CN103923640A - Benzothiazoles fluorescent probe for identifying hydrogen sulfide and application of fluorescent probe - Google Patents
Benzothiazoles fluorescent probe for identifying hydrogen sulfide and application of fluorescent probe Download PDFInfo
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- CN103923640A CN103923640A CN201410179994.8A CN201410179994A CN103923640A CN 103923640 A CN103923640 A CN 103923640A CN 201410179994 A CN201410179994 A CN 201410179994A CN 103923640 A CN103923640 A CN 103923640A
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Abstract
The invention relates to a benzothiazoles fluorescent probe for identifying hydrogen sulfide, and the application of the fluorescent probe, belonging to the field of fine chemical industry. The fluorescent probe is 2-(2-hydroxy phenyl) benzothiazole derivatives, and is prepared by the steps of mixing 2-(2-hydroxy phenyl) benzothiazole with potassium carbonate and 2, 4-dinitro bromobenzene in proportion, and finally purifying by a silica gel column chromatography. The fluorescent probe and the corresponding hydrogen sulfide content detection process are not interfered by biological system matrix and impurities and can be used for quantitative measurement of hydrogen sulfide content in various biological systems. The benzothiazoles fluorescent probe is high in specificity, can be hydrolyzed after being specifically cyclized with the hydrogen sulfide, and namely, is hydrolysate of ether cleavage; the benzothiazoles fluorescent probe is cheap and easily available, can be obtained by chemical synthesis, and is simple and practicable in synthetic process; the benzothiazoles fluorescent probe is high in sensitivity, has good fluorescence emission spectrum characteristic (450-500nm), and can be used for quantitative measurement of the hydrogen sulfide by drawing a standard curve.
Description
Technical field
The present invention relates to a kind of fluorescent probe and application thereof of benzothiazoles identification hydrogen sulfide, it belongs to field of fine chemical.
Background technology
For centuries, hydrogen sulfide (H
2s) be considered to a kind of toxic substance by geology activity or microbial process generation.This colourless, flammable gas has brackish rotten egg smell, and can produce strong impulse effect to mammiferous eyes and respiratory system.Suck excessive hydrogen sulfide and can cause the physiological responses such as the loss of consciousness, respiratory insufficiency, heartbeat stop, when absorbed dose is excessive, can cause death.On the other hand, more and more research is own through starting to challenge this traditional idea now: Mammals self can produce hydrogen sulfide under controlled condition, and thinks that sulfuration oxygen has vital role for maintaining normal physiological function.In mammal body, hydrogen sulfide can be produced by non-enzyme effect, comprises the release in sulphur storehouse in body and the metabolism of polysulfides etc.Also can be participated in catalyzing and synthesizing by plurality of enzymes, comprise cystathionine-polysaccharase (CBS), cystathionine-lyase (CSE), halfcystine transferring enzyme and thin benzylacetone acid transsulfurase.These enzymes can be by different catalytic reaction sulfur-bearings biomolecules produce hydrogen sulfide as halfcystine, high cysteine etc.These several enzymes appear in the tissue of the multiple organs such as heart, vascular system, brain, kidney, lung and pancreas, have illustrated that the distribution of sulfuration oxygen in mammalian body is very extensive.
In mammalian body, hydrogen sulfide can be with downstream egg white matter by the halfcystine generation mercaptolation after translating and be connected in the iron of protoheme in the heart.This process will be controlled multiple physiological response, comprise that damage, vasorelaxation, necrocytosis, vasculogenesis, neuroregulation, inflammation treatment, insulin signaling conduction and oxygen that ischemia reperfusion causes stress wait.In addition, hydrogen sulfide is also as the antioxidant of active oxygen or scavenging agent and play a role.But H
2the concentration level of S is undesired, and oneself is proved relevant with a lot of diseases.The experiment of these initiatives has shown that hydrogen sulfide is a kind of important physiological regulating control gas and be not merely a kind of pollutent.The physiology role of hydrogen sulfide complexity and potential treatment application impels researcher to propose new method for monitoring the generation, circulation of hydrogen sulfide and at different cells, tissue and intraorganic consumption process.
