CN109503634A - 一种异恶唑衍生物及其合成方法和检测硫化氢的应用 - Google Patents
一种异恶唑衍生物及其合成方法和检测硫化氢的应用 Download PDFInfo
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- CN109503634A CN109503634A CN201811324214.9A CN201811324214A CN109503634A CN 109503634 A CN109503634 A CN 109503634A CN 201811324214 A CN201811324214 A CN 201811324214A CN 109503634 A CN109503634 A CN 109503634A
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- hydrogen sulfide
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1025—Heterocyclic compounds characterised by ligands
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
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- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
本发明提供了一种异恶唑衍生物及其合成方法和硫化氢检测中的应用，所述异恶唑衍生物的中文名称为(E)‑5‑(2‑(5,5‑二氟‑10‑(4‑甲氧基苯基)‑1,3,7,9四甲基‑5氢二吡咯并[1,3,2]二氮杂硼‑2‑基)乙烯基)‑3‑甲基‑4‑硝基异恶唑。本发明同时提供了一种快速检测硫化氢的方法，该方法基于所述异恶唑衍生物，在PBS(pH＝7.4)溶液中通过荧光分光光度计定量检测硫化氢的含量。该方法实现了快速简便检测硫化氢。
Description
技术领域
本发明涉及异恶唑衍生物，具体属于一种异恶唑衍生物及其合成方法，以及该衍生物在快速检测硫化氢中的应用。
背景技术
很长时间以来，硫化氢被认为是一种对环境不友好的有臭味的气体，同时也认为它对人的伤害非常大。但是当1989年首次在人脑中发现硫化氢的存在以后，进一步的实验研究表明它和NO、CO同样是一种信号分子，被称为是第三种气体信号分子。研究表明硫化氢作为一种活跃的硫物种(RSS)在生命体内扮演着重要的角色，影响着生命体的健康成长，作为一种信号分子，他可以调剂血管舒张保持血压、调控细胞的生长和凋亡、调节炎症、控制氧化和应激反应及胰岛素信号等。所以，显而易见，硫化氢水平的缺失或异常会导致一些疾病，比如慢性肾病、肝硬化、阿兹海默症、唐氏综合症等。传统的检测方法是气相或液相色谱，但由于有样品破坏性不能原位检测等缺点，所以急需开发新的方法来检测体内的硫化氢。
近年来，出现了一系列检测硫化氢的荧光探针。这些探针主要基于以下机制设计，包括硫解反应，亲核反应，串联迈克尔加成，硫化铜沉淀，还原叠氮等。但其中仍有一些弊端存在，例如：硫解反应和亲核攻击会受到其他硫物质如硫醇的干扰；串联迈克尔加成的副产物较多，反应通常需要很长时间。尽管叠氮化物可以快速响应，但化合物往往不稳定。至于还原硝基的反应通常不产生副产物并会提供一种“开启”响应信号。Pluth课题组开发了第一个基于1,8-萘基带有硝基的荧光探针，但反应时间需要60分钟。然后出现了一系列带有硝基的探针，例如与花青染料和香豆素相连，但它们都需要很长的反应时间。无论使用何种荧光团，都应该解决探针的应用问题。
发明内容
本发明的目的是提供一种异恶唑衍生物及其合成方法，以及该衍生物在检测硫化氢中的应用，该衍生物用于检测硫化氢时应选择性好，响应速度快。
本发明提供的一种异恶唑衍生物，中文名称为(E)-5-(2-(5,5-二氟-10-(4-甲氧基苯基)-1,3,7,9四甲基-5氢二吡咯并[1,3,2]二氮杂硼-2-基)乙烯基)-3-甲基-4-硝基异恶唑，英文名称为
