CN109422721A - 一种硫化氢荧光探针 - Google Patents

一种硫化氢荧光探针 Download PDF

Info

Publication number
CN109422721A
CN109422721A CN201710728327.4A CN201710728327A CN109422721A CN 109422721 A CN109422721 A CN 109422721A CN 201710728327 A CN201710728327 A CN 201710728327A CN 109422721 A CN109422721 A CN 109422721A
Authority
CN
China
Prior art keywords
hydrogen sulfide
fluorescence probe
fluorescence
concentration
beer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201710728327.4A
Other languages
English (en)
Other versions
CN109422721B (zh
Inventor
杨绍祥
田红玉
刘永国
孙宝国
王嘉琳
王皓
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Beijing Technology and Business University
Original Assignee
Beijing Technology and Business University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Beijing Technology and Business University filed Critical Beijing Technology and Business University
Priority to CN201710728327.4A priority Critical patent/CN109422721B/zh
Publication of CN109422721A publication Critical patent/CN109422721A/zh
Application granted granted Critical
Publication of CN109422721B publication Critical patent/CN109422721B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Immunology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Optics & Photonics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)

Abstract

本发明公开了一种硫化氢荧光探针，具体化学结构式如下式所示：

Description

一种硫化氢荧光探针
技术领域
本发明涉及一种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，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。低浓度的硫化氢对眼、呼吸系统及中枢神经都有影响。
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。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。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。
萘环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.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0.88g(6mmol)2-噻吩甲酰氯(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4h。后将温度降至室温，甲醇重结晶得黄色晶体1.37g，产率82.12％。
产物经过核磁氢谱及核磁碳谱表征。
1H NMR(600MHz，DMSO)，δ(ppm)：8.66(s，1H)，8.18(d，J＝8.8Hz，1H)，8.14(m，2H)，8.10(dd，J＝3.7Hz，J＝1.0Hz，1H)，8.02(d，J＝2.16Hz，1H)，7.85(dd，J＝8.46Hz，J＝1.44Hz，1H)，7.67(dd，J＝8.8Hz，J＝2.16Hz，1H)，7.35(dd，J＝4.74Hz，J＝1.0Hz，1H).13CNMR(125MHz，DMSO)：δ(ppm)：160.46，150.73，135.24，136.06，135.45，134.77，131.93，130.89，130.51，129.59，129.35，127.64，123.96，119.68，119.53，108.89.
本发明的荧光探针的荧光强度随着硫化氢浓度的变化如图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.硫化氢荧光探针定量检测啤酒中硫化氢含量
将20μL硫化氢荧光探针，480μLDMSO，1.5mLpH＝7.4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332nm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0.79μM，添加标准溶液后样品浓度分别为4.66μM、10.13μM，添加回收率分别为93％，94％。
依据实施例2可证明本发明的硫化氢荧光探针可用于啤酒中硫化氢含量测定。

Claims (2)

1.一种硫化氢荧光探针，具体化学结构式如下所示：
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。
CN201710728327.4A 2017-08-23 2017-08-23 一种硫化氢荧光探针 Active CN109422721B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201710728327.4A CN109422721B (zh) 2017-08-23 2017-08-23 一种硫化氢荧光探针

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201710728327.4A CN109422721B (zh) 2017-08-23 2017-08-23 一种硫化氢荧光探针

Publications (2)

Publication Number Publication Date
CN109422721A true CN109422721A (zh) 2019-03-05
CN109422721B CN109422721B (zh) 2021-07-23

Family

ID=65498164

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201710728327.4A Active CN109422721B (zh) 2017-08-23 2017-08-23 一种硫化氢荧光探针

Country Status (1)

Country Link
CN (1) CN109422721B (zh)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
WO2016144774A1 (en) * 2015-03-06 2016-09-15 Shell Oil Company Methods of measuring hydrogen sulfide concentrations in reservoir fluids

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016144774A1 (en) * 2015-03-06 2016-09-15 Shell Oil Company Methods of measuring hydrogen sulfide concentrations in reservoir fluids
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

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
NEIL L.等: ""Nematic 2,5-disubstituted thiophenes"", 《J. MATER. CHEM.》 *
XIN ZHOU等: ""Recent Progress on the Development of Chemosensors for Gases"", 《CHEMICAL REVIEWS》 *
李思吾等: ""硫化氢荧光探针"", 《大学化学》 *
顾月清等主编: "《生物医学工程技术》", 30 June 2017, 中国医药科技出版社 *
高敏等: ""检测硫化氢分子的荧光探针"", 《化学进展》 *

Also Published As

Publication number Publication date
CN109422721B (zh) 2021-07-23

Similar Documents

Publication Publication Date Title
Turan et al. Quorum sensing: Little talks for an effective bacterial coordination
Lv et al. Label-free aptasensor for ochratoxin A detection using SYBR Gold as a probe
Li et al. A hand-held optoelectronic nose for the identification of liquors
Zeng et al. Determination of melamine by flow injection analysis based on chemiluminescence system
CN109406475A (zh) 双标记快速响应核酸适配体探针及其检测黄曲霉毒素b1的方法
Goud et al. Tetramethyl-6-carboxyrhodamine quenching-based aptasensing platform for aflatoxin B1: Analytical performance comparison of two aptamers
Khan et al. Switchable fluorescence sensor toward PAT via CA-MWCNTs quenched aptamer-tagged carboxyfluorescein
CN106018624B (zh) 食品中亚硝胺的hplc检测方法
Huang et al. Sensitive turn-on fluorescent detection of tartrazine based on fluorescence resonance energy transfer
Takase et al. Analysis of rotundone in Japanese Syrah grapes and wines using stir bar sorptive extraction (SBSE) with heart-cutting two-dimensional GC-MS
CN113278015B (zh) 一种荧光探针及其制备方法和应用
Rong et al. Ratiometric upconversion fluorometric turn-off nanosensor for quantification of furfural in foods
CN105987893A (zh) 一种利用石墨烯量子点荧光检测血红素的方法
CN110204564A (zh) 一种检测氰根离子的荧光探针及其制备方法和应用
Zeußel et al. Colorimetric Method for Instant Detection of Lysine and Arginine Using Novel Meldrum's Acid‐Furfural Conjugate
Ohtsuki et al. Absolute quantification of dehydroacetic acid in processed foods using quantitative 1H NMR
Dou et al. An indirect competitive fluorescence assay for ochratoxin A based on molecular beacon
CN109422738A (zh) 一种香豆素类硫化氢荧光探针
Li et al. Fluorescence-based aptasensors for small molecular food contaminants: From energy transfer to optical polarization
Ma et al. A versatile Y shaped DNA nanostructure for simple, rapid and one-step detection of mycotoxins
Zhang et al. Development of a graphene oxide nanosheet and double-stranded DNA structure based fluorescent “signal off” aptasensor for ochratoxin A detection in malt
CN109400563B (zh) 一种次氯酸荧光探针及其制备方法和应用
Ghanem et al. Differentiation and identification of cachaça wood extracts using peptide-based receptors and multivariate data analysis
Lu et al. Development and validation of a label-free colorimetric aptasensor based on the HCR and hemin/G-quadruplex DNAzyme for the determination of patulin in fruits and fruit-based products from Xinjiang (China)
CN109422721A (zh) 一种硫化氢荧光探针

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant