CN105541660B - 一种芳基水杨醛‑二苯基‑吖嗪联肼类化合物及制备与应用 - Google Patents

一种芳基水杨醛‑二苯基‑吖嗪联肼类化合物及制备与应用 Download PDF

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CN105541660B
CN105541660B CN201610029731.8A CN201610029731A CN105541660B CN 105541660 B CN105541660 B CN 105541660B CN 201610029731 A CN201610029731 A CN 201610029731A CN 105541660 B CN105541660 B CN 105541660B
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diphenyl
salicylide
azine
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CN105541660A (zh
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唐本忠
王志明
赵祖金
秦安军
赵恩贵
归晨
王京
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South China University of Technology SCUT
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Abstract

本发明属于分析检测材料技术领域，公开了一种芳基水杨醛‑二苯基‑吖嗪联肼类化合物及制备与应用。所述化合物具有式(1)所述的结构通式，其中Ar表示芳香基团或其衍生结构，取代基R1～R10分别选自氢、烷基、烷氧基及芳香基团及相应的衍生结构。所述制备方法为：将二苯基肼衍生物与芳基水杨醛在溶剂中加热至30～90℃反应6～12h，反应产物经分离提纯后即得到芳基水杨醛‑二苯基‑吖嗪联肼类化合物。本发明的化合物表现出了很强的荧光探针特性，对细胞内的亚结构、金属离子都表现出了极强的选择性识别能力，具有极大的开发价值。

Description

一种芳基水杨醛-二苯基-吖嗪联肼类化合物及制备与应用
技术领域
本发明属于分析检测材料技术领域，具体涉及一种芳基水杨醛-二苯基-吖嗪联肼类化合物及制备与应用。
背景技术
随着国家经济的快速发展和人民生活水平的不断提高，个人身体健康的实时监测、疾病的预防和治疗逐渐成为人们更加关注的民生问题。相对于传统的体外化学检验的延迟性和放射线在线检测的危害性，荧光在线显像技术以其高效、绿色、实时性强的优势渐渐走入人们的视野，被广泛应用于细胞免疫学、微生物学、分子生物学、遗传学、神经生物学、病理学、肿瘤学、临床检验学、医学、植物学等方面的科研和民生等领域。
荧光显像技术的关键技术就是荧光物质作为标记探针(或染色剂)的选择。理想的探针分子通过物理或化学作用，特异性吸附在特定的细胞和组织上，在低能量光学辐照下实现二维或三维的成像，通过与荧光颜色、强度和分布情况来判断细胞或组织的健康情况。与普通的化学染色相比，荧光染色的灵敏度要高出100-1000倍，而且通过适当的功能修饰即可实现对活体的在线分析。目前的荧光探针(染料)是以人工合成的芳香环类化合物为主，较大的π电子离域范围可以实现探针分子对光辐射能量的高效吸收，进而通过弛豫、辐射跃迁得到长波长荧光，这个吸收光和发射光间的能量差值被称作斯托克斯位移。斯托克斯位移越小，说明它的吸收光和发射光的能量越接近，非辐射跃迁的比例较小，材料的量子产率可能较高，但化合物通常表现为严重的自吸收现象，干扰成像效果；当斯托克斯位移大时，分子的自吸收现象明显削弱，但是非辐射跃迁比例变大，所得的探针材料往往对光的利用率不高。
