CN111153893B - 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 - Google Patents

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 Download PDF

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CN111153893B
CN111153893B CN202010027255.2A CN202010027255A CN111153893B CN 111153893 B CN111153893 B CN 111153893B CN 202010027255 A CN202010027255 A CN 202010027255A CN 111153893 B CN111153893 B CN 111153893B
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赵宝祥
苗俊英
闫业浩
吴秋蓉
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Abstract

本发明公开了一种用于检测细胞线粒体中SO2衍生物的比率荧光探针,该探针由香豆素衍生物荧光团(能量供体)、哌嗪(连接基团)和(E)‑2‑(4‑(二取代胺基)‑苯乙烯基)‑1,3,3‑三甲基苯并吲哚碘盐(能量受体)三部分构成,其化学结构式如式(I)所示。本发明的探针能够高选择性地与SO2衍生物作用,随着SO2衍生物浓度的增加,其荧光发射强度在490nm处逐渐增强,在620nm处逐渐减弱;二者比值(I490/I620)与SO2衍生物浓度在一定范围内呈线性关系。能够在培养的细胞内实现比率荧光成像,有望在临床医学诊疗中发挥作用,具有广阔的应用前景。

Description

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
技术领域
本发明涉及一种比率荧光探针及其应用,尤其涉及一种基于荧光共振能量转移机理的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;属于有机小分子荧光探针技术领域。
背景技术
SO2作为一种常见的污染物,以HSO3 -/SO3 2-的形式广泛存在于水资源、食物以及有机生物体内。生物体内HSO3 -/SO3 2-浓度异常会引发心血管病、内分泌异常甚至癌症等疾病的发生。对生物体内源性HSO3 -/SO3 2-含量的实时监测,有助于深入研究HSO3 -/SO3 2-在生物体内的生理和病理作用,发展活体内的HSO3 -/SO3 2-荧光成像技术,实时检测细胞内HSO3 -/SO3 2-的浓度与分布具有重大意义。
HSO3 -/SO3 2-荧光探针具有高选择性、高灵敏度、低检测线等优势,逐渐成为科学研究的关注点[Chem.Soc.Rev.,2018,47,8842-8880;J.Am.Chem.Soc.,2014,136,12820-12823.];与之前报道的单发射信号荧光探针相比,比率型荧光探针具有稳定性高、抗干扰能力强等优点;通过计算两个发射峰强度的比值可以实现探针的自校正,进而实现对HSO3 -/SO3 2-的准确定量[Anal.Chem.,2017,89,7038-7045].基于FRET机理的比率荧光探针由能量供体、连接体和能量受体三部分构成。能量供体吸收能量后通过分子内共振过程将能量传递给受体,并使探针表现出增强的受体荧光。随着被检测物种的浓度变化,FRET过程逐渐被阻断,受体无法接受供体的能量,供体和受体的荧光发射强度逐渐发生变化。因此,供体和受体两者的荧光强度比值与HSO3 -/SO3 2-的浓度在一定范围内呈现函数关系。目前,许多荧光探针存在能量传递效率低、两个发射波长之间的距离小等不足,亟待开发新的荧光团,以构筑新型的FRET机理的荧光探针。经检索,有关基于荧光共振能量转移机理的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鲜见报道。
