CN105968094A - Carbazole fluorescent probe for detecting ClO- and preparation method and application thereof - Google Patents
Carbazole fluorescent probe for detecting ClO- and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a carbazole fluorescent probe for detecting ClO- and a preparation method and application thereof. The preparation method of the fluorescent probe comprises the steps that carbazole and bromobutane are dissolved in a DMSO/KOH mixed solution, stirred and heated, and 9-butyl carbazole is generated; a DMF is used as a solvent, POC13 reacts with the product, and 3-formoxyl-9-butyl carbazole is obtained; the 3-formoxyl-9-butylcarbazole and 3-pyridine acetonitrile are mixed in methyl alcohol, potassium tert-butoxide is added, and 1-methyl-3-(9-butylcarbazole-3-cyanogen vinyl)pyridine is generated; the product is dissolved in HCC13, CH3I is added, suction filtration and drying are carried out, and a saffron yellow solid product is obtained. The probe displays high sensitivity and selectivity for CIO- and displays large Stocks displacement when detecting CIO- ions, the detection process is easy and convenient, and the detection result is accurate. By means of laser confocal scanning microscopy, a fluorescence image of the novel fluorescent probe in living cells can be obtained.
Description
Technical field
The present invention relates to carbazoles fluorescent probe, be specifically related to a kind of mensuration ClO-Carbazoles fluorescent probe and its preparation method and application.
Background technology
Hypochlorite ion is to be widely used in a kind of oxidant in our life, such as our disinfectant solution of commonly using, disinfection of drinking water agent, household bleach etc., the most all contain hypochlorous acid.Various microbial bacterials and various inflammation is defendd to play very important effect as important activating oxide a kind of in organism, hypochlorous acid or hypochlorite at immunity of organism.Internal hypochlorous acid is maintained to want very much for the most cellulous normal operation at certain physiological concentration.But the hypochlorous concentration of excess can cause damage and some disease of body tissue cell, such as: nephrotic syndrome, atherosclerosis, cardiovascular disease, cancer etc. disease.Accurately detection hypochlorite ion seems extremely important to some disease of efficient diagnosis.In the method for the detection iron ion being currently known, owing to fluorimetry has quickly response and highly sensitive feature, fluorescent probe is widely studied.
In recent years, people began to focus on design synthesis to ClO-There are the fluorescent probe of specificly-response, therefore many detection ClO-The fluorescent probe of ion is synthesized, but compared with the fluorescent probe of existing synthesis, the problems such as most some preparation method complexity of existence, expensive starting materials, synthesising probing needle poor anti-interference, difference in response, detection limit are higher, therefore provide one to prepare cheap, convenient, detection ClO-There is fluorescent probe highly sensitive, that selectivity good, detection limit is low and method has great importance.
Summary of the invention
Present invention aims to existing detection ClO-Fluorescent probe exist preparation method complexity, the problem such as expensive starting materials, it is provided that a kind of with low cost, prepare and simply measure ClO-Carbazoles fluorescent probe and preparation method thereof.
Another object of the present invention is to provide a kind of quick, detection by quantitative ClO-Fluorescence detection method, and this method detection limit is low, highly sensitive, selectivity is good, cheap, convenient.
A kind of mensuration ClO that the present invention provides-Carbazoles fluorescent probe, it is 1-methyl-3-(9-butyl carbazole-3-acrylonitrile base) pyridine iodide, and its structural formula is:
A kind of mensuration ClO that the present invention provides-The preparation method of carbazoles fluorescent probe, comprise the steps:
1) carbazole, n-butyl bromide are dissolved in DMSO/KOH mixed solution by equimolar amounts, agitating heating, generate 9-butyl carbazole；
2) with DMF as solvent, POCl3With 3-5: 1 reaction in molar ratio of 9-butyl carbazole, obtain 3-formoxyl-9-butyl carbazole；
3) equimolar 3-formoxyl-9-butyl carbazole and 3-pyridylacetonitrile are blended in the methanol of 50 DEG C, add potassium tert-butoxide and at room temperature react, generate 1-methyl-3-(9-butyl carbazole-3-acrylonitrile base) pyridine；
4) by 1-methyl-3-(9-butyl carbazole-3-acrylonitrile base) pyridinium dissolution at HCCl3In, add CH3I reacts, sucking filtration, is dried, obtains crocus solid product；1-methyl-3-(9-butyl carbazole-3-acrylonitrile base) pyridine and CH3The mol ratio of I is 1: 50-60.