吖嗪类化合物，是对包含有一个或几个氮原子的共轭不饱和六元杂环或杂原子化合物的总称，它既包括常见的吡啶、嘧啶、三嗪和噻嗪类结构，也包含逐渐受到关注的芳基共轭型的腙、肼、酰胺类结构。由于分子结构独特的共轭特性及氮原子丰富的杂化形式和电子空间分布，使部分吖嗪类化合物具有显著的荧光特性，其在荧光探针领域的应用逐步活跃起来。联肼结构主要是通过“＝N-N＝”形式将两侧的基团链接起来，使整个分子保持了良好共轭性，相对于类似的偶氮“-N＝N-”结构，联肼的电子离域能力有了很大提高，很适宜构筑高效率的荧光结构。遗憾的是，常规联肼结构中快速的分子内自由转动效应(孤对电子体积小，易于发生顺反异构)和聚集态下的过高的非辐射跃迁比例，导致其荧光量子产率下降严重，很难应用于常规的水系条件下的检测和荧光分析，如，细胞内亚结构的研究、水系中金属离子的监测等。
2001年，唐本忠院士基于其发现的1-甲基-1,2,3,4,5-五苯基噻咯(MPPS)在乙腈溶液中不发光，而在聚集后而产生强烈的荧光的“反常”现象，提出“聚集诱导发光(AIE)”的新观念，通过“分子内旋转受限(RIR)”的工作机理很好的解释了这种现象产生，而且已得到诸多实验结果和理论计算的支持，发展了一个贴有“中国牌”的、具有自主知识产权的材料和理论体系。AIE类材料解决了传统的芳香环荧光生色团在水溶性溶剂中聚集猝灭荧光问题，在生理缓冲溶液或水介质中能够实现高亮度的荧光成像和示踪，与背景中的不发光或弱发光单分子实现高分辨率的区分，很好的定位在目标生物大分子。这种AIE荧光探针的“点亮(light-up)”模式为高灵敏度、对比度的生物研究提供了可能，在生物学、医学等领域具有划时代的意义。
发明内容
基于以上现有技术，本发明的首要目的在于提供一种芳基水杨醛-二苯基-吖嗪联肼类化合物。
本发明的另一目的在于提供一种上述芳基水杨醛-二苯基-吖嗪联肼类化合物的制备方法。
本发明的再一目的在于提供上述芳基水杨醛-二苯基-吖嗪联肼类化合物作为荧光探针材料在化学分析、生物分析和临床医学检测等领域中的应用。
本发明目的通过以下技术方案实现：
一种芳基水杨醛-二苯基-吖嗪联肼类化合物，所述化合物具有如下所述的结构通式：
其中Ar表示芳香基团或其衍生结构，取代基R1～R10分别选自氢、烷基、羟基、烷氧基、硝基、氰基、氨基、巯基、卤素原子、苯基、甲苯基、萘基、呋喃基、噻吩基、吡咯基、吡啶基、吡喃基、喹啉基、吲哚基、羧基或其衍生基团、咔唑基或苯胺基中的一种。
优选地，所述的烷基和烷氧基是指碳原子数为1～12的烷基和烷氧基。
更优选地，所述取代基R1～R10分别选自氢或以下结构式中的一种：
进一步地，当所述取代基R1～R10均为氢，Ar为苯环或苯环衍生物时，所述芳基水杨醛-二苯基-吖嗪联肼类化合物优选具有如下任一项所述的结构式：
其中，A1～A4为氢、烷基、羟基、烷氧基、硝基、氰基、氨基、巯基、卤素取代基、苯基、甲苯基、萘基、呋喃基、噻吩基、吡咯基、吡啶基、吡喃基、喹啉基、吲哚基、羧基或其衍生基团、咔唑基或苯胺基中的一种；优选地，所述的烷基和烷氧基是指碳原子数为1～12的烷基和烷氧基。
进一步地，当所述取代基R1～R10均为氢，Ar为萘环或其衍生物、蒽环或其衍生物、菲环或其衍生物时，所述芳基水杨醛-二苯基-吖嗪联肼类化合物优选具有如下任一项所述的结构式：
其中，B1～B8为氢、烷基、羟基、烷氧基、硝基、氰基、氨基、巯基、卤素取代基、苯基、甲苯基、萘基、呋喃基、噻吩基、吡咯基、吡啶基、吡喃基、喹啉基、吲哚基、羧基或其衍生基团、咔唑基或苯胺基中的一种；优选地，所述的烷基和烷氧基是指碳原子数为1～12的烷基和烷氧基。
优选地，上述结构式中，所述A1～A4、B1-B8分别选自氢或以下结构式中的一种：
进一步地，当所述取代基R1～R10均为氢，Ar为呋喃、噻吩、吡咯、吡啶、吡喃、喹啉(含异喹啉)、吲哚、咔唑、苯胺基或其衍生基团时，所述芳基水杨醛-二苯基-吖嗪联肼类化合物优选具有如下任一项所述的结构式：
