CN109232615A - 一种跨键能量转移型次氯酸荧光探针及其在溶酶体次氯酸检测中应用 - Google Patents

一种跨键能量转移型次氯酸荧光探针及其在溶酶体次氯酸检测中应用 Download PDF

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CN109232615A
CN109232615A CN201811298410.3A CN201811298410A CN109232615A CN 109232615 A CN109232615 A CN 109232615A CN 201811298410 A CN201811298410 A CN 201811298410A CN 109232615 A CN109232615 A CN 109232615A
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hypochlorous acid
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申世立
曹晓群
黄晓晴
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Taishan Medical University
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Abstract

本发明公开了一种基于跨键能量转移的次氯酸比率荧光探针。该探针以咪唑并[1,5‑a]吡啶为能量供体，以罗丹明B为能量受体，以硫代双酰肼为次氯酸响应基团，并引入吗啉结构作为溶酶体定位基团，实现了探针对溶酶体的靶向作用。在没有次氯酸存在时，探针发射能量供体的荧光（462nm），当有次氯酸存在时，探针发射出462nm和589nm的荧光，而462nm处荧光强度却没有变化。次氯酸浓度在0‑3μM的范围时，探针荧光强度的比值I589/I462与次氯酸浓度成良好的线性关系。该探针具有高选择性，高灵敏度，响应快速的特点，并能应用于溶酶体HOCl的检测，具有广阔的应用前景。

