CN109485627A - A kind of coumarin derivative and its synthetic method and the application in detection hydrogen sulfide - Google Patents
A kind of coumarin derivative and its synthetic method and the application in detection hydrogen sulfide Download PDFInfo
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- CN109485627A CN109485627A CN201811326163.3A CN201811326163A CN109485627A CN 109485627 A CN109485627 A CN 109485627A CN 201811326163 A CN201811326163 A CN 201811326163A CN 109485627 A CN109485627 A CN 109485627A
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
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- G—PHYSICS
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- 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"
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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Abstract
The present invention provides a kind of coumarin derivative and its synthetic methods and the application in detection hydrogen sulfide, the Chinese of the derivative is 2- oxo -2H- chromene -7- base 2- ((2,4- dinitrophenyl) thio) benzoic ether, English name is 2-oxo-2H-chromen-7-yl 2- ((2,4-dinitrophenyl) thio) benzoate, it is named as CDP.The present invention provides a kind of coumarin derivative CDP to pass through the content of sepectrophotofluorometer quantitative detection hydrogen sulfide in the solution of DMSO:PBS (7:3, v/v, PBS buffer, pH 7.4) to the method for hydrogen sulfide specific detection.The detection process is easy, sensitive, quick, and testing result is accurate.
Description
Technical field
The present invention relates to coumarin derivative and sulfurated hydrogen detection, a kind of coumarin derivative and its synthesis side are particularly belonged to
Method and the application in detection hydrogen sulfide.
Background technique
Studies have shown that endogenic hydrogen sulfide mostlys come from the enzymolysis of L- hydrogen sulfide, generting machanism is at least with 4
The different enzyme of kind is related: cystathionie-beta-synthetase (CBS), cystathionie-γ-lyases (CSE), the transfer of 3-mercaptopyruvate sulphur
Enzyme (3-MST) and hydrogen sulfide enzyme (CL).These enzymes widely exist in the various tissues of human body and organ.In physiological concentration level
Under, hydrogen sulfide participates in a series of physiological regulating control process, such as adjusts antiotasis, myocardial contraction, nerve conduction and insulin
Secretion etc..Cell cannot once maintain its normal concentration of hydrogen sulfide, will cause artery and pulmonary hypertension, Alzheimer
The diseases such as family name's disease, gastric mucosa damage and cirrhosis.In addition, hydrogen sulfide can also Scavenger of ROS and active nitrogen species.Many researchs
Also show also to regulate and control the strong of human body by various reciprocations between three gasotransmitter hydrogen sulfide, nitric oxide and carbon monoxide
Health and disease.
The requirement that concentration of hydrogen sulfide level detects in biosystem is answered, design choice is good, high sensitivity, has low cell
The fluorescence probe for hydrogen sulfide levels variation in detecting living cells and organizing of toxicity, it has also become have in biomedical advancement
One of advanced subject of challenge.
In the present invention, synthesized a kind of compound based on cumarin, by hydrogen sulfide and compound before the reaction after
Change in fluorescence realizes the specific detection of hydrogen sulfide.
Summary of the invention
The object of the present invention is to provide a kind of coumarin derivative and preparation method thereof, the coumarin derivative can be used for
Sulfurated hydrogen detection, and detection method is simple, easy to operate, good, the high sensitivity of selectivity.
A kind of coumarin derivative provided by the invention, Chinese are 2- oxo -2H- chromene -7- base 2- ((2,4- bis-
Nitrobenzophenone) thio) benzoic ether, English name is 2-oxo-2H-chromen-7-yl 2- ((2,4-dinitrophenyl)
Thio) benzoate is named as CDP structural formula are as follows:
The synthetic method of coumarin derivative CDP provided by the invention a kind of, step are as follows:
By 2- [(2,4- dinitrophenyl) is thio] benzoic acid, 4-dimethylaminopyridine, 1- (3- dimethylamino third
Base) -3- ethyl-carbodiimide hydrochloride and umbelliferone mix in anhydrous methylene chloride, mixture stirred at room temperature
It mixes overnight；Solvent is removed under reduced pressure, gained residue is further purified by silica gel column chromatography, obtains light yellow powder object
CDP；Wherein the molar ratio of 2- [(dinitrophenyl group) is thio] benzoic acid and umbelliferone is 1:1.
The eluant, eluent of the column chromatography is the methylene chloride of volume ratio 20:1 and the mixture of methanol.
The coumarin derivative CDP can be used for sulfurated hydrogen detection.
