CN114656420A - 一种苯并芘衍生物荧光探针在检测生物硫醇中的应用 - Google Patents

一种苯并芘衍生物荧光探针在检测生物硫醇中的应用 Download PDF

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CN114656420A
CN114656420A CN202210211286.2A CN202210211286A CN114656420A CN 114656420 A CN114656420 A CN 114656420A CN 202210211286 A CN202210211286 A CN 202210211286A CN 114656420 A CN114656420 A CN 114656420A
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敬静
张小玲
高梦旭
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Abstract

本发明属于荧光检测技术领域,公开了一种苯并芘衍生物荧光探针在检测生物硫醇中的应用。本发明将苯并芘衍生物荧光探针的二甲基亚砜溶液加入缓冲液中,再加入生物硫醇的水溶液,搅拌20~60min,进行荧光光谱测试。本发明的检测方法检测限低,在水溶液中对Cys/Hcy和GSH的检测限可达到纳摩尔级别;且该荧光探针可以成功地穿过细胞膜,实现活细胞中Hcy/Cys和GSH的鉴别、检测和成像。

Description

一种苯并芘衍生物荧光探针在检测生物硫醇中的应用
技术领域
本发明涉及荧光检测技术领域,尤其涉及一种苯并芘衍生物荧光探针在检测生物硫醇中的应用。
背景技术
在生物体中,生物硫醇包括半胱氨酸(Cys)/同型半胱氨酸(Hcy)、谷胱甘肽(GSH)等,现有研究表明,生物硫醇在维持细胞氧化还原平衡和代谢中起关键作用,并且生物硫醇浓度异常与几种疾病有关,如Cys水平降低与儿童发育异常密切相关;Hcy浓度过高与心血管疾病、阿兹海默症和骨质疏松症有关;GSH在维持细胞的氧化还原动态平衡中起着重要作用。因此,生物硫醇的检测具有重要意义。
目前,现有生物硫醇的检测方法包括高效液相色谱-质谱法、电化学法、电感耦合等离子体-质谱法等,但由于这些方法检测过程较为复杂、所用仪器昂贵、难操作等缺点,限制了生物硫醇检测技术的发展。现阶段,荧光探针检测技术由其灵敏度高、检测限低、操作简单等优点受到广泛关注。研究人员研发了多种不同结构的荧光探针,利用不同的荧光信号组合,来实现单分子区分检测Cys/Hcy、GSH的目的。但现有的荧光探针分子制备过程繁琐,结构复杂,因此,如何提供一种结构简单的荧光探针在生物硫醇检测中的应用对生物硫醇检测技术的发展具有重要意义。
发明内容
本发明的目的在于提供一种苯并芘衍生物荧光探针在检测生物硫醇中的应用,解决现有技术的检测方法存在的上述问题。
为了实现上述发明目的,本发明提供以下技术方案:
本发明提供了一种苯并芘衍生物荧光探针在检测生物硫醇中的应用,将苯并芘衍生物荧光探针的二甲基亚砜溶液加入缓冲液中,再加入生物硫醇的水溶液,搅拌20~60min,进行荧光光谱测试;
其中,所述苯并芘衍生物荧光探针的结构式如下所示:
Figure BDA0003533336860000021
优选的,在上述一种苯并芘衍生物荧光探针在检测生物硫醇中的应用中,所述生物硫醇为半胱氨酸、同型半胱氨酸和谷胱甘肽。
优选的,在上述一种苯并芘衍生物荧光探针在检测生物硫醇中的应用中,所述苯并芘衍生物荧光探针和生物硫醇的摩尔比为1:8~12。
优选的,在上述一种苯并芘衍生物荧光探针在检测生物硫醇中的应用中,所述缓冲液为PBS缓冲液;所述缓冲液的pH值为7~7.7。
优选的,在上述一种苯并芘衍生物荧光探针在检测生物硫醇中的应用中,所述荧光光谱测试的激发波长为345nm或473nm。
经由上述的技术方案可知,与现有技术相比,本发明具有如下有益效果:
本发明的检测方法检测限低,在水溶液中对Cys/Hcy和GSH的检测限可达到纳摩尔级别;且该荧光探针可以成功地穿过细胞膜,实现活细胞中Hcy/Cys和GSH的鉴别、检测和成像。
附图说明
为了更清楚地说明本发明实施例或现有技术中的技术方案,以下将对实施例或现有技术描述中所需要使用的附图作简单地介绍。
图1为实施例1在345nm的激发波长下的荧光光谱;
图2为实施例2在473nm的激发波长下的荧光光谱;
