CN111303072A - Reagent for distinguishing and detecting cysteine and synthetic method and application thereof - Google Patents
Reagent for distinguishing and detecting cysteine and synthetic method and application thereof Download PDFInfo
- Publication number
- CN111303072A CN111303072A CN202010125872.6A CN202010125872A CN111303072A CN 111303072 A CN111303072 A CN 111303072A CN 202010125872 A CN202010125872 A CN 202010125872A CN 111303072 A CN111303072 A CN 111303072A
- Authority
- CN
- China
- Prior art keywords
- cysteine
- solution
- syp
- benzothiazol
- 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.)
- Pending
Links
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 235000018417 cysteine Nutrition 0.000 title claims abstract description 50
- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract description 12
- 238000010189 synthetic method Methods 0.000 title description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000001514 detection method Methods 0.000 claims abstract description 14
- 239000007853 buffer solution Substances 0.000 claims abstract description 12
- -1 (E) -2- (benzothiazol-2-yl) -6- (2- (3- (dicyanomethylene) -5,5-dimethylcyclohex-1-en-1-yl) vinyl) -4-methylphenyl acrylate Chemical compound 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 57
- 239000000243 solution Substances 0.000 claims description 41
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 28
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 claims description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000003756 stirring Methods 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- SMWMPMNQFQRVTR-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-4-methylphenol Chemical compound CC1=CC=C(O)C(C=2SC3=CC=CC=C3N=2)=C1 SMWMPMNQFQRVTR-UHFFFAOYSA-N 0.000 claims description 6
- KBXQWCNIDPFYDM-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-2-hydroxy-5-methylbenzaldehyde Chemical compound S1C(=NC2=C1C=CC=C2)C=1C(=C(C=O)C=C(C=1)C)O KBXQWCNIDPFYDM-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 238000004440 column chromatography Methods 0.000 claims description 6
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 6
- 238000012417 linear regression Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- ZDHOUEDHAXJNJL-UHFFFAOYSA-N 2-(3,5,5-trimethylcyclohex-2-en-1-yl)propanedinitrile Chemical compound CC1=CC(C(C#N)C#N)CC(C)(C)C1 ZDHOUEDHAXJNJL-UHFFFAOYSA-N 0.000 claims description 3
- ILEIUTCVWLYZOM-UHFFFAOYSA-N 2-hydroxy-5-methylbenzaldehyde Chemical compound CC1=CC=C(O)C(C=O)=C1 ILEIUTCVWLYZOM-UHFFFAOYSA-N 0.000 claims description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000012267 brine Substances 0.000 claims description 3
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 3
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 3
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000012488 sample solution Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 239000000523 sample Substances 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 description 3
- 229960003180 glutathione Drugs 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- 238000010586 diagram Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 208000037273 Pathologic Processes Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000011132 hemopoiesis Effects 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 230000009054 pathological process Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004393 prognosis Methods 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- 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"
-
- 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
-
- 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
- C09K2211/1018—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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- General Health & Medical Sciences (AREA)
- Pathology (AREA)
- General Physics & Mathematics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Optics & Photonics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
The invention provides a reagent for distinguishing and detecting cysteine, a synthesis method and application thereof, wherein the reagent is a benzothiazole derivative: the derivative is named as (E) -2- (benzothiazol-2-yl) -6- (2- (3- (dicyanomethylene) -5,5-dimethylcyclohex-1-en-1-yl) vinyl) -4-methylphenyl acrylate in the Chinese, and is named as (E) -2- (benzothiazolyl-2-yl) -6- (2- (3- (dicyanomethylene) -5,5-dimethylcyclohex-1-en-1-yl) vinyl) -4-methylphenylacrylate in the English, and is named as SYP. The detection method is to detect Hepes-CH with pH of 7.43OH‑CH3CN (1:1:1, v/v/v) buffer solution, and the content of cysteine is quantitatively detected by a fluorescence spectrophotometer. The detection process is simple, sensitive and quick, and the detection result is accurate.
Description
Technical Field
The invention relates to cysteine detection, and particularly belongs to a reagent for detecting cysteine, and a synthesis method and application thereof.
Background
Biological thiols, including cysteine (Cys), homocysteine (Hcy) and Glutathione (GSH), have attracted much attention in recent years, primarily because they play a critical role in many physiological and pathological processes, such as reversible redox homeostasis, tissue and human metabolism. Among them, cysteine (Cys) is an important biological thiol, which plays an important role in protein synthesis, detoxification and metabolism, and is also involved in many diseases. Cysteine deficiency can lead to reduced hematopoiesis, psoriasis, neurotoxicity, edema and liver damage, and Cys levels are also overexpressed in cardiovascular disease and alzheimer's disease. Therefore, a sensitive method for detecting biological cells and cysteine in vivo is established, which is convenient for researching the pathology of related diseases and is helpful for related diagnosis and prognosis.
