CN114349717A - 一种基于苯并噻唑衍生物半胱氨酸的荧光探针及其制备方法 - Google Patents
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Abstract
Description
技术领域
本发明涉及半胱氨酸检测的技术领域,尤其是涉及一种基于苯并噻唑衍生物半胱氨酸的荧光探针及其制备方法。
背景技术
含有琉基的半胱氨酸作为构成蛋白质的二十种氨基酸之一,在细胞的生理过程中起着不可替代的作用。例如,半胱氨酸是细胞和组织生长的必备物质,半胱氨酸缺乏与水肿、幼儿发育不良、肝脏损伤等多种疾病相关。因此,实现细胞内半胱氨酸的荧光成像,并给出细胞内半胱氨酸表达与分布的信息,有着重要的生命科学与医学价值。
现有技术中,半胱氨酸含量测定的方法包括气相色谱一质谱联用法、高效液相色谱法、全自动的荧光偏振免疫测定、高效毛细管电泳法、有机小分子荧光探针检测法等。其中,有机小分子荧光探针检测法由于具有简单、便捷、成本低、快速、灵敏及其潜在的细胞内成像等特性,而被广泛使用。目前,已有许多有机小分子荧光探针被开发出来。专利CN103755672 A提供了一种基于香豆素的半胱氨酸荧光探针化合物,该探针的响应时间约为60分钟,响应时间较长。
发明内容
本发明的目的是提供一种基于苯并噻唑衍生物半胱氨酸的荧光探针及其制备方法,荧光探针合成简单,对半胱氨酸的选择性良好、灵敏性高、检测限低,可应用于细胞中的半胱氨酸的检测。
为实现上述目的,本发明提供了一种基于苯并噻唑衍生物半胱氨酸的荧光探针,荧光探针的化学结构式如下所示:
优选的,所述荧光探针在细胞中半胱氨酸检测中的应用。
优选的,所述荧光探针在水溶液中半胱氨酸实时检测中的应用。
一种基于苯并噻唑衍生物半胱氨酸的荧光探针的制备方法,步骤如下:
S1、在无水乙醇中加入氰基联苯酚醛、邻氨基苯硫酚,然后加入双氧水、浓盐酸,室温均匀搅拌,反应结束,抽滤得淡黄色固体II;
S2、在冰浴条件下,将化合物II与丙烯酰氯溶解在干燥的二氯甲烷中,并加入三乙胺,室温搅拌过夜后,真空浓缩得到粗产物,经柱层层析得到化合物I;
优选的,步骤S1中,氰基联苯酚醛、邻氨基苯硫醇、浓盐酸和双氧水的摩尔比为1:1:3:10。
优选的,步骤S2中,化合物II、丙烯酰氯和三乙胺的摩尔比为1:4:4。
优选的,步骤S2中,反应全程在氮气的保护氛围下进行。
因此,本发明采用上述一种基于苯并噻唑衍生物半胱氨酸的荧光探针及其制备方法,其技术效果如下:
(1)荧光探针能与半胱氨酸特异性反应,增强化合物的荧光强度;
(2)荧光探针在检测半胱氨酸过程中不会受到其他氨基酸的干扰,对半胱氨酸具有良好的选择性;
(3)荧光探针能对活细胞中的半胱氨酸进行检测,成像效果好,且对细胞毒性的低。
(4)实现高效快速地检测生物体内半胱氨酸,仅3分钟即可完成半胱氨酸快速检测。
下面通过附图和实施例,对本发明的技术方案做进一步的详细描述。
附图说明
图1是化合物I的1H NMR谱图;
图2是化合物I的选择性光谱图;
图3是化合物I随半胱氨酸浓度变化荧光光谱图;
图4是化合物I加入半胱氨酸的响应时间光谱图。
具体实施方式
以下通过附图和实施例对本发明的技术方案作进一步说明。
除非另外定义,本发明使用的技术术语或者科学术语应当为本发明所属领域内具有一般技能的人士所理解的通常意义。
实施例一
一种基于苯并噻唑衍生物半胱氨酸的荧光探针的制备方法,步骤如下:
(1)将在无水乙醇中加入0.5克氰基联苯酚醛、0.32克邻氨基苯硫酚,然后滴加1.12毫升双氧水、1.74毫升浓盐酸,室温搅拌30min,反应结束,抽滤得淡黄色固体II,收率为80%。
(2)在氮气氛围下,于冰浴中,将0.19克化合物II与0.16毫升丙烯酰氯加入干燥的二氯甲烷,然后滴加0.2毫升三乙胺,室温搅拌过夜,反应结束,真空浓缩得到粗产物,经柱层层析得到化合物I,收率为55%。图1为所得探针的核磁图(400MHz,CDCl3)。
试验测试
(一)探针化合物I对Hela细胞的检测
将试验室通过常规流程培养的Hela细胞进行分组试验,试验组与对照组使用的Hela细胞为同一批细胞状态相近的细胞。
其中,对照组的处理为在Hela细胞中加入10μM的化合物I,在37℃下培养15分钟,细胞基本没有荧光。然后,用PBS洗涤三次后,更换培养基,培养15分钟,细胞基本没有荧光。
试验组的处理为将Hela细胞与10μM的化合物I在37℃下培养15分钟后,用PBS洗涤三次后,更换培养基,再加入半胱氨酸缓冲溶液(25μM)培养15分钟,细胞发出强烈的荧光。
实验表明,化合物I对细胞内的半胱氨酸有良好的成像作用,能检测细胞内的半胱氨酸。
(二)探针化合物I选择性分析
在含有半胱氨酸的DMSO/PBS缓冲液中加入5μM的化合物I,其中,半胱氨酸的浓度为10mM,pH=7.4,DMSO:PBS缓冲液的体积比为3:7,检测结果如图2。
