pH Controlled Intersystem Crossing and Singlet Oxygen Generation of 8‐Azaadenine in Aqueous Solution

Zhou Zhongneng; Hu Zhubin; Zhang Xianwang; Jia Menghui; Wang Xueli; Su Hongmei; Sun Haitao; Chen Jinquan; Xu Jianhua

摘要

Abstract > Azabases are intriguing DNA and RNA analogues and have been used as effective antiviral and anticancer medicines. However, photosensitivity of these drugs has also been reported. Here, pH‐controlled intersystem crossing (ISC) process of 9H 8‐azaadenine (8‐AA) in aqueous solution is reported. Broadband transient absorption measurements reveal that the hydrogen atom at N9 position can greatly affect ISC of 8‐AA and ISC is more favorable when 8‐AA is in its neutral form in aqueous solution. The initial excited ππ* (S <sub>2</sub> ) state evolves through ultrafast internal conversion (IC) (4.2?ps) to the lower‐lying nπ* state (S <sub>1</sub> ), which further stands as a door way state for ISC with a time constant of 160?ps. The triplet state has a lifetime of 6.1?μs. On the other hand, deprotonation at N9 position promotes the IC from the ππ* (S <sub>2</sub> ) state to the ground state (S <sub>0</sub> ) and the lifetime of the S <sub>2</sub> state is determined to be 10?ps. The experimental results are further supported by time‐dependent density functional theory (TDDFT) calculations. Singlet oxygen generation yield is measured to be 13.8?% for the neutral 8‐AA while the deprotonated one exhibit much lower yield (2?%), implying that this compound could be a potential pH‐sensitized photodynamic therapy agent. </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> >氮杂酶是有趣的DNA和RNA类似物，并已被用作有效的抗病毒和抗癌药物。然而，还报道了这些药物的光敏性。这里，据报道，据报道，在水溶液中的9H 8-氮杂腺嘌呤（8-AA）的pH控制的间接系统交叉（ISC）方法。宽带瞬态吸收测量表明，当8-AA在水溶液中的中性形式中时，N9位置的氢原子可以极大地影响8-AA的ISC，ISC更有利。初始激励的ππ*（S <sub> 2 </ sub>）状态通过超快内部转换（IC）（4.2×ps）进化到较低位nπ*状态（s <sub> 1 </ sub>），这进一步作为ISC的门方式，时间常数为160？PS。三重态状态具有6.1Ωμs的寿命。另一方面，n9位置的去质子化从ππ*（s <sub> 2 </ sub>）状态促进IC到地状态（s <sub> 0 </ sub>）和s <sabl的寿命亚> 2 </ sub>状态确定为10？ps。通过时间依赖性密度泛函理论（TDDFT）计算进一步支持实验结果。测量中性8-AA的单次氧产生产率为13.8□，而前质子化的产率低得多的产率（＆lt 2倍），这意味着该化合物可以是潜在的pH-敏化的光动力治疗剂。 </ 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>2019年第5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=Zhou Zhongneng&option=202" target="_blank" rel="nofollow">Zhou Zhongneng;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Hu Zhubin&option=202" target="_blank" rel="nofollow">Hu Zhubin;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhang Xianwang&option=202" target="_blank" rel="nofollow">Zhang Xianwang;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Jia Menghui&option=202" target="_blank" rel="nofollow">Jia Menghui;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wang Xueli&option=202" target="_blank" rel="nofollow">Wang Xueli;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Su Hongmei&option=202" target="_blank" rel="nofollow">Su Hongmei;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Sun Haitao&option=202" target="_blank" rel="nofollow">Sun Haitao;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chen Jinquan&option=202" target="_blank" rel="nofollow">Chen Jinquan;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Xu Jianhua&option=202" target="_blank" rel="nofollow">Xu Jianhua;</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>State Key Laboratory of Precision SpectroscopyEast China Normal UniversityShanghai 200062 China;</p> <p>State Key Laboratory of Precision SpectroscopyEast China Normal UniversityShanghai 200062 China;</p> <p>College of ChemistryBeijing Normal UniversityBeijing 100875 China;</p> <p>Shanghai Institute of Optics and Fine MechanicsShanghai 201800 China;</p> <p>State Key Laboratory of Precision SpectroscopyEast China Normal UniversityShanghai 200062 China;</p> <p>College of ChemistryBeijing Normal UniversityBeijing 100875 China;</p> <p>State Key Laboratory of Precision SpectroscopyEast China Normal UniversityShanghai 200062 China;</p> <p>State Key Laboratory of Precision SpectroscopyEast China Normal UniversityShanghai 200062 China;</p> <p>State Key Laboratory of Precision SpectroscopyEast China Normal UniversityShanghai 200062 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/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=8-azaadenine&option=203" rel="nofollow">8-azaadenine;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=intersystem crossing&option=203" rel="nofollow">intersystem crossing;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=pH&option=203" rel="nofollow">pH;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=singlet oxygen&option=203" rel="nofollow">singlet