CN111116433A - 一种双识别位点硫化氢荧光探针 - Google Patents

一种双识别位点硫化氢荧光探针 Download PDF

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CN111116433A
CN111116433A CN201811283086.8A CN201811283086A CN111116433A CN 111116433 A CN111116433 A CN 111116433A CN 201811283086 A CN201811283086 A CN 201811283086A CN 111116433 A CN111116433 A CN 111116433A
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hydrogen sulfide
fluorescent probe
recognition
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sulfide fluorescent
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杨绍祥
田红玉
刘永国
孙宝国
王皓
武小明
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Beijing Technology and Business University
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    • C—CHEMISTRY; METALLURGY
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    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
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Abstract

本发明公开了一种检测硫化氢的双识别位点荧光探针，具体化学结构式如下所示：

Description

一种双识别位点硫化氢荧光探针
技术领域
本发明涉及一种双识别位点硫化氢荧光探针以及其在检测硫化氢中的应用。
背景技术
硫化氢(H2S)在低浓度时有臭鸡蛋气味，是继NO、CO之后的第三种内源性气体信号分子。它是由膀硫醚-γ-裂解酶、组织膀硫醚-β-合成酶、3-巯基丙酮酸盐转移酶生成并分布在各个组织器官中。H2S作为一种神经递质、免疫调节剂参与了体内大部分的生理过程。然而，H2S含量的异常也会导致许多疾病的发生，比如中风、糖尿病、肿瘤、阿尔茨海默氏症等。除此之外，我们日常饮用的酒类中，由于发酵过程有H2S生成，过多的H2S会影响酒的口感，甚至摄入过多会影响人体健康。
有机小分子荧光探针检测法由于其具有检测快速、操作简便、灵敏高等优点，是一种有效的检测工具，以荧光探针作为检测工具，测定硫化氢的含量，对食品质量与安全研究具有重要的意义。
发明内容
本发明目的是提供一种双识别位点硫化氢荧光探针，它适于在药品、食品、化妆品等产品中检测硫化氢。
更具体的是，本发明涉及一种检测硫化氢的双识别位点荧光探针，它通过下式表示：
Figure BSA0000172983610000011
附图说明
图1是在二甲基亚砜溶液中，随着不同浓度硫化氢的加入，本发明的荧光探针(10μM)的荧光强度变化。嵌入图：硫化氢的浓度。
图2是在二甲基亚砜溶液中，本发明的荧光探针(10μM)荧光强度随着硫化氢浓度变化的标准曲线。
图3在365nm紫外灯下，本发明的荧光探针(10μM)与不同浓度硫化氢(0，0.2，0.4，0.6，0.8，1μM)反应后溶液颜色变化情况。
图4是自然光下，本发明的荧光探针试纸接触硫化氢气体后试纸颜色的变化情况。
具体实施方式
实施例1.检测硫化氢的荧光探针的制备
合成路线如下式所示：
Figure BSA0000172983610000021
化合物1(0.503g，2.9mmol)、10mL三氯甲烷加入到50mL三口烧瓶中，滴加三乙胺(0.303g，3mmol)，冰浴保护下搅拌；用10mL三氯甲烷溶解化合物2(1.548g，5.8mmol)，并逐滴加入到反应三口烧瓶中，冰浴保护下反应0.5h；将反应体系升温至40℃，反应3h，抽滤，三氯甲烷洗涤，干燥，得奶白色固体化合物3。
产物经过核磁氢谱及核磁碳谱表征。
1H NMR(300MHz，DMSO)，δ(ppm)：10.16(s，1H)，9.14(d，J＝2.2Hz，1H)，8.66(s，1H)，8.59(dd，J＝8.7，2.3Hz，1H)，8.29(dd，J＝8.9，2.4Hz，2H)，8.13(d，J＝8.6Hz，1H)，7.97(dd，J＝8.6，1.3Hz，1H)，7.94(d，J＝2.2Hz，1H)，7.47(dd，J＝9.0，2.4Hz，1H).13C NMR(75MHz，DMSO)：δ(ppm)：193.29，152.07，148.65，136.68，135.05，134.44，134.13，133.10，131.76，129.71，128.02，124.29，122.18，121.65，120.56.
实施例2.检测氟离子的荧光探针试纸的制备
将滤纸剪裁成1cm×1cm大小的正方形试纸，并将其浸泡于1mM本发明荧光探针溶液(DMSO溶剂)中，电吹风烘干，得本发明的荧光探针试纸。
本发明的荧光探针的荧光强度随着硫化氢的变化如图1所示，依据该变化可作出该荧光探针(10μM)荧光强度随着硫化氢浓度变化的标准曲线，标准曲线如图2所示，通过该标准曲线的建立，本发明的荧光探针可用于硫化氢的定量检测。本发明的荧光探针与不同浓度硫化氢反应后溶液颜色变化情况如图3所示，随着硫化氢浓度的增加，本发明的荧光探针溶液由无色逐渐变为蓝绿色。如图4所示，本发明的荧光探针试纸接触硫化氢气体后由无色转变为黄色。本发明的荧光探针可用于硫化氢的定性及半定量检测。

Claims (1)

1.一种检测硫化氢的双识别位点荧光探针，具体化学结构式如下所示：
Figure FSA0000172983600000011
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CN103160274A (zh) * 2012-11-30 2013-06-19 山东师范大学 一种检测细胞内硫化氢的荧光探针及其制备方法和应用
CN103805170A (zh) * 2014-01-26 2014-05-21 大连理工常熟研究院有限公司 一种用于识别硫化氢的特异性荧光探针及其应用
CN103923640A (zh) * 2014-04-30 2014-07-16 大连理工常熟研究院有限公司 一种苯并噻唑类识别硫化氢的荧光探针及其应用
CN104860840A (zh) * 2015-04-27 2015-08-26 苏州罗兰生物科技有限公司 一种荧光增强型硫化氢荧光探针的制备及应用
CN105419788A (zh) * 2015-12-25 2016-03-23 济南大学 一种识别硫化氢的小分子荧光探针及其制备方法和应用
CN107141304A (zh) * 2017-05-16 2017-09-08 北京工商大学 一种荧光素类半胱氨酸荧光探针
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