Its synthetic route is as follows:
Step 1) in agitating heating temperature be 60-90 DEG C；
Step 2) in reaction temperature be 60-90 DEG C, response time 8-12h；
Step 3) in room temperature lower response time 4-6h；
Step 4) in reaction temperature 50-70 DEG C, preferably 60 DEG C；Response time 4-6h.
A kind of fluoroscopic examination ClO that the present invention provides-Method, the steps include:
(1) with the fluorescent probe storing solution of DMSO system preparation 1mM；
(2) adding in fluorescence cuvette by 1.6mL water and 0.4mL ethanol and 20 μ L fluorescent probe storing solutions, detect on Fluorescence spectrophotometer, along with treating the addition of test sample, the fluorescence intensity at 440nm gradually strengthens；
(3) with 1.34 × 10-2The ClO of M-Solution, by 1.6mL water and 0.4mL ethanol and 20 μ L fluorescent probe storing solutions addition fluorescence cuvette, adds the ClO of 2 μ L every time-Carry out fluorescence titration experiment, add 55 μ L altogether；With ClO-Concentration is abscissa, with relative intensity of fluorescence (F-F0) it is vertical coordinate drafting figure, obtain ClO-The working curve of concentration, equation of linear regression is: F-F0The unit of=110.798c 9.207, c is 10-5M；Fluorescent probe optimum linear response ClO is obtained by linear fit-In the range of: 0 24.12 × 10-5M, linearly dependent coefficient is R2=0.99819.
Stability experiment proves that fluorescent probe is to ClO-Mensuration there is good light stability.
Experiments verify that, other anion and little molecule not interference system are to ClO-Mensuration.
The probe of the present invention has good cell membrane penetration, can be used for intracellular ClO-Detection.
Compared with prior art, the present invention is as selective enumeration method ClO-Fluorescent probe have the following advantages: 1, the fluorescent probe preparation method of the present invention only needs a step to complete, and reaction condition is simple；2, this fluorescent probe is used for ClO-Detection can obtain a big Stocks displacement, be quick on the draw and there is high selectivity；3, detection means is simple, it is only necessary to by fluorescence spectrophotometer；4, fluorescent probe of the present invention can be used for intracellular ClO-Detection.
Accompanying drawing illustrates:
The ClO of Fig. 1 embodiment 2 fluorescent probe-Fluorescence titration figure
The ClO of Fig. 2 embodiment 3 fluorescent probe-Ultraviolet titration figure
Fig. 3 embodiment 4 fluorescent probe and the fluorescence block diagram of various concurrents
Fig. 4 embodiment 5 fluorescent probe is to ClO-The working curve of response
Fig. 5 embodiment 6 cell imaging figure
Detailed description of the invention
Embodiment 1 measures ClO-The preparation of fluorescent probe
(1) synthesis of 9-butyl carbazole
8.35g (0.050mol) carbazole and the dimethyl sulfoxide of 60mL is added in equipped with the 100mL three-neck flask of magnetic stirring apparatus, thermometer and reflux condensing tube, after stirring makes it dissolve, it is rapidly added 3.0g (0.054mol) potassium hydroxide, it is heated to 90 DEG C, the lower reaction of stirring is the most molten to solid, continues reaction 30min, cooling, loading onto constant pressure funnel, question response liquid is cooled to less than 38 DEG C and is slowly added dropwise 5.5mL (0.051mol) n-butyl bromide.Continue at keeping 90 DEG C to be poured into while hot in the frozen water that diploid is long-pending after stirring reaction 4-6h. has reacted, stand overnight, have white precipitate to separate out.Sucking filtration, washes filter cake with water 2-3 time, removes inorganic matter and dimethyl sulfoxide, is dried to obtain crude product.Gained crude product dehydrated alcohol recrystallization, obtains white needle-like crystals 6.7g, and productivity is 59.8%.
