CN105777591A - 一种姜黄素衍生物及其制备和在检测苯硫酚中的应用 - Google Patents

一种姜黄素衍生物及其制备和在检测苯硫酚中的应用 Download PDF

Info

Publication number
CN105777591A
CN105777591A CN201610153393.9A CN201610153393A CN105777591A CN 105777591 A CN105777591 A CN 105777591A CN 201610153393 A CN201610153393 A CN 201610153393A CN 105777591 A CN105777591 A CN 105777591A
Authority
CN
China
Prior art keywords
dnsc
fluorescence
thf solution
preparation
solution
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
CN201610153393.9A
Other languages
English (en)
Other versions
CN105777591B (zh
Inventor
岳永康
霍方俊
阴彩霞
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.)
Shanxi University
Original Assignee
Shanxi 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 Shanxi University filed Critical Shanxi University
Priority to CN201610153393.9A priority Critical patent/CN105777591B/zh
Publication of CN105777591A publication Critical patent/CN105777591A/zh
Application granted granted Critical
Publication of CN105777591B publication Critical patent/CN105777591B/zh
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
    • C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
    • 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"
    • 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
    • C09K2211/1007—Non-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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B

Landscapes

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

Abstract

本发明提供了一种姜黄素衍生物及其制备和在检测苯硫酚中的应用，所述姜黄素衍生物，名称为bis(2,4‑dinitrobenzenesulfonate)‑curcumin，缩写为DNSC；所述苯硫酚包括苯硫酚衍生物。本发明提供了快速检测苯硫酚及其衍生物的方法，是基于姜黄素衍生物DNSC，在HEPES/MeOH(v/v,1:1,pH 7.4)溶液中定量地检测苯硫酚或其衍生物的含量。DNSC对苯硫酚及其衍生物显示了高的灵敏性和选择性，检测方法过程简便、灵敏、快速，检测结果准确。

