CN108752373A - 一种基于苯硼酯识别过氧化氢的荧光探针 - Google Patents
一种基于苯硼酯识别过氧化氢的荧光探针 Download PDFInfo
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Abstract
本发明公开了一种检测过氧化氢的荧光探针，属于分析化学技术领域。该探针由3‑（苯并[d]噻唑‑2‑基）‑[1,1'‑联苯]‑4‑醇和4‑硼脂溴苄在含有碳酸钾的丙酮溶液中搅拌回流过夜得到。本发明的荧光探针合成简单，使用方便，对过氧化氢具有较好的选择性、灵敏性、检测限低等优点，可应用于细胞中的过氧化氢的检测。
Description
技术领域
本发明提供了一种检测过氧化氢的荧光探针，属于荧光探针技术领域。
技术背景
过氧化氢是人体内活性氧物种其中的一种，通过氧气的代谢及酶的催化而产生。过氧化氢在各种生理过程中发挥重要作用，水平异常与许多类型的疾病如癌症、糖尿病、唐氏综合症和罕见病相关联。近来，已证实是学术界与人类重大疾病相关的活性小分子。基于此，在体内和体外对的检测也引起人们的高度重视。由于过氧化氢重要的生物学作用，发展一种快速、灵敏、简便的检测过氧化氢的方法对于学术研究和早期疾病诊断非常重要。
目前，作为生物体内过氧化氢的检测方法主要有电化学方法、元素分析以及质谱等方法，这些常规方法的样品准备过程复杂，检测过程对样品的损伤较大，而且不能进行实时的监测。与之对比，作为一种价格低廉的检测手段，荧光探针检测法具有灵敏度高、选择性好、响应速度快、能够进行实时可视化检测等优点，近几年来备受研究人员的关注。在现有技术中，专利CN106632441A提供了一种基于四苯基乙烯的过氧化氢荧光探针化合物，专利CN106749359A提供了一种过氧化氢探针化合物，但是此两种化合物都存在制备方法复杂等缺点。
发明内容
针对上述现有技术的不足，本发明提供一种检测过氧化氢的荧光增强型探针，并研究其光谱性质。
本发明所述的一种检测过氧化氢的荧光探针，其特征在于，所述荧光探针的化学结构式如式所示：
上述检测过氧化氢的荧光探针以如下方法制备：
将化合物II和4-硼脂溴苄加入丙酮溶液中，然后加入碳酸钾。搅拌回流过夜，反应结束真空浓缩，柱层析纯化得到白色固体化合物I。
根据本发明，优选的，所述化合物Ⅱ、4-硼脂溴苄和碳酸钾的摩尔比为1:1:1。
本发明所述的荧光探针可用于水溶液中的过氧化氢的实时检测。
进一步优选的，所述荧光探针用于在pH 7.4的DMSO与PBS缓冲液混合液中的过氧化氢的快速检测，检测限为3.61×10-7 mol/L。
本发明所述荧光探针用于在pH 7.4的DMSO与PBS缓冲液混合液中对过氧化氢具有特异性检测的性能。本发明通过实验验证，所述荧光探针在pH 7.4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。随着过氧化氢的加入，在405nm的光激发下，溶液在486nm处发出明亮的蓝色荧光。其它种类活性氧物种的加入对探针的荧光没有影响。因此，本发明的荧光探针化合物对过氧化氢具有很高的选择性。
本发明所述的荧光探针在细胞中检测过氧化氢的应用。
本发明所述荧光探针可以应用于细胞内过氧化氢的检测。具体检测方法为：将10μM的化合物I加入Hela细胞培养液中，在37℃下孵育15分钟，然后加入过氧化氢，细胞发出强烈的荧光。实验表明，化合物I能够识别细胞内的过氧化氢。
本发明的有益效果：
本发明所涉及的一种检测过氧化氢的荧光探针，具有特异性响应过氧化氢、选择性好、能快速识别活细胞中的过氧化氢等优点。
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随过氧化氢浓度变化荧光光谱图。
图4是化合物I与过氧化氢的细胞成像图。
具体实施方式
下面结合附图和具体实施例对本发明进行详细说明，但不限于此。实施例中的各种原料均来自于市场购买。
实施例1
化合物I的合成
将0.14克化合物Ⅱ与0.13克4-硼脂溴苄溶解在丙酮中，在加入60毫克碳酸钾，搅拌回流过夜，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为该探针的核磁图（400MHz, DMSO-d6）。
实施例2 探针化合物I选择性分析
将100个当量的过氧化氢加入含有5 μM的化合物I体积比为3:7的DMSO/PBS缓冲液时的检测结果如图2，当激发光波长为405nm时探针化合物I发出波长为486nm的强烈的荧光，15分钟内达到最强，而且探针化合物I对其他活性氧物种没有明显响应，说明探针化合物I对过氧化氢具有优异的选择性。
实施例3 探针化合物I对过氧化氢滴定实验
将0-40个当量的过氧化氢加入到5 μM探针化合物I的缓冲液中，荧光响应强度随加入过氧化氢量的增加呈规律性增加，检测结果如图3，结果说明探针化合物I对过氧化氢浓度检测范围较广且灵敏度较高。
实施例4 化合物I在识别细胞内的过氧化氢
在10 μM的化合物I加入到Hela细胞的培养液中孵育，然后再加入过氧化氢，洗涤后成像，如图4。结果表明，化合物I能够快速识别细胞内的过氧化氢。
Claims (2)
1.一种检测过氧化氢的荧光探针，其特征在于，所述荧光探针的化学结构式如I所示
。
2.根据权利要求1中所述的一种检测过氧化氢的荧光探针，其特征在于，所述荧光探针可以应用于水体及细胞中的过氧化氢检测。
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Cited By (4)
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| CN109970777A (zh) * | 2019-04-23 | 2019-07-05 | 湘潭大学 | 一种具有检测过氧化氢功能的荧光探针及其制备方法和应用 |
| CN113004310A (zh) * | 2019-12-20 | 2021-06-22 | 湖南超亟化学科技有限公司 | 一种基于dcpo母核的过氧化氢比率型荧光分子探针的制备方法及其应用 |
| CN113004310B (zh) * | 2019-12-20 | 2022-07-08 | 湖南超亟检测技术有限责任公司 | 一种基于dcpo母核的过氧化氢比率型荧光分子探针的制备方法及其应用 |
| CN111393462A (zh) * | 2020-04-10 | 2020-07-10 | 山西大学 | 一种基于双机理的用于检测onoo-的荧光探针及其制备方法和应用 |
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