CN112939957A - 一种苯并吲哚衍生物In-XY1及其合成方法和应用 - Google Patents
一种苯并吲哚衍生物In-XY1及其合成方法和应用 Download PDFInfo
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Abstract
本发明提供了一种苯并吲哚衍生物In‑XY1及其合成方法和应用,所述苯并吲哚衍生物的中文名称为((E)‑2‑(2‑(5‑(4‑(4‑二甲基氨基)苯基)噻吩‑2‑基)乙烯基)‑1,1,3‑三甲基‑1H‑苯并[e]吲哚‑3‑碘化物。本发明将苯并吲哚衍生物In‑XY1作为荧光探针,可实现双通道检测黏度和二氧化硫。具体基于所述苯并吲哚衍生物In‑XY1,在水和甘油不同的体积比混合溶液中通过荧光光谱仪检测黏度的变化,同时在PBS和DMSO(pH=7.4,v/v=9/1)溶液中通过紫外可见分光光度计和荧光光谱仪定量检测二氧化硫的含量。该方法还在细胞和斑马鱼水平实现了双通道检测线粒体的黏度和二氧化硫的变化。
Description
技术领域
本发明涉及苯并吲哚衍生物,具体属于一种苯并吲哚衍生物及其合成方法,以及该衍生物在细胞中检测黏度和二氧化硫的应用。
背景技术
线粒体作为真核细胞重要的细胞器,线粒体的异常与多种疾病的发生息息相关。如神经退行性病变(如阿尔兹海默症、帕金森症)、代谢型疾病(如肥胖症、II型糖尿病)、心血管疾病及癌症等等。二氧化硫(SO2)被人们认为是重要的环境污染物之一。在水溶液中二氧化硫主要以亚硫酸盐(SO3 2-)和亚硫酸氢盐(HSO3 -)两种衍生物形式存在。SO2衍生物被广泛应用于酶抑制剂、抗菌剂、药品,以及食品防腐剂和饮料等,工业当中也已经广泛使用了。然而,流行性病学研究表明吸入或者摄入过多的二氧化硫可能导致呼吸性疾病(如哮喘、肺气肿、慢性支气管炎)、神经紊乱(例如偏头痛、中风等),甚至肺癌。越来越多的证据表明体内SO2的异常水平与线粒体功能障碍密切相关。因此,设计并开发一种可同时检测线粒体中黏度变化和SO2变化的荧光传感器是迫切需要的。
近年来,国内外诸多课题组研究了系列靶向线粒体的近红外探针,用于检测线粒体内活性分子(活性氧,活性氮,硫醇,蛋白酶等),但是对于生理病理过程中线粒体微环境(极性,粘度等)的研究还是不够深入,缺乏有力的研究工具。同时,近年来报道的同时检测黏度和二氧化硫的荧光探针还比较少,这需要研究工作者们更进一步地展开深入研究。
发明内容
本发明的目的是提供一种苯并吲哚衍生物In-XY1及其合成方法,以及该衍生物在细胞水平和斑马鱼中检测黏度和二氧化硫的应用。
本发明提供的一种苯并吲哚衍生物In-XY1,中文名称为(E)-2-(2-(5-(4-(4-二甲基氨基)苯基)噻吩-2-基)乙烯基)-1,1,3-三甲基-1H-苯并[e]吲哚-3-碘化物,英文名称为(E)-2-(2-(5-(4-dimethylamino)phenyl)thiophen-2-yl)vinyl)-1,1,3-trimethyl-1H-benzo[e]indol-3-iumiodide。其结构式为:
In-XY1的合成方法,步骤为:
1)在50mL的圆底烧瓶中,将306mg 4-溴-N,N-二甲基苯胺和150mg四(三苯基膦)钯溶于10mL甲苯中,并将200mg 5-醛基-2-噻吩硼酸溶于8mL乙醇中,再加入2ml的K2CO3(2M),混合物在氩气保护下加热至115℃回流,并且保持5h;冷却至室温,减压除去溶剂甲苯,溶于二氯甲烷,水洗有机相三次,并用无水Na2SO4干燥,减压除去溶剂后的固体通过体积比2:1的二氯甲烷和石油醚作为洗脱液进行柱色谱法纯化,得到橙色化合物1;
2)在50mL的圆底烧瓶中,将1.05g 1,1,2-三甲基-1H-苯并[e]吲哚溶于20ml甲苯中,在氮气保护下,加入0.85g碘甲烷,混合物加热到110℃,回流12h;自然冷却,有沉淀析出,过滤,并用乙醚洗涤产物,得到化合物2;
3)将70mg化合物1和46mg化合物2混合,溶于10ml乙醇中,加热至80℃并保持反应回流8h;自然冷却,减压除去溶剂后的固体通过体积比1:25的甲醇和二氯甲烷作为洗脱液进行柱色谱法纯化,得到蓝黑色粉末即In-XY1。
上述合成的苯并吲哚衍生物In-XY1在细胞水平和斑马鱼中检测黏度和二氧化硫衍生物(SO3 2-)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的亚硫酸钠(作为SO2供体)水溶液,配制2mM的In-XY1的DMSO溶液,配制不同黏度的甘油/乙醇溶液(表1);
