Dual Mechanism of an Intramolecular Charge Transfer (ICT)–FRET‐Based Fluorescent Probe for the Selective Detection of Hydrogen Peroxide

Liang Xiao; Xu Xiaoyi; Qiao Dan; Yin Zheng; Shang Luqing

摘要

Abstract > A dual‐mechanism intramolecular charge transfer (ICT)–FRET fluorescent probe for the selective detection of H <sub>2</sub> O <sub>2</sub> in living cells has been designed and synthesized. This probe used a coumarin–naphthalimide hybrid as the FRET platform and a boronate moiety as the recognition group. Upon the addition of H <sub>2</sub> O <sub>2</sub> , the probe exhibited a redshifted (73?nm) fluorescence emission, and the ratio of fluorescence intensities at λ =558 and 485?nm ( F <sub>558</sub> / F <sub>485</sub> ) shifted notably (up to 100‐fold). Moreover, there was a good linearity ( R 2 =0.9911) between the ratio and concentration of H <sub>2</sub> O <sub>2</sub> in the range of 0 to 60?μ <sc>m</sc> , with a limit of detection of 0.28?μ <sc>m</sc> (signal to noise ratio (S/N)=3). This probe could also detect enzymatically generated H <sub>2</sub> O <sub>2</sub> . Importantly, it could be used to visualize endogenous H <sub>2</sub> O <sub>2</sub> produced by stimulation from epidermal growth factor. </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 XMLNS =“http://www.wiley.com/namespaces/wiley”type =“main”xml：lang =“en”> <标题类型=“main”>抽象</ title> > 双机制分子内电荷转移（ICT） - 用于选择性检测的荧光探针 <sub> 2 </ sub> O. <sub> 2 </ sub> 在活细胞中已经设计和合成。该探针使用香豆素 - 萘硫代胺杂交作为尺寸平台和硼酸盐部分作为识别组。加上h <sub> 2 </ sub> O. <sub> 2 </ sub> ，探针表现出红移（73·NM）荧光发射，荧光强度的比例 λ</ i> = 558和485？nm（ f </ i> <sub> 558 </ sub> / f </ i> <sub> 485 </ sub> ）特别地转移（高达100倍）。而且，有一个很好的线性度（ R </ I> 2 </ sup> = 0.9911）H之间的比率和浓度 <sub> 2 </ sub> O. <sub> 2 </ sub> 在0到60？μ的范围内 <sc> m </ sc> ，检测限为0.28ΩΩ <sc> m </ sc> （信噪比（S / N）= 3）。该探针还可以检测酶促产生的H. <sub> 2 </ sub> O. <sub> 2 </ sub> 。重要的是，它可用于可视化内源性h <sub> 2 </ sub> O. <sub> 2 </ sub> 通过表皮生长因子的刺激产生。 </ p> </摘要> </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-16161/'>《Chemistry, an Asian journal 》</a> <b style="margin: 0 2px;">|</b><span>2017年第24期</span><b style="margin: 0 2px;">|</b> <span>共8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=Liang Xiao&option=202" target="_blank" rel="nofollow">Liang Xiao;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Xu Xiaoyi&option=202" target="_blank" rel="nofollow">Xu Xiaoyi;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Qiao Dan&option=202" target="_blank" rel="nofollow">Qiao Dan;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yin Zheng&option=202" target="_blank" rel="nofollow">Yin Zheng;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Shang Luqing&option=202" target="_blank" rel="nofollow">Shang Luqing;</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>College of Pharmacy &</p> <p>State Key LaboratoryNankai UniversityTianjin 300071 P.R. China;</p> <p>Tianjin Medical UniversityTianjin 300070 P.R. China;</p> <p>College of Pharmacy &</p> <p>State Key LaboratoryNankai UniversityTianjin 300071 P.R. China;</p> <p>College of Pharmacy &</p> <p>State Key LaboratoryNankai UniversityTianjin 300071 P.R. China;</p> <p>College of Pharmacy &</p> <p>State Key LaboratoryNankai UniversityTianjin 300071 P.R. China;</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/159.html" title="化学">化学 ;</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=charge transfer&option=203" rel="nofollow">charge