进一步地，当所述取代基R1～R10均为氢，Ar为四苯乙烯基或其衍生基团时，所述芳基水杨醛-二苯基-吖嗪联肼类化合物优选具有如下任一项所述的结构式：
进一步地，当所述取代基R1～R10不均为氢，Ar为芳香基团或其衍生结构时，所述芳基水杨醛-二苯基-吖嗪联肼类化合物优选具有如下任一项所述的结构式：
上述芳基水杨醛-二苯基-吖嗪联肼类化合物的制备方法，包括如下制备步骤：将二苯基肼衍生物与芳基水杨醛在溶剂中加热至30～90℃反应6～12，反应产物经分离提纯后即得到芳基水杨醛-二苯基-吖嗪联肼类化合物；所述的溶剂是指甲醇、乙醇、乙酸、四氢呋喃、甲苯、苯、氯仿、二氯甲烷、N,N-二甲基甲酰胺(DMF)，N,N-二甲基乙酰胺(DMAC)和N-甲基吡咯烷酮(NMP)中的一种或两种以上的混合；所述的分离提纯是指通过柱层析或重结晶分离提纯；所述重结晶的溶剂为乙醇、四氢呋喃、乙醇、甲苯和N,N-二甲基甲酰胺中的一种。
上述制备方法涉及的合成路线如下式所示：
上述芳基水杨醛-二苯基-吖嗪联肼类化合物单独或和其它试剂结合组成复合型探针结构，制备成荧光淬灭或点亮型探针，应用在传感领域，如对金属离子的选择性识别以及定性、定量研究。
上述芳基水杨醛-二苯基-吖嗪联肼类化合物单独或和其它试剂结合组成复合型探针结构，对生物体结构或组织选择性染色，应用在生物分析、药物监测和临床医学检测领域。
本发明的原理为：通过邻位羟基与肼中的N原子故对电子形成分子内氢键，通过激发态下的分子内质子转移(ESIPT)，实现荧光光谱的有效红移；利用聚集态下分子内氢键和二苯基内旋转受限使该结构具有显著聚集诱导发光性质；通过刚柔结合的分子设计使该类分子具有显著的细胞荧光染色能力，并对特定的金属离子具有较好的选择性识别及线性响应能力。
本发明的化合物及其制备方法具有如下优点及有益效果：
(1)本发明的化合物选择联肼结构作为共轭桥联基元，一方面利用单双键交替的形式保持探针分子的共轭程度，另一方面N原子的孤对电子具有较小的空间位阻，使其能够在一定程度上自由转动从调节空间体积，保证其能容易直接透过细胞膜，对细胞内亚结构进行选择；
(2)本发明的化合物在外围的共轭结构中引入二苯基的取代芳香结构，使分子结构上具有更大的自由度，能够根据细胞亚结构空间要求调整探针结构的构象，也利于离子检测过程中的空间配位要求；
(3)本发明的化合物在联肼两端引入酚羟基结构，与N的孤对电子形成ESIPT态(激发态下分子内的质子转移)，有效的增加斯托克斯位移，防止分子的自吸收现象；二苯基的自由转动引入RIR(分子内受限旋转)机制，强化了此类分子的AIE性能；酚羟基的水溶性也能够显著调节分子的脂水分配系数，从而增加探针直接透过细胞的几率；
(4)本发明的化合物由于分子独特的刚性结构导致荧光探针在脂滴内的荧光情况与固体相似，便于在复杂体系内实现指认和定量分析；系统的调节取代基团结构，能够实现对特定离子的选择性检测和线性定量分析；
(5)本发明的化合物表现出了很强的荧光探针特性，对细胞内的亚结构、金属离子都表现出了极强的选择性识别能力；相对于目前部分商业荧光探针，此类探针结构制备成本较低、分辨率和识别度(区分度)较高，具有极大的开发价值。
附图说明
图1为实施例1所得DBAS在不同极性溶剂下的荧光光谱图；
图2为不同比例水存在下，实施例1所得DBAS四氢呋喃溶液的荧光强度变化曲线图；
图3为实施例1所得DBAS的细胞染色实验结果对比图；
图4为实施例1所得DBAS在水溶液中对不同金属离子的选择实验和干扰实验结果图；
图5为实施例1所得荧光探针在不同铜离子浓度下的荧光强度变化曲线图；
图6为实施例1所得复合探针对不同金属离子的选择实验结果图；
图7为实施例1所得复合探针在不同汞离子含量下的荧光强度变化曲线图；
图8为实施例2所得DBNAS在不同极性溶剂下的荧光光谱图；
