CN113861076B - 一种aie型三苯胺衍生物荧光探针及其制备方法和其在水合肼检测中的应用 - Google Patents
一种aie型三苯胺衍生物荧光探针及其制备方法和其在水合肼检测中的应用 Download PDFInfo
- Publication number
- CN113861076B CN113861076B CN202111258916.3A CN202111258916A CN113861076B CN 113861076 B CN113861076 B CN 113861076B CN 202111258916 A CN202111258916 A CN 202111258916A CN 113861076 B CN113861076 B CN 113861076B
- Authority
- CN
- China
- Prior art keywords
- aie
- fluorescent probe
- dimethylamino
- amino
- hydrazine hydrate
- 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
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 title claims abstract description 49
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 36
- 238000001514 detection method Methods 0.000 title claims abstract description 28
- 125000006617 triphenylamine group Chemical group 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims abstract description 12
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 6
- -1 triphenylamine compound Chemical class 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims description 7
- 238000004809 thin layer chromatography Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 5
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 238000000967 suction filtration Methods 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000005457 ice water Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 2
- 238000001727 in vivo Methods 0.000 claims description 2
- 238000012544 monitoring process Methods 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000523 sample Substances 0.000 abstract description 60
- 238000003384 imaging method Methods 0.000 abstract description 7
- 238000004458 analytical method Methods 0.000 abstract description 6
- MFFDJRYGVWMCQY-FOWTUZBSSA-N chembl3198210 Chemical compound C1=CC(N(C)C)=CC=C1\C=N\C1=CC=CC=C1 MFFDJRYGVWMCQY-FOWTUZBSSA-N 0.000 abstract description 3
- 239000003068 molecular probe Substances 0.000 abstract description 3
- 238000011160 research Methods 0.000 abstract description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 45
- SDWXTQCFTPNNKU-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)-n',n'-bis[2-(pyridin-2-ylmethylamino)ethyl]ethane-1,2-diamine Chemical compound C=1C=CC=NC=1CNCCN(CCNCC=1N=CC=CC=1)CCNCC1=CC=CC=N1 SDWXTQCFTPNNKU-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 9
- 239000000203 mixture Substances 0.000 description 5
- 239000012086 standard solution Substances 0.000 description 5
- 239000011550 stock solution Substances 0.000 description 5
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 239000010413 mother solution Substances 0.000 description 4
- 125000003172 aldehyde group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000000711 cancerogenic effect Effects 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000012632 fluorescent imaging Methods 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- KRRBFUJMQBDDPR-UHFFFAOYSA-N tetrabutylazanium;cyanide Chemical compound N#[C-].CCCC[N+](CCCC)(CCCC)CCCC KRRBFUJMQBDDPR-UHFFFAOYSA-N 0.000 description 2
- 101710134784 Agnoprotein Proteins 0.000 description 1
- 208000014912 Central Nervous System Infections Diseases 0.000 description 1
- 206010023424 Kidney infection Diseases 0.000 description 1
- 208000032376 Lung infection Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 101710138657 Neurotoxin Proteins 0.000 description 1
- 206010037596 Pyelonephritis Diseases 0.000 description 1
- 206010057190 Respiratory tract infections Diseases 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000029918 bioluminescence Effects 0.000 description 1
- 238000005415 bioluminescence Methods 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 208000025222 central nervous system infectious disease Diseases 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000001218 confocal laser scanning microscopy Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 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
- 230000005284 excitation Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000012921 fluorescence analysis Methods 0.000 description 1
- 238000002073 fluorescence micrograph Methods 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000002595 magnetic resonance imaging Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000003471 mutagenic agent Substances 0.000 description 1
- 231100000707 mutagenic chemical Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 239000002581 neurotoxin Substances 0.000 description 1
- 231100000618 neurotoxin Toxicity 0.000 description 1