Disclosure of Invention
The invention aims to provide a reagent for distinguishing and detecting cysteine, a synthesis method and application thereof.
The reagent for distinguishing and detecting cysteine is a benzothiazole derivative, wherein the Chinese name is (E) -2- (benzothiazole-2-yl) -6- (2- (3- (dicyanomethylene) -5,5-dimethylcyclohex-1-en-1-yl) vinyl) -4-methylphenyl acrylate, the English name is (E) -2- (benzothiazolyl-2-yl) -6- (2- (3- (dicyanomethylene) -5,5-dimethylcyclohex-1-en-1-yl) vinyl) -4-methylphenylacrylate, the structure formula is as follows:
the invention provides a synthetic method of a reagent SYP for distinguishing and detecting cysteine, which comprises the following steps:
(1) according to the mol ratio of 1:1: 0.01 adding 2-amino thiophenol, 5-methyl salicylaldehyde and silver nitrate into DMSO, mixing, and stirring at room temperature in the dark for 2 hours; then diluting with dichloromethane by 3 times, washing with brine, combining organic phases, drying with anhydrous sodium sulfate, concentrating, and purifying by column chromatography with ethyl acetate/petroleum ether at a volume ratio of 1:6 to obtain light yellow solid, namely 2-benzothiazol-2-yl-4-methylphenol;
(2) according to a molar ratio of 1.8: 3.9 dissolving the compound 2-benzothiazole-2-yl-4-methylphenol and hexamethylenetetramine in trifluoroacetic acid, and refluxing overnight under stirring; after completion of the reaction and cooling to room temperature, the pH was adjusted using potassium hydroxide until the solid completely precipitated, filtered, washed with water, dried under vacuum and purified by ethyl acetate/petroleum ether column chromatography in a volume ratio of 1:5 to obtain compound 3- (benzothiazol-2-yl) -2-hydroxy-5-methylbenzaldehyde as a yellow solid;
(3) according to the mol ratio of 1:1 adding a compound 3- (benzothiazol-2-yl) -2-hydroxy-5-methylbenzaldehyde and a compound 2- (3,5, 5-trimethylcyclohex-2-en-1-yl) malononitrile into ethanol, adding 0.1 equivalent of piperidine under stirring, mixing, and heating and refluxing for 10 hours; after completion of the reaction and cooling to room temperature, the mixture was filtered, washed with ethanol, and dried under vacuum to give (E) -2- (3- (3- (3-benzothiazol-2-yl) -2-hydroxy-5-methylstyryl) -5, 5-dimethylcyclohex-2-en-1-ylidene) malononitrile as an orange-red solid;
(4) according to the mol ratio of 1: 1.5 addition of the Compound (E) -2- (3- (3- (3-benzothiazol-2-yl) -2-hydroxy-5-methylstyryl) -5, 5-dimethylcyclohex-2-en-1-ylidene) malononitrile and acryloyl chloride to anhydrous CH2Cl2Then the mixture was cooled to 0 ℃ and Et 3 times the equivalent weight was added dropwise with stirring3N, after stirring at 0 ℃ for 1h, the reaction is complete and the mixture is filtered, separately with methanol and CH2Cl2Washed and dried under vacuum to give the compound (E) -2- (benzothiazol-2-yl) -6- (2- (3- (dicyanomethylene) -5,5-dimethylcyclohex-1-en-1-yl) vinyl) -4-methylphenyl acrylate as a yellow solid.
The reagent SYP can be used for distinguishing and detecting cysteine.
The invention provides a method for detecting cysteine, which comprises the following steps:
(1) preparing a Hepes solution with the pH value of 7.4 and the concentration of 10mM, and preparing the solution, methanol and acetonitrile into CH with the volume ratio of 1:1:13OH/CH3CN/Hepes buffer solution, preparing 0.02M cysteine aqueous solution, and dissolving benzothiazole derivative SYP in DMSO to prepare 2mM solution;
(2) 2mL of CH was taken3OH/CH3Adding CN/Hepes buffer solution and 10 mu L of DMSO solution of SYP into a fluorescence cuvette, detecting on a fluorescence spectrophotometer, and gradually increasing the fluorescence intensity at 686nm along with the addition of cysteine aqueous solution of a sample to be detected;
(3) 2mL of CH3OH/CH3Adding CN/Hepes buffer solution into a fluorescence cuvette, simultaneously adding 10 mu L of DMSO solution of SYP, uniformly mixing the system, gradually adding 0.02M cysteine aqueous solution, wherein the volume of the added solution is 0, 2, 4, 5, 6, 7, 8, 10 and 12 mu L, simultaneously measuring the fluorescence intensity at 686nm on a fluorescence spectrometer as 397, 511, 629, 687, 745, 803, 861, 976 and 1093, plotting the cysteine concentration as an abscissa and the fluorescence intensity F as an ordinate to obtain a cysteine concentration working curve; the linear regression equation is: f6865.8C +396.8, with C having a unit of 10-6mol/L；
(4) And when the sample solution is measured, substituting the measured fluorescence intensity into a linear regression equation to obtain the concentration of the cysteine.