(E)-5-(2-(5,5-difluoro-10-(4-methoxyphenyl)-1,3,7,9-tetramethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-2-yl)vinyl)-3-methyl-4-nitroisoxazole，命名为BDP-ZN1。其结构式为：
BDP-ZN1的合成方法，步骤为：
1)按摩尔比1:2～2.5将茴香醛与2,4-二甲基吡咯在脱氧二氯甲烷中搅拌溶解；加入催化量的三氟乙酸，室温下在氩气保护中搅拌该混合溶液10～12小时；随后加入与茴香醛等摩尔的二氯二氰基苯醌，搅拌10～12小时，然后按混合溶液体积的1/10加入三乙胺；继续搅拌10～30分钟后再加入等体积的BF3·Et2O，并将混合物在室温下继续搅拌10～12小时，浓缩后经硅胶柱层析纯化，得到暗红色粉末即化合物1；
2)将DMF和POCl3按体积比1:1混合，冰浴下搅拌15～30分钟，将化合物1和上述混合物一同溶解在1,2-二氯乙烷中，在55～70℃回流2～6小时；然后加入饱和碳酸氢钠水溶液，二氯甲烷萃取，收集有机相，浓缩后经硅胶柱层析纯化得到化合物2；
3)按摩尔比1:1～1.5将化合物2与硝基异恶唑在苯中溶解，加入催化量的冰乙酸和哌啶，在氩气保护下加热至回流，搅拌3～6小时，然后待混合液冷却至室温后浓缩，经硅胶柱层析得到纯的化合物BDP-ZN1。
上述合成的异恶唑衍生物BDP-ZN1用于快速检测硫化氢。
一种检测硫化氢的方法，包括如下步骤：
(1)、配制pH＝7.4、浓度为10mM的PBS缓冲溶液，配制20mM的硫化氢水溶液，配置2mM的BDP-N1的DMSO溶液；
(2)、取1800μL PBS缓冲溶液、200μL DMSO、1μL BDP-ZN1的DMSO溶液于荧光比色皿中，在荧光分光光度仪上检测，随着硫化氢的加入,522nm处的荧光强度的逐渐增强；
(3)、在8个比色皿中，各加1800μL PBS缓冲溶液、200μL DMSO、1μM BDP-ZN1的DMSO溶液，分别加入硫化氢溶液的量为35、70、105、140、175、210、245、280μL，1min后在荧光光谱仪上测定522nm处荧光强度为205.9、275.5、353.8、455.2、539.2、600.7、635.9、719.2，以硫化氢浓度为横坐标，以荧光强度为纵坐标绘制图，得到硫化氢浓度的工作曲线；线性回归方程为：F-F0＝2.14619c-137.4，c的单位为10-6mol/L；
(4)、测定样品溶液时，将测得的荧光强度代入线性回归方程，即可求得硫化氢的浓度。
与现有技术相比，本发明的有益效果：
1、本发明异恶唑衍生物BDP-ZN1的合成只需三步，合成方法简单，操作方便；
2、本发明将异恶唑衍生物BDP-ZN1用于硫化氢检测，由于异恶唑的引入导致硝基的氧化性增强，相比其他还原硝基型荧光探针大大缩短了反应时间，只需要55秒；
3、检测手段简单，只需要借助荧光光谱仪即可实现；
4、检测信号明显，为增强型荧光；
5、通过生物学应用，探针可成为研究硫化氢在细胞中功能的良好传感器，也为疾病的诊断和治疗提供了新的途径
附图说明
图1实施例1制备的BDP-ZN1的核磁氢谱图
图2实施例1制备的BDP-ZN1的核磁碳谱图
图3实施例1制备的BDP-ZN1的质谱图
图4 BDP-ZN1与硫化氢作用的荧光发射图
图5 BDP-ZN1测定硫化氢的工作曲线
图6 BDP-ZN1与各种分析物的荧光柱状图
图7 BDP-ZN1测定硫化氢的时间曲线
图8 BDP-ZN1测定样品的荧光发射图
图9 BDP-ZN1测定内源性硫化氢的细胞成像图
图10 BDP-ZN1测定外源性硫化氢的细胞成像图
具体实施方式
下面结合实施例和附图对本发明做进一步说明，但本发明不受下述实施例的限制。
实施例1
BDP-ZN1的制备和表征
1)将茴香醛(6.0mmol，0.84g)与2,4-二甲基吡咯(13.2mmol，1.26g)在脱氧二氯甲烷(250ml)中搅拌。加入3滴三氟乙酸，继续在室温、氩气保护下搅拌24小时。然后加入二氯二氰基苯醌(6.0mmol，1.36g)，继续搅拌4小时，然后加入三乙胺(15mL)。30分钟之后再加BF3·Et2O(15mL)，并将混合物在室温下搅拌24小时，浓缩混合液后经硅胶柱层析(乙酸乙酯/二氯甲烷/石油醚，1/1/10，V/V，洗脱)纯化，得到所需化合物1，为暗红色粉末；
