CN109082271B - 一种基于苯并吡喃腈衍生物的荧光探针及其制备方法和应用 - Google Patents

一种基于苯并吡喃腈衍生物的荧光探针及其制备方法和应用 Download PDF

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CN109082271B
CN109082271B CN201811248337.9A CN201811248337A CN109082271B CN 109082271 B CN109082271 B CN 109082271B CN 201811248337 A CN201811248337 A CN 201811248337A CN 109082271 B CN109082271 B CN 109082271B
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fluorescent probe
benzopyran
benzopyran nitrile
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CN109082271A (zh
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王元
吴伟娜
王贝贝
薛文招
吕目轩
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Abstract

本发明提供了一种基于苯并吡喃腈衍生物的荧光探针及其制备方法和应用，其中所述苯并吡喃腈衍生物的化学结构式如下：
Figure DDA0001841062590000011
本发明的苯并吡喃腈衍生物生理条件下能选择性的与氰根作用，溶液颜色由淡黄色变为绿色，同时近红外荧光显著增强，特别是作为荧光探针在细胞内氰根的方便检测的应用。

Description

一种基于苯并吡喃腈衍生物的荧光探针及其制备方法和应用
技术领域
本发明属于有机合成领域，具体涉及一种基于苯并吡喃腈衍生物的荧光探针及其制备方法和应用。
背景技术
氰化物被广泛应用于黄金采矿、电镀、冶金等方面，在工业生产上具有很重要的作用。但游离氰根具有很强的毒性，其中氰化钠/钾更是被列为国家一级危险品，受到公安部门的严格管控。尽管如此，氰化物泄露事件时有发生。氰根非常容易被人体吸收，可经口、呼吸道或皮肤进入人体。过量的氰根会导致呕吐、抽搐、失去意志最终导致死亡。因此，氰根的检测在生命科学和环境检测领域有重要的意义。
由于其高选择性和灵敏度，对氰离子检测的荧光化学传感器有了前所未有的发展。但大多数传感器的最大发射在蓝色或绿色光谱区(波长λ<600nm)，很少出现在近红外(NIR)区。事实上，在650-900nm近红外区域具有特殊的优势包括最小吸收干扰，生物样品荧光，低散射和深入的组织渗透。
近年来，氰根的强亲核性是探针设计的主要策略。本发明以苯并吡喃腈为母体荧光团设计了一种荧光探针，利用近红外荧光开启现象检测氰离子。为生物化学系统中氰根的含量检测提供了一种简单、经济、高效的方法。
发明内容
基于氰根的强亲核性是探针设计的主要策略。本发明以噻吩甲酰基作为马赛克基团，与氰根作用后脱除，导致近红外荧光开启。本发明的主要目的在于提供一种可检测氰根的灵敏度高、选择性好的苯并吡喃腈衍生物荧光探针；另一目的是提供该荧光探针的制备方法和应用。
本发明的技术方案是，一种基于苯并吡喃腈衍生物的荧光探针，所述苯并吡喃腈衍生物具有如下结构式：
Figure GDA0002832724720000021
本发明还提供了一种基于苯并吡喃腈衍生物的荧光探针的制备方法，具体制备方法如下：
S1：将2-(2-(4-羟基苯乙烯基)-4H-色满-4-亚乙基)丙二腈和三乙胺首先用二氯甲烷溶解；
S2：冰浴下将噻吩甲酰氯的二氯甲烷溶液滴加到S1所得溶液，室温搅拌反应8-10h；
S3：将S2所得溶液溶剂减压蒸馏，所得固体残渣用二甲基甲酰胺和水混合溶剂重结晶，得到基于所述苯并吡喃腈衍生物的荧光探针。
优选地，上述方法中所述2-(2-(4-羟基苯乙烯基)-4H-色满-4-亚乙基)丙二腈、所述三乙胺和所述噻吩甲酰氯摩尔比为1:1.1:1；所述二甲基甲酰胺和水混合溶剂二者体积比为1:1。
优选地，将0.002-0.004mol 2-(2-(4-羟基苯乙烯基)-4H-色满-4-亚乙基)丙二腈和0.0022-0.0044mol三乙胺溶于0.04-0.08L二氯甲烷溶液中，冰浴下滴加0.002-0.004mol噻吩甲酰氯，常温搅拌8-10h，减压蒸除溶剂，所得固体用二甲基甲酰胺和水按照1:1体积比混合而得的混合溶剂重结晶得到所述苯并吡喃腈衍生物的荧光探针。
本发明还提供了上述一种基于苯并吡喃腈衍生物的荧光探针一种用途，即在作为氰根荧光探针方面的应用，特别是在作为检测细胞内氰根的荧光探针中的应用。
与现有技术相比，本发明的优点和积极效果在于：
本发明通过用酰化反应制备苯并吡喃腈衍生物荧光探针，在多种常见阴离子中，对氰根表现出较高的选择性荧光识别性能，使含有氰根的溶液由浅黄色无荧光变为绿色近红外荧光，具有荧光增强效应并可实现裸眼辨别检测。更为重要的是也可用于生物组织，来检测细胞微环境中氰根的荧光成像检测，具有快速、简便、灵敏度高、选择性强的特点，以及广泛的潜在应用价值。
附图说明
图1为本发明实施例1制得的苯并吡喃腈衍生物荧光探针的1H NMR谱图；
图2为本发明实施例1制得的苯并吡喃腈衍生物荧光探针的质谱谱图；
图3为本发明实施例1制得的苯并吡喃腈衍生物荧光探针的单晶结构图；