Description

一种跨键能量转移型次氯酸荧光探针及其在溶酶体次氯酸检 测中应用
技术领域
本发明涉及一种跨键能量转移型次氯酸荧光探针，该探针能够检测细胞溶酶体内HOCl浓度的变化。
背景技术
细胞内HOCl是在髓过氧化物酶催化作用下，H2O2氧化Cl-离子生成。它在许多细胞生理活动中起着至关重要的作用。例如，当外界病原微生物进入细胞内时，细胞产生HOCl杀灭病原微生物；然而，细胞内HOCl浓度过高，则会引起氧化应激，导致细胞功能障碍，进而引起一系列疾病，比如动脉粥样硬化、关节炎及癌症。因此，开发能够实时检测细胞内HOCl含量的方法，为HOCl相关疾病的研究提供工具，具有重要的意义。
伴随荧光成像技术的发展，利用荧光探针实现细胞内物质荧光成像成为了可能。而相对于传统的分析方法，荧光探针具有操作简单、选择性好、灵敏性高、响应快、对细胞无损伤等优点，近年来利用荧光探针检测HOCl的方法得到了快速发展。
然而，文献中已报道的HOCl探针，大部分基于单个荧光团荧光的变化实现对HOCl的检测，然而这类探针容易受到环境因素的影响，导致测量结果不准确。
采用比率测量的方法可以减少环境因素带来的测量误差，此类方法通过计算荧光强度的比值来实现比率测定。构建此类探针的一个主要思路为：利用荧光团之间的能量传递过程来构造比率探针，如荧光共振能量转移型和跨键能量转移型探针。
荧光共振能量转移型探针的能量供体的荧光发射光谱与能量受体的吸收光谱有一定的重叠，能量传递的效率受到诸多因素的影响，如供体的发射光谱与受体的吸收光谱的重叠程度、供体与受体的跃迁偶极的相对取向、供体与受体之间的距离、受体部分的荧光量子产率等。因此构建此类探针时，荧光团的选择受到较大限制。
与荧光共振能量转移型探针结构类似，跨键能量转移型探针分子中也有两个荧光团，能量从供体通过共轭键直接传递到能量受体，这类探针对荧光团光谱重叠没有要求，且具有更高的能量转移效率。因而构建这类型的探针时，荧光团的选择具有更大的灵活性。
此外，大部分已经报道的次氯酸荧光探针结构并不具有细胞器靶向功能。溶酶体靶向的次氯酸探针更鲜见报道。这对研究溶酶体HOCl的相关疾病研究带来困难。
综上所述，发明人以所述探针以咪唑并[1,5-a]吡啶作为能量供体，罗丹明作为能量受体，硫代双酰肼结构作为次氯酸的响应基团，吗啉结构为溶酶体定位基团，构造了一个跨键能量转移型次氯酸荧光探针。本发明的探针具有溶酶体靶向能力，能够高选择性、高灵敏地检测溶酶体内次氯酸。
发明内容
本发明的目的在于提供一种能应用于细胞溶酶体内HOCl检测的跨键能量转移型荧光探针的制备及应用。
本发明提供的能用于细胞溶酶体内HOCl检测的跨键能量转移型荧光探针（IRh-Ly），其化学结构如下。
本发明所述探针可以用于溶液样品中HOCl的检测。
在HOCl存在条件下，探针分子的硫代双酰肼结构氧化成1,3,4-噁二唑结构，探针同时发射出462 nm和589 nm的荧光，随着次氯酸浓度的增加，589 nm处的荧光逐渐增强，而462 nm处的荧光强度不变，二者的比值（I589/I462）与次氯酸浓度在一定范围内（0-3 μM）呈良好的线性关系。探针可以定量检测HOCl。
另外，该探针还可以用于细胞溶酶体内HOCl变化的检测及细胞成像。
用本发明探针孵育RAW264.7细胞，然后用LPS处理细胞，然后进行共聚焦成像分析，探针蓝色荧光强度不变，而红色荧光强度明显增强，红色/蓝色荧光强度比值增大，因此上述探针可以用于内源性次氯酸的检测。
附图说明
本发明的探针的合成方法，如图1所示。
本发明的探针在不同浓度次氯酸溶液中紫外吸收变化，如图2所示。
本发明的探针在不同浓度次氯酸溶液中荧光发射的变化，如图3所示。
本发明的探针在不同pH缓冲溶液中荧光发射，如图4所示。
本发明的探针对次氯酸的时间响应曲线，如图5所示。
本发明探针靶向溶酶体实验分析，如图6所示。
本发明探针应用于RAW264.7细胞内HOCl的检测，如图7所示。
具体实施方法
实施例1：探针的合成路线见图1。将化合物1（1.2 mmol）溶于7 mL SOCl2中，加热回流2个小时后，减压除去溶剂，得固体2（未提纯，直接用于下一步反应）。将上述化合物2溶于10mL干燥二氯甲烷中，并加入2 mmol三乙胺，常温搅拌10 min，然后将化合物3（1 mmol）的二氯甲烷溶液滴加到上述溶液中，0℃搅拌4 h。将反应液倒入150 mL二氯甲烷中，然后用200mL水洗涤三次，有机相用无水硫酸钠干燥，减压除去溶剂，再进行柱层析分离，得化合物3。
化合物4 (1 mmol)和化合物5 (1.1 mmol)溶于10 mL干燥吡啶中，常温搅拌12 h。将反应液倒入150 mL二氯甲烷中，然后用200 mL水洗涤三次，有机相用无水硫酸钠干燥，减压除去溶剂，再进行柱层析分离，得探针IRh-Ly，产率45%。
以1H NMR、13C NMR及HRMS对其进行结构，数据如下。