图9为不同比例水存在下，实施例2所得DBNAS四氢呋喃溶液的荧光强度变化曲线图；
图10为实施例2所得DBNAS的细胞染色实验结果对比图；
图11为实施例3所得DBAS-2N在不同极性溶剂下的荧光光谱图；
图12为不同比例水存在下，实施例3所得DBAS-2N四氢呋喃溶液的荧光强度变化曲线图；
图13为实施例3所得DBAS-2N在水溶液中对不同金属离子的选择实验和干扰实验结果图；
图14为实施例3所得荧光探针在不同铜离子浓度下的荧光强度变化曲线图。
具体实施方式
下面结合实施例及附图对本发明作进一步详细的描述，但本发明的实施方式不限于此。
实施例1
水杨醛-二苯基-吖嗪联肼(DBAS)的合成，合成路线如下式所示：
具体合成步骤为：将10g二苯基联肼与5ml水杨醛在100ml乙醇溶剂下回流反应2h，反应完成后冷却至-10℃，有大量针装固体析出后低温过滤，粗产品用乙醇重结晶2次，得到淡无色针装晶体水杨醛-二苯基-吖嗪联肼(DBAS)，纯度99％，产率90％。产物鉴定数据为：1H NMR(400MHz,d-DMSO,ppm):11.28(s,1H,-OH),8.75(s,1H),7.64-7.62(m,2H),7.54-7.41(m,7H),7.28-7.24(m,3H),6.29-6.26(m,1H),5.95(d,1H)。MALDI-TOF(m/z):[M+]calcd.C20H14N2O,298.11；found,298.11。
本实施例所得DBAS的光学性质及其在在细胞染色及金属离子传感方面的应用：
(a)DBAS的基本光学性质：
DBAS在不同极性溶剂下的荧光光谱如图1所示，由图1可以看出：随着极性的变化，DBAS的醇式发射(425nm附近)和酮式发射(555nm附近)的比例发生明显变化，为典型的ESIPT发射。而对于ESIPT分子，聚集态多为酮式发射，所以我们检测了该处的聚集发光现象。向DBAS的四氢呋喃溶剂中(溶解单分子态)不断加入一定比例的水，其荧光强度的变化如图2所示，由图2可以看出：DBAS由于溶解度问题慢慢聚集成纳米颗粒，荧光强度明显增强(555nm附近)，称其为AIE性质。由此可以推断出DBAS具有明显的ESIPT和AIE性质，具有荧光探针的潜质。
(b)细胞染色实验：
将DBAS以一定浓度DMSO溶液溶解后滴入细胞培养液中，选择Hela细胞作为研究对象，培养一段时间后采用荧光显微镜对其极性观察，发现DBAS可以顺利的透过细胞壁，并定向的在细胞脂滴处富集，从而显示出黄色荧光(555nm附近)；并与与商用的脂滴探针BODIPY进行共染色对比，结果如图3所示(其中(a)为Hela细胞在明场中的显微结构图，其中馕包状为细胞的脂滴结构；(b)为染色后的细胞在460nm-490nm激发光的暗场下的BODIPY荧光图，(c)为染色后的细胞在330nm-385nm激发光的暗场下的DBAS的荧光图；(d)为将三者重合的荧光图。由图3对比结果显示，DBAS能够特异性的对细胞脂滴进行染色，而且其荧光峰位与固态荧光光谱无明显差异，与商用探针重叠比率可以达到98％以上。说明DBAS可以不经任何修饰直接进入细胞实现靶向荧光染色，并未表现出明显的荧光偏移，AIE和ESIPT现象得到了很好的利用。
(c)离子传感实验：
DBAS在水溶液中对不同金属离子的选择实验和干扰实验结果如图4所示，由图4可以看出，该荧光探针对铜离子存在特异性响应(淬灭荧光)，其在555nm附近的荧光强度明显降低，通过干扰实验结果可以看出，铁和汞离子存在时会对铜离子的检测存在一定影响。DBAS在水溶液中，随着铜离子浓度的增加(0eq～0.2eq)，其荧光强度变化曲线如图5所示，由图5可以看出，该荧光探针的特异性响应与铜离子浓度存在一定线性关系。
将DBAS在水溶液和铜离子组成复合探针，对不同金属离子的选择实验结果如图6所示，由图6可以看出：该复合荧光探针对铁和汞离子存在特异性性响应，并且二者可以通过紫外吸收光谱予以区别。通过对复合探针在不同汞离子含量(Cu2+:Hg2+＝1:0.1～1:1.5)下的荧光强度变化进行测试，结果如图7所示，由图7可以看出：该复合探针存在一定线性响应。