Description

一种姜黄素衍生物及其制备和在检测苯硫酚中的应用
技术领域：
本发明涉及苯硫酚及其衍生物检测分析技术，具体涉及一种姜黄素衍生物及其制备方法和在检测苯硫酚(包括苯硫酚衍生物)中的应用。
背景技术：
苯硫酚及其衍生物是一类具有活性巯基的高毒性芳香类化合物，其广泛应用于农药、医药生产和高分子聚合物合成。报道表明，苯硫酚在鱼类体内的半数致死浓度为0.01-0.4mM(Hell,T.P.,Lindsay,R.C.Toxicologicalpropertiesofthio-andalkylphenolscausingflavortaintinginfishfromtheupperWisconsinRiver[J].J.Environ.Sci.HealthB,1989,24,349360；Amrolia,P.,Sullivan,S.G.,Stern,A.,Munday,R.Toxicityofaromaticthiolsinthehumanredbloodcell[J].J.Appl.Toxicol.,1989,9,113-118)。人体暴露于苯硫酚蒸气中会引起包括中枢神经系统损伤、肢体麻痹、昏迷甚至死亡等一系列严重机体损害(R.Munday,Toxicityofaromaticdisulphides.I.Generationofsuperoxideradicalandhydrogenperoxidebyaromaticdisulphidesinvitro[J].J.Appl.Toxicol.,1985,5,402-408)。目前，苯硫酚及其衍生物已被美国环境保护局列为严重污染物。快速、准确地检测样品中的苯硫酚及其衍生物的含量对于环境监测和生物体健康评估具有极其重要的意义。
荧光探针对苯硫酚衍生物的检测识别广受化学工作者重视。济南大学林伟英教授于2010年最早报道了具有二硝基苯酚醚结构的荧光探针对苯硫酚的识别检测，但该探针受到脂肪族硫醇Cys、Hcy等的干扰(Lin,W.Y.,Long,L.L.,Tan,W.Ahighlysensitivefluorescentprobefordetectionofbenzenethiolsinenvironmentalsamplesandlivingcells.Chem.Commun.,2010,46,1503–1505)。后来，新墨西哥大学Wang教授报道的利用2,4-二硝基苯磺酰胺基团实现了荧光探针对苯硫酚及其衍生物的特异识别(Jiang,W.,Cao,Y.T.Liu,Y.Wang,W.RationaldesignofahighlyselectiveandsensitivefluorescentPETprobefordiscriminationofthiophenolsandaliphaticthiols.Chem.Commun.,2010,46,1944–1946)。但此结构对苯硫酚的识别检测存在着反应过慢的缺陷(通常反应时间处于20-30min之间)，这给易被氧化的苯硫酚的检测带来了不可避免的误差。
针对此现状，我们利用活性较高的2,4-二硝基苯磺酰酯作为识别位点，设计合成了一种姜黄素衍生物DNSC(bis(2,4-dinitrobenzenesulfonate)-curcumin)用于苯硫酚及其衍生物的特异荧光识别检测。该探针对苯硫酚及其衍生物的检测是基于苯硫酚活性巯基对2,4-二硝基苯磺酰酯反应单元的芳香亲核取代(SNAr)过程。
发明内容：
本发明的目的是提供一种姜黄素衍生物及其制备方法，该衍生物可作为检测试剂用于定量检测苯硫酚及其衍生物；在检测苯硫酚及其衍生物时选择性高，响应速度快。
本发明提供的一种姜黄素衍生物，名称为bis(2,4-dinitrobenzenesulfonate)-curcumin，缩写为DNSC，结构式为：
姜黄素衍生物对苯硫酚及其衍生物显示了优良的灵敏性和选择性，检测过程简便、灵敏、快速，检测结果准确。
DNSC的制备：将姜黄素、三乙胺溶于氯仿中，搅拌回流10min后，向体系中逐渐滴加2,4-二硝基苯磺酰氯的氯仿溶液。滴加完毕后回流5小时反应完全。体系冷却到室温后抽滤，甲醇洗涤，滤饼经干燥，得到粗产品。粗产品经柱色谱分离(按体积比乙酸乙酯:石油醚＝1:1)得到黄色纯品。姜黄素、三乙胺和2,4-二硝基苯磺酰氯的摩尔比为1:2-3:2。反应式：
DNSC检测4-甲基苯硫酚(MTP)的方法，步骤为：
(1)、配制pH＝7.4、浓度为10mM的HEPES缓冲溶液，配制2mMDNSC的THF溶液，配制2mMMTP的THF溶液；
(2)、按体积比40:1，将体积比1:1,pH7.4的HEPES/MeOH溶液和DNSC的THF溶液加到干净的荧光比色皿中，在荧光分光光度仪上检测，随着待测样MTP的加入，536nm的荧光强度逐渐增强；
(3)、取2mL体积比1:1,pH7.4的HEPES/MeOH溶液、50μLDNSC的THF溶液加到另一个荧光比色皿中，分别加入体积为0、5、10、15、20、25、30、35、40μL的MTP的THF溶液时，在荧光分光光度仪上测定536nm对应的荧光强度F为102、293、473、694、914、1094、1277、1495、1706，以MTP浓度为横坐标，以相对荧光强度F–F0为纵坐标绘制图，F0＝102，得到MTP浓度的工作曲线；线性回归方程为：F–F0＝40.11c–10.10，c的单位为μM；
(4)、取2mL体积比1:1,pH7.4的HEPES/MeOH溶液、50μLDNSC的THF溶液加入荧光比色皿中，用微量进样器吸取VμL待测样品溶液，加入到此干净的荧光比色皿中，在荧光分光光度仪上检测，将测得的荧光强度代入步骤(3)的线性回归方程，得到浓度c，待测样品MTP浓度C待测样＝(2000+50+V待测样)×c×10-6/V，单位M。
所述的MTP可以用苯硫酚或其它苯硫酚衍生物替代。
与现有技术相比，本发明具有如下有益效果：1、检测体系成本低廉，试剂由天然药物姜黄素和2,4-二硝基苯磺酰氯一步合成，原料便宜，反应条件简单，易于大规模生产；2、本发明的检测方法对苯硫酚及其衍生物显示出高的选择性和灵敏性，其它脂肪族硫醇对苯硫酚及其衍生物的测定没有干扰；3、检测方法响应迅速，检测结果准确；4、检测过程在水溶液中进行；5、检测手段简单，只需要借助荧光分光光度仪即可实现。
附图说明：
图1实施例1DNSC与MTP作用的荧光发射图
图2实施例2DNSC与各种分析物作用的荧光柱状图
图3实施例3测定MTP的工作曲线
图4实施例4测定MTP的动力学图
图5实施例5测定样品的荧光发射图
图6a实施例6制备的姜黄素衍生物的氢谱表征
图6b实施例6制备的姜黄素衍生物的碳谱表征
图6c实施例6制备的姜黄素衍生物的质谱表征
具体实施方式：
实施例1
配制pH＝7.4、浓度为10mM的HEPES缓冲溶液，配制2mMDNSC的THF溶液，配制2mMMTP的THF溶液；取2mL的HEPES/MeOH(v/v,1:1,pH7.4)溶液、50μLDNSC的THF溶液加到一个荧光比色皿中，取MTP的THF溶液，逐渐用微量进样器加到此比色皿中，边加样边在荧光分光光度仪上检测(404nm激发)，随着MTP的加入，536nm处荧光强度逐渐增强。荧光发射图见图1。
实施例2
配制pH＝7.4、浓度为10mM的HEPES缓冲溶液，配制2mMDNSC的THF溶液，分别配制2mMMTP，2mMthiophenol，2mM2-aminobenzenethiol,20mMphenol,20mManiline的THF溶液及20mMCys,Hcy,GSH,mercaptoethanol,NaHS,NaHSO3,NaCN,NaSCN,NaCl的水溶液；在14个荧光比色皿中，各加入2mL的HEPES/MeOH(v/v,1:1,pH7.4)溶液、50μLDNSC的THF溶液，再分别加入1摩尔当量的MTP，thiophenol，2-aminobenzenethiol以及50摩尔当量的各种分析物：phenol，aniline，Cys,Hcy,GSH,mercaptoethanol,NaHS,NaHSO3,NaCN,NaSCN,NaCl在荧光分光光度仪上检测(404nm激发)，绘制不同分析物对应的536nm处荧光强度的柱状图，(见图2)。MTP，thiophenol，2-aminobenzenethiol使得检测体系的荧光强度明显升高，其它的分析物没有引起检测体系荧光强度的变化。
经实验证明，其它分析物不干扰体系对苯硫酚及其衍生物的测定。
实施例3
配制pH＝7.4、浓度为10mM的HEPES缓冲溶液，配制2mMDNSC的THF溶液，配制2mMMTP的THF溶液；取2mL的HEPES/MeOH(v/v,1:1,pH7.4)溶液、50μLDNSC的THF溶液加到一个荧光比色皿中，分别在加入0、5、10、15、20、25、30、35、40μL的MTP的THF溶液时，在荧光分光光度仪上测定536nm对应的荧光强度F为102、293、473、694、914、1094、1277、1495、1706(404nm激发)，以MTP浓度为横坐标，以相对荧光强度F–F0为纵坐标绘制图，F0＝102，得到MTP浓度的工作曲线(见图3)；线性回归方程为：F–F0＝40.11c–10.10，c的单位为μM；
实施例4
配制pH＝7.4、浓度为10mM的HEPES缓冲溶液，配制2mMDNSC的THF溶液，配制2mMMTP的THF溶液；取2mL的HEPES/MeOH(v/v,1:1,pH7.4)溶液、50μLDNSC的THF溶液加到一个荧光比色皿中，加入10摩尔当量MTP的THF溶液，同时在荧光分光光度仪上测定536nm处荧光强度F随时间的变化(见图4)。经实验证明，该检测方法对MTP响应迅速。
实施例5
配制pH＝7.4、浓度为10mM的HEPES缓冲溶液，配制2mMDNSC的THF溶液，配制2mMMTP的THF溶液；取2mL的HEPES/MeOH(v/v,1:1,pH7.4)溶液、50μLDNSC的THF溶液加到一个荧光比色皿中，取MTP的THF溶液28μL，用微量进样器加到此比色皿中，同时在荧光光度仪上测定536nm的对应的荧光强度F为1199(404nm激发)，相对荧光强度F–F0＝1097，通过实施例3的线性回归方程，求得c＝27.60×10-6mol/L，偏差为1.43％。见图5。
实施例6
姜黄素衍生物的制备及表征：
取姜黄素(1mmol,0.368g),三乙胺(3equiv.)溶于20mL氯仿中。搅拌回流10min后，向体系中逐渐滴加2,4-二硝基苯磺酰氯(2equiv.)的氯仿溶液。滴加完毕后回流5小时反应完全。体系冷却到室温后抽滤，甲醇洗涤干燥，得到粗产品。粗产品经柱色谱分离(乙酸乙酯:石油醚＝1:1)得到黄色纯品。
1HNMR(600MHz,DMSO-d6):δ9.09(s,2H),8.66(d,J＝8.6Hz,2H),8.30(d,J＝8.8Hz,2H),7.64(d,J＝15.8Hz,2H),7.54(s,2H),7.36(d,J＝8.3Hz,2H),7.29(d,J＝8.5Hz,2H),7.04(d,J＝16.0Hz,2H),6.19(s,1H),3.59(s,6H)(图6a)。13CNMR(151MHz,DMSO-d6):δ183.5,151.7,151.6,148.2,139.9,138.9,136.3,133.4,132.9,127.8,126.4,124.6,121.9,121.2,113.4,102.6,56.4(图6b)。HRMS[M-H]-:m/zCalcd827.0454,Found827.0468(图6c)。