2)将化合物1(1mmol，0.3g)和预先准备好的DMF/POCl3混合物(6mL/6mL，冰浴搅拌30分钟)溶解在1,2-二氯乙烷中，然后将混合物在65℃回流4小时。浓缩经柱层析乙酸乙酯/二氯甲烷/石油醚，1/1/8，V/V，洗脱)纯化，得到化合物2；
3)将化合物2(0.5mmol，0.14g)与硝基异恶唑(0.55mmol，0.078g)溶解在25mL苯中，加入0.3mL冰乙酸和0.35mL哌啶，加热至回流，氩气保护下回流搅拌5小时，待混合物冷却至室温，浓缩后经柱层析乙酸乙酯/二氯甲烷/石油醚，1/1/8，V/V，洗脱)纯化，得到纯的BDP-N1。1H NMR(600MHz,CDCl3)δ7.74(d,J＝16.6Hz,1H),7.31(d,J＝16.7Hz,1H),7.22(d,J＝8.6Hz,2H),7.08(d,J＝8.6Hz,2H),6.14(s,1H),3.93(s,3H),2.80(s,3H),2.63(s,3H),2.59(s,3H),1.63(s,3H),1.50(s,3H)(见图1)。13C NMR(151MHz,DMSO-d6)δ160.5,146.3,139.9,129.2,123.3,114.8,77.2,55.4,15.0,13.1,11.9(见图2)。ESI-MS m/z:[M+H]+calcd for 507.20；Found 507.20(见图3)。
实施例2
在荧光比色皿中，加入1800μL PBS缓冲溶液、200μL DMSO、1μM BDP-ZN1的DMSO溶液，逐渐加入硫化氢水溶液(0-280μM)，每加入一次，1min后在荧光光谱仪上测定522nm处荧光强度，荧光强度逐渐增强(见图4)。
实施例3
配制pH＝7.4、浓度为10mM的PBS缓冲溶液，并用DMSO配制2mM BDP-ZN1的溶液，配制2mM硫化氢水溶液；在8个比色皿中，取1800μL PBS缓冲溶液、200μL DMSO、1μM BDP-ZN1的DMSO溶液，分别加入硫化氢溶液的量为35、70、105、140、175、210、245、280μM，1min后在荧光光谱仪上测定522nm处荧光强度为205.9、275.5、353.8、455.2、539.2、600.7、635.9、719.2，以硫化氢浓度为横坐标，以荧光强度为纵坐标绘制图，得到硫化氢浓度的工作曲线；线性回归方程为：F-F0＝2.14619c-137.4，c的单位为10-6mol/L(见图5)。
实施例4
配制pH＝7.4、浓度为10mM的PBS缓冲溶液，配制2mM BDP-ZN1的DMSO溶液，配制2mM的硫化氢水溶液；在荧光比色皿中，加1800μL PBS缓冲溶液、200μL DMSO和1μM BDP-ZN1的DMSO溶液，再分别加入10倍当量的其它分析物和硫化氢：NO3 -,P2O7 4-,Cl-,NO2 -,F-,H2O2,HClO,CH3COO-,S2O3 2-,HPO4 2-,CO3 2-,HCO3 -,HSO3 -,Cys,SCN-,H2PO4 -,GSH,SO4 2-,H2S的水溶液，在荧光分光光度仪上检测，绘制不同分析物对应的522nm处荧光强度柱状图(见图6)。硫化氢使得检测体系在522nm处荧光强度明显升高，其它的分析物基本没有引起检测体系荧光强度的变化。
实施例5
配制pH＝7.4、浓度为10mM的PBS缓冲溶液，配制2mM BDP-ZN1的DMSO溶液，配制2mM的硫化氢水溶液；在荧光比色皿中，加1800μL PBS缓冲溶液、200μL DMSO和1μM BDP-ZN1的DMSO溶液，再加入500μL硫化氢水溶液，在522nm处测得其反应时间为55s(见图7)。
实施例6
配制pH＝7.4、浓度为10mM的PBS缓冲溶液，并用DMSO配制2mM BDP-ZN1的溶液，配制20mM硫化氢水溶液；把1μL BDP-ZN1的DMSO溶液加入到1800μL PBS缓冲溶液、200μL DMSO的荧光比色皿中，取硫化氢的溶液250μL，用微量进样器加到此比色皿中，同时在荧光光谱仪上测定522nm处荧光强度为655(见图8)，通过实施例4的线性回归方程，求得c＝3.3×10- 4mol/L。偏差为7.6％。
实施例7