Compared with the prior art, the invention has the following advantages and effects:
1. the benzothiazole derivative is simple to synthesize and low in cost;
2. the benzothiazole derivative can realize the differential detection of cysteine, and has high sensitivity of detection results, short response time and good selectivity;
3. the detection method is simple and can be realized only by means of a fluorescence spectrometer;
4. the invention adopts red channel detection, and has obvious detection signal and strong specificity.
Drawings
FIG. 1 nuclear magnetic hydrogen spectrum of benzothiazole derivative SYP prepared in example 1
FIG. 2 nuclear magnetic carbon spectrum of benzothiazole derivative SYP prepared in example 1
FIG. 3 Mass Spectroscopy of benzothiazole derivative SYP prepared in example 1
FIG. 4 fluorescence emission diagram of the interaction of benzothiazole derivative SYP with cysteine
FIG. 5 fluorescence histogram of benzothiazole derivative SYP and various analytes
FIG. 6 working curve of the benzothiazole derivative SYP for determining cysteine
FIG. 7 fluorescence emission diagram of cysteine sample measured by benzothiazole derivative SYP
FIG. 8 cytographic image of measuring endogenous cysteine by benzothiazole derivative SYP
FIG. 9 imaging of exogenous cysteine cells measured by benzothiazole derivative SYP
Detailed Description
The present invention will be further described with reference to the following examples and drawings, but the present invention is not limited to the following examples.
Example 1
Preparation and characterization of SYP
In a 50mL round bottom flask, 2-aminosulfol (5mmol, 0.625g) and 5-methylsalicylaldehyde (5mmol, 0.681g) were added to 15mL DMSO and silver nitrate (0.05mmol, 0.009g) was added and the mixture was allowed to react for 2 hours at room temperature in the dark with stirring. After completion of the reaction, it was diluted 3-fold with dichloromethane (50mL), washed with brine, the organic phases were combined, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (ethyl acetate/petroleum ether ═ 1:6) to obtain compound (0.893g, 74.07%) as 2-benzothiazol-2-yl-4-methylphenol as a pale yellow solid.1H NMR(600MHz,Chloroform-d)δ8.01(d,J＝8.1Hz,1H),7.93(d,J＝7.9Hz,1H),7.56-7.48(m,2H),7.43(t,J＝7.5Hz,1H),7.21(d,J＝8.3Hz,1H),7.04(d,J＝8.4Hz,1H),2.37(s,3H).13C NMR(150MHz,Chloroform-d)δ169.41,155.79,151.84,133.79,132.60,128.72,128.34,126.67,125.47,122.12,121.52,117.68,116.33,20.51。
In a 25mL single-necked flask, the compound 2-benzothiazol-2-yl-4-methylphenol (1.8mmol, 0.455g) and hexamethylenetetramine (3.9mmol, 0.546g) were dissolved in 15mL of trifluoroacetic acid. The mixture was refluxed overnight with stirring. After completion of the reaction and cooling to room temperature, the pH was adjusted with potassium hydroxide until the solid was completely precipitated, filtered, washed with waterDried under vacuum and purified by column chromatography (ethyl acetate/petroleum ether ═ 1:5) to afford compound 3- (benzothiazol-2-yl) -2-hydroxy-5-methylbenzaldehyde (0.315g, 64.90%) as a yellow solid.1H NMR(600MHz,Chloroform-d)δ10.49(s,1H),8.09(d,J＝7.9Hz,1H),7.97(d,J＝8.0Hz,2H),7.73(s,1H),7.57(t,J＝7.7Hz,1H),7.48(t,J＝7.6Hz,1H),2.44(s,3H).13C NMR(150MHz,Chloroform-d)δ158.55,150.89,135.37,132.97,129.10,127.02,125.96,123.61,122.26,121.63,118.50,20.35。
