CN113061109A - 吗啉-吡啶-部花菁衍生物荧光探针及其制备方法和应用 - Google Patents

吗啉-吡啶-部花菁衍生物荧光探针及其制备方法和应用 Download PDF

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CN113061109A
CN113061109A CN202110338619.3A CN202110338619A CN113061109A CN 113061109 A CN113061109 A CN 113061109A CN 202110338619 A CN202110338619 A CN 202110338619A CN 113061109 A CN113061109 A CN 113061109A
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fluorescent probe
morpholine
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韩学锋
吴伟娜
郭芳芳
宋雨飞
刘爽爽
王元
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Henan University of Technology
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Abstract

本发明提供了一种吗啉‑吡啶‑部花菁衍生物荧光探针及其制备方法和应用，其中所述吗啉‑吡啶‑部花菁衍生物的化学结构式如下：
Figure 100004_DEST_PATH_IMAGE001
本发明的吗啉‑吡啶‑部花菁衍生物荧光探针在纯水相生理条件下能选择性的与羧酸酯酶（CEs）作用，溶液荧光颜色由绿色变成橙黄色，呈现典型的比率荧光信号。特别是作为CEs荧光探针在细胞溶酶体荧光成像中的应用。

Description

吗啉-吡啶-部花菁衍生物荧光探针及其制备方法和应用
技术领域
本发明属于有机合成领域，具体涉及吗啉-吡啶-部花菁衍生物及其制备方法和应用。
背景技术
羧酸酯酶（CEs）作为人体分布的一种重要的水解代谢酶，其在维持人体脂质代谢平衡、药物及毒物的代谢清除中发挥不可忽视的作用。然而，CEs的异常变化又与多种疾病的发生密切相关，例如高血脂、脂肪肝、癌症等疾病。因此，开发快速、灵敏、准确的CEs检测方法具有重要意义。
近年来，荧光分子探针技术由于具有灵敏度高、操作简单、成本低等特点，已经成为检测重要金属离子、阴离子、小分子和生物酶活性的重要手段。但现有绝大多数CEs荧光探针需要有机助溶剂（>10%），无法在纯水相中实现CEs识别，限制了其进一步实际应用。此外，比率荧光探针能够消除环境因素的干扰，达到精确检测的目的。但现有CEs比率荧光探针的报道并不常见。
有鉴于此，特提出本发明。
发明内容
针对现有技术中存在的问题，本发明考虑到部花青衍生物优异的光化学和光物理特性，以含吡啶的部花青衍生物为荧光探针，并引进吗啉环作为溶酶体的定位基团，合成了一种高灵敏度、高选择性的CEs荧光探针。该探针能应用于纯水体系中CEs的测定，具有溶酶体靶向功能，并能应用于溶酶体内CEs浓度的检测。
本发明的主要目的在于提供一种可用于纯水体系和细胞溶酶体内针对CEs的灵敏度高、选择性好的吗啉-吡啶-部花菁衍生物荧光探针；另一目的是提供该荧光探针的制备方法和应用。
为实现上述目的，本发明采用以下技术方案：一种吗啉-吡啶-部花菁衍生物荧光探针，所述吗啉-吡啶-部花菁衍生物具有如下结构式：
Figure 100002_DEST_PATH_IMAGE001
本发明还提供了一种吗啉-吡啶-部花菁衍生物荧光探针的制备方法，具体制备方法如下：
S1：将4-[2-(6-羟基-2-萘基)-乙烯基]-1-[2-(4-吗啉基乙基)]-吡啶溴盐和乙酸酐溶解于二氯甲烷中；
S2：将S1所得溶液滴加三乙胺作催化剂，然后在室温下搅拌反应3-4h；
S3：将S2所得溶液旋蒸，将所得固体残渣用乙酸乙酯清洗，再用乙醇重结晶，得到所述吗啉-吡啶-部花菁衍生物荧光探针。
更进一步地，步骤S2中，4-[2-(6-羟基-2-萘基)-乙烯基]-1-[2-(4-吗啉基乙基)]-吡啶溴盐和三乙胺的摩尔比为1:3。
