CN109053778A - The reagent and its synthetic method of specific detection cyanogen root and application - Google Patents
The reagent and its synthetic method of specific detection cyanogen root and application Download PDFInfo
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Abstract
The present invention provides a kind of reagent of specific detection cyanogen root and its synthetic method and application, the Chinese of the reagent is (E) -2- (2- (5,5- bis- fluoro- -1,7,9 trimethyl -5H-4 λ of 10- (4- methoxyphenyl)4,5λ4Two pyrrolo-es [1,2-C:2', 1'-f] [1,3,2] diaza borax -3- base) vinyl) -1- ethyl -3,3- dimethyl -3H- indoles -1-, structural formula isThe present invention provides a kind of methods of specific detection cyanogen root to pass through the content of sepectrophotofluorometer quantitative detection cyanogen root in MeCN:PBS (10mM, pH=7.4,1:1, v/v).The detection process is easy, sensitive, quick, and testing result is accurate.
Description
Technical field
The present invention relates to a kind of reagent of specific detection cyanogen root and its synthetic method and applications.
Background technique
Cyanogen anion receives significant attention in Anion Recognition field, because it is very harmful to human health, Ke Yitong
Oral cavity is crossed, respiratory tract or skin are absorbed into vivo, cause to faint from fear, and are vomitted, the loss of consciousness and final death.Cyanide it is main in
Malicious mechanism is after cyanide enters blood circulation of human body, with cytochrome oxidase Fe3+Complexing occurs, leads to Fe3+Transmitting
Electronics blocks respiratory chain, leads to death caused by anoxic.It is worth noting that cyanide is not far from us.It has various sources,
Such as production accident, drug, fire hazard aerosol fog or even some foods.However, cyanide is widely used in many fields.For example,
Cyanide is widely used in exploitation of gold deposit and plating in metallurgical industry.In addition, cyanide is in the important original such as synthetic pesticide and pesticide
It is also indispensable when material.Therefore, the cyaniding object detecting method of one kind rapidly and efficiently is developed to environmental monitoring and food analysis
It is extremely important.
Currently, most of fluorescence probe realizes the detection of cyanogen root using fluorescence enhancement type, detection limit is higher.Therefore research is opened
Response of sending out signal a kind of is obvious and detection limits reagent low, that cyanogen root can be detected in cell concentration level seems especially heavy
It wants.
Summary of the invention
The object of the present invention is to provide a kind of easy to operate, good, high sensitivity the detection cyanogen root of selectivity BODIPY to spread out
Biology and preparation method thereof.In the present invention, a kind of compound based on BODIPY has been synthesized, by cyanogen root and compound in parent
The rate of change of fluorescence intensity, realizes the specific detection of cyanogen root before and after core addition reaction.
The present invention provides a kind of two pyrroles of fluorine boron (BODIPY) derivative, structural formulas are as follows:
The present invention also provides the synthetic methods of above-mentioned two pyrroles of fluorine boron (BODIPY) derivative, comprising the following steps: will
Molar ratio is the P-methoxybenzal-dehyde and 2 of 1:2, and 4- dimethyl pyrrole is dissolved in anhydrous dichlormaine, then plus trifluoroacetic acid (TFA),
Mixture is stirred, dichlorocyanobenzoquinone is added later and continues to stir, triethylamine is then added, it is rear that boron trifluoride second is added dropwise
Ether, reaction obtain crude product；The crude product passes through column chromatography eluting to obtain the first compound；To first compound
Dichlorocyanobenzoquinone solution is added dropwise in the solution in tetrahydrofuran (THF)/water, wherein the volume ratio of tetrahydrofuran and water is
The temperature of reaction mixture after storing solution 4 hours at 0 DEG C, is slowly increased to room temperature under protection of argon gas by 100:1, will
Reaction mixture is stood overnight, and by the way that water quenching is added, gained mixture is extracted with dichloromethane and is washed with water, and uses column color
Spectrometry is further purified, and affords second compound with the mixture of ethyl acetate/petroleum ether, wherein ethyl acetate and petroleum
The volume ratio of ether is 1:6；By second compound and 1,3,3- trimethyl -3H- indoles salt are dissolved in benzene, stir under protection of argon gas
It mixes and flows back, it is two pyrroles of fluorine boron (BODIPY) derivative that after reaction, filtering, which with ethanol washing, is dried to obtain black solid,.