A kind of method detecting hydrogen sulfide provided by the invention, step are as follows:
(1), it prepares pH=7.4, the PBS buffer solution that concentration is 10mM, prepares the hydrogen sulfide solution of 20mM；
(2), the DMSO solution of DMSO/PBS (7:3v/v, pH 7.4) solution, 2 μ L CDP for taking 2mL is added to a fluorescence
In cuvette, detected on Fluorescence spectrophotometer, with the addition to test sample hydrogen sulfide, fluorescence intensity at 465nm by
It is cumulative strong；
(3), in 6 cuvettes, the DMSO of each DMSO/PBS (7:3v/v, pH 7.4) solution that 2mL is added, 2 μ LCDP
Solution, the volume for being separately added into hydrogen sulfide solution measure in Fluorescence Spectrometer after being 0,4,8,12,16,20 μ L, 30min
Fluorescence intensity is 603.5,1581,2748,4030,5632,7173 using concentration of hydrogen sulfide as abscissa at 465nm, strong with fluorescence
Degree is that ordinate draws figure, obtains the working curve of concentration of hydrogen sulfide；Equation of linear regression are as follows: F-F0=330.6143c-
281.14, c unit is 10-5mol/L；
(4), when measuring sample solution, the fluorescence intensity measured is substituted into equation of linear regression, hydrogen sulfide can be acquired
Concentration.
Compared with prior art, the invention has the advantages that and effect:
1, the synthetic method of coumarin derivative of the present invention is simple, easy to operate；
2, coumarin derivative of the present invention is able to achieve the specific detection to hydrogen sulfide, it is shown that high sensitivity and fabulous
Selectivity；
3, detection means of the present invention is simple, it is only necessary to can be realized by Fluorescence Spectrometer；
4, present invention detection signal is obvious, is enhanced fluorescence.
Detailed description of the invention
The nucleus magnetic hydrogen spectrum figure of coumarin derivative CDP prepared by Fig. 1 embodiment 1
The nuclear-magnetism carbon spectrogram of coumarin derivative CDP prepared by Fig. 2 embodiment 1
The mass spectrogram of coumarin derivative CDP prepared by Fig. 3 embodiment 1
The fluorescent emission figure of Fig. 4 coumarin derivative CDP and hydrogen sulfide effect
The fluorescence histogram of Fig. 5 coumarin derivative CDP and various analytes
The working curve of Fig. 6 coumarin derivative CDP measurement hydrogen sulfide
The fluorescent emission figure of Fig. 7 coumarin derivative CDP measurement sample
Fig. 8 coumarin derivative CDP cell imaging figure
Specific embodiment
Below with reference to embodiment and attached drawing, the present invention will be further described, but the present invention is not by the limit of following embodiments
System.
Embodiment 1
The preparation and characterization of CDP
By 4-dimethylaminopyridine (12mg, 0.1mmol), 1- (3- dimethylaminopropyl) -3- ethyl carbodiimide
Hydrochloride (192mg, 1mmol) and 2- [(2,4- dinitrophenyl) is thio] benzoic acid (320mg, 1mmol) and 7- hydroxyl are fragrant
Legumin (162mg, 1mmol) mixes in 25mL anhydrous methylene chloride, and mixture is stirred at room temperature overnight.It is removed under reduced pressure molten
Agent, gained residue are further purified by silica gel column chromatography, and with methylene chloride: methanol (20:1, v/v) is used as eluant, eluent, obtains
To light yellow powder object (412mg, 88%).1H NMR(DMSO-d6, 600MHz): δ 8.88 (d, J=2.2Hz, 1H),
8.43-8.28 (m, 2H), 8.08 (d, J=9.6Hz, 1H), 7.86 (d, J=5.4Hz, 3H), 7.79 (d, J=8.5Hz, 1H),
7.36 (s, 1H), 7.24-7.13 (m, 2H), 6.49 (d, J=9.6Hz, 1H) (Fig. 1)13C NMR(DMSO-d6,150MHz):δ
163.3,159.4,153.9,152.2,144.7,144.4,143.6,137.4,134.4,133.3,132.1,131.2,
(130.0,129.4,127.6,121.0,118.2,116.9,115.9,109.8 Fig. 2) .ESI-MS m/z:[M+Na]+Calcd
For 487.0212, Found 487.0210 (Fig. 3)
Embodiment 2
It prepares pH=7.4, the PBS buffer solution that concentration is 10mM, prepares the DMSO solution of 2mM CDP, prepare 20mM sulphur
Change aqueous solution of hydrogen；The DMSO solution of DMSO/PBS (7:3v/v, pH 7.4) solution, 2 μ L CDP for taking 2mL is added to fluorescence cuvette
In, the volume for being gradually added into hydrogen sulfide solution measures 465nm after being 0,4,8,12,16,20 μ L, 30min in Fluorescence Spectrometer
Locating fluorescence intensity is 603.5,1581,2748,4030,5632,7173, and fluorescence intensity gradually increases.Fluorescent emission figure is shown in Fig. 4.