表1配制不同黏度的乙醇/甘油溶液
(2)、将配制的不同黏度的甘油/乙醇溶液、分别加入10μL In-XY1的DMSO溶液于比色皿中,充分混合均匀后,在荧光分光光度仪上检测,随着黏度的增加,740nm处的荧光强度逐渐增强;
(3)、取1800μL PBS缓冲溶液、200μL DMSO、10μL In-XY1的DMSO溶液于比色皿中,在紫外分光光度计上检测,随着SO3 2-的增加(0-100uM),575nm处的吸收逐渐减弱;
(4)、取1800μL PBS缓冲溶液、200μL DMSO、10μL In-XY1的DMSO溶液于比色皿中,在荧光分光光度仪上检测,随着亚硝酸钠的增加(0-100uM),480nm处的荧光强度的逐渐增强。
与现有技术相比,本发明的有益效果:
1、本发明苯并吲哚衍生物In-XY1的合成只需三步,合成方法简单,操作方便;
2、探针In-XY1对黏度的检测,斯托克斯位移较大,近红外发射(740nm),具有高穿透性、低背景荧光、便于活体成像等优点;
3、检测手段简单,双通道(红色通道检测黏度,蓝色通道识别二氧化硫)实现了对黏度和二氧化硫的检测。
4、苯并吲哚碘盐中的正离子,可以有效的靶向线粒体,从而实现了靶向线粒体的黏度和二氧化硫的检测。
附图说明
图1实施例1制备的In-XY1的核磁氢谱
图2实施例1制备的In-XY1的核磁碳谱
图3实施例1制备的In-XY1的质谱图
图4 In-XY1在不同比例甘油乙醇溶液中的荧光光谱图
图5 In-XY1与SO3 2-作用的紫外光谱图
图6 In-XY1与SO3 2-作用的荧光光谱图
图7 In-XY1与各种分析物的荧光柱状图
图8 In-XY1检测黏度细胞成像图
图9 In-XY1测定外源性二氧化硫的细胞成像图
图10 In-XY1线粒体定位成像
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 In-XY1的制备和表征:
In-XY1的合成路线:
In-XY1的合成方法,步骤为:
1)在50mL的圆底烧瓶中,将306mg 4-溴-N,N-二甲基苯胺和150mg四(三苯基膦)钯溶于10mL甲苯中,并将200mg 5-醛基-2-噻吩硼酸溶于8mL乙醇中,再加入2ml的K2CO3(2M),混合物在氩气保护下加热至115℃回流,并且保持5h;冷却至室温,减压除去溶剂甲苯,溶于二氯甲烷,水洗有机相三次,并用无水Na2SO4干燥,减压除去溶剂后的固体通过体积比2:1的二氯甲烷和石油醚作为洗脱液进行柱色谱法纯化,得到橙色化合物1;
2)在50mL的圆底烧瓶中,将1.05g 1,1,2-三甲基-1H-苯并[e]吲哚溶于20ml甲苯中,在氮气保护下,加入0.85g碘甲烷,混合物加热到110℃,回流12h。自然冷却,有沉淀析出,过滤,并用乙醚洗涤产物,得到化合物2;
3)将70mg化合物1和46mg化合物2混合,溶于10ml乙醇中,加热至80℃并保持反应回流8h;自然冷却,减压除去溶剂后的固体通过体积比1:25的甲醇和二氯甲烷作为洗脱液进行柱色谱法纯化,得到蓝黑色粉末即In-XY1。1H NMR(600MHz,DMSO-d6)δ8.71(d,J=15.7Hz,1H),8.41(d,J=8.8Hz,1H),8.26(d,J=8.8Hz,1H),8.19(d,J=8.3Hz,1H),8.13(s,1H),8.04(d,J=8.9Hz,1H),7.79(t,J=7.7Hz,1H),7.69(t,J=7.9Hz,4H),7.11(d,J=15.6Hz,1H),6.83(d,J=8.4Hz,2H),4.14(s,3H),3.03(s,6H),2.00(s,6H).(图1)。13C NMR(151MHz,DMSO)δ181.00,156.65,151.86,144.87,140.05,137.49,137.45,133.26,131.23,130.49,128.77,128.02,127.26,127.18,124.33,123.47,120.22,113.42,112.73,108.36,55.40,53.48,34.47,26.02.(图2)。ESI-MS:[M-I]+Calcd.For 437.2046;Found 437.20451(图3)。
实施例2
配制2.0mL甘油和乙醇(甘油体积含量比例为0%、10%、20%、30%、40%、50%、60%、70%、80%、90%、100%)不同黏度溶液,充分混合均匀,并且超声半小时,赶走溶液中的气泡。然后分别与10μL浓度为2.0mmol/L的探针In-XY1溶液混合于比色皿中,并且充分混合均匀后,测试它们的荧光强度。随着黏度的增加(甘油体积比增加),探针In-XY1在740nm处的荧光逐渐增强(Ex=575nm)(图4)。
