CN105445241B - 高选择性检测肼浓度的方法 - Google Patents
高选择性检测肼浓度的方法 Download PDFInfo
- Publication number
- CN105445241B CN105445241B CN201510755303.9A CN201510755303A CN105445241B CN 105445241 B CN105445241 B CN 105445241B CN 201510755303 A CN201510755303 A CN 201510755303A CN 105445241 B CN105445241 B CN 105445241B
- Authority
- CN
- China
- Prior art keywords
- hydrazine
- probe
- high selectivity
- sample
- fluorescence
- 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.)
- Active
Links
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 title claims abstract description 141
- 238000000034 method Methods 0.000 title claims abstract description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 5
- 239000008280 blood Substances 0.000 claims 3
- 210000004369 blood Anatomy 0.000 claims 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000523 sample Substances 0.000 abstract description 42
- -1 bromobutanoate tricyano furans styrene compounds Chemical class 0.000 abstract description 11
- 238000001514 detection method Methods 0.000 abstract description 8
- 238000004445 quantitative analysis Methods 0.000 abstract description 5
- 238000004451 qualitative analysis Methods 0.000 abstract description 4
- 238000002795 fluorescence method Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- GRHQDJDRGZFIPO-UHFFFAOYSA-N 4-bromobutanoic acid Chemical class OC(=O)CCCBr GRHQDJDRGZFIPO-UHFFFAOYSA-N 0.000 description 8
- 238000002189 fluorescence spectrum Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 239000012491 analyte Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000009834 vaporization Methods 0.000 description 4
- 230000008016 vaporization Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000370738 Chlorion Species 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 238000001506 fluorescence spectroscopy Methods 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- 229940005654 nitrite ion Drugs 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 238000007445 Chromatographic isolation Methods 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 229910017852 NH2NH2 Inorganic materials 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 238000011896 sensitive detection Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
Classifications
-
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
-
- 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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen 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 Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
本发明专利涉及高选择性检测肼浓度的方法。具体而言，本发明使用一类4‑溴丁酸酯三氰基呋喃苯乙烯类化合物作为长波长肼比色荧光探针来在样品中检测肼含量。这类探针不仅能够高选择性地识别肼而且能够在长波长处用荧光法对肼进行灵敏的定量和定性分析。这类探针可以快速对肼实现响应，可以实现对肼的即时检测，可以仅用“裸眼”观察实现对肼的定性和定量分析。这类探针性质稳定，可以长期保存使用。此外，这类探针还具有较强的抗干扰能力。
