CN105801479B - 一种双光子黏度荧光探针及其制备方法和用途 - Google Patents
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Abstract
本发明公开了一种双光子黏度荧光探针及其制备方法和用途，其中双光子黏度荧光探针以喹啉作为母体，结构如下：
Description
一、技术领域
本发明涉及一种双光子黏度荧光探针及其制备方法和用途。
二、背景技术
黏度作为生物体系微环境中的一个重要的性质，细胞中黏度值的变化能够反应细胞的健康状态，或者说黏度与生物体系中多种疾病或生理过程有紧密的联系，特别是细胞质黏度的变化同细胞凋亡有很大关联。如何检测细胞中的黏度对生物体系有很重要的意义，这方面的研究也已经引起了很多科学家们的兴趣。
荧光探针作为一种检测工具有很多的优点，比如：灵敏度高，操作方便，廉价易得等等。检测对象与荧光探针作用能够引起荧光信号的响应变化，从而检测出检测对象的变化。
喹啉作为一种经典的荧光团，不仅具有优良的荧光光谱性质，而且水溶性好，并且细胞毒性低。以喹啉作为荧光团的单光子荧光探针已经被很多文献所报道，但是作为双光子荧光探针的文献报道还很少。检测细胞黏度的双光子荧光探针的报道就更少了。
目前，大部分检测细胞黏度的荧光探针仍为单光子的荧光探针，然而单光子荧光探针具有不少的缺点，如：自荧光干扰很大，激发波长小导致对细胞的光毒性大，容易发生荧光自淬灭等等。双光子荧光探针具有很多单光子荧光探针所不具有的优点，如：细胞光毒性小，不会引起荧光自淬灭，时间空间分辨率高，组织渗透深度大，因而双光子荧光探针已经作为科学家们研究的一个重要课题。
三、发明内容
本发明旨在提供一种双光子黏度荧光探针及其制备方法和用途，所要解决的技术问题是通过分子设计遴选出一种合适的荧光探针结构，以实现双光子成像定性检测细胞黏度，细胞毒性实验表明本发明对细胞几乎没有毒副作用。
本发明双光子黏度荧光探针(MCN)，简称为荧光探针，是以喹啉为母体，其结构式如下：
本发明双光子黏度荧光探针的制备方法，包括如下步骤：
将3.6g化合物1、1.24g丙二腈和0.38g碱性氧化铝溶于二氯甲烷中，室温下搅拌反应4h，将混合物过滤，滤液旋蒸除去溶剂得粗产物，再用柱层析色谱柱分离(以乙酸乙酯/石油醚＝1/4作为洗脱液，v/v)，得到目标产物3.36g(10.04mmol，收率80％)；
所述化合物1的结构式为：
本发明双光子荧光黏度探针MCN的合成过程如下：
本发明双光子黏度荧光探针在定性检测细胞中黏度时作为检测试剂应用。
将本发明荧光探针溶于DMSO中制得1mM的母液，取150μL的该母液于10mL容量瓶中，再用待测溶液定容，配制成15μM。荧光探针单光子和双光子的激发波长分别为400nm和800nm，检测420-780nm波长范围内的荧光光谱变化。
本发明荧光探针检测黏度的机理是荧光探针分子中的喹啉环与丙二腈的C-C单键的旋转，黏度小的体系中，C-C单键的旋转所消耗的能量多，分子受激发到激发态后，能量耗散的方式主要为C-C单键旋转；黏度大的体系中，C-C单键的旋转受到抑制，分子受激发到激发态后，能量耗散的方式主要为荧光发射，在490nm处荧光发射峰随着体系黏度增大逐渐增强。这样设计的目的实现了对黏度的检测。
本发明荧光探针在低粘度体系中荧光量子产率较低，在高黏度体系中荧光量子产率升高了8倍左右。因此，本发明荧光探针能更好地应用于生物检测中。
本发明荧光探针能够对生物细胞体系中的黏度进行转移性的识别，监测分析以及跟踪。
本发明荧光探针结构简单，合成方便。本发明荧光探针是以荧光强弱来检测黏度的强弱。在紫外灯下，肉眼就可以看出其荧光变化，荧光颜色从无变为淡蓝色荧光，操作简便，反应灵敏。本发明荧光探针选择性高，灵敏度高。
四、附图说明
图1是本发明荧光探针(15μM)在纯甘油和纯水中的紫外吸收光谱。
图2是本发明荧光探针(15μM)在不同黏度体系中的荧光浓度光谱图，每条线豆子在静置30min后进行的测试。
图3是本发明荧光探针MCN(1mM)在甘油中在不同的波长激发下双光子吸收截面值。
图4是本发明荧光探针MCN在细胞培养24h后的细胞存活率。从图4中我们可以看出，浓度为15μM时，细胞存活率还有92％左右，说明本发明荧光探针对细胞无毒性作用，因此可以用来做细胞中黏度检测。
图5是本发明荧光探针的双光子共聚焦成像照片，其中图a是荧光探针(10μM)在HeLa细胞中培养30min后，用PBS缓冲溶液(pH＝7.4)冲洗，在双光子荧光共聚焦显微成像，在800nm激发下，荧光发射收集范围460-520nm；图b是HwLa细胞的明场；图c是图a和图b的叠加图。
五、具体实施方式
下面通过实施例对本发明作进一步说明。
实施例1：荧光探针分子MCN的合成
将3.6g化合物1、1.24g丙二腈和0.38g碱性氧化铝溶于40mL二氯甲烷中，室温下搅拌反应4h，将混合物过滤，将滤液旋蒸除去溶剂得粗产物，再用柱层析色谱柱分离(以乙酸乙酯/石油醚＝1/4作为洗脱液，v/v)，得到目标产物3.36g(10.04mmol，收率80％)。
所述化合物1的结构式为：
1H NMR(400MHz,DMSO):δ8.72(s,1H),8.59(d,J＝8.5Hz,1H),8.29(s,1H),8.05(d,J＝8.9Hz,1H),7.96(d,J＝8.8Hz,1H),7.88(d,J＝8.5Hz,1H),7.59(d,J＝8.6Hz,2H),7.04(d,J＝8.6Hz,2H),3.82(s,3H).13C NMR(100MHz,CDCl3):δ160.38,156.99,148.44,147.31,136.87,133.82,133.44,130.40,130.07,128.97,125.50,122.81,114.59,114.29,113.69,112.15,93.67,87.72,87.60,55.40.