- 230000008816 organ damage Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- 150000005838 radical anions Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 208000020029 respiratory tract infectious disease Diseases 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical class C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/61—Carboxylic acid nitriles containing cyano groups and nitrogen atoms being part of imino groups bound to the same carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
- A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Analytical Chemistry (AREA)
- Optics & Photonics (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
本发明涉及一种AIE型三苯胺衍生物荧光探针,化学名称为(Z)‑2‑(4‑(((E)4‑(二甲胺基)苯亚甲基)氨基)苯)3‑(4‑(二苯胺)苯基)丙烯腈,分子式为C36H30N4。一种所述AIE型三苯胺衍生物荧光探针的制备方法,具体制备步骤如下:第一步,制备(E)‑2‑(4‑(4‑(二甲胺基)苯亚甲基)氨基)苯基)乙腈;第二步,制备4‑(二苯胺)苯甲醛;第三步,(E)‑2‑(4‑(4‑(二甲胺基)苯亚甲基)氨基)苯基)乙腈和4‑(二苯胺)苯甲醛在碱性环境下反应,制得所述荧光探针。本发明首次提供了一种具有AIE性能的三苯胺类化合物荧光探针,为有机分析和光化学提供了新型的探针分子,可广泛应用于荧光分析或检测领域。该新型荧光分子探针实现了对水合肼的高灵敏检测,其检测限为0.13µM,可以实现在HeLa细胞中对水合肼含量检测和成像研究。
Description
技术领域
本发明属于有机小分子生物荧光探针技术领域,具体涉及一种AIE型三苯胺衍生物荧光探针、制备方法及其在水合肼检测中的应用。
背景技术
众所周知,水合肼不仅因其易燃易爆的特性而成为导弹和火箭推进系统的推进剂,而且是化学、制药和农业中最重要的反应基础之一。其强大的还原能力还能通过扫氧,有效抑制给水、供热系统的热水锅炉的金属腐蚀。最重要的是,水合肼具有致癌和毒性,在其制造、运输、应用和处置过程中,即使微量泄漏也可能导致严重的环境污染和严重的健康风险,更糟糕的是,由于其水溶性良好,水合肼很容易通过皮肤和口腔接触和吸入,被生物系统吸收。作为一种神经毒素和诱变原,过量接触水合肼可能导致严重的器官损伤,包括肝、肾、肺、中枢神经系统和呼吸道感染等。因此,美国环境保护署(EPA)建议将水合肼作为致癌物质的允许阈值定为10ppb(0.31μM)。由于水合肼的广泛存在和剧毒性,其精准、高灵敏及快速检测主要还是依靠荧光分析法。设计结构新颖的荧光探针分子,丰富其荧光成像方式并提高成像性能,已逐渐成为荧光成像技术发展过程中的热点与难点。
与传统的荧光探针相比,AIE分子生物探针的简单设计和荧光开启特性提供了水介质中特异性分析物和生物过程的直接可视化,具有更高的灵敏度和更好的准确性。不同剂型和表面功能的AIE点生物探针在量子点和小分子染料上表现出吸收率大、发光度高、生物相容性好、无随机闪烁、耐光漂白等先进特性,这些特性使肿瘤细胞检测、长期细胞示踪和肿瘤成像成为可能。最近的研究极大地扩展了AIE荧光剂的生物应用范围,并为荧光生物探针的设计提供了新的策略。预计,AIE生物探针的未来发展将将单光子或多光子荧光与其他形式(如磁共振成像)或功能(如治疗)相结合,以充分展示其作为新一代治疗诊断试剂的潜力。与此同时,分子生物学的发展将提供更特异性的生物受体,这将有助于开发具有高选择性和高灵敏度的下一代AIE生物探针,用于分子传感和成像。近几年,对AIE分子的研究取得了很大的进展,如硅杂环戊二烯及其衍生物、四苯基乙烯(TPE)衍生物以及其它具有AIE现象的分子,在生物检测领域得到了广泛的应用。尽管如此,用于检测水合肼的AIE型荧光探针仍很缺乏,这类探针亟待开发。
发明内容
对目前可用于水合肼检测的AIE型荧光探针缺乏的现状,本发明提供了一种AIE型三苯胺衍生物荧光探针及其制备方法和应用。
为了实现上述发明目的,本发明采用以下技术方案:
一种AIE型三苯胺衍生物荧光探针,其结构式如式Ⅰ所示:
该荧光探针的化学名称为(Z)-2-(4-(((E)4-(二甲胺基)苯亚甲基)氨基)苯)3-(4-(二苯胺)苯基)丙烯腈,分子式为C36H30N4。
一种所述AIE型三苯胺衍生物荧光探针的制备方法,该荧光探针的合成路线如下:
具体制备步骤如下:第一步,制备(E)-2-(4-(4-(二甲胺基)苯亚甲基)氨基)苯基)乙腈;第二步,制备4-(二苯胺)苯甲醛;第三步,(E)-2-(4-(4-(二甲胺基)苯亚甲基)氨基)苯基)乙腈和4-(二苯胺)苯甲醛在碱性环境下反应,制得所述荧光探针。
所述的第一步的合成路线如下:
具体反应步骤如下:将4-(二甲胺基)苯甲醛先溶解在乙醇中,搅拌反应,再加入2-(4-氨基)乙腈,加入醋酸溶液,加热回流,用薄层色谱法监测进程,待反应完成后冷却至室温,然后放冰箱静置一晚,有淡黄色晶体析出,抽滤,再用无水乙醚对沉淀进行洗涤,得到淡黄色固体(纯)产品(E)-2-(4-(4-(二甲胺基)苯亚甲基)氨基)苯基)乙腈。
其中,4-(二甲胺基)苯甲醛与2-(4-氨基)乙腈的物质的量比为0.8-1;反应的pH值为4.5-6.5;加热回流温度为75-85℃。
所述的第二步的合成路线如下:
具体反应步骤如下:将DMF加入到三颈烧瓶内,置于冰浴中,逐滴加入POCl3,在低温下搅拌,将温度增加到室温,然后,加入三苯胺,升温搅拌,冷却至室温,反应混合物缓慢倒入冰水浴中,用NaOH中和,二氯甲烷萃取,合并有机相,有机相用无水MgSO4干燥,过滤,浓缩有机层,用乙酸乙酯:石油醚=1:10(v/v)过柱,得到4-(二苯胺)苯甲醛白色固体;
其中,三苯胺、DMF及POCl3的物质的量比为1:1:1-1:1.2:1.5;低温下搅拌的温度为-10℃-10℃;升温搅拌的时间为10h-15h,具体的温度为40℃-65℃。
所述的第三步的具体步骤如下:
将(E)-2-(4-(4-(二甲胺基)苯亚甲基)氨基)苯基)乙腈溶于有机溶剂中,然后加入4-(二苯胺)苯甲醛,再加入碱,加热回流,搅拌2h,薄层色谱法点板跟踪至反应结束后,抽滤后得到橙色固体(Z)-2-(4-(((E)4-(二甲胺基)苯亚甲基)氨基)苯)3-(4-(二苯胺)苯基)丙烯腈。
所述有机溶剂选自甲苯、乙腈、二氯乙烷、二氯甲烷、N,N-二甲基甲酰胺、四氯化碳、正己烷、四氢呋喃、甲醇或乙醇中的一种;所述的碱选自哌啶、氢氧化钠、碳酸氢钠、叔丁醇钾中的一种;加热回流温度为75-85℃;(E)-2-(4-(4-(二甲胺基)苯亚甲基)氨基)苯基)乙腈、碱与4-(二苯胺)苯甲醛的物质的量比为1:1:1-1:1.2:1.5。
上述制备方法中,反应结束后的后处理方式并无特别的限定,本领域技术人员可依据物料的理化性质,结合公知常识的分离手段,采用常规的物理分离手段来实现目标产物的分离,优选的技术方案为过滤法,更进一步优选,选用减压抽滤。
上述制备方法中,通过薄层色谱法监测反应终点,反应时间无特别的限定。
一种所述的AIE型三苯胺衍生物荧光探针在水合肼检测中的应用。
一种水合肼检测试剂,包括上述荧光探针。
进一步地,所述水合肼检测试剂为体内水合肼检测试剂。
该探针设计的初衷是想通过4-(二甲胺基)苯甲醛中的醛基与2-(4-氨基)乙腈中的氨基通过希夫碱反应,形成C=N双键,提供可以用于水合肼检测的作用位点。
检测原理如下,首先根据相关报道文献推测探针TPAA与N2H4发生相互作用时可能的反应机制是:在N2H4存在的情况下,TPAA的C=N键断裂,由此形成了一个含有氨基的化合物和具有醛基的化合物,该醛基化合物会继续与N2H4作用,得到另一种新化合物,其通过ESI-MS分析数据证实。
有益效果:
1、本发明首次提供了一种具有AIE性能的三苯胺类化合物荧光探针,丰富了水合肼类荧光分子探针的种类,为有机分析和光化学提供了新型的探针分子,可广泛应用于荧光分析或检测领域。
2、该新型荧光分子探针实现了对水合肼的高灵敏检测,其检测限为0.13μM。
3、该荧光探针分子可以实现在HeLa细胞中对水合肼含量检测和成像研究。
附图说明
图1为探针分子TPAA在不同含水量的DMSO-H2O混合液中的荧光图。
图2为探针分子TPAA在DMSO溶液中紫外及荧光图及斯托克斯位移。
图3为探针分子TPAA的DMSO溶液对其他不同类型干扰物的荧光图。
图4为探针分子TPAA的DMSO溶液对不同浓度水合肼的荧光图。
图5为探针分子TPAA的DMSO溶液对水合肼检测动力学图。
图6为探针分子TPAA检测N2H4的机理图。
图7为探针分子TPAA与N2H4响应后终产物的液相质谱图。
图8为探针分子TPAA在HeLa细胞中水合肼的成像图。图中的A1、B1、C1和D1是细胞的绿色通道和蓝色通道的叠加图,随着水合肼浓度的增加,叠加图的光强度增强,A2、B2、C2和D2是细胞的明场图。
具体实施方式
下面结合附图和具体实施例对本发明作进一步详细说明,但不应理解为对本发明的限制。在不背离本发明精神和实质的情况下,对本发明方法、步骤或条件所作的修改或替换,均属于本发明的范围。实施例中未注明具体条件的实验方法及未说明配方的试剂均为按照本领域常规条件。
实施例1
AIE型三苯胺衍生物荧光探针的制备:
第1步、化合物(E)-2-(4-(4-(二甲胺基)苯亚甲基)氨基)苯基)乙腈的制备
将4-(二甲胺基)苯甲醛(0.4470g,3mmol)先溶解在15mL EtOH中,搅拌反应,再加入2-(4-氨基)乙腈(0.4130g,3.5mmol)加热至80℃回流,用薄层色谱法监测进程反应完成后冷却至室温,放入冰箱过夜,有晶体析出,抽滤,得到淡黄色固体产品,产率:90.2%,0.7123g;纯度99%以上。(注:4-(二甲胺基)苯甲醛和2-(4-氨基)乙腈购买于南京晴文生物科技有限公司。)
1H NMR(400MHz,Chloroform-d)δ8.32(s,1H),7.81(d,J=8.3Hz,2H),7.36-7.32(m,2H),7.23(d,J=8.1Hz,2H),6.78-6.74(m,2H),3.79(s,2H),3.09(s,6H)。
第2步、化合物4-(二苯胺)苯甲醛的制备