Tradition comprises that for detection of the method for hydrogen sulfide colorimetric method, polarogram sensing method and vapor-phase chromatography can cause the damage of testing sample conventionally, or can not realize the detection to sulfide in organism at all.The method that fluorescent molecular probe provides the note that induces one, because it has permeability of cell membrane and highly selective, thereby can realize in living things system hydrogen sulfide and the micromolecular detection of other biological.Fluorometry provides important bioinformation by the physiological function for research hydrogen sulfide.If the report that over the past two years, relevant hydrogen sulfide light detected is subject to showing great attention to of research worker.
The invention provides a class 2-(2-hydroxy phenyl) benzothiazole derivant is for specific recognition hydrogen sulfide (H
2s) probe, can generate the hydrolysate with fluorescence properties after itself and hydrogen sulfide are hydrolyzed.This reaction has highly selective, highly sensitive, willing feature.
Summary of the invention
The object of the present invention is to provide a kind of specificity fluorescent probe of identifying hydrogen sulfide, this probe itself has faint fluorescence, with hydrogen sulfide (H
2s) reaction after product has extremely strong fluorescence properties.Utilize this probe reaction can be to hydrogen sulfide (H in multiple biological specimen
2s) content carries out quantitative evaluation.
Technical scheme of the present invention is: a kind of fluorescent probe of benzothiazoles identification hydrogen sulfide, described fluorescent probe is 2-(2-hydroxy phenyl) benzothiazole derivant, its structural formula is as follows:
The preparation method of described fluorescent probe comprises the steps:
(1) according to 2-(2-hydroxy phenyl) benzothiazole: 2,4-binitro bromobenzene: the ratio that salt of wormwood mol ratio is 1:1 ~ 2:2 ~ 3 joins in reaction flask, adds acetonitrile, control temperature of reaction at 40 ~ 80 ℃, stir 8-12h;
(2) by above-mentioned reaction solution process removal of solvent under reduced pressure, residual solid adopts silica gel chromatography to carry out purifying, adopts ethyl acetate: the eluent that normal hexane volume ratio is 1:3 carries out wash-out, obtains fluorescent probe
Described fluorescent probe is applied to the quantitative evaluation of hydrogen sulfide content in biological specimen.As the specific probe of hydrogen sulfide, there is hydrolysis reaction in this probe, measures the content of hydrogen sulfide in cell by the fluorescence intensity of detection by quantitative hydrolysate; Concrete measuring method is:
In system, using 2-(2-hydroxy phenyl) benzothiazole derivant is as specific probe; Concentration and probe concentration is selected 1/ ~ 10 μ M; At conventional damping fluids such as PBS or Tris-HCl: in dimethyl sulfoxide (DMSO) mixing solutions (volume ratio 7:3), temperature of reaction is between 20 ℃ to 60 ℃, and preferably 37 ℃ is the peak optimization reaction time; Reaction system pH is between 5.5 ~ 10.5, and preferably pH7.4 is peak optimization reaction pH value; Reaction times is 5 ~ 120 minutes; Measure hydrolysate fluorescence intensity as the evaluation index of hydrogen sulfide content.
Probe itself has faint fluorescence, and its hydrolysate all has extremely strong fluorescence, and the rapid sensitive that can adopt fluorimetric detector to realize product and substrate detects; Fluoroscopic examination condition is: excitation wavelength 300 nm, carry out the detection of fluorescence emission spectrum at 450 ~ 500 nm.
Beneficial effect of the present invention is: this fluorescent probe is 2-(2-hydroxy phenyl) benzothiazole derivant; Proportionally by 2-(2-hydroxy phenyl) benzothiazole sodium salt and salt of wormwood, 2,4-binitro bromobenzene mixes, and adds DMF, and heating, finally adopts silica gel chromatography to carry out purifying, obtains fluorescent probe.This fluorescent probe and corresponding hydrogen sulfide content testing process can not be subject to the interference of living things system matrix and impurity, can be used for the quantitative assay of hydrogen sulfide content in various living things systems.This should have high specific by probe, can with the cyclisation of hydrogen sulfide specificity after be hydrolyzed, i.e. the hydrolysate of ether bond rupture; Cheap and easy to get, can obtain through chemosynthesis, synthesis technique is simple; Highly sensitive, there is good fluorescence emission spectral property (450～500 nm), by drawing standard curve, carry out hydrogen sulfide quantitative assay.
