CN104531136A - Specific fluorescence probe for identifying thiophenol and application of specific fluorescence probe - Google Patents
Specific fluorescence probe for identifying thiophenol and application of specific fluorescence probe Download PDFInfo
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- CN104531136A CN104531136A CN201410835798.1A CN201410835798A CN104531136A CN 104531136 A CN104531136 A CN 104531136A CN 201410835798 A CN201410835798 A CN 201410835798A CN 104531136 A CN104531136 A CN 104531136A
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Abstract
The invention discloses a specific fluorescence probe for identifying thiophenol and application of the specific fluorescence probe and belongs to the field of fine chemical industry. The specific fluorescence probe is a derivative of 2-benzothiazole-6-naphthol and is prepared by the following steps: mixing the 2-benzothiazole-6-naphthol and 2, 4-dinitrobenzene into an N, N-dimethylformamide solution according to a proportion, heating, and finally, purifying by adopting silica gel chromatography to obtain the fluorescence probe. The fluorescence probe and a corresponding thiophenol content detecting process can not be interfered by matrixes and impurities in a biological system and can be used for quantitatively determining the thiophenol content in various biological systems. The specific fluorescence probe is high in specificity, can be hydrolyzed after being acted with the thiophenol, namely an ether bond is fractured; is cheap and is easy in acquisition, can be obtained by chemical synthesis, is simple and feasible in synthetic process; is high in sensitivity, is good in fluorescence attribute. A hydrolysate can be excited by a two-photon laser with 800nm as an excitation light source, a biological sample is weak in background fluorescence, and the specific fluorescence probe is suitable for detecting the thiophenol content in cells and is capable of quantitatively determining the thiophenol by drawing a standard curve.
Description
Technical field
The invention belongs to field of fine chemical, relating to a kind of specificity fluorescent probe for identifying thiophenol and application thereof.
Background technology
In chemistry, biological, environmental science, develop and seem particularly important for relevant biological activity or the highly sensitive of toxicity molecule, the detection technique of highly selective.Thiophenol belongs to sulfur alcohol compound, is widely used in the preparation of agricultural chemicals, medicine and various Industrial products, is a kind of important industrial chemicals.But, thiophenol has great toxicity, it is 0.01mM-0.4mM to the toxic limit medium dose of fish, human contact's thiophenol liquid or gas all by causing serious central nervous system damage and the injury of other related systems, comprise be short of breath, Muscle weakness, hindlimb paralysis, stupor be even dead.Therefore, consider the harm of thiophenol to environment and human health, develop simple and effective thiophenol detection method and seem particularly necessary.
Summary of the invention
The object of the present invention is to provide a kind of specificity fluorescent probe identifying thiophenol, this probe itself does not have fluorescence, and after reacting with thiophenol, hydrolysate has two-photon fluorescence attribute.This probe can be used for the thiophenol content detecting trace in cell.
Technical scheme of the present invention is: a kind of specificity fluorescent probe for identifying thiophenol, and described fluorescent probe is 2-[4-morpholinodithio base-6-naphthol derivative, and its general structure is as follows:
The preparation method of described fluorescent probe comprises the steps:
(1) according to 2-[4-morpholinodithio-6-naphthols: 2,4-binitro bromobenzene: salt of wormwood mol ratio is that the ratio of 1:1 ~ 2:2 ~ 3 joins in reaction flask, adds DMF, control temperature of reaction at 40 ~ 80 DEG C, stir 8-12h;
(2) above-mentioned reaction solution is removed desolventizing through underpressure distillation, residual solid adopts silica gel chromatography to carry out purifying, adopts ethyl acetate: normal hexane volume ratio is that 1:3 carries out wash-out, obtains fluorescent probe.
Described fluorescent probe is applied to the quantitative evaluation of thiophenol content in biological specimen.As the specific probe of thiophenol, there is hydrolysis reaction, measured the content of thiophenol in cell by the fluorescence intensity of detection by quantitative hydrolysate in this probe.Concrete measuring method is:
Using 2-[4-morpholinodithio base-6-naphthol derivative as specific probe in system; Concentration and probe concentration selects 1 ~ 10 μM; At conventional damping fluids such as PBS or Tris-HCl: in DMF mixing solutions (volume ratio 1:1), temperature of reaction is between 20 DEG C to 60 DEG C, and preferably 25 DEG C is the peak optimization reaction time; Reaction system pH is between 5.5 ~ 10.5, and preferred pH7.4 is peak optimization reaction pH value; Reaction times is 5 ~ 120 minutes; Measure the evaluation index of hydrolysate fluorescence intensity as thiophenol content.