Claims (5)

1.一种姜黄素衍生物DNSC，其特征在于，结构式为：
2.如权利要求1所述的一种姜黄素衍生物DNSC的制备方法，其特征在于，包括如下步骤：将姜黄素、三乙胺溶于氯仿中，搅拌回流10min后，向体系中逐渐滴加2,4-二硝基苯磺酰氯的氯仿溶液，滴加完毕后回流5小时反应完全；体系冷却到室温后抽滤，甲醇洗涤，滤饼经干燥，得到粗产品；粗产品经柱色谱分离，洗脱剂为体积比1:1的乙酸乙酯和石油醚，得到黄色纯品。
3.如权利要求2所述的姜黄素衍生物DNSC的制备方法，其特征在于，所述的姜黄素、三乙胺和2,4-二硝基苯磺酰氯的摩尔比为1:2-3:2。
4.一种快速检测苯硫酚及其衍生物的方法，其特征在于，步骤为：
(1)、配制pH＝7.4、浓度为10mM的HEPES缓冲溶液，配制2mM姜黄素衍生物DNSC的THF溶液，配制2mM4-甲基苯硫酚的THF溶液；
(2)、按体积比40:1，将体积比1:1,pH7.4的HEPES/MeOH溶液和DNSC的THF溶液加到干净的荧光比色皿中，在荧光分光光度仪上检测，随着待测样4-甲基苯硫酚的THF溶液的加入，536nm的荧光强度逐渐增强；
(3)、取2mL的体积比1:1,pH7.4的HEPES/MeOH溶液、50μLDNSC的THF溶液加到另一个荧光比色皿中，分别加入体积为0、5、10、15、20、25、30、35、40μL的4-甲基苯硫酚的THF溶液时，在荧光分光光度仪上测定536nm对应的荧光强度F为102、293、473、694、914、1094、1277、1495、1706，以4-甲基苯硫酚的浓度为横坐标，以相对荧光强度F–F0为纵坐标绘制图，F0＝102，得到4-甲基苯硫酚浓度的工作曲线；线性回归方程为：F–F0＝40.11c–10.10，c的单位为μM；
(4)、取2mL的体积比1:1,pH7.4的HEPES/MeOH溶液、50μLDNSC的THF溶液加入荧光比色皿中，用微量进样器吸取VμL待测样品溶液，加入到此干净的荧光比色皿中，在荧光分光光度仪上检测，将测得的荧光强度代入步骤(3)的线性回归方程，得到浓度c，待测样品4-甲基苯硫酚的浓度C待测样＝(2000+50+V待测样)×c×10-6/V，单位M。
5.如权利要求4所述的检测苯硫酚及其衍生物的方法，其特征在于，所述的4-甲基苯硫酚用苯硫酚或其它苯硫酚衍生物替代。
CN201610153393.9A 2016-03-17 2016-03-17 一种姜黄素衍生物及其制备和在检测苯硫酚中的应用 Expired - Fee Related CN105777591B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610153393.9A CN105777591B (zh) 2016-03-17 2016-03-17 一种姜黄素衍生物及其制备和在检测苯硫酚中的应用