Accompanying drawing explanation
Fig. 1 is 2-(2(2,4-dinitrophenoxy)) benzothiazole
1h-NMR spectrogram.
Fig. 2 is 2-(2(2,4-dinitrophenoxy)) benzothiazole
13c-NMR spectrogram.
Fig. 3 is 2-(2(2,4-dinitrophenoxy)) high resolution mass spectrum of benzothiazole.
Fig. 4 is change in fluorescence result after fluorescent probe reacts with different substances.
Fig. 5 is fluorescence intensity change curve after fluorescent probe reacts with different concns hydrogen sulfide.
Fig. 6 is that fluorescent probe reacts the relation of fluorescence intensity change and time with hydrogen sulfide.
Fig. 7 is co-focusing imaging figure.
Embodiment
The following examples will be further described the present invention, but not thereby limiting the invention.
embodiment 1 2-(2(2,4-dinitrophenoxy)) chemosynthesis of benzothiazole
(1) by the 2-(2-hydroxy phenyl of 0.5 mmol) benzothiazole and 0.625 mmol salt of wormwood, 0.5mmol 2,4-binitro bromobenzene is dissolved in 10 mL acetonitriles, at 80 ℃ of reaction 4 h;
(2) reaction solution is carried out to underpressure distillation;
(3) solid adopts silica gel chromatography to carry out purifying, adopts ethyl acetate-normal hexane (1:3 v/v) to carry out wash-out, obtains faint yellow solid, and characterization result is shown in Fig. 1, Fig. 2 and Fig. 3.
1H?NMR?(400?MHz,?DMSO)?δ?8.98?(d,?J?=?2.8?Hz,?1H),?8.50?(dd,?J?=?7.9,?1.6?Hz,?1H),?8.42?(dd,?J?=?9.3,?2.8?Hz,?1H),?8.11?(d,?J?=?8.0?Hz,?1H),?8.04?(d,?J?=?8.1?Hz,?1H),?7.79?–?7.68?(m,?1H),?7.66?–?7.51?(m,?2H),?7.47?(dd,?J?=?14.4,?7.5?Hz,?2H),?7.24?(d,?J?=?9.3?Hz,?1H).?13C?NMR?(100?MHz,?CDCl3)?δ?160.87?,?155.66?,?152.67?,?150.68?,?141.78?,?139.54?,?135.50?,?132.51?,?131.30?,?128.99?,?127.45?,?126.60,?126.56,?125.72?,?123.46?,?122.25,?122.13,?121.52,?117.80.?HRMS?calcd?for?C16H14NO5?+?([M+H]?+)?394.0492,?found?394.0501。
embodiment 2 2-(2(2,4-dinitrophenoxy)) benzothiazole is for the selectivity of different substances
(1) prepare 99 μ l metabolic reaction systems in advance, the PBS damping fluid (10 mM) that comprises pH 7.4: dimethyl sulfoxide (DMSO) (volume ratio 7:3), fluorion (100 μ M), chlorion (50 μ M), bromide anion (100 μ M), iodide ion (100 μ M), sodium ion (100 μ M), potassium ion (100 μ M), calcium ion (100 μ M), magnesium ion (100 μ M), nitrate ion (100 μ M), Sodium sulfhydrate (100 μ M);
(2) to adding 1 μ l final concentration in reaction system, be 10 μ M 2-(2(2,4-dinitrophenoxy)) benzothiazole initial action;
After (3) 30 min, carry out fluoroscopic examination (λ
ex=300 nm, λ
em=458 nm); Calculate fluorescence intensity (see figure 4) in each system.
embodiment 3 2-(2(2,4-dinitrophenoxy)) benzothiazole and concentration of hydrogen sulfide linear relationship
(1) prepare 99 μ l metabolic reaction systems in advance, comprise the PBS damping fluid (10 mM) of pH 7.4: dimethyl sulfoxide (DMSO) (volume ratio 7:3), hydrogen sulfide (0-100 μ M) reacts 30 minutes under 37 ℃ of conditions;
(2 is 10 μ M 2-(2(2 to adding 1 μ l final concentration in reaction system, 4-dinitrophenoxy)) benzothiazole initial action;
After (3) 30 min, carry out fluoroscopic examination (λ
ex=300 nm, λ
em=458 nm); Calculate fluorescence intensity in each system, set up fluorescence intensity and concentration of hydrogen sulfide typical curve (see figure 5); Typical curve is y=3695.9x-373.09, R2=0.9931, and wherein, y represents 458 nm place fluorescence intensities, x represents Sodium sulfhydrate concentration (hydrazine concentration linear relationship between 0 uM to 100 uM meets).