更进一步地，步骤S1中加入的4-[2-(6-羟基-2-萘基)-乙烯基]-1-[2-(4-吗啉基乙基)]-吡啶溴盐和乙酸酐的摩尔比为1:1.2。
更进一步地，吗啉-吡啶-部花菁衍生物荧光探针的具体制备方法为，将4.41 g 4-[2-(6-羟基-2-萘基)-乙烯基]-1-[2-(4-吗啉基乙基)]-吡啶溴盐（10 mmol）和1.23 g乙酸酐（12 mmol）溶于0.2 L二氯甲烷中，滴加3.04 g三乙胺（30 mmol）作缚酸剂，室温下搅拌3-4 h，TLC追踪反应结束后，旋蒸，所得固体用乙酸乙酯清洗，再用无水乙醇重结晶，得到所述吗啉-吡啶-部花菁衍生物荧光探针。
本发明还提供了上述吗啉-吡啶-部花菁衍生物荧光探针的用途，即在作为CEs荧光探针方面的应用，特别是在作为检测HeLa活细胞溶酶体内CEs的荧光探针中的应用。
与现有技术相比，本发明的优点和积极效果在于：
本发明通过缩合反应制备吗啉-吡啶-部花菁衍生物荧光探针，原料易得，合成和后处理方法简单。在多种常见离子及氨基酸中，对CEs表现出较高的荧光识别性能。探针工作环境中无需任何有机溶剂助溶，非常有利于应用于生物体系，具有广泛的潜在应用价值。
附图说明
图1为本发明实施例1制得的吗啉-吡啶-部花菁衍生物荧光探针的1H NMR谱图；
图2为本发明实施例1制得的吗啉-吡啶-部花菁衍生物荧光探针的13C NMR谱图；
图3为本发明实施例1制得的吗啉-吡啶-部花菁衍生物荧光探针的质谱谱图；
图4为本发明实施例1制得的吗啉-吡啶-部花菁衍生物荧光探针(1×10-5 mol／L)的PBS缓冲溶液 (0.01 mol／L，pH = 7.4)分别加入2×10-5 mol／L阴离子（AcO−、ClO−、CO3 2−、S2− 和HCO3 −)、阳离子（Ca2+、Mg2+、Al3+ 和Fe3+）活性氧物种 （H2O2）和氨基酸（Cys、Ala、Ary、Ser、Asp）的荧光光谱图（a,激发波长为360 nm），和510和580 nm处荧光强度比值F510/F580柱状图（b）。
图5为本发明实施例1制得的吗啉-吡啶-部花菁衍生物荧光探针(1×10-5 mol／L)的PBS缓冲溶液 (0.01 mol／L，pH = 7.4)滴定不同浓度CEs的荧光光谱图, 其图示为510和580 nm处荧光强度比值F510/F580随CEs浓度的线性变化趋势图（激发波长为360 nm）。
图6为在HeLa细胞中，吗啉-吡啶-部花菁衍生物荧光探针与CEs的荧光成像图；HeLa细胞用1×10-5 mol／L 荧光探针培育30分钟后加入CEs且保证CEs的浓度为1×10-3 U/L，继续培育30分钟后，使用Olympus FV500-IX70激光共聚焦显微镜进行荧光成像。
其中：a为荧光探针绿色通道荧光成像图；b为荧光探针红色通道荧光成像图；c为荧光探针绿色通道和红色通道叠加图；d为荧光探针亮场图；e为荧光探针绿色通道、红色通道和亮场叠加图；f为荧光探针+ CEs后绿色通道荧光成像图；g荧光探针+ CEs后红色通道荧光成像图；h为荧光探针+ CEs后绿色通道和红色通道叠加图；i为荧光探针+ CEs后亮场图；j为荧光探针+ CEs后绿色通道、红色通道和亮场叠加图。
图7为在HeLa细胞中，吗啉-吡啶-部花菁衍生物荧光探针与商用溶酶体定位染料LysoTracker Blue共染荧光成像图；HeLa细胞用1×10-5 mol／L 荧光探针和LysoTrackerBlue共同培育30分钟后，使用Olympus FV500-IX70激光共聚焦显微镜进行荧光成像。
其中：a为蓝色通道荧光成像图；b为绿色通道荧光成像图；c为蓝色通道和绿色通道叠加后的图片；d为蓝色通道和绿色通道强度相关图；f为贯穿单个HeLa区域蓝色通道和绿色通道强度分布叠加图。
具体实施方式
下面结合附图和具体实施例进一步详细说明本发明，但本领域技术人员将会理解，下列实施例仅用于说明本发明，而不应视为限定本发明的范围。本发明实施例采用的试剂和原料为常规市场购买得到。
实施例1
本实施例吗啉-吡啶-部花菁衍生物荧光探针的制备方法如下：
将4.41 g 4-[2-(6-羟基-2-萘基)-乙烯基]-1-[2-(4-吗啉基乙基)]-吡啶溴盐（10 mmol）和1.23 g乙酸酐（12 mmol）溶于0.2 L二氯甲烷中，滴加3.04 g三乙胺（30 mmol）作催化剂，室温下搅拌3-4 h，TLC追踪反应结束后，旋蒸，所得固体用乙酸乙酯清洗，再用无水乙醇重结晶，得到所述吗啉-吡啶-部花菁衍生物荧光探针。目标产物的产率为65%。