The compound 3- (benzothiazol-2-yl) -2-hydroxy-5-methylbenzaldehyde (1mmol, 0.269g) and the compound 2- (3,5, 5-trimethylcyclohex-2-en-1-yl) malononitrile (1mmol, 0.291g) were added to 10mL of ethanol, piperidine (0.15mL) was added with stirring, and the mixture was heated under reflux for 10 hours. After the reaction was complete and cooled to room temperature, the mixture was filtered, washed with ethanol, and dried under vacuum to give the compound (E) -2- (3- (3- (3-benzothiazol-2-yl) -2-hydroxy-5-methylstyryl) -5, 5-dimethylcyclohex-2-en-1-ylidene) malononitrile as an orange-red solid. (0.263g, 60.1%).1HNMR(600MHz,Chloroform-d)δ8.01(d,J＝8.1Hz,1H),7.95(d,J＝8.0Hz,1H),7.60-7.54(m,2H),7.53(d,J＝3.9Hz,2H),7.47(t,J＝7.1Hz,1H),7.18(d,J＝16.2Hz,1H),6.89(s,1H),2.63(s,2H),2.57(s,2H),2.42(s,3H),1.12(s,6H).13C NMR(150MHz,Chloroform-d)δ169.49,169.10,154.72,154.55,132.58,131.43,130.82,129.96,129.83,128.82,126.93,125.86,124.56,123.54,122.15,121.63,117.04,113.67,112.88,78.27,77.24,43.08,39.11,32.10,28.06,20.63。
The compound (E) -2- (3- (3- (3-benzothiazol-2-yl) -2-hydroxy-5-methylstyryl) -5, 5-dimethylcyclohex-2-en-1-ylidene) malononitrile (1mmol, 0.44g) and acryloyl chloride (1.5mmol, 122.0mL) were added to 20mL of anhydrous CH2Cl2Then the mixture was cooled to 0 ℃ and Et was added dropwise with stirring3N (3mmol, 0.42 mL). After stirring at 0 ℃ for 1h, the reaction was complete and the mixture was filtered, with methanol and CH, respectively2Cl2Washed and dried under vacuum to give probe (E) -2- (benzothiazol-2-yl) -6- (2- (3- (dicyanomethylene) -5, 5-dimethylcyclohexyl) cyclohexane as a yellow solid-1-en-1-yl) vinyl) -4-methylphenyl acrylate (0.45g, 85.4%).1H NMR(600MHz,DMSO-d6)δ8.18(s,1H),8.10(s,1H),8.08–8.00(m,2H),7.57(s,2H),7.49(s,1H),7.07(d,J＝16.1Hz,1H),6.97(s,1H),6.68(d,J＝14.0Hz,2H),6.34(d,J＝9.3Hz,1H),2.63(s,2H),2.48(s,3H),2.44(s,2H),1.00(s,6H).13C NMR(150MHz,DMSO-d6)δ170.48,162.61,154.43,150.69,147.76,142.49,139.46,134.05,133.21,132.76,132.19,130.57,128.63,128.40,127.47,127.06,126.43,125.13,123.66,122.66,120.82,113.97,113.13,32.13,27.83,20.90.HR-MS m/z:[SYP+H]+calcd for 492.17402; found 492.17378 (see FIG. 1, FIG. 2, FIG. 3, respectively)
Example 2
Preparing Hepes solution with pH of 7.4 and concentration of 10mM, and preparing the solution with methanol and acetonitrile into CH with volume ratio of 1:1:13OH/CH3CN/Hepes buffer solution, 2mM SYP DMSO solution, 0.02M cysteine water solution; take 2mLCH3OH/CH3CN/Hepes solution and 10 mu L of DMSO solution of SYP are added into a fluorescence cuvette, the aqueous solution of cysteine is gradually added into the cuvette by a microsyringe, the detection is carried out on a fluorescence spectrophotometer while the sample is added, and the fluorescence intensity of 686nm is gradually increased along with the addition of cysteine. The fluorescence emission pattern is shown in FIG. 4.
Example 3
Preparing Hepes solution with pH of 7.4 and concentration of 10mM, and preparing the solution with methanol and acetonitrile into CH with volume ratio of 1:1:13OH/CH3CN/Hepes buffer solution, 2mM SYP DMSO solution, 0.02M cysteine water solution; in 18 fluorescence cuvettes, 2mL of CH were added3OH/CH3CN/Hepes solution and 10. mu.L of SYP in DMSO were added to the remaining 17 cuvettes with 10-fold equivalent of each of Cys, Hcy, GSH, NaHS, Ala, Asn, Arg, Asp, Gln, Glu, Gly, His, Ile, Leu, Lys, Met and Phe, and the contents of the 18 cuvettes were examined on a fluorescence spectrophotometer to plot fluorescence intensity histograms at 686nm for the different analytes (see FIG. 5). Cysteine can obviously increase the fluorescence intensity of the detection system at 686nm, and othersThe analyte causes substantially no change in the fluorescence intensity of the detection system.