所述荧光探针在pH7.4的DMSO与PBS缓冲液混合液中以405nm波长的光源作为激发光,其溶液几乎不发光。随着半胱氨酸的加入,溶液在405nm的光激发时,溶液在486nm处发出强烈的明亮的蓝色荧光,而其它种类氨基酸的加入对探针的荧光没有影响。说明,探针化合物I对半胱氨酸具有优异的选择性。
(三)探针化合物I对半胱氨酸浓度变化响应分析
在含有不同浓度的半胱氨酸(0-200μM)的缓冲液中加入5μM探针化合物I,荧光响应强度随加入半胱氨酸量的增加呈规律性增加,检测结果如图3。
所述荧光探针化合物在pH7.4的DMSO与PBS缓冲液混合液中,半胱氨酸的浓度的与荧光强度呈现线性关系,可以定量测定溶液中半胱氨酸的含量。
所述荧光探针在pH7.4的DMSO与PBS混合液中半胱氨酸快速检测中的应用,最低检测限为3.86×10-8mol/L,探针化合物I对半胱氨酸浓度检测范围较广且灵敏度较高。
(四)探针化合物I对半胱氨酸响应时间分析
在含有生物硫醇的DMSO/PBS缓冲液中加入5μM的探针化合物I,对探针化合物I与加入半胱氨酸的响应时间进行了检测,检测结果如图4。
结果显示,在加入半胱氨酸3分钟内,探针化合物I对半胱氨酸的荧光响应强度随时间的增加呈线性增强,在2分钟内就能达到良好的荧光强度。表明,探针化合物I对半胱氨酸的响应较快速,可应用于半胱氨酸的检测。
因此,本发明采用上述一种基于苯并噻唑衍生物半胱氨酸的荧光探针及其制备方法,荧光探针合成简单,对半胱氨酸的选择性良好、灵敏性高、检测限低,可应用于细胞中的半胱氨酸的检测。
最后应说明的是:以上实施例仅用以说明本发明的技术方案而非对其进行限制,尽管参照较佳实施例对本发明进行了详细的说明,本领域的普通技术人员应当理解:其依然可以对本发明的技术方案进行修改或者等同替换,而这些修改或者等同替换亦不能使修改后的技术方案脱离本发明技术方案的精神和范围。
Claims (6)
2.根据权利要求1所述的一种基于苯并噻唑衍生物半胱氨酸的荧光探针,其特征在于:荧光探针在细胞中半胱氨酸检测中的应用。
4.根据权利要求3所述的一种基于苯并噻唑衍生物半胱氨酸的荧光探针的制备方法,其特征在于:步骤S1中,氰基联苯酚醛、邻氨基苯硫醇、浓盐酸和双氧水的摩尔比为1:1:3:10。
5.根据权利要求3所述的一种基于苯并噻唑衍生物半胱氨酸的荧光探针的制备方法,其特征在于:步骤S2中,化合物II、丙烯酰氯和三乙胺的摩尔比为1:4:4。
6.根据权利要求3所述的一种基于苯并噻唑衍生物半胱氨酸的荧光探针的制备方法,其特征在于:步骤S2中,反应全程在氮气的保护氛围下进行。
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CN111303072A (zh) * | 2020-02-27 | 2020-06-19 | 山西大学 | 一种区分检测半胱氨酸的试剂及其合成方法和应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009222466A (ja) * | 2008-03-14 | 2009-10-01 | Sumitomo Chemical Co Ltd | 蛍光システイン誘導体を用いる感作性検定方法及び蛍光システイン誘導体 |
CN108623533A (zh) * | 2018-07-13 | 2018-10-09 | 济南大学 | 一种基于噻唑的检测半胱氨酸的荧光探针及应用 |
CN108690011A (zh) * | 2018-07-13 | 2018-10-23 | 济南大学 | 一种检测半胱氨酸的荧光探针 |
-
2022
- 2022-02-25 CN CN202210179129.8A patent/CN114349717A/zh active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009222466A (ja) * | 2008-03-14 | 2009-10-01 | Sumitomo Chemical Co Ltd | 蛍光システイン誘導体を用いる感作性検定方法及び蛍光システイン誘導体 |
CN108623533A (zh) * | 2018-07-13 | 2018-10-09 | 济南大学 | 一种基于噻唑的检测半胱氨酸的荧光探针及应用 |
CN108690011A (zh) * | 2018-07-13 | 2018-10-23 | 济南大学 | 一种检测半胱氨酸的荧光探针 |
Non-Patent Citations (1)
Title |
---|
路亚男: "生物硫醇和过氧化氢荧光探针的构建及其生物成像研究" * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111303072A (zh) * | 2020-02-27 | 2020-06-19 | 山西大学 | 一种区分检测半胱氨酸的试剂及其合成方法和应用 |
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