CN106632441A - Ratio type fluorescent probe for identifying hydrogen peroxide - Google Patents
Ratio type fluorescent probe for identifying hydrogen peroxide Download PDFInfo
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- CN106632441A CN106632441A CN201611166885.8A CN201611166885A CN106632441A CN 106632441 A CN106632441 A CN 106632441A CN 201611166885 A CN201611166885 A CN 201611166885A CN 106632441 A CN106632441 A CN 106632441A
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 13
- 239000000126 substance Substances 0.000 claims abstract description 4
- 239000000523 sample Substances 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- SVENKGKXRLHCTC-UHFFFAOYSA-N B(O)(O)O.BrCC=1C=CC=CC1 Chemical class B(O)(O)O.BrCC=1C=CC=CC1 SVENKGKXRLHCTC-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 229960001866 silicon dioxide Drugs 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 238000001514 detection method Methods 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 6
- 230000005284 excitation Effects 0.000 description 5
- 238000004448 titration Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 4
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- -1 Tetraphenyl ethylene class compound Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 201000010374 Down Syndrome Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000035977 Rare disease Diseases 0.000 description 1
- 206010044688 Trisomy 21 Diseases 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000004993 emission spectroscopy Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 210000003463 organelle Anatomy 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- 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
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
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- 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
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- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- 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
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Materials Engineering (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
The invention provides a ratio type fluorescent probe, namely TPENS-O, for identifying hydrogen peroxide. The chemical structure formula of the ratio type fluorescent probe is shown in formula (I). The fluorescent probe is used for identifying hydrogen peroxide through fluorescence ratio change. The formula is defined in the description.
Description
Technical field
The present invention relates to a kind of Ratio-type recognizes hydrogen peroxide（H2O2）Fluorescence probe, more particularly to a kind of Ratio-type is special
One identification H2O2Tetraphenyl ethylene class compound fluorescent probe；Belong to organic molecule fluorescence probe field.
Background technology
Hydrogen peroxide (H2O2) play a significant role in various physiology courses, H2O2Horizontal abnormality and perhaps eurypalynous disease
Disease is as associated such as cancer, diabetes, Down's syndrome and rare disease.Recently, H2O2Have proven to be academia and mankind's major disease
Related active small molecular.It is in vivo and external to H based on this2O2Detection also cause the great attention of people.
At present, H2O2Detection means be broadly divided into two classes：Direct method and indirect method.Direct method is that a class is directly utilized
H2O2The method that own physical, chemical property are analyzed detection to it, including the selection of Atomic absorption, emission spectrometry and ion
Property electrode method；Indirect method is that a class utilizes H2O2Recognition site detected, mainly by design synthesis photophysical property compared with
Good fluorescence platform, the fluorescence probe based on the platform carries out being detected in vivo with biology in vitro.But, comprehensive analysis mesh
The H of front report2O2Fluorescence probe is primarily present following deficiency：First, detecting H using Ratiometric fluorescent probe2O2Still very
Difficulty, due to the spectrum characteristic that great majority of synthesising probing needle itself are Fluorescence Increasing type；Second, non-Ratio-type hydrogen peroxide probe
Range of application is more narrow；Because non-Ratio-type probe the detection of hydrogen peroxide is received extraneous factor, such as concentration and probe concentration etc. because
Element affects larger.Based on this, develop new ratio fluorescent probe and recognize that the fluorescence probe of hydrogen peroxide is particularly important in Ratio-type,
There is important actual application value.
The content of the invention
For above-mentioned the deficiencies in the prior art, the invention provides one kind is in detection H2O2Ratiometric fluorescent probe, and grind
Study carefully its spectral quality.
The fluorescence probe of identification hydrogen peroxide of the present invention, it is characterised in that：The fluorescence probe is named as TPENS-
O, its chemical structural formula such as formula（I）It is shown：
（）.
Above-mentioned TPENS-O preparation methods are：
Compound 1 and 4- bromomethyl benzene boric acids ester are made into solvent with DMF, potassium carbonate does alkali, under nitrogen protection room temperature reaction 6h.
After reaction terminates, column chromatography obtains TPENS-O.
Above-mentioned TPENS-O to prepare reaction equation as follows：
Detection H in the fluorescence probe of identification hydrogen peroxide of the present invention2O2。
In above-mentioned application：The fluorescence probe is to realize H in the way of ratio fluorescent changes2O2Identification.