实施例2
取1g二苯基联肼晶体与等摩尔的1-萘基水杨醛在50ml乙醇中60℃反应2h，反应完成后冷却，得到淡黄色晶体，将固体过滤后用75％的乙醇水溶液清洗，得到萘基水杨醛-二苯基-吖嗪联肼(DBNAS)，产品纯度99％，产率>95％。产物鉴定数据为：MALDI-TOF(m/z):[M+]calcd.C24H18N2O,350.41；found,350.65.Anal Calc.for C24H18N2O:C,82.26；H,5.18；N,7.99；O,4.57.Found:C,82.24；H,5.16；N,7.94；O,4.60。产物结构如下式所示：
本实施例所得DBNAS的光学性质及其在细胞内的染色应用：
(a)DBNAS的基本光学性质：
DBNAS在不同极性溶剂下的荧光光谱如图8所示，由图8可以看出：随着极性的变化，DBNAS的醇式发射(440nm附近)和酮式发射(515nm附近)的比例发生明显变化，为典型的ESIPT发射。而对于ESIPT分子，聚集态多为酮式发射，所以我们检测了该处的聚集发光现象。向DBNAS的四氢呋喃溶剂中(溶解单分子态)不断加入一定比例的水，其荧光强度的变化如图9所示，由图9可以看出：DBNAS由于溶解度问题慢慢聚集成纳米颗粒，荧光强度明显增强(530nm附近)，称其为AIE性质。由此可以推断出DBNAS具有明显的ESIPT和AIE性质，具有荧光探针的潜质。
(b)细胞染色实验：
将DBNAS以一定浓度DMSO溶液溶解后滴入细胞培养液中，选择Hela细胞作为研究对象，培养一段时间后采用荧光显微镜对其极性观察，发现DBNAS仍可以顺利的透过细胞壁，并定向的在细胞脂滴处富集，从而显示出绿色荧光(530nm附近)。其结果如图10所示(其中(a)为Hela细胞在明场中的显微结构图，其中馕包状为细胞的脂滴结构；(b)为染色后的细胞在330nm-385nm激发光的暗场下的DBNAS的荧光照片)，由图10中二者对比显示，DBNAS也能够特异性的对细胞脂滴进行染色，而且其荧光峰位与固态荧光光谱无明显差异。说明DBNAS可以不经任何修饰直接进入细胞实现靶向荧光染色，并未表现出明显的荧光偏移，AIE和ESIPT现象得到了很好的利用。
实施例3
DBAS氮乙基衍生物的合成，具体合成步骤如下：
取1g二苯基联肼(或N,N-二乙基氨基二苯基联肼)与等摩尔的N,N-二乙基氨基水杨醛(或水杨醛)在30ml乙醇中60℃反应4h，反应完成后冷却，萃取分液，柱层析得到以下对应产品：
N-DBAS：黄色固体，产率87％。产物鉴定数据为：MALDI-TOF(m/z):[M+]calcd.C24H25N3O:371.47；found,371.88；Anal Calc.for C24H25N3O:C,77.60；H,6.78；N,11.31；O,4.31.found,C,77.55；H,6.74；N,11.30；O,4.32；
DBAS-2N：淡黄色固体，产率85％。产物鉴定数据为：MALDI-TOF(m/z):[M+]calcd.C28H34N4O:442.27；found,442.30；Anal Calc.for C28H34N4O:C,75.98；H,7.74；N,12.66；O,3.61.found,C,75.78；H,7.69；N,12.34；O,3.71；
N-DBAS-2N：黄色固体，产率90％。产物鉴定数据为：MALDI-TOF(m/z):[M+]calcd.C32H43N5O:513.72；found,513.76；Anal Calc.for C32H43N5O:C,74.82；H,8.44；N,13.63；O,3.11.found,C,74.78；H,8.33；N,13.55；O,3.20。
本实施例所得DBAS-2N的光学性质及其在离子传中应用：