The present invention also provides application of above-mentioned two pyrroles of fluorine boron (BODIPY) derivative in cyanogen root detection.
The present invention also provides a kind of methods for detecting cyanogen root, comprising the following steps: (1), prepares pH=7.4, concentration and be
The PBS buffer solution of 10mM, and 2mM (E) -2- (2- (5,5- bis- fluoro- 10- (4- methoxyphenyl)-are prepared with dimethyl sulfoxide
1,7,9 trimethyl -5H-4 λ4,5λ4Two pyrrolo-es [1,2-C:2', 1'-f] [1,3,2] diaza borax -3- base) vinyl) -1-
The dimethyl sulphoxide solution of ethyl -3,3- dimethyl -3H- indoles -1-；(2), by volume 1:1 by PBS buffer solution and second
Nitrile solution is added in 2mL fluorescence cuvette, is detected on Fluorescence spectrophotometer, glimmering at 646nm with the addition to test sample
Luminous intensity gradually decreases, and significantly increases along with 542nm fluorescence intensity；(3), the cyanogen root solution of 20mM is prepared with distilled water,
PBS buffer solution and acetonitrile solution are added in 2mL fluorescence cuvette by 1:1 by volume, are gradually added into the volume of cyanogen root solution
For 0,3,6,9,12,15,18 μ L, while measuring in Fluorescence Spectrometer the ratio of relative intensity of fluorescence at the place 542nm and 646nm
I542/I646It is 0.705,1.970,4.134,11.263,32.964,76.852,97.833, using cyanogen root concentration as abscissa, with
Relative intensity of fluorescence ratio I542/I646It draws and schemes for ordinate, obtain the working curve of cyanogen root concentration c；Equation of linear regression are as follows:
F542/F646The unit of=2.45c+1.25, c are 10-5mol/L；(4), when measuring sample solution, the fluorescence intensity measured is substituted into
Equation of linear regression can acquire cyanogen root concentration c.
Compared with prior art, the invention has the advantages that and effect:
1, the synthesis of the BODIPY derivative is simple, easy to operate；
2, the detection method is able to achieve the specific detection of cyanogen root, it is shown that high sensitivity and fabulous selectivity；
3, detection means is simple, it is only necessary to can be realized by Fluorescence Spectrometer；
4, detection signal is obvious, is Ratio-type fluorescence.
Detailed description of the invention
Fig. 1 shows the nucleus magnetic hydrogen spectrum figure of the probe 1 of the preparation of embodiment 1.
Fig. 2 shows the nuclear-magnetism carbon spectrograms of probe 1 prepared by embodiment 1.
Fig. 3 shows the mass spectrogram of the probe 1 of the preparation of embodiment 1.
Fig. 4 shows the probe 1 in embodiment 2 and the fluorescent emission figure of cyanogen root effect.
Fig. 5 shows the fluorescence histogram of probe 1 and various analytes in embodiment 3.
Fig. 6 shows the working curve of the measurement cyanogen root of the probe 1 in embodiment 4.
Fig. 7 shows the fluorescent emission figure of the measurement sample of the probe 1 in embodiment 5.
Fig. 8 shows the cell imaging figure in embodiment 6.
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.
A kind of BODIPY derivative provided by the invention, Chinese are that (5,5- bis- is fluoro- by 1- (4- azido benzyl) -4-
1,3,7,9 tetramethyl -5H-4 λ4,5λ4[1,3,2] diaza borax -10- base of two pyrrolo-es [1,2-C:2', 1'-f]) pyridine -
1-, English name are 1- (4-azidobenzyl) -4- (5,5-difluoro-1,3,7,9-tetramethyl-5H-4 λ4,5
λ4- dipyrrolo [1,2-c:2', 1'-f] [1,3,2] diazaborinin-10-yl) pyridin-1-ium, it is named as probe
1.Structural formula are as follows:
The synthetic method of probe 1, step are as follows:
1) P-methoxybenzal-dehyde and 2 for being 1:2 by molar ratio, 4- dimethyl pyrrole are dissolved in anhydrous dichlormaine, then plus three
Fluoroacetic acid (TFA) stirs mixture.Dichlorocyanobenzoquinone (DDQ) is added and continues to stir, triethylamine is then added, it is rear to drip
Add boron trifluoride ether.Crude product passes through column chromatography eluting to obtain orange crystal solid chemical compound 1.To compound 2 four
Hydrogen furans (THF)/H2The DDQ solution for being dissolved in THF is added dropwise in solution in O (v/v=100/1), under protection of argon gas.Solution is existed
After being stored 4 hours at 0 DEG C, the temperature of reaction mixture is slowly increased to room temperature, reaction mixture is stood overnight, passes through addition
Water quenching.Gained mixture is extracted with dichloromethane and is washed with water.Crude product is further purified using column chromatography, with (second
Acetoacetic ester/petroleum ether v/v=1:6) mixture affords compound 2, and it is orange solids.