实施例3
取2.0mL体积比为9:1的PBS和DMSO混合溶液、10μL浓度为2.0mmol/L的探针In-XY1DMSO溶液合并于比色皿中,加入不同浓度的SO3 2-水溶液(0-100μM),15min后在紫外可见光吸光光度计上检测In-XY1的吸光度变化。(图5)。随着SO3 2-浓度的增加,探针In-XY1在575nm处的吸光度逐渐减弱。
实施例4
取2.0mL体积比为9:1的PBS和DMSO混合溶液、10μL浓度为2.0mmol/L的探针In-XY1DMSO溶液合并于比色皿中,加入不同浓度的SO3 2-水溶液(0-100μM),15min后在荧光光谱仪上测定探针In-XY1在480nm处的荧光强度。随着SO3 2-浓度的增加,荧光强度逐渐增强(图6)。
实施例5
配制pH=7.4、浓度为10mM的PBS缓冲溶液,配制2mM In-XY1的DMSO溶液,配制20mM的亚硫酸钠水溶液;在荧光比色皿中,加1800μL PBS缓冲溶液、200μL DMSO和10μM In-XY1的DMSO溶液,再分别加入100当量的其它分析物和亚硫酸钠:Mg2+、NaBr、KI、F-、H2O2、Cl-、Ca(NO3)2、Cys、NO2 -、GSH、Hcy、L-谷氨酸、L-赖氨酸、SO4 2-、L-脯氨酸、Gly、Na2S、ClO-、CH3COONa、S2O3 2-、Na2SO3水溶液,在荧光分光光度仪上检测,绘制不同分析物对应的480nm处荧光强度柱状图(见图7)。亚硫酸钠使得检测体系在480nm处荧光强度明显升高,Na2S使得体系荧光强度有些许升高,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6
配制pH=7.4、浓度为10mM的PBS缓冲溶液,配制2mM In-XY1的DMSO溶液,配制20mM的亚硫酸钠水溶液;先将7702细胞中加入2mL的PBS,再将探针溶液加入7702细胞中,使得其浓度为10μM,将7702细胞在37℃下放置20min后,用PBS冲洗细胞三次,再在荧光共聚焦显微镜下进行成像拍照,探针呈现红色荧光。接着,将孵过探针的细胞加入10uM的制霉菌素,并在荧光共聚焦显微镜下观察荧光变化(见图8)。体系在荧光成像仪下显示红色通道荧光明显增强,蓝色通道荧光有所增加。
实施例7
先将7702细胞中加入2mL的PBS,再将探针溶液加入7702细胞中,使得其浓度为10μM,将7702细胞在37℃下放置20min后,用PBS冲洗细胞三次,再在荧光共聚焦显微镜下进行成像拍照,探针呈现红色荧光。然后加入100uM的SO3 2-溶液,20min后在荧光共聚焦显微镜下观察荧光变化(见图9)。体系在荧光成像仪下显示红色通道荧光变暗,蓝色通道荧光变亮。
实施例8
将7702细胞中加入500uM Mito-Tracker Green,在37℃的恒温箱放置20min后,用PBS冲洗三次,再将探针DMSO溶液加入7702细胞中,使得其浓度为10μM,放置20min后,用PBS冲洗细胞三次,再在荧光共聚焦显微镜下进行成像拍照(见图10)。红色通道为探针,绿色通道为Mito-Tracker Green,结果表明探针对线粒体具有良好的靶向性(皮尔逊系数0.90),说明探针能够特异性染色活细胞中的线粒体。
上述实验结果说明In-XY1是双通道检测线粒体的黏度和二氧化硫变化的良好的候选者。
Claims (5)
2.如权利要求1所述的一种苯并吲哚衍生物In-XY1的合成方法,其特征在于,包括如下步骤:
1)在50mL的圆底烧瓶中,将306mg 4-溴-N,N-二甲基苯胺和150mg四(三苯基膦)钯溶于10mL甲苯中,并将200mg 5-醛基-2-噻吩硼酸溶于8mL乙醇中,再加入2ml的K2CO3(2M),混合物在氩气保护下加热至115℃回流,并且保持5h;冷却至室温,减压除去溶剂甲苯,溶于二氯甲烷,水洗有机相三次,并用无水Na2SO4干燥,减压除去溶剂后的固体通过体积比2:1的二氯甲烷和石油醚作为洗脱液进行柱色谱法纯化,得到橙色化合物1;
2)在50mL的圆底烧瓶中,将1.05g 1,1,2-三甲基-1H-苯并[e]吲哚溶于20ml甲苯中,在氮气保护下,加入0.85g碘甲烷,混合物加热到110℃,回流12h;自然冷却,有沉淀析出,过滤,并用乙醚洗涤产物,得到化合物2;