transfer;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=fluorescence&option=203" rel="nofollow">fluorescence;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=FRET&option=203" rel="nofollow">FRET;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=hydrogen peroxide&option=203" rel="nofollow">hydrogen peroxide;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=sensors&option=203" rel="nofollow">sensors;</a> </p> <div class="translation"> 机译：电荷转移;荧光;褶皱;过氧化氢;传感器; 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href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=王晓菲&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,王晓菲</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=谭超华&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,谭超华</a> <span> <a href="/journal-cn-12046/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 化学物理学报 </a> </span> <span> . 2019</span><span> ,第4期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-33265_thesis/02022799516.html">分子内电荷转移双重荧光传感与分子识别</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=江云宝&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 江云宝</a> <span> <a href="/conference-cn-33265/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 全国生物发光分析学术会议 </a> <span> <span> . 1999</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020311544475.html">分子内电荷转移(ICT)荧光探针研究环糊精与表面活性剂及其相互作用以及光诱导ICT荧光传感的初步研究</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=林丽榕&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 林丽榕</a> <span> . 1998</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120105185032.html">通过由电的在分子和电极之间的分子间或分子内电荷转移而发生电子转换的物质组合物</a> <b>[P]</b> . <span> 中国专利： CN1985331A </span> <span> . 2007-06-20</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120107915821.html">用于光伏的基于次甲基二吡咯的材料、能够在极化介质中经历对称性破缺分子内电荷转移的化合物以及包含它们的有机光伏器件</a> <b>[P]</b> . <span> 中国专利： CN105409020A </span> <span> . 2016-03-16</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130419204588.html">ISOLATED NUCLEIC ACID CODING FLUORESCENT BIOSENSOR FOR DETECTION OF HYDROGEN PEROXIDE, EXPRESSION CASSETTE, CELL THAT PRODUCES BIOSENSOR, ISOLATED FLUORESCENT BIOSENSOR FOR DETECTION OF HYDROGEN PEROXIDE, ISOLATED NUCLEIC ACID THAT CODES FLUORESCENT BIOSENSOR, EFFICIENTLY FUSED WITH NUCLEIC ACID THAT CODES SIGNAL OF INTRACELLULAR LOCALISATION</a> <b>[P]</b> . <span> 外国专利：  RU2493260C2 </span> <span> . 2013-09-20</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：用于检测过氧化氢的隔离的核酸编码的荧光生物传感器，表达盒，细胞，用于检测过氧化氢的隔离的荧光生物传感器，分离的核酸，是通过在整个纤维上混合的粗胶体的核酸。 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130419255098.html">Isolated nucleic acids encoding FLUORESCENT DETECTION biosensors for hydrogen peroxide DRAWER Expres, cells producing biosensors BIOSENSOR DEDICATED FLUORESCENT for detecting hydrogen peroxide, an isolated nucleic acid encoding FLUORESCENT biosensor OPERATIONAL fused to nucleic acids encoding intracellular localization SIGNAL</a> <b>[P]</b> . <span> 外国专利：  RU2011148840A </span> <span> . 2013-06-10</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：编码用于过氧化氢的荧光检测生物传感器的分离的核酸DRAWER Expres，产生生物传感器的细胞BIOSENSOR专用的荧光用于检测过氧化氢，一种编码荧光的生物传感器可操作的分离的核酸，与编码细胞内定位的核酸融合 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130419406444.html">VARIABLE COLOR TWO-PHOTON FLUORESCENT PROBES CAPABLE OF MAKING IMAGE OF SELECTIVITY AND ACTIVITY OF HYDROGEN PEROXIDE INSIDE MITOCHONDRIA, A MANUFACTURING METHOD THEREOF, AND AN IMAGING METHOD THEREOF</a> <b>[P]</b> . <span> 外国专利：  KR20130107060A </span> <span> . 2013-10-01</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> 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