将7.75mL的DMF加入到三颈烧瓶内,置于冰浴中,9.5mL的POCl3逐滴加入,在0℃下搅拌40min,将温度增加到室温,然后,加入1g的三苯胺,反应在45℃下搅拌14h,冷却至室温,反应混合物缓慢倒入冰水浴中,用NaOH中和,二氯甲烷萃取,合并有机相,有机相用无水MgSO4干燥,过滤,浓缩有机层,用乙酸乙酯:石油醚=1:10(v/v)过柱,得到白色固体,产率:88.0%,0.98g;纯度99%以上。
1H NMR(400MHz,Chloroform-d)δ9.83(s,1H),7.73-7.67(m,2H),7.40-7.34(m,4H),7.22-7.16(m,6H),7.06-7.01(m,2H)。
第三步、化合物(Z)-2-(4-(((E)4-(二甲胺基)苯亚甲基)氨基)苯)3-(4-(二苯胺)苯基)丙烯腈的制备
将中间体(E)-2-(4-(4-(二甲胺基)苯亚甲基)氨基)苯基)乙腈(0.2634g,1mmol)溶于乙醇中,然后加入4-(二苯胺)苯甲醛(0.2050g,0.75mmol),再加入1.2mmol叔丁醇钾,搅拌数小时,薄层色谱法点板跟踪至反应结束后,趁热抽滤后,用热乙醇洗涤,干燥得到橙色固体(Z)-2-(4-(((E)4-(二甲胺基)苯亚甲基)氨基)苯)3-(4-(二苯胺)苯基)丙烯腈,产率:87.8%,0.3411g;纯度99%以上。
1H NMR(400MHz,DMSO-d6)δ8.48(s,1H),7.92(s,1H),7.87(d,J=9.0Hz,2H),7.75(dd,J=14.5,8.8Hz,4H),7.42-7.37(m,4H),7.32(d,J=8.7Hz,2H),7.20-7.14(m,6H),6.97(d,J=8.9Hz,2H),6.80(d,J=9.1Hz,2H),3.03(s,6H).13C NMR(101MHz,DMSO-d6)δ160.88,152.98,149.74,146.58,141.25,131.24,131.15,130.99,130.38,126.95,126.73,125.99,125.09,124.09,122.20,120.69,111.92.ESI-MS m/z:[probe]+calcd forC36H30N4519.25;Found 519.2。
下面对探针分子TPAA的荧光性质及其在水合肼检测中的应用进行进一步研究。
实施例2探针分子TPAA在不同含水量的DMSO-H2O混合液中的荧光性能测试仪器:日立F7100型分子荧光光谱仪。
实验方法为:将实施例1制得的探针分子TPAA溶解于DMSO中得到1mM的探针母液,常温避光保存,用探针母液分别配制成0%、10%、20%、30%、40%、50%、60%、70%、80%、90%、98%含水量的DMSO-H2O混合液,浓度均为0.1mM。
测量时分别移取1mL不同含水量的DMSO-H2O混合液到1cm比色皿中先后进行荧光光谱测试,如图1所示。随着含水率的增加,荧光强度逐渐增大。当含水量达到40%左右时,558nm处的荧光发射值最高。但随着水分的不断增加,荧光发射强度逐渐降低,是由于溶剂的极性随着含水量的增加而增加,刚性发光分子可以从局部发射(IE)态转移到扭曲分子电荷转移(TICT)态。故选用40%含水量的探针溶液用于TPAA的后续测试。
实施例3探针分子TPAA的紫外吸收光谱及荧光光谱性质测试
测试仪器:PE 950s型紫外光谱仪,日立F7100型分子荧光光谱仪。
实验方法为:将实施例1制得的探针分子TPAA溶解于DMSO溶液中得到1mM的探针母液,常温保存,避光。实验测定中用DMSO和H2O将溶液稀释成0.01mM的标准液进行测试。
测量时移取3mL探针的DMSO溶液到1cm比色皿中先后进行紫外吸收光谱及荧光光谱测试,如图2所示。结果表明:探针TPAA最强紫外吸收峰出现在420nm左右,荧光发射峰出现在537nm左右,斯托克位移达到117nm。这么大的斯托克位移,可以有效的克服因荧光自吸收而在生命体中难以应用的缺陷,实现探针在生命体中的应用。
实施例4探针分子TPAA对其他干扰离子的荧光图
测试仪器:日立F100型分子荧光光谱仪。
实验方法为:将实施例1制得的探针分子TPAA溶解于DMSO中得到1mM的探针母液,常温保存。取水合肼、四丁基氰化铵、ZnSO4、AgNO3、Co(NO3)2、CuSO4、Fe2(SO4)3、PbNO3、NaNO2、NaNO3、KH2PO4、NaHSO4、Na2S、KCl、CaCl2用二次水配置成0.01M母液。实验测定中将探针溶液稀释成10μM的标准溶液进行测试。
测量时移取1mL探针的DMSO溶液到1cm比色皿中分别滴加600μM的过氧化氢、四丁基氰化铵、NaClO、Na2S2O3、Na2HPO4、MgSO4、NaNO2、NaHCO3、NaNO3、KH2PO4、K2CO3、CH3COONa、NaHSO3进行荧光测试。结果如图3所示。结果表明:探针TPAA对水合肼表现出明显的荧光增强现象,而对于一些生物体内常见的金属阳离子和酸根阴离子几乎没有什么影响,进一步说明探针TPAA具有优异的选择性,能够应用于生物体内。
实施例5 TPAA的DMSO溶液对水合肼的定量分析
测试仪器:日立F7100型分子荧光光谱仪。
实验方法为:将实施例1制得的探针分子TPAAA溶解于DMSO中得到1mM的探针母液,常温保存。水合肼用二次水配置成0.01M母液,实验测定中将探针溶液稀释成1μM的标准溶液进行测试。