采用核磁共振仪对制得的吗啉-吡啶-部花菁衍生物进行核磁共振分析，结果如下：
1H NMR (400 MHz, DMSO-d 6 ), δ (ppm): 8.95 (d, J = 4.8 Hz, 2H), 8.37-8.16 (m, 4H), 8.14-7.96 (m, 3H), 7.80-7.63 (m, 2H), 7.42 (d, J = 8.2 Hz, 1H),4.65 (s, 2H), 3.53 (s, 4H), 2.84 (s, 2H), 2.47 (s, 4H), 2.36 (s, 3H)。具体核磁共振氢谱见图1；
13C NMR (400 MHz, DMSO-d 6 ) δ:169.83, 153.23, 149.87, 145.24, 141.11,134.68, 133.23, 131.39, 130.61, 130.03,128.96, 124.90, 124.33, 123.83,123.16, 119.28, 66.67, 58.00, 56.85, 53.31, 21.42。具体核磁共振碳谱见图2；
质谱ESI-MS: m/z = 403.1836 for [M-Br]+。具体质谱谱图见图3。
实施例2
吗啉-吡啶-部花菁衍生物对CEs的光学性质测定
将上述实施例1制得的吗啉-吡啶-部花菁衍生物作为荧光探针在PBS钠缓冲溶液(0.01 mol/L，pH = 7.4)中配制成摩尔浓度为1×10-5 mol/L的溶液，分别在含摩尔浓度为2×10-5 mol/L的阴离子（AcO−、ClO−、CO3 2−、S2− 和HCO3 −)、阳离子（Ca2+、Mg2+、Al3+ 和Fe3+）活性氧物种 （H2O2）和氨基酸（Cys、Ala、Ary、Ser、Asp）的溶液中加入等量的上述荧光探针溶液，采用紫外可见分光光度计或荧光光谱仪进行分析（激发波长为360 nm），所得紫外和荧光光谱图见图4。通过图4可以看出，本发明制得的吗啉-吡啶-部花菁衍生物作为探针只对CEs具有明显响应，比率荧光信号可用于CEs的快速鉴别，而其它离子无变化。
通过图5的滴定光谱计算可以得到CEs检出限为9.8×10-8 U/L，其荧光光谱的线性检测范围为3.0×10-6-8.0×10-6 U/L，因此本发明制得的吗啉-吡啶-部花菁衍生物可用于CEs的荧光定量检测。
实施例3
吗啉-吡啶-部花菁衍生物荧光探针在细胞内CEs的检测实验
HeLa细胞用1×10-5 mol／L的上述实施例1制得的吗啉-吡啶-部花菁衍生物荧光探针在37℃下培育30分钟，加入CEs且保证CEs的浓度为1×10-3 U/L，后再培育30分钟，获得在HeLa细胞的荧光成像图，具体如图6所示，其中：a为荧光探针绿色通道荧光成像图；b为荧光探针红色通道荧光成像图；c为荧光探针绿色通道和红色通道叠加图；d为荧光探针亮场图；e为荧光探针绿色通道、红色通道和亮场叠加图；f为荧光探针+ CEs后绿色通道荧光成像图；g荧光探针+ CEs后红色通道荧光成像图；h为荧光探针+ CEs后绿色通道和红色通道叠加图；i为荧光探针+CEs后亮场图；j为荧光探针+ CEs后绿色通道、红色通道和亮场叠加图。HeLa细胞中加入吗啉-吡啶-部花菁衍生物荧光探针后探针绿色通道和红色通道荧光强，但绿色通道强于红色通道；而再加入CEs后绿色和红色通道荧光均有所减弱，但红色通道强于绿色通道。故本发明实施例1制得的吗啉-吡啶-部花菁衍生物可用于细胞溶酶体中CEs的比率荧光检测。
HeLa细胞用1×10-5 mol／L的上述实施例1制得的吗啉-吡啶-部花菁衍生物荧光探针和商用溶酶体定位染料LysoTracker Blue在37℃下共同培育30分钟，获得在HeLa细胞的荧光成像图，具体如图7所示，其中：a为蓝色通道荧光成像图；b为绿色通道荧光成像图；c为蓝色通道和绿色通道叠加后的图片；d为蓝色通道和绿色通道强度相关图；f为贯穿单个HeLa区域蓝色通道和绿色通道强度分布叠加图。从图7可以看出，HeLa细胞中探针绿色通道荧光和LysoTracker Blue蓝色通道荧光基本吻合，重叠系数为0.91。故本发明实施例1制得的吗啉-吡啶-部花菁衍生物荧光探针可以靶向细胞溶酶体。
以上所述实施例仅是为充分说明本发明而所举的较佳的实施例，其保护范围不限于此。本技术领域的技术人员在本发明基础上所作的等同替代或变换，均在本发明的保护范围之内，本发明的保护范围以权利要求书为准。

