CN108752371A - 一种基于喹啉的双光子过氧化氢荧光探针 - Google Patents
一种基于喹啉的双光子过氧化氢荧光探针 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6‑（苯并[d]噻唑‑2‑基）萘‑2‑醇和4‑硼脂溴苄在丙酮中回流搅拌得到。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
活性氧包括过氧氢自由基（HO2·）,超氧化物自由基（O2·）,过氧自由基（RO2·）,羟基自由基（HO·）,次氯酸（HOCl），单线态氧（1O2）和过氧化氢（H2O2）等。过氧化氢作为一种重要的活性氧物质,在生物机体活动和外界环境中有着极其重要。研究表明,过氧化氢参与生理和病理调节过程,与细胞的增殖分化以及迁移过程息息相关。除此之外,体内适量水平的过氧化氢对生物正常的生理过程是有益的,例如炎症、机体防御等方面也发挥着重要作用；但是很多疾病也是由于过量的过氧化氢而引起的,例如癌症、阿尔察默病等疾病。因此实时定量的检测生物机体和外界环境中的过氧化氢具有非常重要的意义。
目前过氧化氢的检测技术包括电化学法,比色法,气体检测法,荧光法等等。其中由于荧光探针具有操作简单,无辐射,高灵敏度和高分辨率的优势,成为检测过氧化氢的有效手段。近些年,检测过氧化氢的荧光探针已经被报道了很多,然而多数探针都是单光子激发，对细胞、活体的伤害较大。众所周知,双光子有机小分子荧光探针的激发波长一般是单光子激发的两倍左右，因此，其激发波长一般位于近红外区（700-1000nm），这个波段的激发光既具有高度的聚焦和区域激发效果，又不会损伤生物组织，而且还可以实现生物组织内深层成像，另外，由于采用双光子激发，生物自身的荧光不会被激发，相较于单光子激发，双光子激发不仅能有效避免生物体自身荧光物质的背景光的干扰，实现暗场成像，而且还能降低光漂白、光毒性。在现有技术中，专利CN106749359 A提供了一种过氧化氢探针化合物，但是该探针化合物在60分钟完成过氧化氢的检测；另外，由于过氧化氢存在时间短，易与其它物质反应生成新的活性氧物种，因此，设计一种响应时间短，灵敏度高，选择性强的探针具有十分重要的意义。
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，并研究其光谱性质以及细胞内外的应用。
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所示：
。
上述检测过氧化氢的荧光探针以如下方法制备：
化合物I的合成
化合物II，4-硼脂溴苄和碳酸钾溶于丙酮中，回流搅拌过夜，真空浓缩得到粗产物，经柱层层析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；
根据本发明，优选的，化合物I的合成全程在氮气保护下进行。
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，其检测限为1.40×10-7 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响应性能。本发明通过实验验证，将过氧化氢滴入所述荧光探针在pH7.4的DMSO与PBS缓冲液中后，以420nm波长的光源作为激发光，溶液在542nm处发出强烈的黄色荧光。该探针对其它活性氧不响应。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：将化合物I与Hela细胞共同孵育15分钟，然后加入过氧化氢，细胞发出强烈的黄色荧光。实验表明，化合物I能够识别细胞内的过氧化氢。
本发明所涉及的一种检测过氧化氢的荧光探针，展示出选择性高，灵敏度好，可细胞内成像等优点。
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是双光子激发的化合物I在细胞内的成像图。
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0.25克化合物II，0.2克4-硼脂溴苄和0.26克碳酸钾溶于丙酮中，回流搅拌过夜，真空浓缩得到粗产物，经柱层层析得到白色固体化合物I，收率50%。
实施例2 探针化合物I选择性分析
将100当量的过氧化氢滴加入含5 μM的化合物I的DMSO / PBS缓冲液中，检测结果如图2，当激发光波长为420nm时，探针化合物I发出542nm黄色荧光，而且探针化合物I不受其他过氧化物干扰，说明探针化合物I对过氧化氢选择性好。
实施例3 探针化合物I对过氧化氢滴定分析
将0到40当量的过氧化氢滴入到含5 μM探针化合物I的缓冲溶液中时，荧光响应强度随加入过氧化氢量的增加而迅速增加，检测结果如图3，结果说明探针化合物I对过氧化氢浓度的灵敏度较高。
实施例4 化合物I对细胞内过氧化氢的检测
将化合物I与Hela细胞一同孵育后，再加入过氧化氢，细胞在800nm波长的光激发下发出明亮的黄色荧光，成像结果如图4。实验表明，探针化合物I能够识别细胞中的过氧化氢。
Claims (1)
1.一种检测生物硫醇的荧光探针，其特征在于，所述荧光探针的化学结构式如I所示
。
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108129500A (zh) * | 2018-01-11 | 2018-06-08 | 中南大学 | 一种识别过氧化氢的比值型荧光探针的合成与应用 |
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|---|---|---|---|---|
| CN106632441A (zh) * | 2016-12-16 | 2017-05-10 | 济南大学 | 一种识别过氧化氢的比率型荧光探针 |
| CN108129500A (zh) * | 2018-01-11 | 2018-06-08 | 中南大学 | 一种识别过氧化氢的比值型荧光探针的合成与应用 |
Non-Patent Citations (3)
| Title |
|---|
| LINGYU ZENG等: "Two-Photon Fluorescent Probe for Detection of Exogenous and Endogenous Hydrogen Persulfide and Polysulfide in Living Organisms", 《ANAL. CHEM.》 * |
| YANAN LU等: "A fast-response two-photonfluorescent probe for imaging endogenous H2O2in living cells and tissues", 《SPECTROCHIMICA ACTA PART A: MOLECULAR AND BIOMOLECULAR SPECTROSCOPY》 * |
| YUZHI CHEN等: "A Fluorescent Probe for Hydrogen Peroxide in Vivo Based on the Modulation of Intramolecular Charge Transfer", 《ANAL. CHEM.》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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| CN108752371B (zh) | 2020-06-30 |
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