图3为PY-NBD和Cys、Hcy、GSH在PBS中的紫外-可见吸收光谱;
图4为PY-NBD和不同浓度Cys、Hcy、GSH在PBS中的荧光光谱;
其中,A为PY-NBD和0~50μM Cys在345nm的激发波长下的荧光光谱;B为PY-NBD和0~50μM Hcy在345nm的激发波长下的荧光光谱;C为PY-NBD和0~50μM GSH在345nm的激发波长下的荧光光谱;D为PY-NBD和0~50μM Cys在473nm的激发波长下的荧光光谱;E为PY-NBD和0~50μM Hcy在473nm的激发波长下的荧光光谱;F为PY-NBD和0~50μM GSH在473nm的激发波长下的荧光光谱;
图5为HeLa细胞的荧光图像;
其中,A为HeLa细胞的荧光图像;B为红色和绿色通道的归一化平均荧光强度。
具体实施方式
本发明提供一种苯并芘衍生物荧光探针在检测生物硫醇中的应用,将苯并芘衍生物荧光探针的二甲基亚砜溶液加入缓冲液中,再加入生物硫醇的水溶液,搅拌20~60min,进行荧光光谱测试;
其中,苯并芘衍生物荧光探针的结构式如下所示:
Figure BDA0003533336860000031
在本发明中,生物硫醇优选为半胱氨酸、同型半胱氨酸和谷胱甘肽。
在本发明中,苯并芘衍生物荧光探针和生物硫醇的摩尔比优选为1:8~12,进一步优选为1:9~11,更优选为1:10。
在本发明中,苯并芘衍生物荧光探针的二甲基亚砜溶液、生物硫醇的水溶液和缓冲液的体积比为1~3:1~5:10~15,进一步优选为1.2~2.9:2~4:11~14,更优选为2:3:12。
在本发明中,缓冲液优选为PBS缓冲液;缓冲液的pH值优选为7~7.7,进一步优选为7.1~7.6,更优选为7.3;缓冲液的浓度为9~15mM,进一步优选为10~14mM,更优选为11mM。
在本发明中,荧光光谱测试的激发波长优选为345nm或473nm,进一步优选为473nm。
在本发明中,在含有该荧光探针的体系中加入GSH只能触发芘荧光团的蓝色荧光信号,而Hcy、Cys和荧光探针的反应可以产生蓝色和绿色荧光信号,因此,该荧光探针可以同时区分和检测Cys/Hcy和GSH。
本发明还提供一种苯并芘衍生物荧光探针的制备方法,包括以下步骤:
将1-羟基芘、NBD-Cl、三乙胺、N,N-二甲基甲酰胺混合后进行反应,反应结束后加入水,将生成的沉淀过滤、纯化,得到苯并芘衍生物荧光探针。
在本发明中,1-羟基芘、NBD-Cl和三乙胺的摩尔比优选为0.9~1.2:1~1.5:1~1.5,进一步优选为0.94~1.1:1.1~1.4:1.17~1.32,更优选为1.05:1.2:1.3。
在本发明中,1-羟基芘、N,N-二甲基甲酰胺和水的摩尔体积比优选为0.9~1.2mmol:5~15mL:100mL,进一步优选为0.96~1.14mmol:7~14mL:100mL,更优选为0.99mmol:11mL:100mL。
在本发明中,反应在保护气体下进行,保护气体优选为氮气。
在本发明中,反应的温度优选为20~35℃,进一步优选为22~31℃,更优选为27℃;反应的时间优选为20~30h,进一步优选为23~29h,更优选为26h。
在本发明中,纯化优选为硅胶柱纯化;纯化的洗脱剂优选为二氯甲烷和石油醚;二氯甲烷和石油醚的体积比优选为1~3:1~2,进一步优选为1.2~2.8:1.1~1.7,更优选为1.8:1.4。
下面将对本发明实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
实施例1
本实施例提供一种苯并芘衍生物荧光探针及其在检测生物硫醇中的应用:
(1)苯并芘衍生物荧光探针的制备:在氮气保护下,将0.2183g(1mmol)1-羟基芘、0.26g(1.3mmol)NBD-Cl、0.13g(1.3mmol)三乙胺加入9mLN,N-二甲基甲酰胺中,混合均匀后于25℃反应24h,反应结束后加入100mL水,生成黑色沉淀,将沉淀过滤、硅胶柱纯化(洗脱剂:二氯甲烷和石油醚的体积比为1:1),得到橙黄色固体(产率66.67%),即为苯并芘衍生物荧光探针,记为PY-NBD;
(2)PY-NBD在检测生物硫醇中的应用,具体为:将10μL 5μM的PY-NBD的二甲基亚砜溶液加入100μL PBS缓冲液(10mM,pH为7.4)中,再加入10μL 50μM的生物硫醇(Hcy、Cys、GSH)的水溶液,搅拌30min,在345nm的激发波长(狭缝为2.5/2.5nm)以及365~500nm的发射波长下进行荧光光谱测试,结果如图1所示。