embodiment 4 2-(2(2,4-dinitrophenoxy)) benzothiazole is that probe reacts the relation of fluorescence intensity change and time with hydrogen sulfide
(1) prepare 99 μ l metabolic reaction systems in advance, comprise the PBS damping fluid (10 mM) of pH 7.4: dimethyl sulfoxide (DMSO) (volume ratio 7:3), hydrogen sulfide (200 μ M) reacts 30 minutes under 37 ℃ of conditions;
(2 is 10 μ M 2-(2(2 to adding 1 μ l final concentration in reaction system, 4-dinitrophenoxy)) benzothiazole initial action;
After (3) 30 min, carry out fluoroscopic examination (λ
ex=300 nm, λ
em=458 nm); Calculate fluorescence intensity in each system, set up fluorescence intensity and hydrogen sulfide reaction times linear relationship curve (see figure 6).
hydrogen sulfide content in embodiment 5 quantitative assay human lung adenocarcinoma A549 cells
(1) human lung adenocarcinoma A549 clone is incubated on cover glass, and the substratum of employing is DMEM substratum (containing 10% calf serum) and 100 μ g/ml's is dual anti-, and culture environment is in 5% CO2gas incubator of 37 ℃;
(2) before using, attached cell adopts the DMEM substratum that does not contain serum to rinse 3 times, and adding final concentration is the 2-(2(2 of 10 μ M, 4-dinitrophenoxy)) benzothiazole, in 37 ℃ of temperature, incubate 40 minutes;
(3) afterwards, adopt PBS damping fluid to rinse 3 times.Observation of cell under laser confocal microscope, carrys out content (see figure 7) in showed cell by fluorescence distribution position and intensity.
hydrogen sulfide content in embodiment 6 quantitative assay human bloods
(1) to 380 μ l through PBS: in 10% human normal plasma of dimethyl sulphoxide solution (volume ratio 7:3) dilution, add the final concentration of hydrogen sulfide of 20 μ l to be respectively 0 μ M, 50 μ M, 100 μ M, 150 μ M, 200 μ M, 250 μ M, 300 μ M hydrogen sulfide solutions;
(2) to adding 1 μ l final concentration in reaction system, be 10 μ M 2-(2(2,4-dinitrophenoxy)) benzothiazole initial action;
(3) carry out fluoroscopic examination (λ
ex=300 nm, λ
em=458 nm); Calculate signal to noise ratio S/N>10, detect fluorescence intensity signals in different hydrogen sulfide content blood plasma.
Claims (2)
1. a fluorescent probe for benzothiazoles identification hydrogen sulfide, is characterized in that: described fluorescent probe is 2-(2-hydroxy phenyl) benzothiazole sodium salt derivative, its structural formula is as follows:
The preparation method of described fluorescent probe comprises the steps:
(1) according to 2-(2-hydroxy phenyl) benzothiazole: 2,4-binitro bromobenzene: the ratio that salt of wormwood mol ratio is 1:1 ~ 2:2 ~ 3 joins in reaction flask, adds acetonitrile, control temperature of reaction at 40 ~ 80 ℃, stir 8-12h;
(2) by above-mentioned reaction solution process removal of solvent under reduced pressure, residual solid adopts silica gel chromatography to carry out purifying, adopts ethyl acetate: the eluent that normal hexane volume ratio is 1:3 carries out wash-out, obtains fluorescent probe.
2. the fluorescent probe of a kind of benzothiazoles identification hydrogen sulfide according to claim 1, is characterized in that: described fluorescent probe is applied to the quantitative evaluation of hydrogen sulfide content in biological specimen.