1H NMR (400 MHz), δ (ppm): 0.88 (t, 3H, J = 7.2 Hz), 1.06 (t, 6H, J =6.8 Hz), 1.31 (m, 2H), 1.67 (m, 2H), 2.36 (br, 4H), 2.94 (t, 2H, J = 7.2 Hz),3.27 (br, 4H), 3.31 (br, 4H), 3.49 (br, 4H), 3.57 (t, 4H, J = 4.8 Hz), 3.70(br, 2H), 6.34 (s, 1H), 6.40 (m, 2H), 6.53 (d, 1H, J = 8.0 Hz), 6.65 (s, 2H),6.78 (d, 1H, J = 6.8 Hz), 7.18 (d, 1H, J = 6.8 Hz), 7.36 (m, 4H), 7.65 (t,2H, J = 7.6 Hz), 7.90 (s, 1H), 8.03 (d, 1H, J = 6.8 Hz), 8.18 (d, 1H, J = 7.2Hz), 10.83 (s, 1H).
13C NMR (100 MHz), δ (ppm): 189.9, 169.4, 163.05, 153.7, 153.5, 152.0,149.2, 148.9, 140.2, 139.6, 136.4, 134.8, 133.8, 130.1, 129.9, 129.5, 129.2,127.4, 125.1, 124.1, 123.6, 122.4, 120.5, 117.8, 111.4, 110.0, 108.4, 107.5,103.4, 101.7, 97.5, 73.8, 66.6, 62.4, 53.6, 47.9, 44.1, 29.0, 25.6, 22.1,14.1, 12.8.
HRMS m/z: calcd for C52H56ClN8O4S [M+H]+: 923.3834; obtained: 923.3862。
实施例2：配制1 μM探针的PBS缓冲溶液（含30%乙醇，pH 5.00）。再分别加入0,0.25, 0.5, 1, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0 μM HOCl溶液。如图2所示，伴随次氯酸浓度的增大，探针在565 nm处，出现一个强的吸收峰，这说明HOCl的加入，导致了罗丹明结构从闭环到开环结构的转变。
实施例3：配制1 μM探针的PBS缓冲溶液（含30%乙醇，pH 5.00）。分别向上述缓冲溶液中加入0, 0.25, 0.5, 1, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0 μM HOCl次氯酸，然后进行荧光光谱分析，结果显示探针在589 nm处的荧光发射随着次氯酸浓度的增加而变强，如图3所示，图（a）为探针在不同浓度HOCl中荧光发射图，图(b)为探针在589 nm和462 nm处荧光强度比值（I589/I462）与HOCl浓度的关系。
实施例4： 配制1 μM探针的PBS缓冲溶液（含30%乙醇），PBS的pH分别为pH 4.0,4.5, 5.0, 5.5, 6.0, 6.5, 7.0, 7.4, 8, 9, 10, 向上述溶液中加入0 μM或3μM次氯酸，然后进行荧光光谱分析，结果显示，在弱酸性环境中，探针对次氯酸有更好的响应，说明探针能适用于溶酶体的弱酸环境，如图4所示。
实施例5：配制1 μM探针的PBS缓冲溶液（含30%乙醇，pH 5.00）。分别向上述缓冲溶液中加入0和3.0 μM HOCl次氯酸，然后进行荧光光谱分析探针的荧光强度比值I589/I462随时间的变化。实验结果显示，探针在20 s内即可到达最大值，探针具有很高的灵敏度，可以实现对HOCl的实时检测，如图5所示。
实施例6：先用本发明所述探针1 μM，孵育RAW264.7细胞30分钟；再加入溶酶体标记物Lyso Tracker Deep Red 继续孵育30分钟。使用激光共聚焦显微镜进行荧光成像，分别收集探针蓝光（410-520 nm）的荧光成像照片，同时收集Lyso Tracker Deep Red的荧光照片。然后进行叠加分析，如图6所示。图6a为本发明探针的荧光图像；图6b为Lyso TrackerDeep Red的荧光图像；图6c为6a、6b的叠加图；图6d为亮场图像；共定位系数为0.96。
实施例7：对照组：先用本发明所述探针1 μM，孵育RAW264.7细胞30分钟；使用激光共聚焦显微镜进行荧光成像，收集蓝光（410-520 nm）和红光（560-700 nm）的荧光，并统计两个光的比值。
实验组：先用LPS （1 μg/mL）刺激细胞6小时，随后加入PMA（1 μg/mL）继续培养30分钟，随后在无血清培养基中加入1 μM本发明所述探针，培养30分钟；使用激光共聚焦显微镜进行荧光成像，收集蓝光（410-520 nm）和红光（560-700 nm）的荧光，并统计两个光的比值。结果如图7所示。实验结果表明，在细胞受刺激后，探针的荧光强度比值明显增加，本发明所述的探针，可以实现RAW264.7细胞内HOCl的检测。

Claims (3)

1.本发明提供一种跨键能量转移型HOCl比率荧光探针（IRh-Ly）的合成及应用，其结构式如下。
2.如权利1所述的探针在检测溶液样品中HOCl的应用。
3.如权利1所述的探针在检测细胞溶酶体中HOCl的应用。
CN201811298410.3A 2018-11-02 2018-11-02 一种跨键能量转移型次氯酸荧光探针及其在溶酶体次氯酸检测中应用 Pending CN109232615A (zh)

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