CN117470821A - 一种萘二甲酰亚胺类荧光探针在黏度检测中的应用 - Google Patents
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Abstract
本发明公开了一种萘二甲酰亚胺类荧光探针在黏度检测中的应用。本发明公开的荧光探针化学名称为：4‑甲基‑N‑(2‑(6‑((2‑乙基吗啉)氨基)‑1,3‑二氧‑1H‑苯并[de]异喹啉‑2)乙基)苯磺酰胺。该探针同时具有黏度响应特性，可实现溶液和细胞黏度的检测。因此，本发明荧光探针能够用于污水黏度及生物黏度微环境的检测。
Description
技术领域
本发明属于化学医药技术领域，具体涉及一种萘二甲酰亚胺类荧光探针在黏度检测中的应用。
背景技术
黏度是化学工业生产领域的一项重要指标，它反映的是流体流动时内部摩擦的物理量。黏度也可以反应细胞内的微环境变化，他与生物分子相互作用，代谢产物扩散和信号传导等密不可分。因此，可以检测黏度变化对化学和生物学意义重大。目前，检测黏度的方法主要有黏度计法等，这些方法需要的液体量较大，且无法检测细胞内的黏度变化。
随着科技的发展，荧光法因其灵敏度高，反应迅速等优点，成为检测溶液及细胞黏度的一种重要的方法。萘二甲酰亚胺衍生物因其良好的光稳定性，量子产率较高等优点，广泛应用于荧光探针领域。
然而，目前的萘二甲酰亚胺衍生物往往都是对溶液或细胞内的极性响应(Sensorsand Actuators B:Chemical,2021,329:129148)，对黏度响应的萘二甲酰亚胺衍生物较少。
因此，对萘二甲酰亚胺衍生物进行黏度响应方面的研究，以期利用其良好的荧光性能，实现其对黏度的检测，从而筛选出安全、高效的黏度敏感型萘二甲酰亚胺类荧光探针，对于实现此类荧光探针的产业价值具有重要意义。
发明内容
发明目的：本发明目的在于提供一种萘二甲酰亚胺类荧光探针在黏度检测中的应用。本发明提供的萘二甲酰亚胺类荧光探针可以检测溶液和细胞黏度。由于黏度与多种疾病(癌症等)有关，因此，本发明荧光探针能够用于制备黏度敏感型肿瘤诊断试剂，用于制备肿瘤的荧光成像试剂或放射性显像试剂。
技术方案：本发明的目的通过下述技术方案实现：
本发明提供了一种萘二甲酰亚胺类荧光探针在黏度检测中的应用,所述萘二甲酰亚胺荧光探针化学名称为：4-甲基-N-(2-(6-((2-乙基吗啉)氨基)-1,3-二氧-1H-苯并[de]异喹啉-2)乙基)苯磺酰胺，其结构式为：
所述萘二甲酰亚胺类荧光探针用于检测溶液和细胞黏度。
所述萘二甲酰亚胺类荧光探针用于污水黏度及生物黏度微环境的检测。
本发明使用所述萘二甲酰亚胺类荧光探针进行黏度检测时，一种优选地实施方式是，将所述萘二甲酰亚胺类探针加入混合溶液，通过检测所述溶液的荧光强度IF，按照方程logIF＝3.33+0.06logη来计算所述溶液的黏度η，其中，所述溶液的黏度η≥1cP。
进一步地，所述混合溶液的黏度范围是5cP-500cP。
进一步地，所述萘二甲酰亚胺类荧光探针在混合溶液中的浓度为1-15μM。
更进一步地，所述萘二甲酰亚胺类荧光探针在混合溶液中的浓度为10μM。
由于本发明所述的萘二甲酰亚胺类荧光探针能够应用于黏度检测中，因此还可以将所述萘二甲酰亚胺类荧光探针用于制备黏度敏感型肿瘤诊断试剂，用于制备肿瘤的荧光成像试剂或放射性显像试剂。
本发明采用所述萘二甲酰亚胺类荧光探针进行黏度检测时，使用的黏度测试装置为荧光光谱仪，所述荧光光谱仪包括有荧光信号处理器和存储器，所述存储器存储有计算程序，通过荧光信号处理器得到荧光强度值，将其带入计算程序执行时能够实现以下步骤：将溶液的荧光强度IF带入方程logIF＝3.33+0.06logη中，计算得到所述溶液的黏度η。
有益效果：
