CN108752371B - Two-photon hydrogen peroxide fluorescent probe based on quinoline - Google Patents
Two-photon hydrogen peroxide fluorescent probe based on quinoline Download PDFInfo
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- CN108752371B CN108752371B CN201810767815.0A CN201810767815A CN108752371B CN 108752371 B CN108752371 B CN 108752371B CN 201810767815 A CN201810767815 A CN 201810767815A CN 108752371 B CN108752371 B CN 108752371B
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title claims abstract description 86
- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 21
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title description 4
- 239000000126 substance Substances 0.000 claims description 3
- 239000000523 sample Substances 0.000 abstract description 15
- 238000001514 detection method Methods 0.000 abstract description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 6
- 230000035945 sensitivity Effects 0.000 abstract description 5
- 238000010992 reflux Methods 0.000 abstract description 3
- -1 thiazole-2-yl Chemical group 0.000 abstract description 3
- 229910052796 boron Inorganic materials 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 abstract description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 abstract 1
- 125000005605 benzo group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 230000005284 excitation Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000007853 buffer solution Substances 0.000 description 5
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000003384 imaging method Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 238000002795 fluorescence method Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000003642 reactive oxygen metabolite Substances 0.000 description 1
- 238000003375 selectivity assay Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000011895 specific detection Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
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- 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
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Abstract
The invention discloses a fluorescent probe for detecting hydrogen peroxide, and belongs to the technical field of analytical chemistry. The probe is obtained by refluxing and stirring 6- (benzo [ d ] thiazole-2-yl) naphthalene-2-ol and 4-boron lipid benzyl bromide in acetone. The fluorescent probe disclosed by the invention is simple to synthesize, convenient to use, and has the advantages of good selectivity, sensitivity, low detection limit and the like on hydrogen peroxide, and can be applied to detection of hydrogen peroxide in cells.
Description
Technical Field
The invention provides a fluorescent probe for detecting hydrogen peroxide, and belongs to the technical field of fluorescent probes.
Technical Field
The active oxygen comprises hydrogen peroxide radical (HO)2Cndot.), superoxide radical (O)2Cnidium lactone (RO), peroxy Radical (RO)2H), hydroxyl radical (HO H), hypochlorous acid (HOCl), singlet oxygen (H) (H), and1O2) And hydrogen peroxide (H)2O2) And the like. Hydrogen peroxide is an important active oxygen species, and is extremely important in living organisms and the external environment. Research shows that hydrogen peroxide is involved in physiological and pathological regulation processes and is closely related to the proliferation and differentiation and migration processes of cells. In addition, a moderate level of hydrogen peroxide in the body is beneficial to the normal physiological processes of the organism, such as inflammation, body defense and the like; however, many diseases are also caused by excessive hydrogen peroxide, such as cancer and Alzheimer's disease. Therefore, the method has very important significance in real-time quantitative detection of the hydrogen peroxide in the living organisms and the external environment.
Current techniques for detecting hydrogen peroxide include electrochemical methods, colorimetric methods, gas detection methods, fluorescence methods, and the like. The fluorescent probe has the advantages of simple operation, no radiation, high sensitivity and high resolution, and is an effective means for detecting hydrogen peroxide. In recent years, many fluorescent probes for detecting hydrogen peroxide have been reported, but most of the probes are single-photon excited and have great damage to cells and living bodies. As is known, the excitation wavelength of a two-photon organic small-molecule fluorescent probe is generally about twice of that of single-photon excitation, so that the excitation wavelength is generally positioned in a near infrared region (700 + 1000 nm), the excitation light in the band has high focusing and region excitation effects, does not damage biological tissues, and can realize deep imaging in the biological tissues. In the prior art, patent CN 106749359A provides a hydrogen peroxide probe compound, but the probe compound completes the detection of hydrogen peroxide in 60 minutes; in addition, because the hydrogen peroxide has short existence time and is easy to react with other substances to generate new active oxygen species, the design of the probe with short response time, high sensitivity and strong selectivity has very important significance.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a fluorescence-enhanced probe for detecting hydrogen peroxide, and researches the spectral property and the application inside and outside cells.
The invention relates to a fluorescent probe for detecting hydrogen peroxide, which is characterized in that the chemical structural formula of the fluorescent probe
Shown in the figure:
the fluorescent probe for detecting hydrogen peroxide is prepared by the following method:
synthesis of Compound I
Dissolving the compound II, 4-boron ester benzyl bromide and potassium carbonate in acetone, refluxing and stirring overnight, vacuum concentrating to obtain a crude product, and performing column chromatography to obtain a white solid compound I.
According to the invention, the compound II, the 4-borolipid benzyl bromide and the potassium carbonate are preferably in a molar ratio of 1:1: 1;
according to the invention, the synthesis of compound I is preferably carried out entirely under nitrogen protection.
The fluorescent probe can be used for detecting hydrogen peroxide in aqueous solution in real time.