发明内容
针对现有技术的不足,本发明要解决的问题是提供一种基于荧光共振能量转移机理的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。
本发明所述的用于检测细胞线粒体中SO2衍生物的比率荧光探针,其特征在于:所述比率荧光探针由香豆素衍生物荧光团(能量供体)、哌嗪(连接基团)和(E)-2-(4-(二取代胺基)-苯乙烯基)-1,3,3-三甲基苯并吲哚碘盐(能量受体)三部分构成;其化学结构式如式(I)所示:
Figure BDA0002362920200000021
上述用于检测细胞线粒体中SO2衍生物的比率荧光探针的制备方法是:根据已报道方法制备出4-(4-(7-(二乙氨基-2-氧代-2H-色烯-3-甲酰基)哌嗪-1-基)苯甲醛,然后与1,2,3,3-四甲基苯并吲哚-1-碘盐进行脱水缩合反应,即制得所述用于检测细胞线粒体中SO2衍生物的比率荧光探针。制备化学反应式如下:
Figure BDA0002362920200000022
本发明所述用于检测细胞线粒体中SO2衍生物的比率荧光探针在检测含SO2衍生物的样品中的应用。
其中:所述含SO2衍生物样品优选是培养的细胞或含SO2衍生物的溶液。
本发明提供的用于检测细胞线粒体中SO2衍生物的比率荧光探针在无SO2衍生物的存在下,能量供体被激发光激发后将能量传递给能量受体,进而使探针表现出增强的受体荧光;与SO2衍生物反应时,能量受体中的功能双键与SO2衍生物发生加成反应,能量受体结构改变,生成新的加成产物如图1所示;同时,FRET能量转移过程被阻断,当荧光探针与SO2衍生物加成产物被激发时,表现为供体发射荧光。当SO2衍生物的浓度变化时,两个发射波长的荧光强度随之发生改变;从而实现了对SO2衍生物的比率检测。实验还显示,本发明所述的荧光探针能够靶向线粒体的SO2衍生物(图6)。
具体的:配制本发明所述的用于检测细胞线粒体中SO2衍生物的比率荧光探针的测试溶液(DMSO/PBS缓冲液,v/v=3:7,pH=7.4),分别加入一定量的活性氧、活性氮以及金属离子的水溶液,如:1O2,Fe2+,H2O2,HClO,HO·,OH-,t-BuOOH,t-BuOO,NO3 -,CN-,GSH,Fe3+,Cys,H2S,Ca2+,Hg2+,Pb2+等。对上述溶液进行荧光测试,结果表明上述探针对SO2衍生物有很好的选择性,见图2。
本发明所述的荧光探针随SO2衍生物浓度的增加,探针在490nm处荧光强度逐渐增强,620nm处荧光强度逐渐减弱;二者比值相对SO2衍生物浓度在一定范围内呈线性关系。可以确定该探针能够定量检测低浓度的SO2衍生物,见图3。
激光扫描共聚焦显微镜设置激发波长为405nm,绿色通道收集波长为405-495nm,红色通道收集波长为555-700nm。
在加入上述探针的HepG2活细胞中,用激光扫描共聚焦显微镜观察不加GSH/Na2S2O3和加入GSH/Na2S2O3(GSH/Na2S2O3:促进细胞代谢内源性产生SO2衍生物)的细胞荧光显微成像变化。可以看出不存在GSH/Na2S2O3的细胞红色通道荧光较强,绿色通道荧光较弱;实验组(加GSH/Na2S2O3)红色通道荧光较对照组减弱,绿色通道荧光较对照组明显增强;其绿色通道荧光与红色通道荧光强度统计值的比值变化非常明显,见图4。
在加入本发明所述的荧光探针的L-O2活细胞中,用激光扫描共聚焦显微镜观察加入GSH/Na2S2O3和NaHSO3的细胞荧光显微成像变化。可以看出加入GSH/Na2S2O3的实验组红色通道荧光较强,绿色通道荧光较弱,两者与对照组无明显差别;加入Na2HSO3的细胞红色通道荧光较弱,绿色通道荧光较强;其绿色通道荧光与红色通道荧光强度统计值的比值变化非常明显,见图5。