(a)DBAS-2N的基本光学性质：
DBAS-2N在不同极性溶剂下的荧光光谱如图11所示，由图11可以看出：随着极性的变化，DBAS-2N的醇式发射(435nm附近)和酮式发射(545nm附近)的比例发生明显变化，为典型的ESIPT发射。而对于ESIPT分子，聚集态多为酮式发射，所以我们检测了该处的聚集发光现象。向DBAS-2N的四氢呋喃溶剂中(溶解单分子态)不断加入一定比例的水，其荧光强度的变化如图12所示，由图12可以看出：DBAS-2N由于溶解度问题慢慢聚集成纳米颗粒，荧光强度明显增强(545nm附近)，称其为AIE性质。由此可以推断出DBAS-2N具有明显的ESIPT和AIE性质，具有荧光探针的潜质。
(b)离子传感实验：
DBAS-2N在水溶液中对不同金属离子的选择实验和干扰实验结果如图13所示，由图13通过对比发现，该荧光探针对铜离子存在特异性性响应(淬灭荧光)，其在545nm附近的荧光强度明显降低，通过干扰实验结果可以看出，铁和汞离子存在时会对铜离子的检测存在一定影响。DBAS-2N在水溶液中，随着铜离子浓度的增加(0eq～0.15eq)，其荧光强度变化曲线如图14所示，由图14可以看出，该荧光探针的特异性响应与铜离子浓度存在一定线性关系。
实施例4
DBNAS衍生物的合成，具体合成步骤如下：
取1gN,N-二乙基氨基二苯基联肼与等摩尔的1-萘基水杨醛在50ml乙醇中60℃反应2h，反应完成后冷却，得到淡黄色晶体，将晶体过滤后，用75％的乙醇水溶液清洗，得到萘基水杨醛-N,N-二乙基氨基二苯基-吖嗪联肼(DBNAS-2N)，产品纯度99％，产率>95％。
产物鉴定数据如下：MALDI-TOF(m/z):[M+]calcd.C32H36N4O,492.65；found,492.77.Anal Calc.for C32H36N4O:C,78.01；H,7.37；N,11.37；O,3.25.Found:C,77.86；H,7.35；N,11.35；O,3.30。产物结构如下式所示：
实施例5
四苯乙烯水杨醛-二苯基-吖嗪联肼(m-TPE-DBAS)的合成，合成路线如下式所示：
具体合成步骤为：采用Sizuki偶联得到四苯乙烯基水杨醛衍生物结构后，取等摩尔的二苯基联肼晶体与其在20ml乙醇中60℃反应4h，反应完成后冷却，得到淡黄色粉末，将粉末过滤后，用75％的乙醇溶液清洗，得到粗产品，经层析提纯得到四苯乙烯水杨醛-二苯基-吖嗪联肼(m-TPE-DBAS)，产率为85％。
产物鉴定数据如下:MALDI-TOF(m/z):[M+]calcd.C40H30N2O:554.24；found,554.36；Anal Calc.for C40H30N2O:C,86.61；H,5.45；N,5.05；O,2.88；found,C,C,86.58；H,5.35；N,5.01；O,2.92。
上述实施例为本发明较佳的实施方式，但本发明的实施方式并不受上述实施例的限制，其它的任何未背离本发明的精神实质与原理下所作的改变、修饰、替代、组合、简化，均应为等效的置换方式，都包含在本发明的保护范围之内。

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1.一种芳基水杨醛-二苯基-吖嗪联肼类化合物的应用，其特征在于：所述芳基水杨醛-二苯基-吖嗪联肼类化合物单独制备成荧光淬灭型探针，应用于铜离子的选择性识别以及定性、定量研究，或与铜离子组成复合荧光点亮型探针，应用于铁和汞离子的选择性识别以及定性、定量研究；或所述的芳基水杨醛-二苯基-吖嗪联肼类化合物制备成荧光探针，对细胞脂滴选择性染色，应用在生物分析、药物监测和临床医学检测领域；所述的芳基水杨醛-二苯基-吖嗪联肼类化合物具有如下任一项所述的结构式：
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