CN109422667B - 一种萘甲腈类硫化氢荧光探针 - Google Patents
一种萘甲腈类硫化氢荧光探针 Download PDFInfo
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Abstract
本发明公开了一种萘甲腈类硫化氢荧光探针,具体化学结构式如下式所示:
Description
技术领域
本发明涉及一种萘甲腈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,低浓度的硫化氢对眼、呼吸***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。
由于葡萄酒自身的强还原作用,在葡萄酒的贮藏过程中,一些硫化物会转化为硫化氢。硫化氢是啤酒中主要的硫化物之一,其味阈值为10μg/L,对啤酒风味影响很大,优质成熟啤酒含量为(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。所以,当硫化氢含量较高时不仅会对啤酒、葡萄酒本身的品质产生影响,也存在一定的食品安全问题。所以开展硫化氢在酒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顶空气相色谱法、亚甲基蓝分光光度法、荧光光度法测定、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。
萘甲腈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甲腈类硫化氢荧光探针,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,本发明涉及一种萘甲腈类硫化氢荧光探针,它通过下式表示:
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.萘甲腈类硫化氢荧光探针的制备
合成路线如下式所示:
将1.01g(6mmol)6-羟基-2-萘甲腈(1)与1.12g(6mmol)2,4-二硝基氟苯(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5h。后将温度降至室温,甲醇重结晶得黄色晶体1.67g,产率83.5%。
产物经过核磁氢谱及核磁碳谱表征。
1H NMR(600MHz,DMSO),δ(ppm):8.94(d,J=2.79Hz,1H),8.65(s,1H),8.47(dd,J=9.21Hz,J=2.79Hz,1H),8.23(d,J=9.03Hz,1H),8.08(d,J=8.61Hz,1H),7.85(m,2H),7.62(dd,J=9.03Hz,J=2.46Hz,1H),7.39(d,J=9.21Hz,1H).13C NMR(125MHz,DMSO),δ(ppm):154.80,154.34,142.71,140.52,135.95,134.80,132.27,130.21,130.18,129.44,127.95,122.44,121.85,121.46,119.45,116.60,108.78.
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.萘甲腈类硫化氢荧光探针定量检测啤酒中硫化氢含量
将20μL萘甲腈类硫化氢荧光探针,480μL DMSO,1.5mL pH=7.0的缓冲溶液加入到比色皿。再将20μL啤酒样加入,25℃条件下反应15分钟,以287nm激发波长进行荧光检测,再分别添加5μM、10μM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。所测啤酒样硫化氢浓度为1.82μM,添加标准溶液后样品浓度分别为6.26μM、11.16μM,添加回收率分别为92%,95%。
依据实施例2可证明本发明的萘甲腈类硫化氢荧光探针可用于啤酒中硫化氢含量测定。
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