3)将70mg化合物1和46mg化合物2混合,溶于10ml乙醇中,加热至80℃并保持反应回流8h;自然冷却,减压除去溶剂后的固体通过体积比1:25的甲醇和二氯甲烷作为洗脱液进行柱色谱法纯化,得到蓝黑色粉末即In-XY1。
3.如权利要求1所述的苯并吲哚衍生物In-XY1在制备双通道检测黏度和二氧化硫的探针中的应用。
4.一种双通道检测黏度和二氧化硫的方法,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Na2SO3水溶液,配制2mM的In-XY1的DMSO溶液,配制不同黏度的甘油/乙醇溶液;
(2)、将配制的不同黏度的甘油/乙醇溶液,分别加入10μLIn-XY1的DMSO溶液于荧光比色皿中,充分混合均匀后,在荧光分光光度仪上检测探针In-XY1随着黏度的增加荧光强度在740nm处的变化;
(3)、取1800μL PBS缓冲溶液、200μL DMSO、10μLIn-XY1的DMSO溶液于比色皿中,在紫外可见光吸光光度计上监测探针In-XY1随着SO3 2-的增加在575nm处的吸光度变化;
(4)、取1800μL PBS缓冲溶液、200μL DMSO、10μLIn-XY1的DMSO溶液于比色皿中,在荧光分光光度仪上检测探针In-XY1随着SO3 2-的增加在480nm处的荧光强度变化。
5.如权利要求1所述的苯并吲哚衍生物In-XY1在制备细胞成像试剂中的应用。
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113354627A (zh) * | 2021-06-22 | 2021-09-07 | 浙江工业大学 | 一种用于检测粘度的近红外荧光化合物及其制备与应用 |
CN114181204A (zh) * | 2021-12-13 | 2022-03-15 | 洛兮医疗科技(杭州)有限公司 | 一种检测粘度的近红外荧光探针及其制备和应用 |
CN114605371A (zh) * | 2022-02-21 | 2022-06-10 | 山西大学 | 一种苯并吡喃衍生物bp-ⅲ及其合成方法和应用 |
CN115260083A (zh) * | 2022-07-01 | 2022-11-01 | 山西医科大学 | 一种线粒体靶向的粘度响应荧光探针的制备方法及应用 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080274907A1 (en) * | 2006-10-27 | 2008-11-06 | Invitrogen Corporation | Fluorogenic ph sensitive dyes and their method of use |
CN103134787A (zh) * | 2013-02-25 | 2013-06-05 | 太原理工大学 | 一种比率型氰离子荧光探针分子的应用方法 |
CN109053549A (zh) * | 2018-10-12 | 2018-12-21 | 济南大学 | 一种定位线粒体检测粘度的双光子荧光探针及其合成方法和应用 |
CN110078714A (zh) * | 2019-05-16 | 2019-08-02 | 济南大学 | 一种定位线粒体的双光子粘度探针及其制备方法和应用 |
CN110143966A (zh) * | 2019-06-03 | 2019-08-20 | 山西大学 | 一种螺吡喃-萘酰亚胺衍生物及其合成方法和应用 |
US20190375941A1 (en) * | 2018-06-11 | 2019-12-12 | Institute For Stem Cell Biology And Regenerative Medicine (Instem) | Compounds as fluorescent probes, synthesis and applications thereof |
CN111153893A (zh) * | 2020-01-10 | 2020-05-15 | 山东大学 | 一种用于检测细胞线粒体中so2衍生物的比率荧光探针及其应用 |
CN112142721A (zh) * | 2020-09-04 | 2020-12-29 | 武汉大学深圳研究院 | 一种可靶向线粒体的近红外二区噻喃盐荧光化合物及其制备方法与应用 |
US20210000965A1 (en) * | 2017-10-25 | 2021-01-07 | Georgia State University Research Foundation, Inc | Enrichment-triggered chemical delivery system |