Probe itself does not have fluorescence, and product has two-photon fluorescence attribute, and the rapid sensitive that fluorimetric detector can be adopted to realize product and substrate detects; Fluoroscopic examination condition is: excitation wavelength is 342nm, and emission wavelength is 512nm.
Beneficial effect of the present invention is: fluorescent probe is 2-[4-morpholinodithio base-6-naphthol derivative; According to 2-[4-morpholinodithio-6-naphthols: 2,4-binitro bromobenzene: salt of wormwood mol ratio is that the ratio of 1:1 ~ 2:2 ~ 3 joins in reaction flask, adds DMF, control temperature of reaction at 40 ~ 80 DEG C, stir 8-12h; , finally adopt silica gel chromatography to carry out purifying, obtain fluorescent probe.This fluorescent probe and corresponding thiophenol content detection process can not be subject to the interference of living things system matrix and impurity, can be used for the quantitative assay of thiophenol content in various living things system.This fluorescent probe has high specific, can with thiophenol specific catalytic after be hydrolyzed, i.e. the hydrolysis reaction of ether bond rupture; Cheap and easy to get, can obtain through chemosynthesis, synthesis technique is simple; Highly sensitive, be applicable to detecting thiophenol content in cell, carry out thiophenol quantitative assay by drawing standard curve.Such probe is two-photon fluorescence probe, and the effective background fluorescence that reduces is on the impact of measuring result.
The invention provides a class 2-[4-morpholinodithio base-6-naphthol derivative for the probe of specific recognition thiophenol, after itself and thiophenol react, the hydrolysate with two-photon fluorescence attribute can be generated.This reaction has highly selective, highly sensitive, willing feature.This probe can be used for the thiophenol content detecting trace in cell.
Accompanying drawing explanation
Fig. 1 2-[4-morpholinodithio base-6-(2,4-dinitrophenoxy) naphthalene is change in fluorescence result after probe and different substances react;
Fig. 2 2-[4-morpholinodithio base-6-(2,4-dinitrophenoxy) naphthalene is fluorescence intensity change curve after probe and different concns thiophenol react;
Fig. 3 2-[4-morpholinodithio base-6-(2,4-dinitrophenoxy) naphthalene is the relation that probe and thiophenol react fluorescence intensity change and time;
Fig. 4 2-[4-morpholinodithio base-6-(2,4-dinitrophenoxy) naphthalene cell imaging picture;
Fig. 5 2-[4-morpholinodithio base-6-(2,4-dinitrophenoxy) naphthol derivative general structure.
Embodiment
The following examples will be further described the present invention, but not thereby limiting the invention.
The chemosynthesis of embodiment 1 2-[4-morpholinodithio base-6-(2,4-dinitrophenoxy) naphthalene
(1) be dissolved in 10mL DMF by the 2-[4-morpholinodithio base-6-naphthols of 0.5mmol and 2, the 4-binitro bromobenzenes of 0.625mmol salt of wormwood and 0.6mmol, 80 DEG C are reacted 12 hours;
(2) by reaction solution underpressure distillation, light yellow solid residue is obtained;
(3) solid adopts silica gel chromatography to carry out purifying, adopts ethyl acetate-hexane (1:3v/v) to carry out wash-out, obtains 188mg light yellow solid powder.
1H NMR(400MHz,DMSO)δ8.96(d,J＝2.2Hz,1H)，8.81(s,1H)，8.48(dd,J＝9.2,2.3Hz,1H)，8.37(d,J＝8.9Hz,1H)，8.30(d,J＝8.5Hz,1H)，8.21(d,J＝8.0Hz,1H)，8.11(d,J＝7.5Hz,2H)，7.89(s,1H)，7.59(t,J＝7.6Hz,2H)，7.51(t,J＝7.4Hz,1H)，7.37(d,J＝9.2Hz,1H)。
Embodiment 2 2-[4-morpholinodithio base-6-(2,4-dinitrophenoxy) naphthalene is for the selectivity of different substances
(1) prepare 99 μ L metabolic reaction systems in advance, comprise the PBS damping fluid (10mM) of pH 7.4: DMF (volume ratio 1:1), mercaptoethanol (100 μMs), p-Nitrobenzenethiol (100 μMs), halfcystine (100 μMs), homocysteine (100 μMs), gsh (100 μMs), Sodium sulfhydrate (100 μMs), thiophenol (100 μMs);
(2) in reaction system, add 1 μ L final concentration is 10 μMs of 2-[4-morpholinodithio base-6-(2,4-dinitrophenoxy) naphthalene initial actions;
(3) after 20min, carry out fluoroscopic examination, calculate fluorescence intensity (see Fig. 1) in each system.