(2) synthesis of 3-formoxyl-9-butyl carbazole
2.23g (0.01mol) 9-butyl carbazole is dissolved in 7.7mL DMF (0.10mol) under magnetic stirring, under ice-water bath, the dropping of 4.9mL (0.05mol) phosphorus oxychloride is entered, it is warmed up to 90 DEG C of reaction 10h, it is cooled in about the 50 DEG C trash ices that reactant liquor is poured into 2 times of volumes (be previously added 50mL chloroform), stirring, separatory, continuation 50mL chloroform extraction twice (each 50mL), merge organic layer, washing organic layer is once, add appropriate anhydrous magnesium sulfate to be dried overnight, after filtering desiccant, concentration of organic layers is to 5-10mL, column chromatography for separation carries out gradient elution (first VEthyl acetate:VPetroleum ether=1:8, rear VEthyl acetate:VPetroleum ether=1:4), obtain product 0.78g, productivity 31.1%.
(3) synthesis of compound [1] (1-methyl-3-(9-butyl carbazole-3-acrylonitrile base) pyridine)
0.75g (3mmol) 3-formoxyl-9-butyl carbazole and 0.32mL (3mmol) 3-pyridylacetonitrile are dissolved in the methanol of about 50 DEG C that 20mL is dried, add 0.5g (4.5mmol) potassium tert-butoxide.When reactant mixture stirs 5h at room temperature, after having reacted, sucking filtration, washs twice solvent of filter cake with a small amount of methanol, is dried, obtains yellow solid product 0.57g, productivity 54.3%.
(4) synthesis of compound [2] (1-methyl-3-(9-butyl carbazole-3-acrylonitrile base) pyridine iodide)
0.35g (1mmol) compound [1] is dissolved in 15mL chloroform under magnetic stirring, add 3.7mL (0.06mol) iodomethane, at 60 DEG C during stirring reaction 5h, after having reacted, sucking filtration, wash twice solvent of filter cake with a small amount of chloroform, be dried, gained crocus solid is carried out column chromatography for separation (eluent VMethanol:VDichloromethane=1:10), obtain crocus solid product 0.22g, productivity 43.8%.
Fluorescent probe is used1H NMR characterizes, and result is as follows:
1H NMR(600MHz,DMSO-d6null):δ9.412(s,1H),8.987(d,J=6.0Hz,1H),8.858(d,J=8.4Hz,1H),8.812(s,1H),8.529(s,1H),8.257(q,J=9.0Hz,2H),8.171(d,J=7.8Hz,1H),7.888(d,J=9.0Hz,1H),7.736(d,J=7.8Hz,1H),7.578(t,J=7.2Hz,1H),7.348(t,J=7.2Hz,1H),4.497(m,J=7.2Hz,5H),1.817(m,J=7.2Hz,2H),1.342(m,J=7.8Hz,2H),0.908(t,J=7.2Hz,3H).
13C NMR(150MHz,DMSO-d6):δ149.82,144.66,143.03,141.10,142.63,135.31,128.19,127.67,127.41,124.17,123.98,122.89,122.31,120.84,117.93,110.88,99.43,48.85,42.90,31.18,20.22,14.19.
The ClO of embodiment 2 fluorescent probe-Fluorescence titration
In 1.6mL water and 0.4mL ethanol system, add 20 μ L fluorescent probe storing solutions carry out ClO-Fluorescence titration is tested, and detects on Fluorescence spectrophotometer, and along with treating the addition of test sample, the fluorescence intensity at 440nm gradually strengthens.Instrument parameter: the slit width of excitation wavelength and transmitting wavelength is respectively 2.5nm, 5.0nm, and voltage is 600V, and the maximum excitation wavelength of fluorescent probe solution is: λexFor 370nm (see Fig. 1).
The ClO of embodiment 3 fluorescent probe-Ultraviolet titrates
In 1.6mL water and 0.4mL ethanol system, add 30 μ L fluorescent probe storing solutions carry out ClO-Ultraviolet titration experiments, detects on UV detector, and along with treating the addition of test sample, the uv absorption intensity at 415nm gradually weakens (see Fig. 2).
Embodiment 4 fluorescent probe and the fluorescence block diagram of various concurrents
In cuvette, add 1.6mL water and 0.4mL ethanol and 20 μ L fluorescent probe storing solutions, then be separately added into other concurrent (F-,Cl-,Br-,I-,CO3 2-,HCO3 -,NO3 -,SO4 2-,AcO-,SCN-,S2O3 2-, HSO3 -,SO3 2-,HS-,PO4 3-,H2O2, GSH, Cys) so that it is ultimate density is 5mM, adds ClO immediately-So that it is ultimate density is 25 × 10-5M, surveys its fluorescence spectrum, the block diagram (see Fig. 3) of the fluorescence intensity at drafting different anions correspondence 440nm respectively.