Embodiment 3
It prepares pH=7.4, the PBS buffer solution that concentration is 10mM, prepares the DMSO solution of 2mM CDP, prepare 20mM's
Hydrogen sulfide solution；In fluorescence cuvette, each DMSO/PBS (7:3v/v, pH 7.4) solution that 2mL is added and 2 μ L CDP's
DMSO solution, then it is separately added into other analytes and hydrogen sulfide of 10 times of equivalents: Cys, Hcy, GSH, S2O3 2-,SO3 2-,Br-,
Cl-,F-,HSO3 -,NO2 -,S2O4 2-,S2O5 2-,SCN-,CO3 2-,HCO3 -Aqueous solution, detected on Fluorescence spectrophotometer, draw
Fluorescence intensity histogram at the corresponding 465nm of different analytes (see Fig. 5).Hydrogen sulfide makes detection architecture fluorescence at 465nm
Intensity is significantly raised, and other analytes do not cause the variation of detection architecture fluorescence intensity substantially.
Embodiment 4
It prepares pH=7.4, the PBS buffer solution that concentration is 10mM, and prepares the solution of 2mM CDP with DMSO, prepare
20mM hydrogen sulfide solution；In 8 cuvettes, each DMSO/PBS (7:3v/v, pH 7.4) solution, 2 μ LCDP that 2mL is added
DMSO solution, be separately added into hydrogen sulfide solution volume be 0,4,8,12,16,20 μ L, 3min after surveyed in Fluorescence Spectrometer
Determining fluorescence intensity at 465nm is 603.5,1581,2748,4030,5632,7173, using concentration of hydrogen sulfide as abscissa, with fluorescence
Intensity is that ordinate draws figure, obtains the working curve of concentration of hydrogen sulfide；Equation of linear regression are as follows: F-F0=330.6143c-
281.14, c unit is 10-5mol/L.See Fig. 6.
Embodiment 5
It prepares pH=7.4, the PBS buffer solution that concentration is 10mM, and prepares the solution of 2mM CDP with DMSO, prepare
20mM hydrogen sulfide solution；The DMSO solution of 2 μ L CDP is added to DMSO/PBS (7:3v/v, pH 7.4) solution of 2mL
In fluorescence cuvette, the 10 μ L of solution of hydrogen sulfide is taken, is added in this cuvette with microsyringe, while in Fluorescence Spectrometer
Measuring 465nm fluorescence intensity is 3790, by the equation of linear regression of embodiment 4, acquires c=10.219 × 10-5mol/L.Partially
Difference is 2.1%.See Fig. 7.
Embodiment 6
It prepares pH=7.4, the PBS buffer solution that concentration is 10mM, and prepares the solution of 2mM CDP with DMSO, prepare
20mM hydrogen sulfide solution；The DMSO solution of 5 μ L CDP is added in the PBS of 2mL；HepG-2 cell is added in probe solution
In culture solution, so that its concentration is 5 μM, with HepG-2 cell at 37 DEG C, 15min is reacted, system is several under phosphorimager
Do not have fluorescence (Fig. 8 b)；5 μ L SNP (stimulation of endogenous hydrogen sulfide) solution are added in the PBS of 2mL, solution is added
In HepG-2 cell culture fluid, it is incubated for 15min at 37 DEG C, adds 5 μM of probe solution, 15min, body are incubated at 37 DEG C
It ties up under phosphorimager and is displayed in blue fluorescence (Fig. 8 a)；Probe solution is added in HepG-2 cell culture fluid, so that its is dense
Degree is 5 μM, with HepG-2 cell at 37 DEG C, reacts 15min, adds the hydrogen sulfide of external source, and making its concentration is respectively 50 μ
M reacts 15min at 37 DEG C, and system is displayed in blue fluorescence (Fig. 8 c) under phosphorimager；HepG- is added in probe solution
In 2 cell culture fluids, so that its concentration is 5 μM, with HepG-2 cell at 37 DEG C, 15min is reacted, the vulcanization of external source is added
Hydrogen, making its concentration is respectively 100 μM, at 37 DEG C, reacts 15min, system is displayed in blue fluorescence (figure under phosphorimager
8d)。
Claims (5)
1. a kind of coumarin derivative CDP, which is characterized in that structural formula are as follows:
2. a kind of synthetic method of coumarin derivative CDP as described in claim 1, which is characterized in that steps are as follows:
By 2- [(2,4- dinitrophenyl) is thio] benzoic acid, 4-dimethylaminopyridine, 1- (3- dimethylaminopropyl) -3-
Ethyl-carbodiimide hydrochloride and umbelliferone mix in anhydrous methylene chloride, and mixture was stirred at room temperature
Night；Solvent is removed under reduced pressure, gained residue is further purified by silica gel column chromatography, obtains light yellow powder object CDP；
Wherein the molar ratio of 2- [(dinitrophenyl group) is thio] benzoic acid and umbelliferone is 1:1.
