CN110724069A - 一种萘甲腈类甲醛荧光探针 - Google Patents

一种萘甲腈类甲醛荧光探针 Download PDF

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CN110724069A
CN110724069A CN201810774838.4A CN201810774838A CN110724069A CN 110724069 A CN110724069 A CN 110724069A CN 201810774838 A CN201810774838 A CN 201810774838A CN 110724069 A CN110724069 A CN 110724069A
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formaldehyde
fluorescent probe
naphthalocyanine
formaldehyde fluorescent
food
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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

本发明公开了一种萘甲腈类甲醛荧光探针，具体化学结构式如下所示：

Description

一种萘甲腈类甲醛荧光探针
技术领域
本发明涉及一种萘甲腈类甲醛荧光探针以及其在检测甲醛中的应用。
背景技术
甲醛是最简单的醛，被认为是潜在的强致突变物质之一，早已经被世界卫生组织定为致癌和致畸物质。最新研究证明，甲醛与淋巴细胞增殖存在剂量-效应关系，低浓度时对细胞增殖起促进作用，高浓度时会引起细胞异常增值，具有潜在的致癌性。甲醛还是许多活生物体中的代谢中间体，并用作组织固定剂和防腐剂。正常生理***中内源性甲醛的产生是通过组蛋白去甲基化，DNA甲基化和氨基脲敏感性胺氧化酶产生的。在正常的生理大脑中，甲醛的浓度范围为0.2-0.4毫摩尔/L。在这个水平上，甲醛对通过DNA去甲基化循环和认知能力的记忆形成至关重要。相反，患者甲醛异常累积可能会诱发多种疾病，包括癌症，神经退行性疾病，糖尿病，慢性肝脏和心脏病。食物中甲醛含量的测定以及检测方法越来越受到关注。食物中含有甲醛，如蔬菜、水果、肉类和海鲜，这些食物中存在微量的甲醛是正常现象，是由自身细胞代谢产生的内源性甲醛，一般含量很少。此外，甲醛因其具有防腐功能，虽然国家食药监总局已经明确禁止将甲醛用作食品防腐剂，但还是有不法商贩将其用作食品防腐剂。研究表明，在食品包装、储存和运输过程中的甲醛残留物可能对人体健康产生严重威胁。
近年来，许多甲醛响应荧光探针已经被国外报道和用来进行可视化活细胞中的甲醛含量的检测，但其在食品甲醛含量的检测中应用较少。
发明内容
本发明目的是提供一种萘甲腈类甲醛荧光探针，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甲醛荧光探针，它通过下式表示：
Figure BSA0000167183410000011
附图说明
图1是在磷酸缓冲盐溶液中，随着不同浓度甲醛的加入，本发明的荧光探针(10μM)的荧光强度变化。嵌入图：甲醛的浓度。
图2是在磷酸缓冲盐溶液中，本发明的荧光探针(10μM)荧光强度随着甲醛浓度变化的标准曲线。
具体实施方式
实施例1.萘甲腈类甲醛荧光探针的制备
合成路线如下式所示：
Figure BSA0000167183410000021
在50mL的三口烧瓶中依次加入6-羟基-2-萘甲腈(1.000g，6mmol)、K2CO3(1.658g，12mmol)、10mL丙酮，加热回流。恒压滴液漏斗缓慢滴加溶有溴乙酸乙酯的10mL丙酮溶液。回流3h，冷却至室温，蒸除溶剂得到燕麦状白色中间体3。将中间体3(1.180g，4.7mmol)、64％水合肼(2.507g，47mmol)加入到20mL甲醇溶液中，加热回流2.5h。得到的粗产物，蒸除溶剂后用甲醇洗三次，抽滤、烘干得1.080g白色粉末状固体产物，产率89％。产物经过核磁氢谱及核磁碳谱表征。1H NMR(600MHz，DMSO)，δ(ppm)：9.47(s，1H)，8.46(s，1H)，8.00(d，J＝8.9Hz，1H)，7.94(d，J＝8.9Hz，1H)，7.72(dd，J＝8.5Hz，J＝1.3Hz，1H)，7.42(m，2H)，4.67(s，2H)，4.37(s，2H).13C NMR(125MHz，DMSO)：δ(ppm)：166.65，158.60，136.41，134.43，130.65，128.57，128.04，127.44，121.07，119.90，107.79，106.42，66.00.
本发明的荧光探针的荧光强度随着甲醛的变化如图1所示，依据该变化可作出荧光探针(10μM)荧光强度随着甲醛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甲醛的定量检测。
实施例2.萘甲腈类甲醛荧光探针定量检测海带中甲醛含量
将购自超市的海带样品精确称取1.000g，搅碎后放入30mL样品瓶中，加入25mL超纯水室温浸提12h。将20μL萘甲腈类甲醛荧光探针，480μL DMSO，1.5mL pH＝7.0的缓冲溶液加入到比色皿。再将20μL浸提溶液加入，25℃条件下反应30分钟，以300nm激发波长进行荧光检测，再分别添加150μM、250μM甲醛标准溶液，进行荧光检测，根据荧光强度与甲醛浓度的标准曲线，将上述检测值换算成甲醛浓度，计算添加回收率。所测海带中甲醛浓度为12.62μM(0.7572mg/kg)，添加标准溶液后样品浓度分别为174.7μM、265.0μM，添加回收率分别为107.44％，100.90％。
依据实施例2可证明本发明的萘甲腈类甲醛荧光探针可用于食物中甲醛含量测定。

Claims (1)

1.一种萘甲腈类甲醛荧光探针，具体化学结构式如下所示：
Figure FSA0000167183400000011
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CN105542752A (zh) * 2015-12-14 2016-05-04 济南大学 一种甲醛荧光探针及其制备方法和应用
CN105542756A (zh) * 2016-02-03 2016-05-04 浙江理工大学 一种检测甲醛的荧光探针及其制备方法与应用
CN108047060A (zh) * 2017-12-01 2018-05-18 河南省农业科学院农业质量标准与检测技术研究所 一种识别检测甲醛的芘衍生物荧光探针分子及其制备方法和应用
CN108219776A (zh) * 2018-02-05 2018-06-29 三峡大学 一种增强型荧光探针、制备方法及在检测甲醛上的应用
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CN105542756A (zh) * 2016-02-03 2016-05-04 浙江理工大学 一种检测甲醛的荧光探针及其制备方法与应用
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