综上,本发明公开的用于检测SO2衍生物的比率荧光探针能够靶向线粒体并高选择性地与SO2衍生物作用,随着SO2衍生物浓度的增加,其荧光发射强度在490nm处逐渐增强,在620nm处逐渐减弱;二者比值(I490/I620)与SO2衍生物浓度在一定范围内呈线性关系。提示该荧光探针不仅可以定量检测溶液体系中的SO2衍生物,而且能够用于活细胞内的SO2衍生物比率成像;有望在临床医学诊疗中发挥作用,具有广阔的应用前景。
附图说明
图1为本发明所述的荧光探针与SO2衍生物反应生成产物的核磁共振谱(1H NMR)。
图2为本发明所述的荧光探针对各种活性氧、活性氮等被分析物响应的荧光强度及其比率柱状图。
图3为本发明所述的荧光探针在490nm与620nm处的荧光强度变化,及其比值与SO2衍生物浓度间的线性关系图。
图4为本发明所述的荧光探针对HepG2细胞内源性SO2衍生物共聚焦荧光成像图,绿色通道(405-495nm)和红色通道(555-700nm)。
其中:(A)为所示条件下的细胞成像图;(B)为与(A)对应的条件下绿色通道荧光强度与红色通道荧光强度比值柱状图。
图5为本发明所述的荧光探针对L-O2细胞内源性和外源性SO2衍生物共聚焦荧光成像图,绿色通道(405-495nm)和红色通道(555-700nm)。Ctr(对照组):细胞用该SO2衍生物探针(1μM)溶液孵化1小时后的绿色和红色通道成像;GSH/Na2S2O3:细胞首先使用500μM GSH和250μM Na2S2O3孵化1h后,再用1μM该探针溶液继续孵化1小时;Na2HSO3:细胞先用该SO2衍生物探针(1μM)溶液孵化1小时后再用不同浓度的NaHSO3(50μM和100μM)培养1小时成像中。
其中:(A)为所示条件下的细胞成像图;(B)为与(A)对应的条件下绿色通道荧光强度与红色通道荧光强度比值柱状图;Ctr:对照组(只加入本发明的探针)。
图6为本发明所述的荧光探针靶向线粒体的SO2衍生物的HeLa细胞成像示意图
其中:(a)为本发明的探针成像图,λex=405nm,绿色通道:410-495nm;(b)为靶向线粒体的商品染料Mito Tracker Deep Red成像图,λex=639nm,红色通道:640-700nm;(c)为(a)与(b)的叠加图;(d)为共定位系数示意图(系数为0.91)。
具体实施方式
下面结合具体附图和实施例对本发明内容进行详细说明。如下所述例子仅是本发明的较佳实施方式而已,应该说明的是,下述说明仅仅是为了解释本发明,并非对本发明作任何形式上的限制,凡是依据本发明的技术实质对实施方式所做的任何简单修改,等同变化与修饰,均属于本发明技术方案的范围内。
下述实施例中,所使用的材料、试剂、菌株、载体等,如无特殊说明,均可从商业途径得到。
实施例1
4-(4-(7-(二乙氨基-2-氧代-2H-色烯-3-甲酰基)哌嗪-1-基)苯甲醛(217mg,0.5mmol)与1,2,3,3-四甲基苯并吲哚-1-碘盐(176.2mg,0.5mmol)溶于30mL乙醇,在哌啶(0.5mL)催化下回流12h,柱色谱分离(二氯甲烷:甲醇=30:1),得到紫黑色粉末即为用于检测细胞线粒体中SO2衍生物的比率荧光探针(缩写为探针ZACA),产率57.1%。
结构确认谱图数据:
IR(KBr)ν:3065,2970,1721,1563.
MS(z/m):639.3314,Found:639.3310.
1H NMR(400MHz,DMSO-d6):δ=8.41(d,J=16.0Hz,1H),8.38(d,J=9.2Hz,1H),8.24(d,J=9.2Hz,1H),8.18(d,J=8.4Hz,1H),8.14(d,J=8.8Hz,2H),8.05(s,1H),8.02(d,J=9.2Hz,1H),7.78(t,J=7.2Hz,1H),7.68(t,J=7.2Hz,1H),7.53(d,J=9.2Hz,1H),7.41(d,J=16.0Hz,1H),7.13(d,J=8.8Hz,2H),6.77(dd,J=7.2Hz and J=2.0Hz,1H),6.58(d,J=2.0Hz,1H),4.15(s,3H),3.45-3.75(m,12H),2.00(s,6H),1.14(t,J=7.8Hz,6H);