由图1可知,PY-NBD与Hcy/Cys/GSH都可以成功发生亲核取代反应释放出芘荧光团,在345nm的激发光的激发下发射出蓝色的荧光。
实施例2
本实施例提供一种苯并芘衍生物荧光探针及其在检测生物硫醇中的应用,具体参见实施例1,不同之处在于:应用中,激发波长为473nm(狭缝为5/5nm),发射波长为493~650nm。荧光光谱测试结果如图2所示。
由图2可知,在473nm的激发光的激发下,只有加入了Hcy、Cys的体系可以发射出绿色的荧光。这是因为亲核取代发生后,不发荧光的NBD衍生物中只有S-NBD-Hcy和S-NBD-Cys可以发生分子内重排,产生可以发出绿色荧光信号的N-NBD-Hcy和N-NBD-Cys。S-NBD-GSH因为与S-NBD-Hcy和S-NBD-Cys之间分子结构的差异,无法发生分子内重排所以也不会有荧光信号产生。
紫外-可见吸收光谱:将10μL 5μM的PY-NBD的二甲基亚砜溶液加入100μL PBS缓冲液(10mM,pH为7.4)中,再加入10μL 50μM的生物硫醇(Hcy、Cys、GSH)的水溶液,搅拌30min,进行紫外-可见吸收光谱测试,结果如图3所示。由图3可知,探针在340nm处显示出强吸收带。随着Cys或Hcy的加入,340nm处的吸收峰降低,而出现了两个新的吸收峰。随着GSH的引入,仅观察到一个新的吸收峰。
荧光滴定实验和检测限:将10μL 5μM的PY-NBD的二甲基亚砜溶液加入100μLPBS缓冲液(10mM,pH为7.4)中,再加入10μL不同浓度(0~50μM)的生物硫醇(Hcy、Cys、GSH)的水溶液,搅拌30min,进行荧光光谱测试,结果如图4所示。由图4可知,通过荧光滴定实验在0~50μM范围内,PY-NBD的荧光强度分别随着Cys、Hcy和GSH浓度的增加而逐渐增加。PY-NBD(5μM)的荧光强度与生物硫醇的浓度在0~15μM之间获得了良好的线性关系。此外,PY-NBD对Cys、Hcy和GSH的检测限(根据公式LOD=3σ/K计算,其中σ为空白测量的标准偏差,K为荧光之间的斜率410nm或546nm处的强度和分析物浓度)均达到毫摩尔级。
细胞实验:采用含10%胎牛血清和1%抗生素的RPMI 1640(Hyclone)培养基进行HeLa细胞培养,细胞培养条件为37℃和5%CO2的加湿气氛;对照组的PY-NBD浓度为5μM,孵育时间为30min;实验组用300μM生物硫醇清除剂NEM(N-乙基马来酰亚胺)预处理细胞30min,然后用50μM Cys、Hcy或GSH处理细胞30min;最后,将5μM PY-NBD加入HeLa细胞,孵育30min。在成像前,用磷酸盐缓冲盐水(PBS,pH为7.4)清洗细胞三次,以去除多余的化合物。HeLa细胞的荧光图像如图5所示。由图5可知,PY-NBD可以成功地穿过细胞膜,实现活细胞中Hcy、Cys和GSH的鉴别、检测和成像。通过双通道的细胞成像荧光强度可以更直观和准确的检测和鉴别细胞内源和外源Hcy/Cys和GSH。
以上所述仅是本发明的优选实施方式,应当指出,对于本技术领域的普通技术人员来说,在不脱离本发明原理的前提下,还可以做出若干改进和润饰,这些改进和润饰也应视为本发明的保护范围。

Claims (5)

1.一种苯并芘衍生物荧光探针在检测生物硫醇中的应用,其特征在于,将苯并芘衍生物荧光探针的二甲基亚砜溶液加入缓冲液中,再加入生物硫醇的水溶液,搅拌20~60min,进行荧光光谱测试;
其中,所述苯并芘衍生物荧光探针的结构式如下所示:
Figure FDA0003533336850000011
2.根据权利要求1所述的一种苯并芘衍生物荧光探针在检测生物硫醇中的应用,其特征在于,所述生物硫醇为半胱氨酸、同型半胱氨酸和谷胱甘肽。
3.根据权利要求1或2所述的一种苯并芘衍生物荧光探针在检测生物硫醇中的应用,其特征在于,所述苯并芘衍生物荧光探针和生物硫醇的摩尔比为1:8~12。
4.根据权利要求3所述的一种苯并芘衍生物荧光探针在检测生物硫醇中的应用,其特征在于,所述缓冲液为PBS缓冲液;所述缓冲液的pH值为7~7.7。
5.根据权利要求1或4所述的一种苯并芘衍生物荧光探针在检测生物硫醇中的应用,其特征在于,所述荧光光谱测试的激发波长为345nm或473nm。
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