CN105906623B - 一种吡啶并[1,2‑a]苯并咪唑羧酸类pH荧光探针及其应用 - Google Patents

一种吡啶并[1,2‑a]苯并咪唑羧酸类pH荧光探针及其应用 Download PDF

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CN105906623B
CN105906623B CN201610347388.1A CN201610347388A CN105906623B CN 105906623 B CN105906623 B CN 105906623B CN 201610347388 A CN201610347388 A CN 201610347388A CN 105906623 B CN105906623 B CN 105906623B
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benzimidazole
fluorescence
pyrido
carboxylic acids
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葛燕青
段桂运
曹晓群
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Taishan Medical University
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Abstract

本发明公开了一种吡啶并[1,2‑a]苯并咪唑羧酸类pH荧光探针,所述探针是4‑甲基吡啶并[1,2‑a]苯并咪唑‑3‑羧酸,其化学结构式如式(1)所示。本发明的荧光探针在二甲基亚砜的水溶液中对pH有独特的荧光选择性和较高的灵敏度,与现有探针相比,具有pH相应范围窄,不受背景干扰,适用于强酸性环境pH检测等显著优点,具有巨大的应用前景。

Description

一种吡啶并[1,2-a]苯并咪唑羧酸类pH荧光探针及其应用
技术领域
本发明涉及有机小分子荧光探针领域,尤其涉及一种新型pH荧光探针4-甲基吡啶并[1,2-a]苯并咪唑-3-羧酸及其应用。
背景技术
pH作为细胞健康的一个重要指标,在细胞生长,扩散,调亡,自噬,离子运输,以及其他细胞过程中起着重要作用。其微小变化便可能导致细胞功能素乱和严重疾病,如大肠癌,乳腺癌,囊性纤维化,神经退行性疾病甚至阿尔茨海默氏症。但目前常用的玻璃电极测pH的方法不适用于生命领域pH的检测。
荧光探针选择性好,灵敏度高,操作简单,成本低并且可以实现实时监测,现已作为一种首选的测试工具应用于细胞内pH值的测定。尽管已有多种pH荧光探针被报道,但是目前对于酸性条件下细胞内pH的研究还不够深入。为此,开发新型理想的酸性pH探针,检测细胞内氢离子的浓度以及分布对研究细胞的生理、病理过程具有极为重要的意义。
吡啶并[1,2-a]苯并咪唑类化合物因受制于有限的合成方法,其在光学领域的应用报到很少,其而作为pH荧光探针的应用更是未见文献报道。
发明内容
针对现有技术的不足,本发明的目的在于提供一种pH荧光探针新分子吡啶并[1,2-a]苯并咪唑羧酸及其应用。
本发明的技术方案是:一种吡啶并[1,2-a]苯并咪唑羧酸pH荧光探针,其化学结构式如式(1)所示:
本发明还包括吡啶并[1,2-a]苯并咪唑羧酸pH荧光探针的应用,式(1)化合物在二甲亚砜的水溶液中对pH有独特的荧光选择性。
本发明还包括吡啶并[1,2-a]苯并咪唑羧酸pH荧光探针的合成方法,在95%的乙醇溶液中,将4-甲基吡啶并[1,2-a]苯并咪唑-3-羧酸乙酯与氢氧化钠按照1:2投料比例,80℃下回流反应2-5小时,得到4-甲基吡啶并[1,2-a]苯并咪唑-3-羧酸。
配制吡啶并[1,2-a]苯并咪唑羧酸的二甲亚砜溶液,分别加入到不同pH的二甲亚砜的水溶液中(二甲亚砜:水=2:8),通过荧光光谱测试来研究对不同pH的选择性,测其荧光发射波谱强度变化发现: pH由4.0变化至6.0的过程中,430 nm处荧光强度明显增强,如图1所示。因此,吡啶并[1,2-a]苯并咪唑羧酸作为pH荧光探针具有巨大的应用前景。
附图说明
图1:不同pH的二甲亚砜水溶液(二甲亚砜:水=2:8)的荧光光谱图。
图2:荧光探针新分子的核磁氢谱。
图3:荧光探针新分子的核磁碳谱。
具体实施方式
实施例1:式(1)化合物的合成方案如下式所示:
具体合成步骤如下:
在50 mL圆底烧瓶中依次加入2.54g(10.0 mmol)4-甲基吡啶并[1,2-a]苯并咪唑-3-羧酸乙酯,0.80g(20.0 mmol)氢氧化钠,20 mL95%的乙醇,80℃下回流反应2-5小时,倒入300 mL水中,浓盐酸调pH至5-6,析出大量固体,抽滤,干燥得1.32g黄色固体产品,产率58.4%。
核磁共振氢谱测定:1H NMR(400 MHz,DMSO-d6):δ9.44 (d, J = 8.0 Hz, 1H),8.62 (d, J = 8.0 Hz, 1H), 8.00 (d, J = 8.0 Hz, 1H), 7.83-7.67(m, 3H),2.89 (s,3H). 13C NMR(100 MHz,CDCl3):166.97, 129.25, 128.10, 126.24, 124.55, 115.69,114.91, 114.40, 15.01.
如图2,图3所示。
实施例2:
取吡啶并[1,2-a]苯并咪唑羧酸0.0023g,溶于10mL二甲亚砜,得探针母液,浓度为10-3M。分别取100微升探针母液,加入到10mL不同pH的二甲亚砜的水溶液中(二甲亚砜:水=2:8)测其荧光发射强度变化发现:pH由4.0变化至6.0的过程中,430 nm处荧光强度明显增强,如图1所示。

Claims (2)

1.一种吡啶并[1,2-a]苯并咪唑羧酸类pH荧光探针,其特征在于:它是4-甲基吡啶并[1,2-a]苯并咪唑-3-羧酸,其化学结构式如式(1)所示:
C:\Documents and Settings\Administrator\Local Settings\Temp\360zip$Temp\360$8\481105e3-09ec-4236-92d1-fb7eb6fb9654\100001\100001.xml.files\image001.jpg
式(1)化合物在二甲基亚砜的水溶液中对pH有独特的荧光选择性。
2.权利要求1所述4-甲基吡啶并[1,2-a]苯并咪唑-3-羧酸pH荧光探针的合成方法,其特征在于:在95%的乙醇溶液中,将4-甲基吡啶并[1,2-a]苯并咪唑-3-羧酸乙酯与氢氧化钠按照1:2投料比例,80℃下回流反应2-5小时,得到4-甲基吡啶并[1,2-a]苯并咪唑-3-羧酸。
CN201610347388.1A 2016-05-24 2016-05-24 一种吡啶并[1,2‑a]苯并咪唑羧酸类pH荧光探针及其应用 Expired - Fee Related CN105906623B (zh)

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CN109694706A (zh) * 2017-10-20 2019-04-30 泰山医学院 一种氰基呋喃半花菁类so32-比率型荧光探针及其应用
CN109722238A (zh) * 2017-10-27 2019-05-07 泰山医学院 吡啶修饰的吡啶并[1,2-a]苯并咪唑类SO32-比率荧光探针及其应用
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