采用标准加入法测试探针分子对水合肼的荧光响应,移取1mL的探针母液(10μM)至比色皿中,每次加入1μL的水合肼检测荧光强度变化,水合肼含量加到600μM不再继续加入,如图4所示,随着水合肼含量的增加,在537nm处的荧光峰强度不断增强,因此,该探针对水合肼有较高的灵敏度,可用于生物体内微量水合肼的检测。
实施例6探针分子TPAA在水合肼存在下的动力学实验
测试仪器:日立F7100型分子荧光光谱仪。
实验方法为:将实施例1制得的探针分子TPAA溶解于DMSO中得到1mM的探针母液,常温保存。水合肼用二次水配置成0.01M母液。实验测定中将溶液稀释成10μM的标准溶液进行测试。
移取1mL的探针母液(10μM)至比色皿中,设置荧光激发波长为420nm,分别测试探针,探针+水合肼溶液在不同的时间(0分钟、1分钟、2分钟、3分钟、5分钟、10分钟、15分钟、20分钟、25分钟)荧光强度的变化,如图5所示。实验结果表明,开始探针溶液的荧光强度随时间的增加而增强,探针+水合肼在20min内荧光强度达到最高值,后荧光强度趋于稳定,说明该探针响应迅速且稳定性较好。
实施例7探针分子TPAA机理探究实验
实验方法:首先根据相关报道文献推测探针TPAA与N2H4发生相互作用时可能的反应机制是:如图6在N2H4存在的情况下,TPAA的C=N键断裂,由此形成了一个含有氨基的化合物(1)和具有醛基的化合物(2),该醛基化合物会继续与N2H4作用,得到化合物(3),然后通过液相质谱ESI-MS分析数据证实(m/z:calculated for164.2和388.2;图7)。
实施例8探针分子TPAA在HeLa细胞中对水合肼的成像研究。
实验方法为:将实施例1制得的探针分子TPAA溶解于DMSO中得到1mM的探针母液,常温保存。实验测定中用DMSO和H2O将溶液稀释成0.01mM的标准液进行测试。
为了证明探针在生物系统的实际应用,在共聚焦荧光显微镜下对细胞进行了在不同pH值下的生物荧光成像实验。将HeLa细胞接到培养皿中在37℃条件下培养24h,然后将TPAA标准液(10μM)加入到培养皿中,加入不同浓度的水合肼(50、100、150μM)继续孵育1小时后进行荧光成像,如图8所示。实验结果表明探针分子TPAA在随着水合肼浓度增加,荧光在不断增强。这些结果表明,探针TPAA可以作为检测细胞内水合肼的荧光标签进入细胞,因而具有在生物体内检测水合肼的潜力。
需要说明的是,以上内容仅仅说明了本发明的技术思想,不能以此限定本发明的保护范围,对于本技术领域的普通技术人员来说,在不脱离本发明原理的前提下,还可以做出若干改进和润饰,这些改进和润饰均落入本发明权利要求书的保护范围之内。
Claims (10)
1.一种AIE型三苯胺衍生物荧光探针,其特征在于:其结构式如式Ⅰ所示:
;
式Ⅰ。
2.一种如权利要求1所述AIE型三苯胺衍生物荧光探针的制备方法,其特征在于:该荧光探针的合成路线如下:
;
具体制备步骤如下:第一步,制备(E)-2-(4-(4-(二甲胺基)苯亚甲基)氨基)苯基)乙腈;第二步,制备4-(二苯胺)苯甲醛;第三步,(E)-2-(4-(4-(二甲胺基)苯亚甲基)氨基)苯基)乙腈和4-(二苯胺)苯甲醛在碱性环境下反应,制得所述荧光探针。
3.根据权利要求2所述AIE型三苯胺衍生物荧光探针的制备方法,其特征在于:所述的第一步的合成路线如下:
;
具体反应步骤如下:将4-(二甲胺基)苯甲醛先溶解在乙醇中,搅拌反应,再加入2-(4-氨基)乙腈,加入醋酸溶液,加热回流,用薄层色谱法监测进程,待反应完成后冷却至室温,然后放冰箱静置一晚,有淡黄色晶体析出,抽滤,再用无水乙醚对沉淀进行洗涤,得到淡黄色固体(E)-2-(4-(4-(二甲胺基)苯亚甲基)氨基)苯基)乙腈。
4.根据权利要求3所述AIE型三苯胺衍生物荧光探针的制备方法,其特征在于:其中,4-(二甲胺基)苯甲醛与2-(4-氨基)乙腈的物质的量比为0.8-1;反应的pH值为4.5-6.5;加热回流温度为75-85℃。
5.根据权利要求2所述AIE型三苯胺衍生物荧光探针的制备方法,其特征在于:所述的第二步的合成路线如下:
;
具体反应步骤如下:将DMF加入到三颈烧瓶内,置于冰浴中,逐滴加入POCl3,在低温下搅拌,将温度增加到室温,然后,加入三苯胺,升温搅拌,冷却至室温,反应混合物缓慢倒入冰水浴中,用NaOH中和,二氯甲烷萃取,合并有机相,有机相用无水MgSO4干燥,过滤,浓缩有机层,用乙酸乙酯和石油醚过柱,得到4-(二苯胺)苯甲醛白色固体,所述乙酸乙酯与石油醚体积比为1:10。
6.根据权利要求5所述AIE型三苯胺衍生物荧光探针的制备方法,其特征在于:其中,三苯胺、DMF及POCl3的物质的量比为1:1:1-1:1.2:1.5;低温下搅拌的温度为-10℃-10℃;升温搅拌的时间为10 h-15 h,具体的温度为40℃-65℃。
7.根据权利要求2所述AIE型三苯胺衍生物荧光探针的制备方法,其特征在于:所述的第三步的具体步骤如下:
将(E)-2-(4-(4-(二甲胺基)苯亚甲基)氨基)苯基)乙腈溶于有机溶剂中,然后加入4-(二苯胺)苯甲醛,再加入碱,加热回流,搅拌2h,薄层色谱法点板跟踪至反应结束后,抽滤后得到橙色固体(Z)-2-(4-(((E)4-(二甲胺基)苯亚甲基)氨基)苯)3-(4-(二苯胺)苯基)丙烯腈。