Embodiment 3 2-[4-morpholinodithio base-6-(2,4-dinitrophenoxy) naphthalene and thiophenol concentration linear relationship
(1) prepare 99 μ L metabolic reaction systems in advance, comprise the PBS damping fluid (10mM) of pH 7.4: DMSO (volume ratio 1:9), thiophenol (0-200 μM), react 30 minutes under 25 DEG C of conditions;
(2) in reaction system, add 1 μ L final concentration is 10 μMs of 2-[4-morpholinodithio base-6-(2,4-dinitrophenoxy) naphthalene initial actions;
(3) after 20min, carry out fluoroscopic examination, calculate fluorescence intensity in each system.(see Fig. 2).
Embodiment 4 2-[4-morpholinodithio base-6-(2,4-dinitrophenoxy) naphthalene is the relation that probe and thiophenol react fluorescence intensity change and time
(1) prepare 99 μ L metabolic reaction systems in advance, comprise the PBS damping fluid (10mM) of pH 7.4: DMSO (volume ratio 1:9), thiophenol (50 μMs), react 30 minutes under 25 DEG C of conditions;
(2 in reaction system, add 1 μ L final concentration be 10 μMs of 2-[4-morpholinodithio base-6-(2,4-dinitrophenoxy) naphthalene initial actions;
(3) after 20min, carry out fluoroscopic examination, calculate fluorescence intensity in each system, set up fluorescence intensity and thiophenol reaction times linear relationship curve (see Fig. 3).
Thiophenol content in embodiment 5 quantitative assay human pulmonary epithelial cells
(1) human pulmonary epithelial cells system is incubated on cover glass, and the substratum of employing is the dual anti-of DMEM substratum (containing 10% calf serum) and 100 μ g/mL, and culture environment is in 5% CO2gas incubator of 25 DEG C.
(2) before using, attached cell adopts does not rinse 3 times containing the DMEM substratum of serum, adds 2-[4-morpholinodithio base-6-(2, the 4-dinitrophenoxy) naphthalene that final concentration is 50 μMs, incubate 30 minutes in 25 DEG C of temperature, another group adds the thiophenol that final concentration is 100 μMs.
(3), after, PBS wash buffer 3 times are adopted.Observation of cell under laser confocal microscope, carrys out thiophenol content (see Fig. 4) in showed cell by fluorescence distribution position and intensity.A () and (c) is light field, (b) and (d) is respectively the cell picture not adding thiophenol, add thiophenol, and excitation wavelength is 800nm.
Claims (3)
1. for identifying a specificity fluorescent probe for thiophenol, it is characterized in that: described fluorescent probe is 2-[4-morpholinodithio-6-naphthol derivative, and its structural formula is as follows:
The preparation method of described fluorescent probe comprises the steps:
(1) according to 2-[4-morpholinodithio-6-naphthols: 2,4-binitro bromobenzene: salt of wormwood mol ratio is that the ratio of 1:1 ~ 2:2 ~ 3 joins in reaction flask, adds DMF, control temperature of reaction at 40 ~ 80 DEG C, stir 8-12h;
(2) by above-mentioned reaction solution through removal of solvent under reduced pressure, residual solid adopts silica gel chromatography to carry out purifying, adopts ethyl acetate: normal hexane volume ratio is that 1:3 carries out wash-out, obtains fluorescent probe.
2. an application for the specificity fluorescent probe for identifying thiophenol according to claim 1, is characterized in that: described fluorescent probe is applied to the quantitative evaluation of thiophenol content in environmental samples.
3. the application of the specificity fluorescent probe for identifying thiophenol according to claim 1, it is characterized in that: described fluorescent probe hydrolysate can be excited by two-photon laser, using 800nm as excitation light source, biological sample background fluorescence is faint, is applicable to detecting thiophenol content in cell.