Related experiment confirms：Fluorescence probe TPENS-O of the present invention ratio fluorescents in mixed system change obvious,
And the 430nm fluorescent quenchings under conditions of hydrogen peroxide is present, 550nm Fluorescence Increasings, it was demonstrated that the probe is probably hydrogen peroxide
Probe（Fig. 1）.In H2O2In Choice tests, when being excited with 360nm light, only H2O2Occurrence rate type is changed significantly（Fig. 2）；
In H2O2In titration experiments（Fig. 3）, with the gradually increase of hydrogen peroxide, probe TPENS-O ratio fluorescents change obvious.Infer,
The probe can detect in the cell the hydrogen peroxide activated molecule of organelle.
Based on above-mentioned experimental result, the single-minded identification H of ratio of the present invention is may certify that2O2Fluorescence probe be a class
New high selectivity fluorescent probe molecule, the recognition mechanism of the probe is the recognition site boron of hydrogen peroxide in clearance fluorogen
There is fluorophore fluorescence transmitting caused by oxidation reaction and change in acid esters, recognize product Fluorescence Increasing with hydrogen peroxide.Its identification is anti-
Answer product such as（II）It is shown：
（I）.
The compound fluorescent probe and the close traditional mistake of its function of the Ratio-type identification hydrogen peroxide that the present invention is provided
Hydrogen oxide fluorescence probe is compared with significant advantage, and compound of the present invention is examined in vitro to active small molecular high selectivity
Survey and synthesizing mean also has novelty and simplicity.The fluorescence probe of the present invention is changing into detection peroxide by ratio fluorescent
Change hydrogen and fluorescence platform is provided, the probe and its research are studied as theoretical foundation has been established in application for biology, indicate that the probe is being lived
The realization of the detection of intracellular hydrogen peroxide provides important tool.
Description of the drawings
Fig. 1：Probe itself and its fluorescence spectrum in the presence of hydrogen peroxide.The nm of excitation wavelength 360.
Fig. 2：Selectivity of the probe to hydrogen peroxide.Excitation wavelength is 360 nm；The concentration of probe mother liquor：10-3M, selects
Property ion concentration be 0.05 mM.
Wherein：Excitation wavelength is 360nm；The concentration of probe mother liquor：10-3M, the concentration of selective ion is 0.05 mM.
Fig. 3：H2O2Titration figure.
H2O2Titration experiments；Wherein excitation wavelength is 360 nm；The concentration of probe mother liquor:10-3M, takes 10 μ L probes female
Liquid dilution 2ml is carried out, and adds different amounts of H2O2Titration.
Specific embodiment
Embodiment 1
The synthesis of TPENS-O：
0.35g (1mmol) compound 1,0.25g (1.1mmol) 4- bromomethyl benzene boric acid esters, potassium carbonate 50mg are dissolved in
In 20mL DMF, the h of room temperature reaction 6 under nitrogen protection, reaction terminates, and uses mobile phase CH2Cl2/CH3OH=100:1, cross silica gel
Post obtains TPENS-O.
1H NMR (400 MHz, DMSO-d 6) δ 8.11 (d, J = 2.1 Hz, 1H), 8.06 (d, J = 7.9
Hz, 1H), 7.97 (d, J = 8.1 Hz, 1H), 7.73 (d, J = 7.7 Hz, 1H), 7.57 (d, J = 7.7
Hz, 1H), 7.50 – 7.46 (m, 0H), 7.41 – 7.36 (m, 0H), 7.16 – 7.14 (m, 2H), 7.15
– 7.12 (m, 3H), 7.04 (d, J = 1.8 Hz, 1H), 7.01 (d, J = 1.9 Hz, 1H), 6.99 (s,
0H), 5.40 (s, 1H), 1.31 (s, 6H)。
Embodiment 2
Responses of the TPENS-O to hydrogen peroxide：
Prepare the 10 of 1 part of 10 mL in advance-3The probe of the M present inventionN, N- dimethyl formamide solution, then takes respectively 5 μ L and adds
In entering two identical 5mL volumetric flasks, add hydrogen peroxide equivalent for 50 times of probe equivalent in one of bottle, use PBS/
DMF(V:V=1:1) solution is diluted to 3mL, then carries out fluoroscopic examination（λEx= 360nm）, as a result see Fig. 1.