Example 4
Preparing Hepes solution with pH of 7.4 and concentration of 10mM, and preparing the solution with methanol and acetonitrile into CH with volume ratio of 1:1:13OH/CH3CN/Hepes buffer solution, 2mM SYP DMSO solution, 0.02M cysteine water solution; 2mL of CH was added to each of 9 cuvettes3OH/CH3CN/Hepes solution and 10 mu L of DMSO solution of SYP, then adding cysteine solution respectively, the volumes of the added solutions are 0, 2, 4, 5, 6, 7, 8, 10 and 12 mu L respectively, simultaneously measuring the fluorescence intensity at 686nm on a fluorescence spectrometer as 397, 511, 629, 687, 745, 803, 861, 976 and 1093, plotting the cysteine concentration as abscissa and the fluorescence intensity F as ordinate to obtain a working curve of the cysteine concentration; the linear regression equation is: f6865.8C +396.8, with C having a unit of 10-6mol/L, see FIG. 6.
Example 5
Preparing Hepes solution with pH of 7.4 and concentration of 10mM, and preparing the solution with methanol and acetonitrile into CH with volume ratio of 1:1:13OH/CH3CN/Hepes buffer solution, 2mM SYP DMSO solution and 2mM cysteine aqueous solution are prepared; in the fluorescence cuvette, 2mL of CH were added3OH/CH3CN/Hepes solution and 10. mu.L of SYP in DMSO, 10. mu.L of cysteine solution was taken and added to the cuvette using a microsyringe, and the fluorescence intensity at 686nm was 973 on a fluorescence spectrometer, and C was determined to be 9.93X 10 by the linear regression equation of example 4-5mol/L, relative deviation from the theoretical value of 0.7%, see FIG. 7.
Example 6
Preparing 10mM pH 7.4Hepes buffer solution, preparing 2mM SYP DMSO solution, and preparing 0.02M cysteine aqueous solution; add 5. mu.L of SYP in DMSO to 2mL Hepes; adding the probe solution into a Hela cell culture dish to ensure that the concentration of the probe solution is 5 mu M, reacting the probe solution with Hela cells for 30 minutes at 37 ℃, and enabling the system to have red fluorescence under a fluorescence imager; another set of cells was added with 1mM NEM (thiol scavenger) and allowed to wait 30 minutes, and then 2mL of 10 μ M probe solution was added to it, after half an hour of incubation, the system showed no red fluorescence under the fluorescence imager, indicating that there was endogenous cysteine in the cells. See fig. 8. The dishes were then washed 2-3 times with Hepes buffer and incubated with 20. mu.M of exogenous Cys for 30 minutes, and the system showed time-dependent red fluorescence under a fluorescence imager, as shown in FIG. 9.
Claims (4)
1. A reagent SYP for distinguishing and detecting cysteine is characterized in that the structural formula is as follows:
2. a method for the synthesis of a reagent SYP for the differential detection of cysteine according to claim 1, comprising the following steps:
(1) according to the mol ratio of 1:1: 0.01 adding 2-amino thiophenol, 5-methyl salicylaldehyde and silver nitrate into DMSO, mixing, and stirring at room temperature in the dark for 2 hours; then diluting with dichloromethane by 3 times, washing with brine, combining organic phases, drying with anhydrous sodium sulfate, concentrating, and purifying by column chromatography with ethyl acetate/petroleum ether at a volume ratio of 1:6 to obtain light yellow solid, namely 2-benzothiazol-2-yl-4-methylphenol;
(2) according to a molar ratio of 1.8: 3.9 dissolving the compound 2-benzothiazole-2-yl-4-methylphenol and hexamethylenetetramine in trifluoroacetic acid, and refluxing overnight under stirring; after completion of the reaction and cooling to room temperature, the pH was adjusted using potassium hydroxide until the solid completely precipitated, filtered, washed with water, dried under vacuum and purified by ethyl acetate/petroleum ether column chromatography in a volume ratio of 1:5 to obtain compound 3- (benzothiazol-2-yl) -2-hydroxy-5-methylbenzaldehyde as a yellow solid;
(3) according to the mol ratio of 1:1 adding a compound 3- (benzothiazol-2-yl) -2-hydroxy-5-methylbenzaldehyde and a compound 2- (3,5, 5-trimethylcyclohex-2-en-1-yl) malononitrile into ethanol, adding 0.1 equivalent of piperidine under stirring, mixing, and heating and refluxing for 10 hours; after completion of the reaction and cooling to room temperature, the mixture was filtered, washed with ethanol, and dried under vacuum to give (E) -2- (3- (3- (3-benzothiazol-2-yl) -2-hydroxy-5-methylstyryl) -5, 5-dimethylcyclohex-2-en-1-ylidene) malononitrile as an orange-red solid;
(4) according to the mol ratio of 1: 1.5 addition of the Compound (E) -2- (3- (3- (3-benzothiazol-2-yl) -2-hydroxy-5-methylstyryl) -5, 5-dimethylcyclohex-2-en-1-ylidene) malononitrile and acryloyl chloride to anhydrous CH2Cl2Then the mixture was cooled to 0 ℃ and Et 3 times the equivalent weight was added dropwise with stirring3N, after stirring at 0 ℃ for 1h, the reaction is complete and the mixture is filtered, separately with methanol and CH2Cl2Washed and dried under vacuum to give the compound (E) -2- (benzothiazol-2-yl) -6- (2- (3- (dicyanomethylene) -5,5-dimethylcyclohex-1-en-1-yl) vinyl) -4-methylphenyl acrylate as a yellow solid.