-
2021
- 2021-02-03 CN CN202110146323.1A patent/CN112939957B/zh active Active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080274907A1 (en) * | 2006-10-27 | 2008-11-06 | Invitrogen Corporation | Fluorogenic ph sensitive dyes and their method of use |
CN103134787A (zh) * | 2013-02-25 | 2013-06-05 | 太原理工大学 | 一种比率型氰离子荧光探针分子的应用方法 |
US20210000965A1 (en) * | 2017-10-25 | 2021-01-07 | Georgia State University Research Foundation, Inc | Enrichment-triggered chemical delivery system |
US20190375941A1 (en) * | 2018-06-11 | 2019-12-12 | Institute For Stem Cell Biology And Regenerative Medicine (Instem) | Compounds as fluorescent probes, synthesis and applications thereof |
CN109053549A (zh) * | 2018-10-12 | 2018-12-21 | 济南大学 | 一种定位线粒体检测粘度的双光子荧光探针及其合成方法和应用 |
CN110078714A (zh) * | 2019-05-16 | 2019-08-02 | 济南大学 | 一种定位线粒体的双光子粘度探针及其制备方法和应用 |
CN110143966A (zh) * | 2019-06-03 | 2019-08-20 | 山西大学 | 一种螺吡喃-萘酰亚胺衍生物及其合成方法和应用 |
CN111153893A (zh) * | 2020-01-10 | 2020-05-15 | 山东大学 | 一种用于检测细胞线粒体中so2衍生物的比率荧光探针及其应用 |
CN112142721A (zh) * | 2020-09-04 | 2020-12-29 | 武汉大学深圳研究院 | 一种可靶向线粒体的近红外二区噻喃盐荧光化合物及其制备方法与应用 |
Non-Patent Citations (1)
Title |
---|
ZHANG, XIYUAN等: "Dual-emission NIR fluorescent probe sensitive response biological microenvironment and sulfur dioxide", 《SENSORS AND ACTUATORS B: CHEMICAL》 * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113354627A (zh) * | 2021-06-22 | 2021-09-07 | 浙江工业大学 | 一种用于检测粘度的近红外荧光化合物及其制备与应用 |
CN113354627B (zh) * | 2021-06-22 | 2022-03-25 | 浙江工业大学 | 一种用于检测粘度的近红外荧光化合物及其制备与应用 |
CN114181204A (zh) * | 2021-12-13 | 2022-03-15 | 洛兮医疗科技(杭州)有限公司 | 一种检测粘度的近红外荧光探针及其制备和应用 |
CN114181204B (zh) * | 2021-12-13 | 2023-07-11 | 洛兮医疗科技(杭州)有限公司 | 一种检测粘度的近红外荧光探针及其制备和应用 |
CN114605371A (zh) * | 2022-02-21 | 2022-06-10 | 山西大学 | 一种苯并吡喃衍生物bp-ⅲ及其合成方法和应用 |
CN115260083A (zh) * | 2022-07-01 | 2022-11-01 | 山西医科大学 | 一种线粒体靶向的粘度响应荧光探针的制备方法及应用 |
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