图4为本发明实施例1制得的苯并吡喃腈衍生物荧光探针的DMSO/H2O(体积比9:1)溶液(1×10-5mol/L)分别加入AcO-，Br-，Cl-，ClO-，CN-，F-，I-，PO4 3-，PPi，HSO3 -，S2-，N3 -和SCN-等阴离子(5×10-4mol/L))的紫外吸收光谱图；
图5为本发明实施例1制得的苯并吡喃腈衍生物荧光探针的DMSO/H2O(体积比9:1)溶液(5×10-5mol/L)滴定不同浓度CN-的紫外吸收光谱图；
图6为本发明实施例1制得的苯并吡喃腈衍生物荧光探针的DMSO/H2O(体积比9:1)溶液(1×10-5mol/L)分别加入AcO-，Br-，Cl-，ClO-，CN-，F-，I-，PO4 3-，PPi，HSO3 -，S2-，N3 -和SCN-等阴离子(5×10-4mol/L))的荧光光谱图；
图7为本发明实施例1制得的苯并吡喃腈衍生物荧光探针的DMSO/H2O(体积比9:1)溶液(5×10-5mol/L)滴定不同浓度CN-的荧光光谱光图；
图8为在HeLa细胞中，苯并吡喃腈衍生物荧光探针与CN-的荧光成像图；HeLa细胞用1×10-5mol/L荧光探针培育30分钟后加入5×10-5mol/LCN-，继续培育30分钟后使用Olympus FV500-IX70激光共聚焦显微镜进行荧光成像。
其中：a为荧光探针荧光成像图；b为荧光探针明场下的成像图；c为荧光探针明场图和荧光图叠加后的图片；d为荧光探针+CN--荧光成像图；e为荧光探针+CN--明场下的成像图；f为荧光探针+CN-明场图和荧光图叠加后的图片。
具体实施方式
下面结合附图和具体实施例进一步详细说明本发明，本发明实施例采用的试剂和原料为常规市场购买得到。
实施例1：
苯并吡喃腈衍生物的合成
Figure GDA0002832724720000041
将0.624g 2-(2-(4-羟基苯乙烯基)-4H-色满-4-亚乙基)丙二腈和1.265g三乙胺溶于40mL二氯甲烷中，冰浴下滴加0.588g噻吩甲酰氯,常温搅拌8h。减压蒸除溶剂，将固体残渣用二甲基甲酰胺和水混合溶剂(1：1，体积比)重结晶即为目标产物，目标产物的产率为56％。
采用核磁共振仪对制得的苯并吡喃腈衍生物进行核磁共振分析，结果如下：
1H NMR(400MHz，DMSO-d6)δ:8.74-8.76(d，J＝8.4Hz，1H)，8.12-8.13(d，J＝5.2Hz，1H)，8.05-8.06(d，J＝3.6Hz，1H)，7.93-7.97(t，J＝8.0Hz，1H)，7.87-7.89(d，J＝8.8Hz，2H)，7.83(s，1H)，7.79-7.81(d，J＝8.8Hz，1H)，7.62-7.66(t，J＝8.0Hz，1H)，7.55-7.59(d，J＝16.0Hz，1H)，7.41-7.43(t，J＝8.4Hz，2H)，7.32-7.35(t，J＝4.4Hz，1H)，7.07(s，1H).具体核磁图谱见图1；
质谱：ESI-MS:ESI-MS:m/z＝423.0930[M+H]+(calcd.423.08).具体质谱谱图见图2；
本发明制得的荧光探针的单晶结构图见图3。
实施例2
苯并吡喃腈衍生物对氰根的光学性质测定
将上述实施例1制得的苯并吡喃腈衍生物作为荧光探针在DMSO/H2O(体积比9:1)介质中配制成摩尔浓度为1×10-5mol/L的溶液，分别在含摩尔浓度为5×10-4mol/L的AcO-，Br-，Cl-，ClO-，CN-，F-，I-，PO4 3-，PPi，HSO3 -，S2-，N3 -和SCN-等阴离子的溶液中加入等量的上述荧光探针溶液，采用紫外可见光谱仪进行分析，所得紫外光谱图见图4。通过图4可以看出，本发明实施例1制得的苯并吡喃腈衍生物作为荧光探针只对氰根具有明显响应，探针溶液颜色由淡黄色变为绿色，其它离子无变化。通过图5紫外滴定光谱看出620纳米和438纳米处的吸光度比值与氰根在1.2×10-4-3.75×10-4mol/L浓度范围内线性相关，通过计算得到为检出限达1.68×10-6mol/L。
将上述实施例1制得的苯并吡喃腈衍生物作为荧光探针在DMSO/H2O(体积比9:1)介质中配制成摩尔浓度为1×10-5mol/L的溶液，分别在含摩尔浓度为5×10-4mol/L的AcO-，Br-，Cl-，ClO-，CN-，F-，I-，PO4 3-，PPi，HSO3 -，S2-，N3 -和SCN-等阴离子的溶液中加入等量的上述荧光探针溶液，采用荧光光谱仪进行分析，所得荧光光谱图见图6。通过图6可以看出，本发明实施例1制得的苯并吡喃腈衍生物作为荧光探针只对氰根具有明显响应，探针溶液由无荧光变为明显近红外荧光，其它离子无变化。通过图7荧光滴定光谱看出717纳米处的荧光强度与氰根在7.5×10-5-4.0×10-4mol/L浓度范围内线性相关，因此本发明实施例1制得的苯并吡喃腈衍生物可用于氰根的比色定性检测。
实施例3
苯并吡喃腈衍生物荧光探针在细胞内氰根的检测实验
HeLa细胞用1×10-5M的上述实施例1制得的苯并吡喃腈衍生物荧光探针培育0.5小时后加入CN-，继续培育0.5小时后使用Olympus FV500-IX70激光共聚焦显微镜进行荧光成像，获得在HeLa细胞的荧光成像图，具体如图7所示，其中a为上述荧光探针荧光成像图；b为上述荧光探针明场下的成像图；c为上述荧光探针明场图和荧光图叠加后的图片；d为上述荧光探针+CN-荧光成像图；e为上述荧光探针+CN-明场下的成像图；f为上述荧光探针+CN-明场图和荧光图叠加后的图片。HeLa细胞中加入苯并吡喃腈衍生物荧光探针无荧光发射，而再加入CN-后荧光明显增强。故本发明实施例1制得的苯并吡喃腈衍生物可用于细胞中CN-的定性检测。
以上所述实施例仅是为充分说明本发明而所举的较佳的实施例，其保护范围不限于此。本技术领域的技术人员在本发明基础上所作的等同替代或变换，均在本发明的保护范围之内，本发明的保护范围以权利要求书为准。