Tests prove that, other anion not interference system is to ClO-Detection.
Embodiment 5 fluorescent probe is to ClO-Response working curve
With 1.34 × 10-2The ClO of M-Solution, by 1.6mL water and 0.4mL ethanol and 20 μ L fluorescent probe storing solutions addition fluorescence cuvette, adds the ClO of 2 μ L every time-Carry out fluorescence titration experiment, add 55 μ L altogether；With ClO-Concentration is abscissa, with relative intensity of fluorescence (F-F0) it is vertical coordinate drafting figure, obtain ClO-The working curve of concentration, equation of linear regression is: F-F0The unit of=110.798c 9.207, c is 10-5M；Fluorescent probe optimum linear response ClO is obtained by linear fit-In the range of: 0-24.12 × 10-5M, linearly dependent coefficient is R2=0.99819 (see Fig. 4).
Embodiment 6ClO-Cell imaging
With the fluorescent probe storing solution of DMSO solution system preparation 1mM before experiment.Take above-mentioned 20 μ L fluorescent probe storing solutions and add the culture medium containing adherent Hela cell, be placed in the 5%CO of 37 DEG C2After incubator hatches 35min, clean three times gently with phosphate buffer (PBS, pH 7.4), to remove the probe storing solution being introduced into cell of excess in culture medium.After being fixed by cell under Olympus ZEISS LSM 880 laser confocal microscope, carry out fluorescence imaging (10 times of object lens, 63 times of oily mirrors) by linear scanning.Respectively with the laser excitation that wavelength is 405nm and 488nm, collect blue-fluorescence and the yellow fluorescence of 500-600nm that emission band is 425-500nm.Such as Fig. 5, probe shows faint yellow fluorescence and blue-fluorescence under confocal fluorescent imager, adds 5 μ L 1.34 × 10 immediately-2The ClO of M-, yellow fluorescence gradually weakens, and blue-fluorescence gradually strengthens.
Claims (7)
1. one kind measures ClO-Carbazoles fluorescent probe, be characterised by, it is 1-methyl-3-(9-butyl carbazole-3-acrylonitrile
Base) pyridine iodide, its structural formula is:
2. a kind of mensuration ClO as claimed in claim 1-The preparation method of carbazoles fluorescent probe, it is characterised in that include
Following steps:
1) carbazole, n-butyl bromide are dissolved in DMSO/KOH mixed solution by equimolar amounts, agitating heating, generate 9-butyl
Carbazole；
2) with DMF as solvent, POCl3With 3-5: 1 reaction in molar ratio of 9-butyl carbazole, obtain 3-formoxyl-9-butyl
Carbazole；
3) equimolar 3-formoxyl-9-butyl carbazole and 3-pyridylacetonitrile are blended in the methanol of 50 DEG C, add potassium tert-butoxide
At room temperature react, generate 1-methyl-3-(9-butyl carbazole-3-acrylonitrile base) pyridine；
4) by 1-methyl-3-(9-butyl carbazole-3-acrylonitrile base) pyridinium dissolution at HCCl3In, add CH3I reacts, sucking filtration,
It is dried, obtains crocus solid product；1-methyl-3-(9-butyl carbazole-3-acrylonitrile base) pyridine and CH3The mol ratio of I is
1∶50-60。
3. a kind of mensuration ClO as claimed in claim 2-The preparation method of carbazoles fluorescent probe, it is characterised in that described
Step 1) in agitating heating temperature be 60-90 DEG C.
4. a kind of mensuration ClO as claimed in claim 2-The preparation method of carbazoles fluorescent probe, it is characterised in that described
Step 2) in reaction temperature be 60-90 DEG C, response time 8-12h.
5. a kind of mensuration ClO as claimed in claim 2-The preparation method of carbazoles fluorescent probe, it is characterised in that described
Step 3) in room temperature lower response time 4-6h.
6. a kind of mensuration ClO as claimed in claim 2-The preparation method of carbazoles fluorescent probe, it is characterised in that described
Step 4) in reaction temperature 50-70 DEG C, response time 4-6h.