本发明所述萘二甲酰亚胺类荧光探针通过引入萘二甲酰亚胺衍生物，使得分子具有良好的光学性能，此外，多个单键的引入，使其对黏度响应灵敏。因此，本发明所述萘二甲酰亚胺类荧光探针能够用于黏度检测，能够用于污水黏度及生物黏度微环境的检测。由于黏度与多种疾病(癌症等)有关，因此，本发明所述萘二甲酰亚胺类荧光探针能够用于制备肿瘤诊断试剂，用于制备肿瘤的荧光成像试剂或放射性显像试剂。
附图说明
图1为萘二甲酰亚胺类荧光探针EL(10μM)在不同溶剂中的吸收谱图。
图2为萘二甲酰亚胺类荧光探针EL(10μM)在不同浓度H2O-Gly混合物中的荧光光谱。
图3为萘二甲酰亚胺类荧光探针EL在530nm处的荧光强度值。
图4为萘二甲酰亚胺类荧光探针EL在HeLa细胞中的共聚焦图片及其所对应的荧光强度值。
具体实施方式
下面通过具体实施例对本发明技术方案进行详细说明，但是本发明的保护范围不局限于所述实施例。
各实施例中物质均来自于市售产品。
其中，4-(2-乙氨基)吗啉等购买于百灵威科技公司。
吸收光谱的测试仪器为Hitachi U-2910分光光度计；荧光光谱仪器为Hitachi F-2700分光光度计，细胞成像仪器为lecia共聚焦显微镜。
实施例1萘二甲酰亚胺类荧光探针(简称为EL)的合成
其中，取代基X为卤素。本实施例中，X选自溴。
将N-(2-(6-溴-1,3-二氧-1H-苯并异喹啉-2(3H))乙基)-4-甲基苯并磺酰胺，即化合物1(0.472g，1mmol)和4-(2-乙氨基)吗啉(0.4mL，3mmol)溶于20mL甲醇中，在烧瓶中搅拌1h。搅拌后在85℃下回流8h，冷却至室温后，用石油醚洗涤。以CH2Cl2和CH3OH混合物(CH2Cl2和CH3OH的体积比为10:1～6:1)为洗脱液，进行柱色谱分离提纯，得到0.46g黄色固体，化学命名为：4-甲基-N-(2-(6-((2-乙基吗啉)氨基)-1,3-二氧-1H-苯并[de]异喹啉-2)乙基)苯磺酰胺，即为荧光探针分子，简称为EL。
通过对化合物的氢谱、碳谱进行分析，确认上述化合物的结构无误。表征结果如下：
1H NMR(400MHz,CDCl2),δ(ppm):8.45(d,J＝8.0Hz,1H),8.34(d,J＝8.4Hz,1H),8.19(d,J＝7.6Hz,1H),7.66(t,J＝7.8Hz,1H),7.47(d,J＝8.4Hz,2H),6.69-6.74(m,3H),6.49(s,1H),5.32(t,J＝0.8Hz,2H),4.20(t,J＝5.4Hz,2H),3.77(t,J＝4.4Hz,4H),3.37-3.48(m,4H),2.87(s,2H),2.59(s,3H),1.91(s,3H)。
13C NMR(100MHz,CDCl2),δ(ppm):166.27,165.78,151.25,144.01,138.25,136.00,132.45,131.15,130.44,127.81,126.11,123.87,121.61,110.79,105.82,68.20,57.11,44.41,40.28,40.08,22.12,0.90。
实施例2萘二甲酰亚胺类荧光探针EL在不同溶剂中的光物理性质测试实验
用不同种类的有机溶剂(所用有机溶剂见图1)配制含10μM EL的测试溶液，将上述溶液用紫外分光光度计测试其吸收光谱，结果见图1。
从图1中可以看出：荧光探针EL在350-500nm处存在较大的吸光度值，在450-650nm处有较大的荧光峰，这说明该荧光化合物可以用350-500nm的光激发，其发射光谱的范围为450-650nm。
实施例3萘二甲酰亚胺类荧光探针EL的黏度测试实验
实验方法：
(1)用DMSO配制浓度为1mM的探针母液。
(2)将H2O和甘油以不同比例(0，10％，20％，30％，40％，50％，60％，70％，80％，90％，100％的甘油)混合配制成不同黏度值的混合溶剂，然后分别加入荧光探针EL配制成含10μM EL的测试溶液。