Claims (6)

1.一种吗啉-吡啶-部花菁衍生物荧光探针，其特征在于所述吗啉-吡啶-部花菁衍生物荧光探针具有如下结构式：
Figure DEST_PATH_IMAGE001
。
2.根据权利要求1所述的吗啉-吡啶-部花菁衍生物荧光探针的制备方法，其特征在于，包括如下步骤：
S1：将4-[2-(6-羟基-2-萘基)-乙烯基]-1-[2-(4-吗啉基乙基)]-吡啶溴盐和乙酸酐溶解于二氯甲烷中；
S2：将S1所得溶液滴加三乙胺作催化剂，然后在室温下搅拌反应3-4h；
S3：将S2所得溶液旋蒸，将所得固体残渣用乙酸乙酯清洗，再用乙醇重结晶，得到所述吗啉-吡啶-部花菁衍生物荧光探针。
3.根据权利要求2所述的吗啉-吡啶-部花菁衍生物荧光探针的制备方法，其特征在于：所述步骤S1中加入的4-[2-(6-羟基-2-萘基)-乙烯基]-1-[2-(4-吗啉基乙基)]-吡啶溴盐和乙酸酐的摩尔比为1:1.2。
4.根据权利要求2所述的吗啉-吡啶-部花菁衍生物荧光探针的制备方法，其特征在于：所述步骤S2中，4-[2-(6-羟基-2-萘基)-乙烯基]-1-[2-(4-吗啉基乙基)]-吡啶溴盐和三乙胺的摩尔比为1:3。
5.根据权利要求2所述的吗啉-吡啶-部花菁衍生物荧光探针的制备方法，其特征在于步骤如下：将4.41 g 4-[2-(6-羟基-2-萘基)-乙烯基]-1-[2-(4-吗啉基乙基)]-吡啶溴盐和1.23 g乙酸酐溶于0.2 L二氯甲烷中，滴加3.04 g三乙胺作缚酸剂，常温下搅拌反应3-4h，TLC追踪反应结束后，旋蒸，所得固体用乙酸乙酯清洗，再用乙醇重结晶，得到所述吗啉-吡啶-部花菁衍生物荧光探针。
6.根据权利要求1所述的吗啉-吡啶-部花菁衍生物荧光探针作为羧酸酯酶荧光探针在细胞溶酶体荧光成像中的应用。
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114835636A (zh) * 2022-05-27 2022-08-02 安徽大学 一种萘-乙烯基吡啶基双响应型荧光探针及其制备方法和用途
CN117430804A (zh) * 2023-11-28 2024-01-23 渤海大学 纯水环境快速检测次氯酸根荧光探针的制备方法

