CN110724114B - 一种检测亚硫酸氢根及硫化氢的荧光探针 - Google Patents

一种检测亚硫酸氢根及硫化氢的荧光探针 Download PDF

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CN110724114B
CN110724114B CN201810774837.XA CN201810774837A CN110724114B CN 110724114 B CN110724114 B CN 110724114B CN 201810774837 A CN201810774837 A CN 201810774837A CN 110724114 B CN110724114 B CN 110724114B
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hydrogen sulfide
fluorescent probe
bisulfite
detecting
detecting bisulfite
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杨绍祥
田红玉
刘永国
梁森
孙宝国
王皓
武小明
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Beijing Technology and Business University
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Abstract

本发明公开了一种检测亚硫酸氢根及硫化氢的荧光探针，具体化学结构式如下所示：

Description

一种检测亚硫酸氢根及硫化氢的荧光探针
技术领域
本发明涉及一种检测亚硫酸氢根及硫化氢的荧光探针以及其在检测亚硫酸氢根及硫化氢中的应用。
背景技术
硫化氢(H2S)在低浓度时有臭鸡蛋气味。吸入少量高浓度硫化氢可于短时间内致命，是一种急性剧毒。
H2S作为一种免疫调节剂、神经递质参与了体内大部分的生理过程。然而，H2S含量的异常也导致许多疾病的发生，肿瘤、糖尿病、中风、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。
亚硫酸盐和亚硫酸氢盐主要通过人呼吸空气污染物SO2、体内含硫氨基酸氧化及作为防腐剂添加到食品中被摄入这三种方式在人体内积累。尤其它的抗菌性、抗氧化、延长食品保质期是作为防腐剂的重要原因且被广泛应用到食品及饮料中。当体内含量异常，会对人体健康造成危害，严重时引发一系列疾病：呼吸道疾病、肺癌、皮肤过敏等。中国食品安全国家标准GB5009.34-2016规定亚硫酸盐和亚硫酸氢盐含量在食品中的含量不超过1mg/kg。
有机小分子荧光探针检测法由于其具有简单、便捷、成本低、快速、灵敏及其潜在的成像等特性，已被证明是一种非常有效的检测方法，目前许多的有机小分子荧光探针被开发出来。因此，利用荧光探针分析手段检测亚硫酸氢根及硫化氢的含量，对食品质量安全及生物研究具有重要的意义。
发明内容
本发明目的是提供一种检测亚硫酸氢根及硫化氢的荧光探针，它适于在食品、药品、化妆品等产品中检测亚硫酸氢根及硫化氢。
更具体的是，本发明涉及一种检测亚硫酸氢根及硫化氢的荧光探针，它通过下式表示：
Figure BSA0000167183360000011
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是在二甲基亚砜溶液中，随着不同浓度亚硫酸氢根的加入，本发明的荧光探针(10μM)的荧光强度变化。嵌入图：亚硫酸氢根的浓度。
图4是在二甲基亚砜溶液中，本发明的荧光探针(10μM)荧光强度随着亚硫酸氢根浓度变化的标准曲线。
具体实施方式
实施例1.检测亚硫酸氢根及硫化氢的荧光探针的制备
合成路线如下式所示：
Figure BSA0000167183360000021
将1.00g(5.81mmol)化合物1，0.58g(7.16mmol)哌啶，10mL三氯甲烷加入到三口烧瓶中，升温到40℃。将1.74g(9.99mmol)化合物2溶于20mL三氯甲烷，缓慢滴加到三口烧瓶中。加热到70℃，反应3.5小时，后将温度降至室温，甲醇重结晶得化合物3。将0.20g(0.61mmol)化合物3，0.12g(0.65mmol)化合物4，0.19g(1.84mmol)三乙胺，20mL DMF加入到三口烧瓶中，加热到80℃，反应8小时，后将温度降至室温，水洗三次，甲醇重结晶得产物5。
产物经过核磁氢谱及核磁碳谱表征。
1H NMR(300MHz，DMSO)δ8.96(d，J＝2.8Hz，1H)，8.71(s，1H)，8.60(s，1H)，8.49(dd，J＝9.2，2.8Hz，1H)，8.35-8.28(m，1H)，8.23(dd，J＝8.4，3.2Hz，2H)，8.12(dd，J＝8.1，2.6Hz，2H)，7.87(d，J＝2.2Hz，1H)，7.66-7.51(m，3H)，7.42(d，J＝9.2Hz，1H).13C NMR(75MHz，DMSO)δ163.72，154.64，154.45，153.41，148.42，142.58，140.45，135.85，134.86，133.17，132.82，130.85，130.50，130.24，129.05，127.70，126.92，126.41，123.70，123.04，122.49，121.48，121.27，116.78，116.68，106.22.
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。
本发明的荧光探针的荧光强度随着亚硫酸氢根的变化如图3所示，依据该变化可作出该荧光探针(10μM)荧光强度随着亚硫酸氢根浓度变化的标准曲线，标准曲线如图4所示，通过该标准曲线的建立，本发明的荧光探针可用于亚硫酸氢根的定量检测。

Claims (1)

1.一种检测亚硫酸氢根及硫化氢的荧光探针，具体化学结构式如下所示：
Figure FSA0000167183350000011
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