实施例2：荧光探针分子的双光子测试
将本发明荧光探针溶于DMSO中制得1mM的母液，取150μL的该母液于10mL容量瓶中，再用不同体积比的甘油/水混合溶液(甘油与水的体积比分别为50:50、60:40、70:30、80:20、90:10、95:5、99:1)定容，配制成15μM。荧光探针单光子和双光子的激发波长分别为400nm和800nm，检测420-780nm波长范围内的荧光光谱变化。
利用双光子测试技术，测试荧光探针(MCN)在不同黏度体系中的双光子吸收截面，从图3可以看出，荧光探针分子在甘油中的最大双光子吸收截面为400GM，双光子激发波长在800nm。
实施例3：细胞毒性测试
MTT(3-(4，5-二甲基噻唑-2)-2，5-二苯基四氮唑溴盐)实验是根据已报道的文章，做一些细胞毒性测试。分别在同一批细胞中加入0，5，10，15，20，25μM的荧光探针，此条件是在37℃、含5％CO2的细胞培养箱中孵育24小时，根据细胞存活度的公式：细胞存活率％＝OD570(样品)/OD570(对照组)×100，可算得细胞存活率(图4)。从图4中我们可以看出，浓度为15μM时，细胞存活率还有92％左右，说明了本发明荧光探针对细胞无毒性作用，因此可以用来检测细胞中的黏度。
实施例4：细胞成像测试
HeLa细胞由DEME(invitrogen)培养液培养，成像前一天，HeLa细胞放于平底表面皿中，成像时HeLa细胞和10μM的荧光探针MCN的DMSO溶液于37℃、含5％CO2的细胞培养箱中孵育0.5小时，用中性的PBS缓冲溶液或培养液充分洗涤后，用双光子荧光共聚焦成像，得图5b。
Claims (4)
1.一种双光子黏度荧光探针，其特征在于其结构式如下：
2.一种权利要求1所述的双光子黏度荧光探针的制备方法，其特征在于包括如下步骤：
将3.6g化合物1、1.24g丙二腈和0.38g碱性氧化铝溶于二氯甲烷中，室温下搅拌反应4h，将混合物过滤，将滤液旋蒸除去溶剂得粗产物，柱层析分离后得到目标产物；
所述化合物1的结构式为：
3.根据权利要求2所述的制备方法，其特征在于：
柱层析分离的洗脱液为乙酸乙酯和石油醚按体积比1:4混合得到。
4.一种权利要求1所述的双光子黏度荧光探针的用途，其特征在于：非诊断或治疗目的的在定性检测细胞中黏度时作为检测试剂的应用。
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| CN108484590B (zh) * | 2018-05-18 | 2021-02-26 | 安徽大学 | 一种基于咔唑的双光子粘度荧光探针及其制备方法和用途 |
| CN109535098B (zh) * | 2018-10-17 | 2022-04-19 | 南京工业大学 | 一种用于黏度检测的近红外荧光探针及其制备和应用 |
| CN110229101B (zh) * | 2019-05-31 | 2020-11-03 | 浙江工业大学 | 用于检测黏度的aie荧光化合物及其制备与应用 |
| CN111892923B (zh) * | 2020-08-19 | 2022-05-31 | 安徽大学 | 一种基于二腈乙烯基的双光子荧光粘度探针及其制备方法和用途 |
| CN112592283B (zh) * | 2021-01-25 | 2022-06-07 | 井冈山大学 | 一种用于酒类饮品粘度检测的荧光化合物及其制备和应用 |
| CN113045596B (zh) * | 2021-03-24 | 2022-09-13 | 台州学院 | 一种过氧亚硝基阴离子和粘度双响应型荧光探针及其制备和应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080193640A1 (en) * | 2007-02-09 | 2008-08-14 | Jun Zhang | Wood preserving composition for treatment of in-service poles, posts, piling, cross-ties and other wooded structures |
| CN103614135A (zh) * | 2013-11-29 | 2014-03-05 | 安徽大学 | 一种双光子荧光探针及其制备方法和用途 |
-
2016
- 2016-04-29 CN CN201610290214.6A patent/CN105801479B/zh active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080193640A1 (en) * | 2007-02-09 | 2008-08-14 | Jun Zhang | Wood preserving composition for treatment of in-service poles, posts, piling, cross-ties and other wooded structures |
| CN103614135A (zh) * | 2013-11-29 | 2014-03-05 | 安徽大学 | 一种双光子荧光探针及其制备方法和用途 |
Non-Patent Citations (1)
| Title |
|---|
| 基于喹啉母核的金属离子荧光化学传感器的研究;汪恕欣;《安徽大学硕士学位论文》;20121031;全文 * |
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