3. Use of a reagent SYP according to claim 1 for the detection of cysteine.
4. A method for detecting cysteine comprising the steps of:
(1) preparing a Hepes solution with the pH value of 7.4 and the concentration of 10mM, and preparing the solution, methanol and acetonitrile into CH with the volume ratio of 1:1:13OH/CH3CN/Hepes buffer solution, preparing 0.02M cysteine aqueous solution, and dissolving benzothiazole derivative SYP in DMSO to prepare 2mM solution;
(2) 2mL of CH was taken3OH/CH3Adding CN/Hepes buffer solution and 10 mu L of DMSO solution of SYP into a fluorescence cuvette, detecting on a fluorescence spectrophotometer, and gradually increasing the fluorescence intensity at 686nm along with the addition of cysteine to be detected;
(3) 2mLCH3OH/CH3Adding CN/Hepes buffer solution into a fluorescence cuvette, simultaneously adding 10 μ L of DMSO solution of SYP, uniformly mixing the system, gradually adding 0.02M cysteine aqueous solution, wherein the volume of the added solution is 0, 2, 4, 5, 6, 7, 8, 10 and 12 μ L, and simultaneously measuring the fluorescence intensity at 686nm on a fluorescence spectrometerDegree 397, 511, 629, 687, 745, 803, 861, 976 and 1093, plotting the cysteine concentration as abscissa and the fluorescence intensity F as ordinate to obtain a working curve of the cysteine concentration; the linear regression equation is: f6865.8C +396.8, with C having a unit of 10-6mol/L；
(4) And when the sample solution is measured, substituting the measured fluorescence intensity into a linear regression equation to obtain the concentration of the cysteine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010125872.6A CN111303072A (en) | 2020-02-27 | 2020-02-27 | Reagent for distinguishing and detecting cysteine and synthetic method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010125872.6A CN111303072A (en) | 2020-02-27 | 2020-02-27 | Reagent for distinguishing and detecting cysteine and synthetic method and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111303072A true CN111303072A (en) | 2020-06-19 |
Family
ID=71154696
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010125872.6A Pending CN111303072A (en) | 2020-02-27 | 2020-02-27 | Reagent for distinguishing and detecting cysteine and synthetic method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111303072A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111675632A (en) * | 2020-06-22 | 2020-09-18 | 湖南师范大学 | Fluorescent molecular probe for detecting genotoxin Colibactin through visual imaging as well as preparation method and application of fluorescent molecular probe |
| CN112939886A (en) * | 2021-02-04 | 2021-06-11 | 山西大学 | Near-infrared fluorescent probe capable of detecting content of GSTs (glutathione S-terminal transferase) as well as synthetic method and application thereof |
Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101329279A (en) * | 2008-07-18 | 2008-12-24 | 山西大学 | Method for rapidly testing cysteine in water solution |
| CN102323233A (en) * | 2011-07-09 | 2012-01-18 | 山西大学 | Reagent and method for detecting homocysteine (HCY) |
| CN102928392A (en) * | 2012-10-29 | 2013-02-13 | 山西大学 | Cysteine detection method |
| CN103788076A (en) * | 2014-01-22 | 2014-05-14 | 山西大学 | Reagent and method for detecting cysteine |
| CN105181666A (en) * | 2015-09-23 | 2015-12-23 | 山西大学 | Reagent and method for conducting fluorescence detection on cysteine |
| CN108129365A (en) * | 2018-01-03 | 2018-06-08 | 湖南韵邦生物医药有限公司 | A kind of fluorescence probe, preparation method and the application of near infrared detection cysteine |
| CN108623533A (en) * | 2018-07-13 | 2018-10-09 | 济南大学 | A kind of fluorescence probe for detecting cysteine and application based on thiazole |
| CN109336915A (en) * | 2018-10-11 | 2019-02-15 | 贺州学院 | A kind of cysteine fluorescence probe and its preparation method and application |