7. a fluoroscopic examination ClO-Method, it is characterised in that step is:
(1) with the fluorescent probe storing solution as claimed in claim 1 of DMSO system preparation 1mM；
(2) by 1.6mL water and 0.4mL ethanol and 20 μ L fluorescent probe storing solutions addition fluorescence cuvette, glimmering
Detecting on light spectrophotometer, along with treating the addition of test sample, the fluorescence intensity at 440nm gradually strengthens；
(3) with 1.34 × 10-2The ClO of M-Solution, by 1.6mL water and 0.4mL ethanol and 20 μ L fluorescent probes deposit
Liquid adds in fluorescence cuvette, adds the ClO of 2 μ L every time-Carry out fluorescence titration experiment, add 55 μ L altogether；With ClO-Concentration is
Abscissa, with relative intensity of fluorescence (F-F0) it is vertical coordinate drafting figure, obtain ClO-The working curve of concentration, linear regression side
Cheng Wei: F-F0The unit of=110.798c 9.207, c is 10-5M；Obtain fluorescent probe optimum linear by linear fit to respond
ClO-In the range of: 0 24.12 × 10-5M, linearly dependent coefficient is R2=0.99819.
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| CN108219774A (en) * | 2017-10-19 | 2018-06-29 | 泰山医学院 | A kind of quinolines of pyrido [1,2-a] benzimidazole substitution detect hypochlorous fluorescence probe and its application |
| CN108822019A (en) * | 2018-08-21 | 2018-11-16 | 济南大学 | Polar fluorescence probe of a kind of detection fat drips and its preparation method and application |
| CN108840818A (en) * | 2018-06-25 | 2018-11-20 | 山西大学 | It is a kind of for detecting the synthesis and application of the ratio colour pattern carbazoles fluorescence probe of hydrogen sulfide |
| CN110272731A (en) * | 2019-07-15 | 2019-09-24 | 山西大学 | A kind of fluorescence probe DCCO and its preparation method and application |
| CN111205242A (en) * | 2020-02-24 | 2020-05-29 | 山西大学 | Benzothiazole derivative and synthesis method and application thereof |
| CN112724069A (en) * | 2021-01-28 | 2021-04-30 | 内蒙古农业大学 | Carbazolyl ethanone fluorescent probe compound for identifying and detecting iron and mercury |
| CN114573571A (en) * | 2022-03-15 | 2022-06-03 | 安徽大学 | Carbazole derivative fluorescent probe containing dicyano isophorone base and preparation method and application thereof |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106916140A (en) * | 2017-03-13 | 2017-07-04 | 山西大学 | Carbazole nitrogen containing derivative and its production and use |
| CN108219774A (en) * | 2017-10-19 | 2018-06-29 | 泰山医学院 | A kind of quinolines of pyrido [1,2-a] benzimidazole substitution detect hypochlorous fluorescence probe and its application |
| CN108840818A (en) * | 2018-06-25 | 2018-11-20 | 山西大学 | It is a kind of for detecting the synthesis and application of the ratio colour pattern carbazoles fluorescence probe of hydrogen sulfide |
| CN108840818B (en) * | 2018-06-25 | 2021-09-28 | 山西大学 | Synthesis and application of colorimetric carbazole fluorescent probe for detecting hydrogen sulfide |
| CN108822019A (en) * | 2018-08-21 | 2018-11-16 | 济南大学 | Polar fluorescence probe of a kind of detection fat drips and its preparation method and application |
| CN108822019B (en) * | 2018-08-21 | 2019-08-13 | 济南大学 | Polar fluorescence probe of a kind of detection fat drips and its preparation method and application |
| CN110272731A (en) * | 2019-07-15 | 2019-09-24 | 山西大学 | A kind of fluorescence probe DCCO and its preparation method and application |
| CN110272731B (en) * | 2019-07-15 | 2021-05-14 | 山西大学 | Fluorescent probe DCCO and preparation method and application thereof |
| CN111205242A (en) * | 2020-02-24 | 2020-05-29 | 山西大学 | Benzothiazole derivative and synthesis method and application thereof |
| CN112724069A (en) * | 2021-01-28 | 2021-04-30 | 内蒙古农业大学 | Carbazolyl ethanone fluorescent probe compound for identifying and detecting iron and mercury |
| CN114573571A (en) * | 2022-03-15 | 2022-06-03 | 安徽大学 | Carbazole derivative fluorescent probe containing dicyano isophorone base and preparation method and application thereof |
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