Description
技术领域
本发明涉及高选择性检测肼浓度的方法。具体而言，本发明涉及使用4-溴丁酸酯三氰基呋喃苯乙烯类化合物作为肼高选择长波长比色荧光探针的方法及对肼高选择性识别的应用。
背景技术
肼(NH2NH2)因其具有较强的还原性而广泛的应用于有机合成等工业领域中。此外，肼作为抗菌药物在医药领域也得到了应用。但是，研究表明肼具有强毒性，能够增强肺癌、鼻炎癌以及肝癌的发病率。现在肼已被美国环保署和世界卫生组织列为人类一个潜在的致癌物质。众所周知，肼具有较强的挥发性，易于引起包括大气和水在内的环境污染。因此，开发高选择灵敏检测肼的方法是非常必要的。
目前，检测肼的传统分析方法主要包括气相色谱法、液相色谱法和电化学方法等。最近，荧光探针由于其灵敏度高、操作方便等优点而得到了快速发展，但是目前报道的肼荧光探针仍存在一些不足，例如选择性差、灵敏度低、响应速度慢、合成复杂以及激发和发射波长相对较短等。另外，比色探针由于不需要借助先进的昂贵仪器仅用“裸眼”观察即可达到定量和定性分析的目的而受到广泛关注。因此，发展高选择性、高灵敏度、合成简单的长波长肼比色荧光探针是本领域技术人员研究的热点。
发明内容
本领域急需一种高选择性检测肼浓度的方法。具体而言，本发明的发明人制备一种高选择高灵敏长波长肼比色荧光探针，从而能够有效检测肼。为此，本发明合成了一类新颖的长波长肼比色荧光探针，其合成简单、稳定性高、和/或选择性高，和/或能够识别肼。
具体而言，本发明提供了一种长波长肼比色荧光探针，其为4-溴丁酸酯三氰基呋喃苯乙烯类化合物。
本发明还提供了肼比率荧光探针的制备方法，其是通过将相应的4-羟基三氰基呋喃苯乙烯类化合物与4-溴丁酸反应制得。
在本发明的长波长肼比色荧光探针的制备方法中，反应温度是20～150℃；反应时间是1h～24h；4-羟基三氰基呋喃苯乙烯类化合物与4-溴丁酸的摩尔比为约1：1至1：8。
本发明的长波长肼比色荧光探针可与肼进行作用，引起荧光和吸收光谱的变化(同时伴随着颜色的变化)，从而实现对肼的定性和定量检测。
具体而言，本发明的长波长肼比色荧光探针分别与其他分析物进行作用均不能导致荧光光谱的明显改变，从而实现对肼的选择性识别，进而可任选地用于排除其他分析物的存在对肼的定性和定量测定的干扰。
可选择地，本发明的长波长肼比色荧光探针的稳定性好，进而能够长期保存使用。
进一步的，本发明的长波长肼比色荧光探针是高选择肼比色长波长荧光探针，且合成简单，有利于商业化的推广应用。
附图说明
图1是不同浓度肼(0～500μM)对探针(20μM)吸收和荧光光谱的影响。
图2是不同浓度肼引起探针(40μM)溶液颜色的变化图
图3是不同分析物(200μM)对探针(20μM)荧光光谱以及探针利用荧光光谱法定量分析肼(200μM)的影响。
具体实施方式：
本发明提出了上述高选择性长波长肼比色荧光探针的合成路线、方法及其光谱性能。
本发明的长波长肼比色荧光探针是一类4-溴丁酸酯三氰基呋喃苯乙烯类化合物，其具有以下结构通式
上式中：R1，R2，R3，R4为氢原子，直链或支链烷基，直链或支链烷氧基，磺酸基，酯基，羧基；R1，R2，R3和R4可以相同或不同。
该类长波长肼比色荧光探针的合成路线和方法如下：
本发明的方法所采用的上述高选择性识别肼长波长比色荧光探针的显著特征是能够在长波长处高选择性地识别肼，和/或在其他高浓度分析物的存在下能够准确对肼进行定性和定量分析。重要的是，本发明的方法中所采用的长波长肼比色荧光探针还能够用“裸眼”观察的方法进行定性和定量分析。
下面将通过借助以下实施例来更详细地说明本发明。以下实施例仅是说明性的，应该明白，本发明并不受下述实施例的限制。
实施例1
(方案1)将4-羟基苯乙烯三氰基呋喃(303mg，1.0mmol)、4-溴丁酸(166mg，1.0mmol)、4-二甲氨基吡啶(122mg，1.0mmol)和二环己基碳二亚胺(412mg，2.0mmol)溶于20mL干燥的二氯甲烷中，50℃下反应4h后，减压蒸发得到粗产品，然后使用二氯甲烷进行柱色谱分离，得到浅黄色纯净产品140mg，产率为31﹪。
(方案2)将4-羟基苯乙烯三氰基呋喃(303mg，1.0mmol)、4-溴丁酸(166mg，1.0mmol)、4-二甲氨基吡啶(122mg，1.0mmol)和二环己基碳二亚胺(412mg，2.0mmol)溶于20mL干燥的二氯甲烷中，50℃下反应10h后，减压蒸发得到粗产品，然后使用二氯甲烷进行柱色谱分离，得到浅黄色纯净产品293mg，产率为65﹪。
(方案3)将4-羟基苯乙烯三氰基呋喃(303mg，1.0mmol)、4-溴丁酸(166mg，1.0mmol)、4-二甲氨基吡啶(122mg，1.0mmol)和二环己基碳二亚胺(412mg，2.0mmol)溶于20mL干燥的二氯甲烷中，50℃下反应15h后，减压蒸发得到粗产品，然后使用二氯甲烷进行柱色谱分离，得到浅黄色纯净产品320mg，产率为71﹪。
(方案4)将4-羟基苯乙烯三氰基呋喃(303mg，1.0mmol)、4-溴丁酸(332mg，2.0mmol)、4-二甲氨基吡啶(224mg，2.0mmol)和二环己基碳二亚胺(824mg，4.0mmol)溶于20mL干燥的二氯甲烷中，50℃下反应15h后，减压蒸发得到粗产品，然后使用二氯甲烷进行柱色谱分离，得到浅黄色纯净产品401mg，产率为89﹪。
1H-NMR(400MHz,CDCl3)δ(*10-6):1.81(s,6H),2.28-2.34(m,2H),2.82(t,J＝6Hz,2H),3.56(t,J＝6Hz,2H),7.00(d,J＝16Hz,2H),7.24(s,1H),7.63-7.70(m,3H).13C-NMR(100MHz,CDCl3)δ(*10-6):26.44,27.39,32.36,32.55,58.16,97.77,100.35,110.12,110.78,111.52,115.03,122.83,130.32,131.45,146.03,153.87,170.56,173.57,175.15.ESI-MS calcd for C22H19BrN3O3[M+H]+452,found 452.