| CN109516969A (en) * | 2018-11-08 | 2019-03-26 | 山西大学 | One kind coumarin derivative containing carboxyl and its synthetic method and application |
| CN109678763A (en) * | 2018-12-06 | 2019-04-26 | 华南理工大学 | A kind of near-infrared biological thiol fluorescence probe and its preparation method and application |
| CN110028463A (en) * | 2019-04-11 | 2019-07-19 | 青岛科技大学 | A kind of fluorescence probe and its synthetic method and application with big Stokes shift |
| CN110143954A (en) * | 2019-06-03 | 2019-08-20 | 山西大学 | A kind of coumarin derivative and its synthetic method and application |
| CN110204536A (en) * | 2019-06-10 | 2019-09-06 | 山西大学 | It is a kind of for distinguish detection Cys/Hcy and GSH fluorescence probe and preparation method thereof |
| CN114349717A (en) * | 2022-02-25 | 2022-04-15 | 明士新材料有限公司 | Benzothiazole derivative cysteine-based fluorescent probe and preparation method thereof |
-
2020
- 2020-02-27 CN CN202010125872.6A patent/CN111303072A/en active Pending
Patent Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101329279A (en) * | 2008-07-18 | 2008-12-24 | 山西大学 | Method for rapidly testing cysteine in water solution |
| CN102323233A (en) * | 2011-07-09 | 2012-01-18 | 山西大学 | Reagent and method for detecting homocysteine (HCY) |
| CN102928392A (en) * | 2012-10-29 | 2013-02-13 | 山西大学 | Cysteine detection method |
| CN103788076A (en) * | 2014-01-22 | 2014-05-14 | 山西大学 | Reagent and method for detecting cysteine |
| CN105181666A (en) * | 2015-09-23 | 2015-12-23 | 山西大学 | Reagent and method for conducting fluorescence detection on cysteine |
| CN108129365A (en) * | 2018-01-03 | 2018-06-08 | 湖南韵邦生物医药有限公司 | A kind of fluorescence probe, preparation method and the application of near infrared detection cysteine |
| CN108623533A (en) * | 2018-07-13 | 2018-10-09 | 济南大学 | A kind of fluorescence probe for detecting cysteine and application based on thiazole |
| CN109336915A (en) * | 2018-10-11 | 2019-02-15 | 贺州学院 | A kind of cysteine fluorescence probe and its preparation method and application |
| CN109516969A (en) * | 2018-11-08 | 2019-03-26 | 山西大学 | One kind coumarin derivative containing carboxyl and its synthetic method and application |
| CN109678763A (en) * | 2018-12-06 | 2019-04-26 | 华南理工大学 | A kind of near-infrared biological thiol fluorescence probe and its preparation method and application |
| CN110028463A (en) * | 2019-04-11 | 2019-07-19 | 青岛科技大学 | A kind of fluorescence probe and its synthetic method and application with big Stokes shift |
| CN110143954A (en) * | 2019-06-03 | 2019-08-20 | 山西大学 | A kind of coumarin derivative and its synthetic method and application |
| CN110204536A (en) * | 2019-06-10 | 2019-09-06 | 山西大学 | It is a kind of for distinguish detection Cys/Hcy and GSH fluorescence probe and preparation method thereof |
| CN114349717A (en) * | 2022-02-25 | 2022-04-15 | 明士新材料有限公司 | Benzothiazole derivative cysteine-based fluorescent probe and preparation method thereof |
Non-Patent Citations (5)
| Title |
|---|
| HAIXIAN REN,等: "An NIR ESIPT-based fluorescent probe with large stokes shift for specific detection of Cys and its bioimaging in cells and mice", 《SENSORS AND ACTUATORS, B:CHEMICAL》, vol. 319, 8 May 2020 (2020-05-08), pages 128248, XP086175659, DOI: 10.1016/j.snb.2020.128248 * |
| MEIQING ZHU,等: "An ICT-based ratiometric fluorescent probe for cysteine and its application in biological issues", 《JOURNAL OF MOLECULAR LIQUIDS》, vol. 296, 8 October 2019 (2019-10-08), pages 1 - 11832, XP086039021, DOI: 10.1016/j.molliq.2019.111832 * |
| 刘柳,等: "用于检测巯基化合物的荧光探针的研究进展", 《化学与生物工程》, vol. 33, no. 02, 29 February 2016 (2016-02-29), pages 1 - 7 * |
| 罗静,等: "荧光化学传感器的研究进展", 《功能高分子学报》, vol. 23, no. 04, 31 December 2010 (2010-12-31), pages 413 - 422 * |
| 谢光杰,等: "选择性生物小分子硫醇荧光探针的研究进展", 《化学研究与应用》, vol. 28, no. 09, 30 September 2016 (2016-09-30), pages 1177 - 1185 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111675632A (en) * | 2020-06-22 | 2020-09-18 | 湖南师范大学 | Fluorescent molecular probe for detecting genotoxin Colibactin through visual imaging as well as preparation method and application of fluorescent molecular probe |