13C NMR(100MHz,DMSO-d6):δ=181.74,164.81,158.96,157.18,154.33,153.12,151.86,144.73,140.05,137.20,133.98,133.18,131.11,130.68,130.47,128.69,127.29,126.97,124.41,123.32,116.08,114.20,113.34,109.96,107.64,107.13,96.80,53.38,45.83,44.66,34.45,26.24,12.78,8.95。
上述荧光探针ZACA的制备反应如下式所示:
Figure BDA0002362920200000051
实施例2
配制用于检测细胞线粒体中SO2衍生物的比率荧光探针的测试溶液(DMSO/PBS缓冲液,v/v=3:7,pH=7.4)。向装有5μM该探针的10mL容量瓶中,用微量进样器分别加入20当量的:1O2,Fe2+,H2O2,HClO,HO·,OH-,t-BuOOH,t-BuOO,NO3 -,CN-,GSH,Fe3+,Cys,H2S,Ca2+,Hg2 +,Pb2+。作用15min后进行荧光测试。
结果表明,本发明所述的探针只对SO2衍生物有很好的响应和选择性,见图2。
实施例3
向装有5μM本发明所述荧光探针的10mL容量瓶中,用微量进样器分别加入梯度浓度的SO2衍生物,作用0.5h后进行荧光测试。
结果表明,本发明所述的荧光探针随SO2衍生物浓度的增加,490nm处荧光强度逐渐增强,620nm处荧光强度逐渐减弱;490nm处荧光强度与620nm处荧光强度的比值相对SO2衍生物浓度在一定范围内呈线性关系,见图3。可以确定本发明所述的荧光探针能够定量检测低浓度的SO2衍生物。
实施例4细胞内荧光成像测试
激光扫描共聚焦显微镜设置激发波长为405nm,绿色通道收集波长为405-495nm,红色通道收集波长为555-700nm。
将HepG2和L-O2细胞转移到小的玻璃瓶中孵化24h后,分组实验。
对照组:细胞用本发明所述的荧光探针(1μM)溶液孵化1小时,然后PBS洗涤三次后用激光扫描共聚焦显微镜进行成像检测。可以看出对照组的细胞红色通道荧光较强,绿色通道荧光较弱。且本发明所述的荧光探针能够靶向线粒体的SO2衍生物,见图6。
试验组:细胞先用500μM GSH和250μM Na2S2O3孵化1h后,再用1μM本发明所述的荧光探针溶液继续孵化1小时;用激光扫描共聚焦显微镜进行成像检测。可以看出该组红色通道荧光较对照组减弱,绿色通道荧光较对照组明显增强;其绿色通道荧光与红色通道荧光强度统计值的比值变化非常明显,见图4。
或者,试验组:L-O2细胞先用1μM本发明所述的荧光探针溶液孵化1小时后再用不同浓度的NaHSO3(50μM和100μM)或GSH/Na2S2O3培养1小时;用激光扫描共聚焦显微镜进行成像检测。可以看出加入GSH/Na2S2O3的实验组红色通道荧光较强,绿色通道荧光较弱,两者与对照组无明显差别;加入Na2HSO3的细胞红色通道荧光较弱,绿色通道荧光较强;其绿色通道荧光与红色通道荧光强度统计值的比值变化非常明显,见图5。

Claims (1)

1.一种用于检测细胞线粒体中SO2衍生物的比率荧光探针,其特征在于:所述比率荧光探针由能量供体香豆素衍生物荧光团、连接基团哌嗪和能量受体(E)-2-(4-(二取代胺基)-苯乙烯基)-1,3,3-三甲基苯并吲哚碘盐三部分构成;其化学结构式如式(I)所示:
Figure FDA0003324574920000011
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