实施例2
本发明的发明人进行了如下测试：(a)不同浓度肼(0～500μM)对探针(20μM)吸收光谱的影响，插入图是595nm处吸光度与410nm处吸光度的比值与加入的肼浓度之间的线性关系。(b)不同浓度肼(0～500μM)对探针(20μM)荧光光谱的影响；插入图是610nm处荧光强度与加入的肼浓度之间的线性关系。上述测定是在乙醇和水(5:5，V/V)含有5mM磷酸盐缓冲溶液(PBS)，pH值7.4的体系中，且所有光谱测试都是在25℃下肼加入作用20min后测得的。结果参见图1。
从图1a可以看出，伴随着探针溶液中肼浓度的增加，410nm处的吸收峰逐渐降低，同时595nm处产生新的吸收峰并逐渐升高，且在120～250μM肼浓度范围内和595nm处吸光度与410nm处吸光度的比值成良好的线性关系。从图1b可以看出，伴随着探针溶液中肼浓度的增加，610nm处荧光发射峰逐渐升高，且在50～500μM肼浓度范围内和610nm处荧光强度成良好的线性关系。因此，本发明的探针能较精确地确定待测样本中肼的含量。
实施例3
由图2可以清晰的看出：不同浓度肼(从左至右:0,0.2,0.4,0.6,0.8,1.0mM)存在下探针溶液(40μM)的颜色由黄色逐渐变成蓝色。因此，本发明的探针仅用“裸眼”观察即可完成样本中肼的定性和定量分析检测。
实施例4
不同分析物(200μM)对探针(20μM)荧光光谱的影响。分析物包括：乙二胺EDA、二乙胺DEA、三乙胺TEA、正丁胺nBA、氯离子Cl-、硫酸根离子SO4 2-、硝酸根离子NO3 -、亚硝酸根离子NO2 -和肼，它们的浓度均为200μM。所有测试条件是在乙醇和水(5:5，V/V)含有5mM磷酸盐缓冲溶液(PBS)，pH值7.4的体系中完成，且所有光谱都是在25℃下分析物加入作用20min后测得的。移取10μL的探针储备液(10mM)放进5mL比色管中，然后加入2.5mL乙醇，250μL 100mMPBS，再移取10μL上述分析物储备液(100mM)加入比色管内，然后用超纯水定容至5mL。摇匀，静置20min，即可测定。结果如图3灰色柱状图所示。
从图3灰色柱状图可以看出，探针对肼具有很高的选择性，能够专一性地和肼进行反应。其原因可能是腈首先与溴原子发生分子间的亲核取代反应，然后肼上的另外一个氮原子又发生了分子内亲核取代反应胺解掉了酯基导致的。
不同分析物(200μM)对探针(20μM)荧光光谱法定量分析肼(200μM)的影响。分析物包括：乙二胺EDA、二乙胺DEA、三乙胺TEA、正丁胺nBA、氯离子Cl-、硫酸根离子SO4 2-、硝酸根离子NO3 -、亚硝酸根离子NO2 -和肼，它们的浓度均为200μM。所有测试条件是在乙醇和水(3:7，V/V)含有5mM磷酸盐缓冲溶液(PBS)，pH值7.4的体系中完成，且所有光谱都是在25℃下分析物加入作用20min后测得的。结果如图3黑色柱状图所示。
从图3黑色柱状图可以看出，环境中存在的其他常见分析物不会明显干扰探针对肼的定性与定量检测。
Claims (7)
1.检测样品中肼含量的方法，其包括使具有如下结构的化合物与样品接触的步骤：
其中：R1，R2，R3，R4为独立地选自由氢原子、直链或支链烷基、直链或支链烷氧基、磺酸基、酯基和羟基组成的组；且其中的R1，R2，R3和R4相同或不同。
2.根据权利要求1所述的方法，其中所述的化合物为如下结构的化合物：
3.根据权利要求1或2的方法，其还包括在化合物与样品接触后检测荧光强度的步骤。
4.根据权利要求1或2的方法，其中所述的样品为血液或食品。
5.根据权利要求1或2的方法，其中所述的样品为血液。
6.权利要求1或2中所定义的化合物在检测样品中肼浓度中的用途。
7.根据权利要求6的用途，其中所述的样品为血液或食品。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510755303.9A CN105445241B (zh) | 2015-11-09 | 2015-11-09 | 高选择性检测肼浓度的方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510755303.9A CN105445241B (zh) | 2015-11-09 | 2015-11-09 | 高选择性检测肼浓度的方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105445241A CN105445241A (zh) | 2016-03-30 |
| CN105445241B true CN105445241B (zh) | 2018-02-02 |
Family
ID=55555690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510755303.9A Active CN105445241B (zh) | 2015-11-09 | 2015-11-09 | 高选择性检测肼浓度的方法 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105445241B (zh) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106243122B (zh) * | 2016-08-01 | 2017-12-26 | 济南大学 | 一种检测肼的荧光探针及其应用 |