| CN111675632B (en) * | 2020-06-22 | 2021-06-22 | 湖南师范大学 | Fluorescent molecular probe for detecting genotoxin Colibactin through visual imaging as well as preparation method and application of fluorescent molecular probe |
| CN112939886A (en) * | 2021-02-04 | 2021-06-11 | 山西大学 | Near-infrared fluorescent probe capable of detecting content of GSTs (glutathione S-terminal transferase) as well as synthetic method and application thereof |
| CN112939886B (en) * | 2021-02-04 | 2022-05-31 | 山西大学 | Near-infrared fluorescent probe capable of detecting content of GSTs (glutathione S-terminal transferase) as well as synthetic method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108484622B (en) | Synthesis of multi-signal fluorescent probe and application thereof in simultaneous differential detection of Hcy, Cys and GSH | |
| CN108997326B (en) | Thiol fluorescent probe and preparation method and application thereof | |
| CN107602502B (en) | ESIPT type fluorescent probe for biological mercaptan detection and application | |
| CN105712964B (en) | Preparation method and application of thiol fluorescent probe based on coumaroyl hydrazide | |
| CN110041317A (en) | A kind of naphthalimide fluorescence probe and its preparation and application | |
| CN110498758B (en) | Near-infrared fluorescent probe for identifying glutathione and preparation and application thereof | |
| CN109293595A (en) | A kind of near infrared fluorescent probe and its preparation method and application detecting hydrogen sulfide | |
| CN111303072A (en) | Reagent for distinguishing and detecting cysteine and synthetic method and application thereof | |
| Liu et al. | Oxidized-morpholine dressing ratiometric fluorescent probe for specifically visualizing the intracellular glutathione | |
| CN111205242A (en) | Benzothiazole derivative and synthesis method and application thereof | |
| CN110143954A (en) | A kind of coumarin derivative and its synthetic method and application | |
| CN111253356A (en) | Coumarin-benzopyrylium salt derivative and synthesis method and application thereof | |
| CN111205243B (en) | Reagent for distinguishing and detecting thiophenol as well as synthesis method and application thereof | |
| CN111285836A (en) | Preparation and application of near-infrared fluorescent probe | |
| CN111217799A (en) | Indole salt-coumarin derivative and synthesis method and application thereof | |
| CN111073634B (en) | Nitroreductase fluorescent probe based on nitroreduction and sulfur-nitrogen transposition and preparation method thereof | |
| Wei et al. | Mitochondria-targeted ratiometric fluorescent imaging of cysteine | |
| CN112939963B (en) | Benzopyranoate derivative and synthesis method and application thereof | |
| CN105985299B (en) | A kind of fluorescence probe of highly selective hypersensitive analysis ferrous ion | |
| CN108383774A (en) | It is a kind of based on the cysteine fluorescence probe of end group acetylenic ketone and its preparation and application | |
| CN109485627B (en) | Coumarin derivative, synthesis method thereof and application of coumarin derivative in detection of hydrogen sulfide | |
| CN110452236B (en) | Coumarin cysteine fluorescent probe and preparation method and application thereof | |
| CN110894193B (en) | Synthesis of novel fluorescent probe and application of novel fluorescent probe in cysteine detection | |
| CN109422736A (en) | The weary oxygen fluorescence probe in 2nd area of near-infrared and its preparation method and application | |
| CN111116511A (en) | Benzothiazole biological thiol probe and preparation method and application thereof |
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 | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20200619 |
|
| RJ01 | Rejection of invention patent application after publication |