CN109422669B - 一种萘酚类硫化氢荧光探针 - Google Patents

一种萘酚类硫化氢荧光探针 Download PDF

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CN109422669B
CN109422669B CN201710732757.3A CN201710732757A CN109422669B CN 109422669 B CN109422669 B CN 109422669B CN 201710732757 A CN201710732757 A CN 201710732757A CN 109422669 B CN109422669 B CN 109422669B
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hydrogen sulfide
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杨绍祥
田红玉
刘永国
孙宝国
王皓
王嘉琳
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Beijing Technology and Business University
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Abstract

本发明公开了一种萘酚类硫化氢荧光探针，具体化学结构式如下式所示：

Description

一种萘酚类硫化氢荧光探针
技术领域
本发明涉及一种萘酚类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，对眼、呼吸系统及中枢神经都有影响。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。
硫化氢是啤酒中主要的硫化物之一，对啤酒风味影响很大，其味阈值为10μg/L，优质成熟啤酒含量仅为(1～5)μg/L。当啤酒中含量超过10μg/L时，就能感到明显的“酵母臭味”、“生酒味”、“洋葱味”，当含量达到50μg/L时，呈臭鸡蛋味，与双乙酰、乙醛共存时产生一股强烈的青草味。在葡萄酒的贮藏过程中，由于葡萄酒自身的强还原作用，会使一些硫化物转化为硫化氢。所以，当硫化氢含量较高时不仅会对啤酒、葡萄酒的品质产生影响，也会造成一定的食品安全问题。所以开展硫化氢在食品中的含量检测方法研究具有重要的实际意义。
目前，硫化氢含量测定的方法有亚甲基蓝分光光度法、荧光光度法测定、顶空气相色谱法、气相分子吸收光谱法等。在各种方法中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。
萘酚类化合物具有较强的荧光强度，成为荧光探针使用非常广泛的荧光基团之一。
发明内容
本发明目的是提供一种萘酚类硫化氢荧光探针，它适于在食品、药品、化妆品等产品中检测硫化氢。
更具体的是，本发明涉及一种萘酚类硫化氢荧光探针，它通过下式表示：
Figure BSA0000149585620000011
附图说明
图1是在磷酸缓冲盐溶液中，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：半胱氨酸的浓度。
图2是在磷酸缓冲盐溶液中，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。
具体实施方式
实施例1.萘酚类硫化氢荧光探针的制备
合成路线如下式所示：
Figure BSA0000149585620000021
将1.01g(6mmol)6-氰基-2-萘酚(1)与1.60g(6mmol)2，4-二硝基苯磺酰氯(2)加入到50mL三口烧瓶中，再将一滴三乙胺加入到其中，加入10mL三氯甲烷，加热回流2h。后将温度降至室温，甲醇重结晶得黄色晶体1.97g，产率82.4％。
产物经过核磁氢谱及核磁碳谱表征。
1H NMR(600MHz，DMSO)，δ(ppm)：9.14(d，J＝2.3Hz，1H)，8.66(s，1H)，8.59(dd，J＝8.7Hz，J＝2.3Hz，1H)，8.28(d，J＝8.7Hz，1H)，8.17(d，J＝8.8Hz，2H)，7.96(d，J＝2.4Hz，1H)，7.88(dd，J＝8.5Hz，J＝1.4Hz，1H)，7.50(dd，J＝9.0Hz，J＝2.4Hz，1H)；13C NMR(125MHz，DMSO)：δ(ppm)：162.08，148.63，148.61，135.20，134.82，134.15，132.15，131.28，131.11，130.08，128.0，128.03，122.81，121.66，120.62，119.22，110.04.
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。
实施例2.萘酚类硫化氢荧光探针定量检测葡萄酒中硫化氢含量
将20μL萘酚类硫化氢荧光探针，480μL DMSO，1.5mL pH＝7.4的缓冲溶液加入到比色皿。再将20μL葡萄酒样加入，25℃条件下反应40分钟，以330nm激发波长进行荧光检测，再分别添加10μM、15μM硫化氢标准溶液，进行荧光检测，根据荧光强度与浓度的标准曲线，将上述检测值换算成硫化氢浓度，计算添加回收率。所测葡萄酒样硫化氢浓度为2.32μM，添加标准溶液后样品浓度分别为11.15μM、15.57μM，添加回收率分别为91％，93％。
依据实施例2可证明本发明的萘酚类硫化氢荧光探针可用于葡萄酒中硫化氢含量测定。

Claims (2)

1.一种萘酚类硫化氢荧光探针，具体化学结构式如下所示：
Figure FSA0000149585610000011
2.权利要求1所述荧光探针在食品、药品、化妆品中检测硫化氢的应用。
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104447421A (zh) * 2014-10-28 2015-03-25 苏州罗兰生物科技有限公司 一种新型半胱氨酸和同型半胱氨酸荧光探针的制备与应用
CN104531136A (zh) * 2014-12-29 2015-04-22 大连理工常熟研究院有限公司 一种用于识别苯硫酚的特异性荧光探针及其应用
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

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104447421A (zh) * 2014-10-28 2015-03-25 苏州罗兰生物科技有限公司 一种新型半胱氨酸和同型半胱氨酸荧光探针的制备与应用
CN104531136A (zh) * 2014-12-29 2015-04-22 大连理工常熟研究院有限公司 一种用于识别苯硫酚的特异性荧光探针及其应用
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

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