More preferably, the fluorescent probe is used for rapidly detecting hydrogen peroxide in a DMSO and PBS buffer solution mixed solution with the pH of 7.4, and the detection limit is 1.40 × 10-7mol/L。
The fluorescent probe disclosed by the invention has specific response performance to hydrogen peroxide in a mixed solution of DMSO and PBS buffer solution with the pH value of 7.4. The invention is verified by experiments that after the hydrogen peroxide is dripped into DMSO and PBS buffer solution with the pH value of 7.4, a light source with the wavelength of 420nm is used as exciting light, and the solution emits strong yellow fluorescence at 542 nm. The probe is not responsive to other reactive oxygen species. Therefore, the fluorescent probe compound of the present invention has high selectivity for hydrogen peroxide.
The fluorescent probe disclosed by the invention is applied to detecting hydrogen peroxide in cells.
The fluorescent probe can be applied to the detection of hydrogen peroxide in cells. The specific detection method comprises the following steps: compound I was incubated with Hela cells for 15 minutes, and then hydrogen peroxide was added and the cells fluoresced strongly yellow. Experiments show that the compound I can recognize hydrogen peroxide in cells.
The fluorescent probe for detecting hydrogen peroxide disclosed by the invention has the advantages of high selectivity, good sensitivity, capability of imaging in cells and the like.
Drawings
FIG. 1 is a drawing of Compound I1H NMR spectrum.
FIG. 2 is a graph of the selectivity spectrum of Compound I.
FIG. 3 is a fluorescence spectrum of Compound I as a function of hydrogen peroxide concentration.
Fig. 4 is an image of compound I excited by two photons in a cell.
Detailed Description
The present invention will be described in detail below with reference to the accompanying drawings and specific embodiments, but is not limited thereto. The various materials in the examples were purchased from the market.
EXAMPLE 1 Synthesis of Compound I
0.25 g of compound II, 0.2 g of 4-boratabenzyl bromide and 0.26 g of potassium carbonate were dissolved in acetone, stirred under reflux overnight, concentrated under vacuum to give a crude product, which was chromatographed on a column to give compound I as a white solid in 50% yield.
EXAMPLE 2 Probe Compound I Selectivity assay
100 equivalents of hydrogen peroxide is added into DMSO/PBS buffer solution containing 5 mu M of compound I, the detection result is shown in figure 2, when the wavelength of the excitation light is 420nm, the probe compound I emits 542nm yellow fluorescence, and the probe compound I is not interfered by other peroxides, which indicates that the probe compound I has good selectivity on hydrogen peroxide.
EXAMPLE 3 Probe Compound I titration analysis for Hydrogen peroxide
When 0 to 40 equivalents of hydrogen peroxide was dropped into the buffer solution containing 5. mu.M of the probe compound I, the fluorescence response intensity rapidly increased with the increase in the amount of hydrogen peroxide added, and the results of the detection are shown in FIG. 3, which indicates that the probe compound I had a high sensitivity to the hydrogen peroxide concentration.
EXAMPLE 4 detection of intracellular Hydrogen peroxide by Compound I
After compound I and Hela cells are incubated together, hydrogen peroxide is added, the cells emit bright yellow fluorescence under the excitation of light with the wavelength of 800nm, and the imaging result is shown in figure 4. Experiments show that the probe compound I can recognize hydrogen peroxide in cells.
Claims (1)
1. A fluorescent probe for detecting hydrogen peroxide is characterized in that the chemical structural formula of the fluorescent probe is shown as I
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810767815.0A CN108752371B (en) | 2018-07-13 | 2018-07-13 | Two-photon hydrogen peroxide fluorescent probe based on quinoline |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810767815.0A CN108752371B (en) | 2018-07-13 | 2018-07-13 | Two-photon hydrogen peroxide fluorescent probe based on quinoline |
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| Publication Number | Publication Date |
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| CN108752371A CN108752371A (en) | 2018-11-06 |
| CN108752371B true CN108752371B (en) | 2020-06-30 |
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Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106632441A (en) * | 2016-12-16 | 2017-05-10 | 济南大学 | Ratio type fluorescent probe for identifying hydrogen peroxide |
| CN108129500A (en) * | 2018-01-11 | 2018-06-08 | 中南大学 | A kind of synthesis and application of the ratio type fluorescence probe for identifying hydrogen peroxide |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106632441A (en) * | 2016-12-16 | 2017-05-10 | 济南大学 | Ratio type fluorescent probe for identifying hydrogen peroxide |
| CN108129500A (en) * | 2018-01-11 | 2018-06-08 | 中南大学 | A kind of synthesis and application of the ratio type fluorescence probe for identifying hydrogen peroxide |
Non-Patent Citations (3)
| Title |
|---|
| A fast-response two-photonfluorescent probe for imaging endogenous H2O2in living cells and tissues;Yanan Lu等;《Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy》;20170914;第190卷;第353-359页 * |
| A Fluorescent Probe for Hydrogen Peroxide in Vivo Based on the Modulation of Intramolecular Charge Transfer;Yuzhi Chen等;《Anal. Chem.》;20170418;第89卷;第5278-5284页 * |
| Two-Photon Fluorescent Probe for Detection of Exogenous and Endogenous Hydrogen Persulfide and Polysulfide in Living Organisms;Lingyu Zeng等;《Anal. Chem.》;20150206;第87卷;第3004-3010页 * |
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