Salicylic Acids Applied to Detection of Aggregated Proteins

Zhang Jun; Wang Jun; Sandberg Alexander; Wu Xiongyu; Nystr?m Sofie; LeVine Harry; Konradsson Peter; Hammarstr?m Per; Durbeej Bo; Lindgren Mikael

摘要

Abstract > Two analogues to the fluorescent amyloid probe 2,5‐bis(4′‐hydroxy‐3′‐carboxy‐styryl)benzene (X‐34) were synthesized based on the trans ‐stilbene pyrene scaffold (Py1SA and Py2SA). The compounds show strikingly different emission spectra when bound to preformed Aβ1–42 fibrils. This remarkable emission difference is retained when bound to amyloid fibrils of four distinct proteins, suggesting a common binding configuration for each molecule. Density functional theory calculations show that Py1SA is twisted, while Py2SA is more planar. Still, an analysis of the highest occupied molecular orbitals (HOMOs) and lowest unoccupied molecular orbitals (LUMOs) of the two compounds indicates that the degree of electronic coupling between the pyrene and salicylic acid (SA) moieties is larger in Py1SA than in Py2SA. Excited state intramolecular proton transfer (ESIPT) coupled‐charge transfer (ICT) was observed for the anionic form in polar solvents. We conclude that ICT properties of trans ‐stilbene derivatives can be utilized for amyloid probe design with large changes in emission spectra and decay times from analogous chemical structures depending on the detailed physical nature of the binding site. </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><Abstract Type =“main”XML：Lang =“en”> <标题类型=“main”>抽象</ title> >两种类似物到荧光淀粉样蛋白探针2,5-BIS（4'-羟基-3基于 Trans </ i> - 硅烯芘支架（Py1SA和Py2SA）合成“-Carboxy-Styryl）苯（X-34）。当与预成型Aβ1-42原纤维结合时，化合物显示出惊人的不同发射光谱。当与四个不同蛋白质的淀粉样蛋白原纤维结合时，保留这种显着的发射差异，表明每个分子的共同结合构型。密度函数理论计算表明py1sa扭曲，而py2sa更加平坦。仍然，对两种化合物的最高占用分子轨道（HOMOS）和最低的未占用分子轨道（LUMOS）的分析表明，芘和水杨酸（SA）部分之间的电子偶联程度在Py1SA中较大，而不是py2SA。激发状态分子内质子转移（ESIPT）耦合电荷转移（ICT）在极性溶剂中的阴离子形式观察到。我们得出结论，反式 - / i> -stilbene衍生物的ICT性质可用于淀粉样蛋白探针设计，其根据粘合位点的详细物理性质，从类似化学结构的发射光谱和衰减时间发生大变化。 </ p> </ abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" >著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-16300/'>《Chemphyschem: A European journal of chemical physics and physical chemistry》</a> <b style="margin: 0 2px;">|</b><span>2018年第22期</span><b style="margin: 0 2px;">|</b><span>共9页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhang Jun&option=202" target="_blank" rel="nofollow">Zhang Jun;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wang Jun&option=202" target="_blank" rel="nofollow">Wang Jun;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Sandberg Alexander&option=202" target="_blank" rel="nofollow">Sandberg Alexander;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wu Xiongyu&option=202" target="_blank" rel="nofollow">Wu Xiongyu;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Nystr?m Sofie&option=202" target="_blank" rel="nofollow">Nystr?m Sofie;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=LeVine Harry&option=202" target="_blank" rel="nofollow">LeVine Harry;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Konradsson Peter&option=202" target="_blank" rel="nofollow">Konradsson Peter;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Hammarstr?m Per&option=202" target="_blank" rel="nofollow">Hammarstr?m Per;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Durbeej Bo&option=202" target="_blank" rel="nofollow">Durbeej Bo;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lindgren Mikael&option=202" target="_blank" rel="nofollow">Lindgren Mikael;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>Division of Chemistry Department of Physics Chemistry and BiologyLink?ping University581 83 Link?ping Sweden;</p> <p>Division of Theoretical Chemistry Department of Physics Chemistry and BiologyLink?ping University581 83 Link?ping Sweden;</p> <p>Division of Chemistry Department of Physics Chemistry and BiologyLink?ping University581 83 Link?ping Sweden;</p> <p>Division of Chemistry Department of Physics Chemistry and BiologyLink?ping University581 83 Link?ping Sweden;</p> <p>Division of Chemistry Department of Physics Chemistry and BiologyLink?ping University581 83 Link?ping Sweden;</p> <p>Sanders-Brown Center on AgingUniversity of KentuckyKY 40536–0230 Lexington USA;</p> <p>Division of Chemistry Department of Physics Chemistry and BiologyLink?ping University581 83 Link?ping Sweden;</p> <p>Division of Chemistry Department of Physics Chemistry and BiologyLink?ping University581 83 Link?ping Sweden;</p> <p>Division of Theoretical Chemistry Department of Physics Chemistry and BiologyLink?ping University581 83 Link?ping Sweden;</p> <p>Division of Chemistry Department of Physics Chemistry and BiologyLink?ping University581 83 Link?ping Sweden;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li > <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span><a href="https://www.zhangqiaokeyan.com/clc/1186.html" title="物理化学（理论化学）、化学物理学">物理化学（理论化学）、化学物理学;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=amyloid detection&option=203" rel="nofollow">amyloid detection;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=ESIPT&option=203" rel="nofollow">ESIPT;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=fluorescent probe&option=203" rel="nofollow">fluorescent probe;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=ICT&option=203" rel="nofollow">ICT;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=pyrene&option=203" rel="nofollow">pyrene;</a> </p> <div class="translation"> 机译：淀粉样蛋白检测;eSipt;荧光探针;ICT;芘; </div> </li> </ul> </div> </div> <div class="literature cardcommon"> <div 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translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：ESIPT新型咪唑基化合物的激发态分子内质子转移激发蓝光荧光及其合成方法 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130412138048.html">DIPYRRIN BASED MATERIALS FOR PHOTOVOLTAICS COMPOUNDS CAPABLE OF UNDERGOING SYMMETRY BREAKING INTRAMOLECULAR CHARGE TRANSFER IN A POLARIZING MEDIUM AND ORGANIC PHOTOVOLTAIC DEVICES COMPRISING THE SAME</a> <b>[P]</b> . <span> 外国专利：  IN2014DN09797A </span> <span> . 2016-04-22</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：基于双吡啶的光电化合物，可在具有相同对称性的偏光和有机光电器件中经历对称性断裂，分子内电荷转移 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130414253223.html">DIPYRRIN BASED MATERIALS FOR PHOTOVOLTAICS, COMPOUNDS CAPABLE OF UNDERGOING SYMMETRY BREAKING 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Intramolecular Proton and Charge Transfer of Pyrene‐based transtrans ‐Stilbene Salicylic Acids Applied to Detection of Aggregated Proteins

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