2) by compound 2 and 1,3,3- trimethyl -3H- indoles salt are dissolved in benzene, stir and flow back under protection of argon gas,
After reaction, filtering with ethanol washing, is dried to obtain black solid, is required product probe 1.
The present invention also provides a kind of method for detecting cyanogen root, steps are as follows:
(1), it prepares pH=7.4, the PBS buffer solution that concentration is 10mM, and prepares 2mM with dimethyl sulfoxide (DMSO)
(E) -2- (2- (5,5- bis- fluoro- 10- (4- methoxyphenyl) -1,7,9 trimethyl -5H-4 λ4,5λ4Two pyrrolo-es [1,2-C:2',
1'-f] [1,3,2] diaza borax -3- base) vinyl) and -1- ethyl -3,3- dimethyl -3H- indoles -1- DMSO solution；
(2), PBS buffer solution and acetonitrile solution are added in 2mL fluorescence cuvette by 1:1 by volume, in fluorescence spectrophotometer
It is detected on photometer, with the addition to test sample, fluorescence intensity at 646nm is gradually decreased, along with 542nm fluorescence intensity
It significantly increases；
(3), solution (is configured) by NaCN with the cyanogen root that distilled water prepares 20mM, by volume 1:1 by PBS buffer solution and
Acetonitrile solution is added in 2mL fluorescence cuvette, and the volume for being gradually added into cyanogen root solution is 0,3,6,9,12,15,18 μ L, while
The ratio I at 542nm with relative intensity of fluorescence at 646nm is measured in Fluorescence Spectrometer542/I646For 0.705,1.970,4.134,
11.263,32.964,76.852,97.833, using cyanogen root concentration as abscissa, with relative intensity of fluorescence ratio I542/I646It is vertical
Coordinate draws figure, obtains the working curve of cyanogen root concentration c；Equation of linear regression are as follows: F542/F646The unit of=2.45c+1.25, c
It is 10-5mol/L；
(4), when measuring sample solution, the fluorescence intensity measured is substituted into equation of linear regression, the dense of cyanogen root can be acquired
Degree.
Embodiment 1
The preparation and characterization of probe 1
The P-methoxybenzal-dehyde (0.545g, 4mmol) and 2,4- dimethyl pyrrole for being 1:2.175 by molar ratio
(0.833g, 8.7mmol) is dissolved in anhydrous dichlormaine (300mL), then plus trifluoroacetic acid (TFA) (1mL), stir mixture.It is added
Dichlorocyanobenzoquinone (0.98g, 4mmol) simultaneously continues to stir 4h, and triethylamine (9mL) then is added, is added dropwise after 15min borontrifluoride
Borate ether (9mL).Crude product passes through column chromatography eluting to obtain orange crystal solid chemical compound 1.To compound 1 (142mg,
0.4mmol) in 8mL THF/H2The DDQ solution (360mg, 1.58mmol) for being dissolved in THF is added dropwise in O (v/v=100/1), in argon
Under gas shielded.After solution is stored 4 hours at 0 DEG C, the temperature of reaction mixture is slowly increased to room temperature, by reaction mixture
It stands overnight, by the way that water (20mL) quenching is added.Gained mixture is extracted with dichloromethane and is washed with water.Use column chromatography
Crude product is further purified, affords compound 2 with (ethyl acetate/petroleum ether v/v=1:6) mixture, is orange solids.
2) compound 2 (80mg, 0.22mmol) and 1,3,3- trimethyl -3H- indoles salt (70mg, 0.22mmol) is molten
In 20mL benzene, after stirring simultaneously back flow reaction 4h under protection of argon gas, filtering with ethanol washing, is dried to obtain black solid, is
Required product probe 1.