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610153393.9A CN105777591B (zh) 2016-03-17 2016-03-17 一种姜黄素衍生物及其制备和在检测苯硫酚中的应用

Publications (2)

Publication Number Publication Date
CN105777591A true CN105777591A (zh) 2016-07-20
CN105777591B CN105777591B (zh) 2017-06-23

Family

ID=56393861

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610153393.9A Expired - Fee Related CN105777591B (zh) 2016-03-17 2016-03-17 一种姜黄素衍生物及其制备和在检测苯硫酚中的应用

Country Status (1)

Country Link
CN (1) CN105777591B (zh)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106543202A (zh) * 2016-10-31 2017-03-29 湖南师范大学 一种新型检测苯硫酚荧光分子探针的制备方法和应用
CN111073633A (zh) * 2018-10-22 2020-04-28 北京工商大学 一种萘环类苯硫酚荧光探针

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4985333A (en) * 1988-04-22 1991-01-15 Tokyo Ohka Kogyo Co., Ltd. Positive-working photosensitive composition with three difference 1,2-naphthoquinone diazide sulfonic acid esters to include the ester of curcumin
CN103351335A (zh) * 2013-05-28 2013-10-16 中南大学 一种荧光增强检测含巯基氨基酸的荧光分子探针的合成及应用
CN103589423A (zh) * 2013-11-20 2014-02-19 陕西省计量科学研究院 一种含n,n-二乙基对甲氨基酚的荧光探针及其在检测苯硫酚中的应用
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
CN104804728A (zh) * 2015-04-27 2015-07-29 苏州罗兰生物科技有限公司 一种荧光增强型苯硫酚荧光探针的制备及应用
CN105348214A (zh) * 2015-12-02 2016-02-24 齐鲁工业大学 一种苯并恶嗪酮类苯硫酚荧光探针及其制备方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4985333A (en) * 1988-04-22 1991-01-15 Tokyo Ohka Kogyo Co., Ltd. Positive-working photosensitive composition with three difference 1,2-naphthoquinone diazide sulfonic acid esters to include the ester of curcumin
CN103351335A (zh) * 2013-05-28 2013-10-16 中南大学 一种荧光增强检测含巯基氨基酸的荧光分子探针的合成及应用
CN103589423A (zh) * 2013-11-20 2014-02-19 陕西省计量科学研究院 一种含n,n-二乙基对甲氨基酚的荧光探针及其在检测苯硫酚中的应用
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
CN104804728A (zh) * 2015-04-27 2015-07-29 苏州罗兰生物科技有限公司 一种荧光增强型苯硫酚荧光探针的制备及应用
CN105348214A (zh) * 2015-12-02 2016-02-24 齐鲁工业大学 一种苯并恶嗪酮类苯硫酚荧光探针及其制备方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
AYA SHIBATA等: "Rhodamine-based fluorogenic probe for imaging biological thiol", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106543202A (zh) * 2016-10-31 2017-03-29 湖南师范大学 一种新型检测苯硫酚荧光分子探针的制备方法和应用
CN106543202B (zh) * 2016-10-31 2018-08-07 湖南师范大学 一种新型检测苯硫酚荧光分子探针的制备方法和应用
CN111073633A (zh) * 2018-10-22 2020-04-28 北京工商大学 一种萘环类苯硫酚荧光探针