| CN106431986B (zh) * | 2016-09-29 | 2017-12-26 | 济南大学 | 一种检测肼的荧光探针及其应用 |
| CN106608862B (zh) * | 2016-11-16 | 2019-02-01 | 商丘师范学院 | 一种长波长检测肼的荧光探针及其合成方法与应用 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5719061A (en) * | 1994-10-20 | 1998-02-17 | The United States Of America As Represented By The Secretary Of The Navy | Fluorescent detection of hydrazine, monomethylhydrazine, and 1,1-dimethylhydrazine by derivatization with aromatic dicarboxaldehydes |
| WO2005005956A2 (en) * | 2003-07-08 | 2005-01-20 | Stanford University | Fluorophore compounds and their use in biological systems |
| CN103923071A (zh) * | 2014-04-30 | 2014-07-16 | 大连理工常熟研究院有限公司 | 一种用于识别肼的特异性荧光探针及其应用 |
| CN104531138A (zh) * | 2014-12-29 | 2015-04-22 | 大连理工常熟研究院有限公司 | 一种用于识别肼的特异性荧光探针及其应用 |
| JP2015087234A (ja) * | 2013-10-30 | 2015-05-07 | ダイハツ工業株式会社 | ヒドラジン濃度検出装置 |
| CN105017196A (zh) * | 2015-07-21 | 2015-11-04 | 山东大学 | 一种检测肼的近红外比率荧光探针及其应用 |
-
2015
- 2015-11-09 CN CN201510755303.9A patent/CN105445241B/zh active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5719061A (en) * | 1994-10-20 | 1998-02-17 | The United States Of America As Represented By The Secretary Of The Navy | Fluorescent detection of hydrazine, monomethylhydrazine, and 1,1-dimethylhydrazine by derivatization with aromatic dicarboxaldehydes |
| WO2005005956A2 (en) * | 2003-07-08 | 2005-01-20 | Stanford University | Fluorophore compounds and their use in biological systems |
| JP2015087234A (ja) * | 2013-10-30 | 2015-05-07 | ダイハツ工業株式会社 | ヒドラジン濃度検出装置 |
| CN103923071A (zh) * | 2014-04-30 | 2014-07-16 | 大连理工常熟研究院有限公司 | 一种用于识别肼的特异性荧光探针及其应用 |
| CN104531138A (zh) * | 2014-12-29 | 2015-04-22 | 大连理工常熟研究院有限公司 | 一种用于识别肼的特异性荧光探针及其应用 |
| CN105017196A (zh) * | 2015-07-21 | 2015-11-04 | 山东大学 | 一种检测肼的近红外比率荧光探针及其应用 |
Non-Patent Citations (2)
| Title |
|---|
| "A highly selective long-wavelength fluorescent probe for the detection of human carboxylesterase 2 and its biomedical applications;Lei Feng等;《Chemical Communications》;20141231;第50卷(第93期);第14519-14522页 * |
| Fluorescent push–pull pH-responsive probes for ratiometric detection of intracellular pH;Martin Ipuy 等;《Organic & Biomolecular Chemistry》;20141230;第12卷;第3641-3648页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105445241A (zh) | 2016-03-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Zhou et al. | Design principles of spectroscopic probes for biological applications | |