8.根据权利要求7所述AIE型三苯胺衍生物荧光探针的制备方法,其特征在于:所述有机溶剂选自甲苯、乙腈、二氯乙烷、二氯甲烷、N,N-二甲基甲酰胺、四氯化碳、正己烷、四氢呋喃、甲醇或乙醇中的一种;所述的碱选自哌啶、氢氧化钠、碳酸氢钠、叔丁醇钾中的一种;加热回流温度为75-85℃;(E)-2-(4-(4-(二甲胺基)苯亚甲基)氨基)苯基)乙腈、碱与4-(二苯胺)苯甲醛的物质的量比为1:1:1-1:1.2:1.5。
9.一种如权利要求1所述的AIE型三苯胺衍生物荧光探针在制备水合肼检测试剂中的应用。
10.根据权利要求9所述的AIE型三苯胺衍生物荧光探针在制备水合肼检测试剂中的应用,其特征在于:所述的水合肼检测试剂为体内水合肼检测试剂。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202111258916.3A CN113861076B (zh) | 2021-10-27 | 2021-10-27 | 一种aie型三苯胺衍生物荧光探针及其制备方法和其在水合肼检测中的应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202111258916.3A CN113861076B (zh) | 2021-10-27 | 2021-10-27 | 一种aie型三苯胺衍生物荧光探针及其制备方法和其在水合肼检测中的应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN113861076A CN113861076A (zh) | 2021-12-31 |
CN113861076B true CN113861076B (zh) | 2023-08-08 |
Family
ID=78998642
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202111258916.3A Active CN113861076B (zh) | 2021-10-27 | 2021-10-27 | 一种aie型三苯胺衍生物荧光探针及其制备方法和其在水合肼检测中的应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN113861076B (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114736153B (zh) * | 2022-05-16 | 2023-08-25 | 扬州工业职业技术学院 | 一种aie型偶氮酶荧光小分子探针及其制备方法 |
CN114736139B (zh) * | 2022-05-17 | 2023-12-15 | 浙江科技学院 | 一种检测汽车制动液的荧光化合物及其制备方法和应用 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109970600A (zh) * | 2019-03-26 | 2019-07-05 | 菏泽学院 | 一种三苯胺衍生物希夫碱类有机荧光探针及其制备方法 |
CN112110913A (zh) * | 2019-06-20 | 2020-12-22 | 湖南超亟化学科技有限公司 | 一种可用于水合肼检测的新型荧光探针及试纸的制备和应用 |
-
2021
- 2021-10-27 CN CN202111258916.3A patent/CN113861076B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109970600A (zh) * | 2019-03-26 | 2019-07-05 | 菏泽学院 | 一种三苯胺衍生物希夫碱类有机荧光探针及其制备方法 |
CN112110913A (zh) * | 2019-06-20 | 2020-12-22 | 湖南超亟化学科技有限公司 | 一种可用于水合肼检测的新型荧光探针及试纸的制备和应用 |
Non-Patent Citations (1)
Title |
---|
Fluorescent probes for detecting glutathione: Bio-imaging and two reaction mechanisms;Ying Xia 等;《Dyes and Pigments》(第163期);441-446 * |
Also Published As
Publication number | Publication date |
---|---|
CN113861076A (zh) | 2021-12-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Chen et al. | A novel imidazo [1, 5-α] pyridine-based fluorescent probe with a large Stokes shift for imaging hydrogen sulfide | |
Yang et al. | A NIR ratiometric probe for hydrazine “naked eye” detection and its imaging in living cell | |
CN113861076B (zh) | 一种aie型三苯胺衍生物荧光探针及其制备方法和其在水合肼检测中的应用 | |
Huo et al. | Isophorone-based aldehyde for “ratiometric” detection of cyanide by hampering ESIPT | |