oxygen;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=transient absorption&option=203" rel="nofollow">transient absorption;</a> </p> <div class="translation"> 机译：8-氮杂腺嘌呤;跨越式交叉;pH;单线氧;瞬态吸收; </div> </li> </ul> </div> </div> <div class="literature cardcommon"> <div class="similarity "> <h3 class="all_title" id="enpatent66">相似文献</h3> <div class="similaritytab clearfix"> <ul> <li class="active" >外文文献</li> <li >中文文献</li> <li >专利</li> </ul> </div> <div class="similarity_details"> <ul > <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704022115631.html">pH Controlled Intersystem Crossing and Singlet Oxygen Generation of 8‐Azaadenine in Aqueous Solution</a> <b>[J]</b> . <span> <a 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href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=李云飞&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,李云飞</a> <span> <a href="/journal-cn-9151/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 化工学报 </a> </span> <span> . 2005</span><span> ,第003期</span> </span> </div> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/academic-journal-cn_polyester-industry_thesis/0201248162724.html">氧气在醋酸水溶液中的溶解度估算</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=徐海波&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 徐海波</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=王勤波&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,王勤波</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=李希&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,李希</a> <span> <a href="/journal-cn-9195/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 聚酯工业 </a> </span> <span> . 2005</span><span> ,第005期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-6185_thesis/020221623804.html">碳酸氢钠溶液中钴离子活化氧气氧化氨基酚产生羟基自由基的研究</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=施薇&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 施薇</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=徐爱华&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,徐爱华</a> <span> <a href="/conference-cn-6185/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 第七届全国环境化学学术大会 </a> <span> <span> . 2013</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020316251886.html">叙事治疗单次小组在舒缓晚期癌症患者精神压力中的运用--以南昌市R医院三个单次小组为例</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=谢婷&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 谢婷</a> <span> . 2020</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/061201653096.html">用于产生用于消毒剂用途的pH受控的次卤酸水溶液的电解装置</a> <b>[P]</b> . <span> 中国专利： CN101713080B </span> <span> . 2015.05.13</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120105905782.html">用于产生用于消毒剂用途的pH受控的次卤酸水溶液的电解装置</a> <b>[P]</b> . <span> 中国专利： CN101713080A </span> <span> . 2010-05-26</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130429984386.html">STORAGE-STABLE FORMULATION OF OXIDATION-SENSITIVE PHENOLIC DRUG, ESPECIALLY PARACETAMOL, COMPRISES AQUEOUS DRUG SOLUTION DEOXYGENATED BY A TEMPERATURE-CONTROLLED MANUFACTURING PROCESS OF THE FORMULATION</a> <b>[P]</b> . <span> 外国专利：  WO2008135601A3 </span> <span> . 2009-06-18</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：氧化敏感的酚类药物（尤其是甲萘酚）的存储稳定配方，包括通过温度控制的制造过程脱氧的水性药物溶液 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130429984387.html">STORAGE-STABLE FORMULATION OF OXIDATION-SENSITIVE PHENOLIC DRUG, ESPECIALLY PARACETAMOL, COMPRISES AQUEOUS DRUG SOLUTION DEOXYGENATED BY A TEMPERATURE-CONTROLLED MANUFACTURING PROCESS OF THE FORMULATION</a> <b>[P]</b> . <span> 外国专利：  WO2008135601A2 </span> <span> . 2008-11-13</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：氧化敏感的酚类药物（尤其是甲萘酚）的存储稳定配方，包括通过温度控制的制造过程脱氧的水性药物溶液 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130429895031.html">Storage-stable formulation of oxidation-sensitive phenolic drug, especially paracetamol, comprises aqueous drug solution deoxygenated by a temperature-controlled manufacturing process of the formulation</a> <b>[P]</b> . <span> 外国专利：  EP1992334A1 </span> <span> . 2008-11-19</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：氧化敏感性酚类药物，尤其是对乙酰氨基酚的储存稳定制剂，包括通过制剂的温度控制制造过程脱氧的药物水溶液 </span> </p> </li> </ul> </div> </div> </div> <div class="theme cardcommon" style="overflow: auto;display:none"> <h3 class="all_title" id="enpatent55">相关主题</h3> <ul id="subject"> </ul> </div> </div> </div> </div> <div class="right rightcon"> <div class="details_img cardcommon clearfix" style="margin-bottom: 10px;display:none;" > </div> </div> </div> <div id="thesis_get_original1" class="downloadBth" style="bottom: 19px;z-index: 999;" onclick="ywcd('0704022115631','4',7,2,1,'',this,24)" class="delivery" prompt="010401" 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