(3)将上述溶液用荧光光谱仪测试其荧光发射光谱，对其荧光光谱进行拟合得到相应的曲线。
图2为萘二甲酰亚胺类荧光探针EL(10μM)在不同浓度H2O-Gly混合物中的荧光光谱。图中，曲线从下至上对应溶液中的甘油比例依次为(0，10％，20％，30％，40％，50％，60％，70％，80％，90％，100％)。
如图所示，随着甘油比例的增加，有机小分子荧光化合物的荧光强度逐渐增加，表明该有机小分子荧光化合物对黏度的变化响应明显。
为了进一步验证探针可以量化溶液粘度变化，本发明采用黏度测试装置测量了探针在530nm处的荧光强度进行拟合。本发明使用的黏度测试装置为荧光光谱仪，包括有荧光信号处理器和存储器，存储器存储有计算程序，通过荧光信号处理器得到荧光强度值，将其带入计算程序执行时能够实现以下步骤：将溶液的荧光强度IF带入方程logIF＝3.33+0.06logη中，计算得到所述溶液的黏度η。
从图3中可以看出：有机小分子荧光化合物EL的荧光强度IF和黏度η符合–Hoffmann方程，通过拟合得到方程logIF＝3.33+0.06logη。因此，通过测试EL在不同溶液中的荧光强度即可得到溶液的黏度值。
实施例4萘二甲酰亚胺类荧光探针EL检测细胞内的黏度
用DMSO配制浓度为1mM的探针母液。取2μM EL染色正常培养的HeLa细胞(ATCC)作为对照组，染色时间为15min。实验组用制霉菌素处理HeLa细胞45min，以此增加HeLa细胞的黏度，然后用2μM EL染色该HeLa细胞。最后，用激光共聚焦显微镜分别成像实验组和对照组的细胞，并用激光共聚焦显微镜记录细胞的荧光强度值。萘二甲酰亚胺荧光探针EL在HeLa细胞中的共聚焦图片及其所对应的荧光强度值见图4。其中，图4A为EL在HeLa细胞中的共聚焦图片；图4B为其所对应的荧光强度值。
从图中可以看出，相比于对照组，实验组的图像较亮，其荧光强度值也较大，这进一步验证了制菌霉素可以增加细胞内的黏度值。由此可见，荧光探针EL能够用于检测细胞内的黏度。
如上所述，尽管参照特定的优选实施例已经表示和表述了本发明，但其不得解释为对本发明自身的限制。在不脱离所附权利要求定义的本发明的精神和范围前提下，可对其在形式上和细节上作出各种变化。
Claims (8)
1.一种萘二甲酰亚胺类荧光探针在黏度检测中的应用,其特征在于，所述萘二甲酰亚胺荧光探针化学名称为：4-甲基-N-(2-(6-((2-乙基吗啉)氨基)-1,3-二氧-1H-苯并[de]异喹啉-2)乙基)苯磺酰胺，其结构式为：
2.根据权利要求1所述的应用，其特征在于，所述萘二甲酰亚胺类荧光探针用于检测溶液和细胞黏度。
3.根据权利要求1所述的应用，其特征在于，所述萘二甲酰亚胺类荧光探针用于检测污水黏度及生物黏度微环境。
4.根据权利要求1-3任一项所述的应用，其特征在于，将所述萘二甲酰亚胺类荧光探针加入混合溶液，通过检测所述溶液的荧光强度IF，按照方程logIF＝3.33+0.06logη来计算所述溶液的黏度η，其中，所述溶液的黏度η≥1cP。
5.根据权利要求4所述的应用，其特征在于，所述溶液的黏度范围是5cP-500cP。
6.根据权利要求4所述的应用，其特征在于，所述萘二甲酰亚胺类荧光探针在混合溶液中的浓度为1-15μM。
7.根据权利要求6所述的应用，其特征在于，所述萘二甲酰亚胺类荧光探针在混合溶液中的浓度为10μM。
8.根据权利要求1所述的应用，其特征在于，所述萘二甲酰亚胺类荧光探针用于制备黏度敏感型肿瘤诊断试剂，用于制备肿瘤的荧光成像试剂或放射性显像试剂。
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