Conclusion：Show that the probe is responded to hydrogen peroxide.
Embodiment 3
Selectivity of the TPENS-O to hydrogen peroxide (see Fig. 2)：
Wherein：Excitation wavelength is 360 nm；The concentration of probe mother liquor：10-3M, the concentration of selective ion is 0.1mM.Take 5 μ L
Probe mother liquor dilution 3ml is carried out, after take the above-mentioned dilution of 3mL, add various ions to carry out spectrum test, wherein various ions
Concentration is 0.1mM.The test environment of probe is PBS/DMF (V:V = 1:1) cushioning liquid.
Conclusion：Test result shows that probe TPENS-O has high selectivity to hydrogen peroxide.
Embodiment 4
The titration of hydrogen peroxide：
10 mL concentration are prepared for 0.05 mM H2O2The aqueous solution and the present invention probe mother liquor（Concentration is 10-3M）As standby
With.Concentration of hydrogen peroxide from 0 equivalent is titrated into 200 equivalents and fluoroscopic examination is carried out（λEx= 360nm, λEm= 430nm, λEm
= 550nm）, fluorescence intensity in each system is calculated, set up fluorescence intensity and concentration of hydrogen peroxide calibration curve (see Fig. 3).
Claims (2)
1. it is a kind of identification hydrogen peroxide Ratiometric fluorescent probe, it is characterised in that：The fluorescence probe is named as TPENS-O,
Its chemical structural formula such as formula（I）It is shown：
（）.
2. Ratiometric fluorescent probe according to claim 1, it is characterised in that be prepared from using following preparation method：
By 1mmol compounds 1,1.1mmol 4- bromomethyl benzene boric acid esters, potassium carbonate 50mg, in being dissolved in 20mL DMF, in nitrogen protection
The lower h of room temperature reaction 6, after reaction terminates, uses mobile phase CH2Cl2/CH3OH=100:1 crosses silicagel column obtains TPENS-O,
Chemical reaction is as follows：
。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611166885.8A CN106632441A (en) | 2016-12-16 | 2016-12-16 | Ratio type fluorescent probe for identifying hydrogen peroxide |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611166885.8A CN106632441A (en) | 2016-12-16 | 2016-12-16 | Ratio type fluorescent probe for identifying hydrogen peroxide |
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Family
ID=58823729
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| CN201611166885.8A Withdrawn CN106632441A (en) | 2016-12-16 | 2016-12-16 | Ratio type fluorescent probe for identifying hydrogen peroxide |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107311957A (en) * | 2017-06-21 | 2017-11-03 | 海南大学 | One kind is based on aggregation-induced emission and excited state intramolecular proton transfer compound and its preparation method and application |
| CN108148087A (en) * | 2018-02-23 | 2018-06-12 | 银川高新区广煜科技有限公司 | Long wavelength's hydrogen peroxide fluorescence probe |
| CN108752371A (en) * | 2018-07-13 | 2018-11-06 | 济南大学 | A kind of two-photon hydrogen peroxide fluorescence probe based on quinoline |
| CN108752373A (en) * | 2018-07-13 | 2018-11-06 | 济南大学 | A kind of fluorescence probe identifying hydrogen peroxide based on benzene boron ester |
| CN109060739A (en) * | 2018-07-13 | 2018-12-21 | 中国科学院上海微系统与信息技术研究所 | A method of detection hydrogen peroxide |
| CN110057801A (en) * | 2019-05-10 | 2019-07-26 | 中国医学科学院药用植物研究所 | A kind of ratio fluorescent probe and its hydrogen peroxide and glucose detection application based on aggregation-induced emission property |
| CN110172070A (en) * | 2019-06-05 | 2019-08-27 | 商丘师范学院 | A kind of fluorescence probe and its synthetic method and application detecting viscosity and hydrogen peroxide |
| CN111393462A (en) * | 2020-04-10 | 2020-07-10 | 山西大学 | Dual-mechanism-based fluorescent probe for detecting ONOO-, and preparation method and application thereof |
| CN111875560A (en) * | 2020-07-09 | 2020-11-03 | 山东师范大学 | Ratio type two-photon fluorescent probe and preparation method and application thereof |