1H NMR(600MHz,CDCl3): δ 8.66 (d, J=18Hz, 1H), 8.18 (s, 1H), 7.92 (s, J=18Hz,
1H), 7.58 (d, J=12Hz, 4H), 7.22 (d, J=6Hz, 2H), 7.09 (d, J=6Hz, 2H), 6.27 (s, 1H), 5.10 (m,
J=18Hz, 2H), 3.92 (s, 3H), 2.71 (s, 3H), 1.87 (s, 3H), 1.65 (m, J=18Hz, 3H), 1.60 (m, J=
18Hz, 6H), 1.28 (s, 3H) (Fig. 1)13C NMR(150MHz,CDCl3):δ180.1,165.8,160.8,149.8,143.6,
143.1,142.3,140.6,130.9,129.6,128.8,125.7,125.3,122.7,115.0,114.2,113.2,55.4,
51.9,44.2,29.7,27.1,22.7,19.2,15.7,15.4,14.5,14.1 (Fig. 2) .ESI-MS m/z:[M]+calcd
for 538.2836；Found 538.2837 (Fig. 3).
Embodiment 2
It prepares pH=7.4, the PBS buffer solution that concentration is 10mM, and prepares 1 solution of 2mM probe with DMSO；20 μ L are visited
The DMSO solution of needle 1 is added in the fluorescence cuvette of 2mL MeCN:PBS (10mM, pH=7.4,1:1, v/v), takes cyanogen root molten
Liquid is gradually added in this cuvette with microsyringe, is detected on Fluorescence spectrophotometer in sample-adding, with adding for cyanogen root
Enter, fluorescence intensity reduces at 646nm, and gradually increases along with fluorescence intensity at 542nm.Fluorescent emission figure is shown in Fig. 4.
Embodiment 3
It prepares pH=7.4, the PBS buffer solution that concentration is 10mM, and prepares 1 solution of probe of 2mM with DMSO；At 20
In fluorescence cuvette, the DMSO of each MeCN:PBS (10mM, pH=7.4,1:1, v/v) solution that 2mL is added and 20 μ L probes 1 is molten
Liquid, then it is separately added into the various analytes of 3 molar equivalent cyanogen roots and 30 molar equivalents: Cys, Hcy, GSH, F-,Cl-,Br-,
NO3-,N3-,HSO3 -,AcO-,CO3 2-,HCO3-,S2-,SCN-,ClO4-,SO4 2-,HPO4 2-,H2PO4 2-,NO2 -In fluorescence spectrophotometry
Detected on instrument, draw at the corresponding 542nm of different analytes and at 646nm relative intensity of fluorescence ratio histogram, (see figure
5).Cyanogen root makes probe 1 at 542nm and the fluorescence intensity significant change of 646nm, and other analytes do not cause bright substantially
Aobvious change in fluorescence.
Embodiment 4
It prepares pH=7.4, the PBS buffer solution that concentration is 10mM, the cyanogen root solution of 20mM is prepared with distilled water, respectively will
2mL MeCN:PBS (10mM, pH=7.4,1:1, v/v) solution is added in 7 cuvettes, is gradually added into the body of cyanogen root solution
Product is 0,5,10,15,20,25,30 μ L, while relative intensity of fluorescence at the place 542nm and 646nm is measured in Fluorescence Spectrometer
Ratio I542/I646It is 0.705,1.970,4.134,11.263,32.964,76.852,97.833, with cyanogen root concentration for horizontal seat
Mark, with relative intensity of fluorescence ratio I542/I646It draws and schemes for ordinate, obtain the working curve of cyanogen root concentration c；Linear regression side
Journey are as follows: F542/F646The unit of=2.45c+1.25, c are 10-5mol/L；See Fig. 6.
Embodiment 5
It prepares pH=7.4, the PBS buffer solution that concentration is 10mM, and prepares 1 solution of 2mM probe with DMSO；20 μ L are visited
The DMSO solution of needle 1 is added in the fluorescence cuvette of 2mL MeCN:PBS (10mM, pH=7.4,1:1, v/v) solution, takes cyanogen
The 24 μ L of solution of root, is added in this cuvette with microsyringe, while being measured at 542nm and 646nm in Fluorescence Spectrometer
Fluorescence intensity is 1249 and 21, the ratio (I at 542nm with relative intensity of fluorescence at 646nm542/I646) it is 49.476, pass through reality
The equation of linear regression for applying example 4, acquires c=23.8 × 10-5mol/L.Deviation is 0.8%.See Fig. 7.