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106588846A (zh) * 2016-12-08 2017-04-26 曲阜师范大学 一种双比率型多功能高灵敏羧酸酯酶检测荧光探针的制备方法及应用
CN108164450A (zh) * 2018-02-08 2018-06-15 赣南师范大学 一种羧酸酯酶荧光探针及其制备方法和应用
CN109438326A (zh) * 2018-11-12 2019-03-08 潍坊医学院 一种用于检测羧酸酯酶的荧光探针及其制备方法与专用检测试剂盒
CN110818703A (zh) * 2019-11-22 2020-02-21 河南理工大学 一种吡咯-部花菁衍生物荧光探针及其制备方法和应用
CN112521376A (zh) * 2020-12-16 2021-03-19 河南理工大学 色烯-吡啶衍生物荧光探针、制备方法及应用
WO2021170781A1 (en) * 2020-02-28 2021-09-02 Technische Universität Berlin Fluorescent probes for detection of calcifications
CN114196395A (zh) * 2020-09-17 2022-03-18 中国科学院大连化学物理研究所 一种硫酸酯酶的水溶性荧光探针及其合成方法和应用
CN114436995A (zh) * 2022-02-25 2022-05-06 河南理工大学 吗啉-茚酮-查尔酮衍生物荧光探针及其制备方法和应用

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106588846A (zh) * 2016-12-08 2017-04-26 曲阜师范大学 一种双比率型多功能高灵敏羧酸酯酶检测荧光探针的制备方法及应用
CN108164450A (zh) * 2018-02-08 2018-06-15 赣南师范大学 一种羧酸酯酶荧光探针及其制备方法和应用
CN109438326A (zh) * 2018-11-12 2019-03-08 潍坊医学院 一种用于检测羧酸酯酶的荧光探针及其制备方法与专用检测试剂盒
CN110818703A (zh) * 2019-11-22 2020-02-21 河南理工大学 一种吡咯-部花菁衍生物荧光探针及其制备方法和应用
WO2021170781A1 (en) * 2020-02-28 2021-09-02 Technische Universität Berlin Fluorescent probes for detection of calcifications
CN114196395A (zh) * 2020-09-17 2022-03-18 中国科学院大连化学物理研究所 一种硫酸酯酶的水溶性荧光探针及其合成方法和应用
CN112521376A (zh) * 2020-12-16 2021-03-19 河南理工大学 色烯-吡啶衍生物荧光探针、制备方法及应用
CN114436995A (zh) * 2022-02-25 2022-05-06 河南理工大学 吗啉-茚酮-查尔酮衍生物荧光探针及其制备方法和应用

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
FANG-FANG GUO ET AL.: "A water-soluble lysosome-targetable fluorescent probe for carboxylesterase detection and its application in biological imaging" *
GUANG CHEN ET AL.: "A bright two-photon fluorescence probe with large stokes shift for deep tissue imaging of H2S during metabolism" *
JIANGUO WANG ET AL.: "A fast responsive, highly selective and light-up fluorescent probe for two-photon imaging of carboxylesterase in living cells" *
SHUWEI ZHANG ET AL.: "A novel fluorescent probe with one-excitation and dual-emission for selective and simultaneous detection of Glutathione and Arginine in NIR and blue regions" *
SHUWEI ZHANG ET AL.: "A water-soluble near-infrared fluorescent probe for sensitive and selective detection of cysteine" *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114835636A (zh) * 2022-05-27 2022-08-02 安徽大学 一种萘-乙烯基吡啶基双响应型荧光探针及其制备方法和用途
CN114835636B (zh) * 2022-05-27 2023-06-13 安徽大学 一种萘-乙烯基吡啶基双响应型荧光探针及其制备方法和用途
CN117430804A (zh) * 2023-11-28 2024-01-23 渤海大学 纯水环境快速检测次氯酸根荧光探针的制备方法
CN117430804B (zh) * 2023-11-28 2024-04-05 渤海大学 纯水环境快速检测次氯酸根荧光探针的制备方法

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