| Zhang et al. | A compact fluorescent probe based on o-phthalaldehyde for ultrasensitive detection of hydrazine in gas and solution phases | |
| Peng et al. | A novel fluorescent probe for selective detection of hydrogen sulfide in living cells | |
| CN107417671A (zh) | 一种含喹啉取代的香豆素衍生物及其制备方法和在比率型pH荧光探针上的应用 | |
| Fang et al. | Coumarinocoumarin-based fluorescent probe for the sensitive and selective detection of hydrazine in living cells and zebra fish | |
| CN109867611A (zh) | 一种用于红酒和活体内硫化氢检测的水溶性双光子硫化氢荧光探针及其制备方法和应用 | |
| CN105445241B (zh) | 高选择性检测肼浓度的方法 | |
| 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 | |
| CN105418559B (zh) | 高灵敏性检测肼的试剂盒及其应用 | |
| CN105400508A (zh) | 肼浓度的检测方法 | |
| CN109897080A (zh) | 高选择超灵敏肝癌特异性过氧化亚硝酸盐探针及其应用 | |
| CN104529956B (zh) | 高灵敏度高选择性甲醛比色荧光双通道指示剂及其应用 | |
| CN103755620A (zh) | 一种镁离子荧光探针及其制备方法与应用 | |
| CN104132920A (zh) | 一种荧光猝灭测定Ag+或F-的方法 | |
| CN105418560B (zh) | 长波长肼比色荧光探针及其制备方法 | |
| CN110452250A (zh) | 一种荧光素母体结构的检测肼用荧光探针 | |
| CN108774226A (zh) | 一种用于检测银离子的荧光探针及其制备方法与应用 | |
| CN111233928B (zh) | 一种香豆素衍生物Mito-Cys及其制备方法和应用 | |
| CN105985291B (zh) | 一种快速高选择性分析氟离子的比色荧光探针 | |
| CN105418500A (zh) | 高选择性肼比率荧光探针及其制备方法 | |
| CN105199715B (zh) | 一种基于罗丹明b衍生物的荧光探针及其制备方法和应用 | |
| Liu et al. | An imidazo [1, 5-α] pyridines-based ratiometric fluorescent probe for sensing sulfur dioxide derivatives in real samples based on a FRET mechanism | |
| CN109734710A (zh) | 一种检测半胱氨酸的荧光探针及其合成方法与应用 | |
| CN113004200B (zh) | 基于萘酰亚胺衍生物的甲醛浓度和pH值双响应型探针及其制备和应用 | |
| CN110563609B (zh) | 一种检测亚硒酸根的近红外荧光探针的制备方法及应用 |
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 | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20240627 Address after: 518000, Building B, No. 49 Fengqi Road, Fucheng'ao Community, Pinghu Street, Longgang District, Shenzhen City, Guangdong Province. The first floor of Building 2 and the entire building of Building 3 Patentee after: Shenzhen Municipal Institute testing Co.,Ltd. Country or region after: China Address before: 362200, next to 1003 Quan'an Middle Road, Meiling Street, Jinjiang City, Quanzhou City, Fujian Province Patentee before: Jinjiang shangjingfuben Environmental Protection Technology Co.,Ltd. Country or region before: China |
|
| TR01 | Transfer of patent right |