3. the preparation method of coumarin derivative CDP as described in claim 1, which is characterized in that the elution of the column chromatography
Agent is the methylene chloride of volume ratio 20:1 and the mixture of methanol.
4. application of the coumarin derivative CDP as described in claim 1 in sulfurated hydrogen detection.
5. a kind of method for detecting hydrogen sulfide, includes the following steps:
(1), it prepares pH=7.4, the PBS buffer solution that concentration is 10mM, the hydrogen sulfide solution of 20mM is prepared, by claim
Coumarin derivative CDP described in 1 is dissolved in the solution that DMSO is configured to 2mM；
(2), the DMSO solution of DMSO/PBS (7:3v/v, pH 7.4) solution, 2 μ L CDP for taking 2mL is added to a fluorescence colorimetric
It in ware, is detected on Fluorescence spectrophotometer, with the addition to test sample hydrogen sulfide, the fluorescence intensity at 465nm is gradually increased；
(3), in 6 cuvettes, each DMSO/PBS (7:3v/v, pH 7.4) solution, DMSO of 2 μ LCDP that 2mL is added is molten
Liquid, the volume for being separately added into hydrogen sulfide solution measure 465nm after being 0,4,8,12,16,20 μ L, 30min in Fluorescence Spectrometer
Locating fluorescence intensity is 603.5,1581,2748,4030,5632,7173 using concentration of hydrogen sulfide as abscissa, is vertical with fluorescence intensity
Coordinate draws figure, obtains the working curve of concentration of hydrogen sulfide；Equation of linear regression are as follows: F-F0=330.6143c-281.14, c's
Unit is 10-5mol/L；
(4), when measuring sample solution, the fluorescence intensity measured is substituted into equation of linear regression, the concentration of hydrogen sulfide can be acquired.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111763187A (en) * | 2020-07-13 | 2020-10-13 | 湖南科技大学 | Coumarin-based hydrogen sulfide fluorescent probe and preparation method and application thereof |
| CN112939918A (en) * | 2021-02-05 | 2021-06-11 | 山西大学 | Coumarin derivative CTT and synthesis method and application thereof |
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| CN107383037A (en) * | 2017-07-18 | 2017-11-24 | 渤海大学 | A kind of long wave elongated H2S fluorescence probes and its synthetic method and application |
| CN108358906A (en) * | 2018-03-14 | 2018-08-03 | 中南大学 | One species specificity distinguishes the fluorescence probe of different mercaptan |
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| CN107383037A (en) * | 2017-07-18 | 2017-11-24 | 渤海大学 | A kind of long wave elongated H2S fluorescence probes and its synthetic method and application |
| CN108358906A (en) * | 2018-03-14 | 2018-08-03 | 中南大学 | One species specificity distinguishes the fluorescence probe of different mercaptan |
Non-Patent Citations (2)
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| LEI YANG，等: "A Triple-Emission Fluorescent Probe for Discriminatory Detection of Cysteine/Homocysteine, Glutathione/Hydrogen Sulfide, and Thiophenol in Living Cells", 《ACS SENS.》 * |
| YANG YANG，等: "Dual-Site and Dual-Excitation Fluorescent Probe That Can Be Tuned for Discriminative Detection of Cysteine, Homocystein, and Thiophenols", 《ANAL. CHEM.》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111763187A (en) * | 2020-07-13 | 2020-10-13 | 湖南科技大学 | Coumarin-based hydrogen sulfide fluorescent probe and preparation method and application thereof |
| CN112939918A (en) * | 2021-02-05 | 2021-06-11 | 山西大学 | Coumarin derivative CTT and synthesis method and application thereof |
| CN112939918B (en) * | 2021-02-05 | 2022-07-19 | 山西大学 | Coumarin derivative CTT and synthesis method and application thereof |
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