Liu et al. | A novel N-nitrosation-based ratiometric fluorescent probe for highly selective imaging endogenous nitric oxide in living cells and zebrafish | |
Tan et al. | A new fluorescent and colorimetric probe for trace hydrazine with a wide detection range in aqueous solution | |
Gunnlaugsson et al. | Novel sodium-selective fluorescent PET and optically based chemosensors: towards Na+ determination in serum | |
Ge et al. | A ratiometric fluorescent probe for sensing Cu2+ based on new imidazo [1, 5-a] pyridine fluorescent dye | |
Huo et al. | The synthesis, characterization of three isomers of rhodamine derivative and their application in copper (II) ion recognition | |
CN105924449B (zh) | 一种检测汞离子反应型荧光素类荧光探针制备与应用 | |
Wang et al. | A fluorescent and colorimetric chemosensor for nitric oxide based on 1, 8-naphthalimide | |
CN111100476B (zh) | 一种pH荧光探针的合成及应用 | |
CN108752377B (zh) | 一种检测过氧亚硝基阴离子的荧光探针、合成方法和应用 | |
US8623239B2 (en) | Compound and functional luminescent probe comprising the same | |
CN104031039B (zh) | 氧杂蒽类染料及其制备方法和应用 | |
Wang et al. | An AIE and PET fluorescent probe for effective Zn (ii) detection and imaging in living cells | |
Huang et al. | A fluorescent probe based on triphenylamine with AIE and ICT characteristics for hydrazine detection | |
Xu et al. | A novel fluorescent probe for hydrazine based on acetyl-deprotection and iminocoumarin formation | |
CN114591632B (zh) | 一类氮杂吲哚-半花菁染料、其合成方法及应用 | |
Kang et al. | A facile Zn (II) probe based on intramolecular charge transfer with fluorescence red-shift | |
Huang et al. | A pyridyl functionalized rhodamine chemodosimeter for selective fluorescent detection of mercury ions and cell imaging | |
Gao et al. | Recent development of organic small-molecule and nanomaterial fluorescent probes for hydrazine | |
Pan et al. | The preparation of a special fluorescent probe with an aggregation-induced emission effect for detecting hydrazine in water | |
Xia et al. | Phenothiazine-based fluorescent probes for the detection of hydrazine in environment and living cells | |
Wang et al. | A switch-on fluorophore using water molecules via hydrogen bonding and its application for bio-imaging of formaldehyde in living cells |
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 |