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Cited By (10)
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| CN104449677A (en) * | 2014-12-29 | 2015-03-25 | 大连理工常熟研究院有限公司 | Specific fluorescent probe for recognizing fluorine ions and application of specific fluorescent probe |
| CN104479669A (en) * | 2014-11-18 | 2015-04-01 | 辽宁大学 | Preparation method and applications of enhanced type fluorescent probe for detecting hydrogen sulfide |
| CN105086995A (en) * | 2015-05-21 | 2015-11-25 | 湖南城市学院 | Preparation and application of probe for hydrogen sulfide (H2S) based on protection-deprotection mechanism |
| CN106083760A (en) * | 2016-02-16 | 2016-11-09 | 中国科学院理化技术研究所 | Fluorescent chemical sensor capable of selectively detecting hydrogen sulfide, preparation method and application |
| CN106496217A (en) * | 2016-10-31 | 2017-03-15 | 湖南师范大学 | A kind of new detection H2The preparation method and application of S fluorescent molecular probes |
| CN107782707A (en) * | 2017-10-12 | 2018-03-09 | 华南师范大学 | Application of the three benzothiazolyl benzene in nitryl aromatic explosive fluoroscopic examination |
| CN111072650A (en) * | 2018-10-22 | 2020-04-28 | 北京工商大学 | Benzothiazole hydrogen sulfide fluorescent probe |
| CN111116433A (en) * | 2018-10-31 | 2020-05-08 | 北京工商大学 | Double-recognition-site hydrogen sulfide fluorescent probe |
| CN112876425A (en) * | 2021-02-06 | 2021-06-01 | 许昌学院 | Hydrogen sulfide fluorescent probe and preparation method and application thereof |
| CN115160237A (en) * | 2022-08-03 | 2022-10-11 | 王威 | Fluorescent probe for detecting hydrogen sulfide and preparation method and application thereof |
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| CN104479669A (en) * | 2014-11-18 | 2015-04-01 | 辽宁大学 | Preparation method and applications of enhanced type fluorescent probe for detecting hydrogen sulfide |
| CN104449677A (en) * | 2014-12-29 | 2015-03-25 | 大连理工常熟研究院有限公司 | Specific fluorescent probe for recognizing fluorine ions and application of specific fluorescent probe |
| CN105086995A (en) * | 2015-05-21 | 2015-11-25 | 湖南城市学院 | Preparation and application of probe for hydrogen sulfide (H2S) based on protection-deprotection mechanism |
| CN106083760B (en) * | 2016-02-16 | 2018-09-14 | 中国科学院理化技术研究所 | Fluorescent chemical sensor capable of selectively detecting hydrogen sulfide, preparation method and application |
| CN106083760A (en) * | 2016-02-16 | 2016-11-09 | 中国科学院理化技术研究所 | Fluorescent chemical sensor capable of selectively detecting hydrogen sulfide, preparation method and application |
| CN106496217A (en) * | 2016-10-31 | 2017-03-15 | 湖南师范大学 | A kind of new detection H2The preparation method and application of S fluorescent molecular probes |
| CN107782707A (en) * | 2017-10-12 | 2018-03-09 | 华南师范大学 | Application of the three benzothiazolyl benzene in nitryl aromatic explosive fluoroscopic examination |
| CN107782707B (en) * | 2017-10-12 | 2020-07-17 | 华南师范大学 | Application of triphenylthiazolyl benzene in fluorescence detection of nitro aromatic explosives |
| CN111072650A (en) * | 2018-10-22 | 2020-04-28 | 北京工商大学 | Benzothiazole hydrogen sulfide fluorescent probe |
| CN111072650B (en) * | 2018-10-22 | 2021-04-06 | 北京工商大学 | Benzothiazole hydrogen sulfide fluorescent probe |
| CN111116433A (en) * | 2018-10-31 | 2020-05-08 | 北京工商大学 | Double-recognition-site hydrogen sulfide fluorescent probe |
| CN112876425A (en) * | 2021-02-06 | 2021-06-01 | 许昌学院 | Hydrogen sulfide fluorescent probe and preparation method and application thereof |
| CN112876425B (en) * | 2021-02-06 | 2022-05-06 | 许昌学院 | Hydrogen sulfide fluorescent probe and preparation method and application thereof |
| CN115160237A (en) * | 2022-08-03 | 2022-10-11 | 王威 | Fluorescent probe for detecting hydrogen sulfide and preparation method and application thereof |
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