配制pH＝7.4、浓度为10mM的PBS缓冲溶液，并用DMSO配制2mM BDP-ZN1的溶液，配制20mM硫化氢水溶液；把5μL BDP-ZN1的DMSO溶液加入到2mL的PBS中；将探针溶液加入HepG-2细胞培养液中，使得其浓度为5μM，与HepG-2细胞在37℃下，孵育30分钟后用PBS溶液冲洗三次，进行激光共聚焦成像，此时细胞内没有荧光，如图9a；把5μL SNP(硝普钠：刺激内源性硫化氢)溶液加入到2mL的PBS中，将溶液加入HepG-2细胞培养液中，在37℃下孵育60分钟后用PBS溶液冲洗三次，进行激光共聚焦成像，细胞内同样无荧光，如图9b；向孵育过SNP细胞中再加入5μM的探针溶液，在37℃下孵育30分钟后用PBS溶液冲洗三次，进行激光共聚焦成像，此时细胞在荧光成像仪下显示出明显绿色荧光，如图9c；将探针溶液加入HepG-2细胞培养液中，使得其浓度为5μM，与HepG-2细胞在37℃下，孵育30分钟后用PBS溶液冲洗三次，再加入外源的硫化氢，使其浓度分别为50μM、100μM、200μM，在37℃下，孵育30分钟，随后均用PBS缓冲溶液冲洗三次，进行激光共聚焦成像，此时细胞在荧光成像仪下显示出不同程度的绿色荧光，如图10。
上述实验结果说明BDP-ZN1是检测细胞内硫化氢良好的候选者。
Claims (5)
1.一种异恶唑衍生物BDP-ZN1，其特征在于，结构式为：
2.如权利要求1所述的一种异恶唑衍生物BDP-ZN1的合成方法，其特征在于，包括如下步骤：
1)按摩尔比1:2～2.5将茴香醛与2,4-二甲基吡咯在脱氧二氯甲烷中搅拌溶解；加入催化量的三氟乙酸，室温下在氩气保护中搅拌该混合溶液10～12小时；随后加入与茴香醛等摩尔的二氯二氰基苯醌，搅拌10～12小时，然后按混合溶液体积的1/10加入三乙胺；继续搅拌10～30分钟后再加入等体积的BF3·Et2O，在室温下继续搅拌10～12小时，浓缩后经硅胶柱层析纯化，得到暗红色粉末即化合物1；
2)将DMF和POCl3按体积比1:1混合，冰浴下搅拌15～30分钟，将化合物1和上述混合物一同溶解在1,2-二氯乙烷中，在55～70℃回流2～6小时；然后加入饱和碳酸氢钠水溶液，二氯甲烷萃取，收集有机相，浓缩后经硅胶柱层析纯化得到化合物2；
3)按摩尔比1:1～1.5将化合物2与硝基异恶唑在苯中溶解，加入催化量的冰乙酸和哌啶，在氩气保护下加热至回流，搅拌3～6小时，然后待混合液冷却至室温后浓缩，经硅胶柱层析得到纯的化合物BDP-ZN1。
3.如权利要求1所述的异恶唑衍生物BDP-ZN1在硫化氢检测中的应用。
4.一种特异性检测硫化氢的方法，其特征在于，包括如下步骤：
(1)、配制pH＝7.4、浓度为10mM的PBS缓冲溶液，配制20mM的硫化氢水溶液，配置2mM的BDP-ZN1的DMSO溶液；
(2)、取1800μL PBS缓冲溶液、200μL DMSO、1μL BDP-ZN1的DMSO溶液于荧光比色皿中，在荧光分光光度仪上检测，随着硫化氢的加入，522nm处的荧光强度的逐渐增强；
(3)、在8个比色皿中，各加入1800μL PBS缓冲溶液、200μL DMSO、1μM BDP-ZN1的DMSO溶液，分别加入硫化氢溶液的量为35、70、105、140、175、210、245、280μM，1min后在荧光光谱仪上测定522nm处荧光强度为205.9、275.5、353.8、455.2、539.2、600.7、635.9、719.2，以硫化氢浓度为横坐标，以荧光强度为纵坐标绘制图，得到硫化氢浓度的工作曲线；线性回归方程为：F-F0＝2.14619c-137.4，c的单位为10-6mol/L；
(4)、测定样品溶液时，将测得的荧光强度代入线性回归方程，即可求得硫化氢的浓度。
5.如权利要求1所述的异恶唑衍生物BDP-ZN1在制备细胞成像试剂中的应用。
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111234250A (zh) * | 2020-02-18 | 2020-06-05 | 盐城工学院 | 一种双向荧光硫化氢探针及其应用 |
| CN111234250B (zh) * | 2020-02-18 | 2021-12-10 | 盐城工学院 | 一种双向荧光硫化氢探针及其应用 |
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