Claims (5)

1.一种基于苯并吡喃腈衍生物的荧光探针，其特征在于，所述苯并吡喃腈衍生物具有如下结构式：
Figure FDA0002832724710000011
2.根据权利要求1所述的一种基于苯并吡喃腈衍生物的荧光探针的制备方法，其特征在于，包括如下步骤：
S1：将2-(2-(4-羟基苯乙烯基)-4H-色满-4-亚乙基)丙二腈和三乙胺首先用二氯甲烷溶解；
S2：冰浴下将噻吩甲酰氯的二氯甲烷溶液滴加到S1所得溶液，室温搅拌反应8-10h；
S3：将S2所得溶液溶剂减压蒸馏，所得固体残渣用二甲基甲酰胺和水混合溶剂重结晶，得到基于所述苯并吡喃腈衍生物的荧光探针。
3.根据权利要求2所述的一种基于苯并吡喃腈衍生物的荧光探针的制备方法，其特征在于，所述2-(2-(4-羟基苯乙烯基)-4H-色满-4-亚乙基)丙二腈、所述三乙胺和所述噻吩甲酰氯摩尔比为1:1.1:1；所述二甲基甲酰胺和水混合溶剂二者体积比为1:1。
4.根据权利要求2所述的基于苯并吡喃腈衍生物的荧光探针的制备方法，其特征在于，将0.002-0.004mol 2-(2-(4-羟基苯乙烯基)-4H-色满-4-亚乙基)丙二腈和0.0022-0.0044mol三乙胺溶于0.04-0.08L二氯甲烷溶液中，冰浴下滴加0.002-0.004mol噻吩甲酰氯，常温搅拌8-10h，减压蒸除溶剂，所得固体用二甲基甲酰胺和水按照1:1体积比混合而得的混合溶剂重结晶得到所述苯并吡喃腈衍生物的荧光探针。
5.权利要求1所述的一种苯并吡喃腈衍生物的荧光探针在作为氰根荧光探针方面的应用。
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