| CN111875628A (en) * | 2020-08-14 | 2020-11-03 | 中国药科大学 | Fluorescent probe with aggregation-induced emission characteristic, preparation method and application |
| CN113004310A (en) * | 2019-12-20 | 2021-06-22 | 湖南超亟化学科技有限公司 | Preparation method and application of hydrogen peroxide ratio type fluorescent molecular probe based on DCPO parent nucleus |
| CN113248543A (en) * | 2021-03-29 | 2021-08-13 | 南开大学 | Enzyme activity detection system, detection method and application of histone demethylase LSD1 |
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- 2016-12-16 CN CN201611166885.8A patent/CN106632441A/en not_active Withdrawn
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107311957A (en) * | 2017-06-21 | 2017-11-03 | 海南大学 | One kind is based on aggregation-induced emission and excited state intramolecular proton transfer compound and its preparation method and application |
| CN108148087A (en) * | 2018-02-23 | 2018-06-12 | 银川高新区广煜科技有限公司 | Long wavelength's hydrogen peroxide fluorescence probe |
| CN108752371B (en) * | 2018-07-13 | 2020-06-30 | 济南大学 | Two-photon hydrogen peroxide fluorescent probe based on quinoline |
| CN109060739A (en) * | 2018-07-13 | 2018-12-21 | 中国科学院上海微系统与信息技术研究所 | A method of detection hydrogen peroxide |
| CN108752373A (en) * | 2018-07-13 | 2018-11-06 | 济南大学 | A kind of fluorescence probe identifying hydrogen peroxide based on benzene boron ester |
| CN108752373B (en) * | 2018-07-13 | 2020-03-27 | 济南大学 | Fluorescent probe for identifying hydrogen peroxide based on phenylboronate |
| CN108752371A (en) * | 2018-07-13 | 2018-11-06 | 济南大学 | A kind of two-photon hydrogen peroxide fluorescence probe based on quinoline |
| CN110057801B (en) * | 2019-05-10 | 2021-08-06 | 中国医学科学院药用植物研究所 | Fluorescence ratiometric probe based on aggregation-induced emission property and application of fluorescence ratiometric probe in detection of hydrogen peroxide and glucose |
| CN110057801A (en) * | 2019-05-10 | 2019-07-26 | 中国医学科学院药用植物研究所 | A kind of ratio fluorescent probe and its hydrogen peroxide and glucose detection application based on aggregation-induced emission property |
| CN110172070B (en) * | 2019-06-05 | 2021-11-02 | 商丘师范学院 | Fluorescent probe for detecting viscosity and hydrogen peroxide as well as synthesis method and application thereof |
| CN110172070A (en) * | 2019-06-05 | 2019-08-27 | 商丘师范学院 | A kind of fluorescence probe and its synthetic method and application detecting viscosity and hydrogen peroxide |
| CN113004310A (en) * | 2019-12-20 | 2021-06-22 | 湖南超亟化学科技有限公司 | Preparation method and application of hydrogen peroxide ratio type fluorescent molecular probe based on DCPO parent nucleus |
| CN113004310B (en) * | 2019-12-20 | 2022-07-08 | 湖南超亟检测技术有限责任公司 | Preparation method and application of hydrogen peroxide ratio type fluorescent molecular probe based on DCPO parent nucleus |
| CN111393462A (en) * | 2020-04-10 | 2020-07-10 | 山西大学 | Dual-mechanism-based fluorescent probe for detecting ONOO-, and preparation method and application thereof |
| CN111875560A (en) * | 2020-07-09 | 2020-11-03 | 山东师范大学 | Ratio type two-photon fluorescent probe and preparation method and application thereof |
| CN111875628A (en) * | 2020-08-14 | 2020-11-03 | 中国药科大学 | Fluorescent probe with aggregation-induced emission characteristic, preparation method and application |
| CN111875628B (en) * | 2020-08-14 | 2022-04-08 | 中国药科大学 | Fluorescent probe with aggregation-induced emission characteristic, preparation method and application |
| CN113248543A (en) * | 2021-03-29 | 2021-08-13 | 南开大学 | Enzyme activity detection system, detection method and application of histone demethylase LSD1 |
| CN113248543B (en) * | 2021-03-29 | 2022-08-26 | 南开大学 | Enzyme activity detection system, detection method and application of histone demethylase LSD1 |
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Application publication date: 20170510 |