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| CN104804728A (en) * | 2015-04-27 | 2015-07-29 | 苏州罗兰生物科技有限公司 | Preparation and application of fluorescence-enhanced thiophenol fluorescence probe |
| CN105348214A (en) * | 2015-12-02 | 2016-02-24 | 齐鲁工业大学 | Benzoxazinone thiophenol fluorescent probe and preparation method thereof |
| CN105419783A (en) * | 2015-11-24 | 2016-03-23 | 齐鲁工业大学 | Thiophenol fluorescent probe based on 7-lignocaine-3-hydroxycoumarin structure and preparation method thereof |
| CN105419788A (en) * | 2015-12-25 | 2016-03-23 | 济南大学 | Small-molecular fluorescent probe for recognizing H2S, preparation method and application thereof |
| CN105777591A (en) * | 2016-03-17 | 2016-07-20 | 山西大学 | Curcumin derivative and application thereof in preparation and detection of thiophenol |
| CN108484561A (en) * | 2018-04-04 | 2018-09-04 | 济南大学 | A kind of preparation and application of long wavelength's colorimetric fluorescence probe of quick high-selectivity analysis benzenethiol |
| CN109180561A (en) * | 2018-11-14 | 2019-01-11 | 中国科学院海洋研究所 | The application of chalcones fluorescence probe thiophenols in detection aqueous solution |
| CN109422669A (en) * | 2017-08-24 | 2019-03-05 | 北京工商大学 | A kind of aphthols hydrogen sulfide fluorescence probe |
| CN109422667A (en) * | 2017-08-23 | 2019-03-05 | 北京工商大学 | A kind of naphthonitrile class hydrogen sulfide fluorescence probe |
| CN110724114A (en) * | 2018-07-16 | 2020-01-24 | 北京工商大学 | Fluorescent probe for detecting bisulfite and hydrogen sulfide |
| CN111072650A (en) * | 2018-10-22 | 2020-04-28 | 北京工商大学 | Benzothiazole hydrogen sulfide fluorescent probe |
| CN111205243A (en) * | 2020-02-27 | 2020-05-29 | 山西大学 | Reagent for distinguishing and detecting thiophenol and synthetic method and application thereof |
| CN113804662A (en) * | 2021-08-30 | 2021-12-17 | 大连理工大学 | Rapid detection method special for dichlorvos pesticide residue in fresh fruits and vegetables |
| CN114018880A (en) * | 2021-10-22 | 2022-02-08 | 杭州食疗晶元生物科技有限公司 | Method for identifying purified water and natural mineral water based on endogenous active intermediate |
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| CN104804728A (en) * | 2015-04-27 | 2015-07-29 | 苏州罗兰生物科技有限公司 | Preparation and application of fluorescence-enhanced thiophenol fluorescence probe |
| CN105419783A (en) * | 2015-11-24 | 2016-03-23 | 齐鲁工业大学 | Thiophenol fluorescent probe based on 7-lignocaine-3-hydroxycoumarin structure and preparation method thereof |
| CN105419783B (en) * | 2015-11-24 | 2017-11-21 | 齐鲁工业大学 | A kind of benzenethiol fluorescence probe based on the Hydroxycoumarin class formation of 7 lignocaine 3 and preparation method thereof |
| CN105348214A (en) * | 2015-12-02 | 2016-02-24 | 齐鲁工业大学 | Benzoxazinone thiophenol fluorescent probe and preparation method thereof |
| CN105419788A (en) * | 2015-12-25 | 2016-03-23 | 济南大学 | Small-molecular fluorescent probe for recognizing H2S, preparation method and application thereof |
| CN105419788B (en) * | 2015-12-25 | 2017-12-29 | 济南大学 | A kind of small-molecule fluorescent probe for identifying hydrogen sulfide and its preparation method and application |
| CN105777591A (en) * | 2016-03-17 | 2016-07-20 | 山西大学 | Curcumin derivative and application thereof in preparation and detection of thiophenol |
| CN105777591B (en) * | 2016-03-17 | 2017-06-23 | 山西大学 | A kind of curcumin derivate and its preparation and the application in benzenethiol is detected |
| CN109422667A (en) * | 2017-08-23 | 2019-03-05 | 北京工商大学 | A kind of naphthonitrile class hydrogen sulfide fluorescence probe |
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| CN109422669B (en) * | 2017-08-24 | 2021-01-26 | 北京工商大学 | Naphthol hydrogen sulfide fluorescent probe |
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| CN111072650B (en) * | 2018-10-22 | 2021-04-06 | 北京工商大学 | Benzothiazole hydrogen sulfide fluorescent probe |
| CN111072650A (en) * | 2018-10-22 | 2020-04-28 | 北京工商大学 | Benzothiazole hydrogen sulfide fluorescent probe |
| CN109180561A (en) * | 2018-11-14 | 2019-01-11 | 中国科学院海洋研究所 | The application of chalcones fluorescence probe thiophenols in detection aqueous solution |
| CN109180561B (en) * | 2018-11-14 | 2021-07-27 | 中国科学院海洋研究所 | Application of chalcone fluorescent probe in detection of thiophenol compounds in aqueous solution |
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