Also Published As

Publication number Publication date
CN105777591B (zh) 2017-06-23

Similar Documents

Publication Publication Date Title
Li et al. An aza-coumarin-hemicyanine based near-infrared fluorescent probe for rapid, colorimetric and ratiometric detection of bisulfite in food and living cells
Zhang et al. Lysosomal-targeted two-photon fluorescent probe to sense hypochlorous acid in live cells
Yang et al. A NIR ratiometric probe for hydrazine “naked eye” detection and its imaging in living cell
Zeng et al. A distinctive mitochondrion-targeting, in situ-activatable near-infrared fluorescent probe for visualizing sulfur dioxide derivatives and their fluctuations in vivo
Dai et al. A simple and effective coumarin-based fluorescent probe for cysteine
Park et al. A near-infrared “turn-on” fluorescent probe with a self-immolative linker for the in vivo quantitative detection and imaging of hydrogen sulfide
Dai et al. An effective colorimetric and ratiometric fluorescent probe for bisulfite in aqueous solution
Liu et al. Mitochondria-targeted and FRET based ratiometric fluorescent probe for SO2 and its cell imaging
Guan et al. A near-infrared fluorescent sensor for selective detection of cysteine and its application in live cell imaging
Shang et al. Development of a two-photon fluorescent turn-on probe with far-red emission for thiophenols and its bioimaging application in living tissues
Yu et al. A colorimetric and near-infrared fluorescent probe for biothiols and its application in living cells
Wang et al. A highly sensitive and selective near-infrared fluorescent probe for imaging hydrazine in living tissues and mice
Chen et al. A novel fluorescent probe for sensitive detection and imaging of hydrazine in living cells
Li et al. A ratiometric fluorescent probe for fast detection of hydrogen sulfide and recognition of biological thiols
Wu et al. A new fluorescent chemodosimeter for ultra-sensitive determination of toxic thiophenols in environmental water samples and cancer cells
Wang et al. A novel pyrazoline-based selective fluorescent probe for detecting reduced glutathione and its application in living cells and serum
Hou et al. Development of fluorescent probes for hydrogen polysulfides by using cinnamate ester as the recognition unit
Yang et al. A novel mitochondria-targeted ratiometric fluorescent probe for endogenous sulfur dioxide derivatives as a cancer-detecting tool
Yu et al. A colorimetric and near-infrared fluorescent turn-on probe for in vitro and in vivo detection of thiophenols
Wang et al. A mitochondria-targeted ratiometric probe for the fluorescent and colorimetric detection of SO2 derivatives in live cells
Hong et al. A dicyanoisophorone-based near-infrared fluorescent probe and its application for detecting thiophenols in water and living cells
CN110015992A (zh) 一种用于二氧化硫/亚硫酸(氢)盐检测的荧光探针及其制备方法和应用
CN109678763A (zh) 一种近红外生物硫醇荧光探针及其制备方法和应用
CN105622624A (zh) 一种罗丹明b衍生物、制备方法及其作为荧光探针的应用
Xu et al. A highly selective ratiometric fluorescent and chromogenic probe for sulfite and its applications in imaging of living cells and zebrafish in vivo

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20170623

Termination date: 20200317