Embodiment 6
The probe 1DMSO solution of 2mM is prepared with DMSO；Probe DMSO solution is added in HepG-2 cell culture fluid, is made
Obtaining its concentration is 10 μM, is incubated for 30 minutes at 37 DEG C with HepG-2 cell.System is in Laser Scanning Confocal Microscope red channel at this time
In show red fluorescence, and green channel only has very faint green fluorescence.Respectively by 50 μM, 100 μM, 150 μM of cyanogen roots it is molten
After liquid and above-mentioned pretreated HepG-2 cell are incubated for 30 minutes again, system is shown in Laser Scanning Confocal Microscope green channel at this time
Strong green fluorescence, and the fluorescence of red channel disappears substantially, sees Fig. 8.
It will be understood by those skilled in the art that above embodiments are only exemplary embodiments, without departing substantially from spirit herein
In the case where range, a variety of variations can be carried out, replaced and changed.
Claims (4)
1. a kind of two pyrroles of fluorine boron (BODIPY) derivative, which is characterized in that structural formula are as follows:
2. the synthetic method of two pyrroles of fluorine boron (BODIPY) derivative according to claim 1, comprising the following steps:
The P-methoxybenzal-dehyde and 2 for being 1:2 by molar ratio, 4- dimethyl pyrrole are dissolved in anhydrous dichlormaine, then plus trifluoroacetic acid
(TFA), mixture is stirred, dichlorocyanobenzoquinone is added later and continues to stir, triethylamine is then added, is added dropwise afterwards borontrifluoride
Borate ether, reaction obtain crude product；
The crude product passes through column chromatography eluting to obtain the first compound；
Dichlorocyanobenzoquinone solution is added dropwise in the solution in tetrahydrofuran (THF)/water to first compound, wherein four
The volume ratio of hydrogen furans and water is 100:1, under protection of argon gas, after solution is stored 4 hours at 0 DEG C, by reaction mixture
Temperature be slowly increased to room temperature, reaction mixture is stood overnight, by the way that water quenching is added, gained mixture extracts with methylene chloride
It takes and is washed with water, be further purified using column chromatography, afford the second chemical combination with the mixture of ethyl acetate/petroleum ether
Object, wherein the volume ratio of ethyl acetate and petroleum ether is 1:6；
By second compound and 1,3,3- trimethyl -3H- indoles salt are dissolved in benzene, stir and flow back under protection of argon gas, instead
Ying Hou, filtering, with ethanol washing, is dried to obtain black solid, is two pyrroles of fluorine boron (BODIPY) derivative.
3. application of two pyrroles of fluorine boron (BODIPY) derivative according to claim 1 in cyanogen root detection.
4. a kind of method for detecting cyanogen root, comprising the following steps:
(1), prepare pH=7.4, concentration be 10mM PBS buffer solution, and with dimethyl sulfoxide prepare 2mM (E) -2- (2- (5,
5- bis- fluoro- 10- (4- methoxyphenyl) -1,7,9 trimethyl -5H-4 λ4,5λ4Two pyrrolo-es [1,2-C:2', 1'-f] [1,3,2]
Diaza borax -3- base) vinyl) -1- ethyl -3,3- dimethyl -3H- indoles -1- dimethyl sulphoxide solution；
(2), PBS buffer solution and acetonitrile solution are added in 2mL fluorescence cuvette by 1:1 by volume, in fluorescence spectrophotometry
It is detected on instrument, with the addition to test sample, gradually decreasing for fluorescence intensity at 646nm is significant along with 542nm fluorescence intensity
Enhancing；
(3), the cyanogen root solution of 20mM is prepared with distilled water, PBS buffer solution and acetonitrile solution are added to 2mL by 1:1 by volume
In fluorescence cuvette, the volume for being gradually added into cyanogen root solution is 0,3,6,9,12,15,18 μ L, while being surveyed in Fluorescence Spectrometer
Determine the ratio I at 542nm with relative intensity of fluorescence at 646nm542/I646For 0.705,1.970,4.134,11.263,32.964,
76.852,97.833, using cyanogen root concentration as abscissa, with relative intensity of fluorescence ratio I542/I646It draws and schemes for ordinate, obtain
The working curve of cyanogen root concentration c；Equation of linear regression are as follows: F542/F646The unit of=2.45c+1.25, c are 10-5mol/L；
(4), when measuring sample solution, the fluorescence intensity measured is substituted into equation of linear regression, cyanogen root concentration c can be acquired.
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| CN111233909A (en) * | 2020-03-03 | 2020-06-05 | 山西大学 | Reagent for detecting cyanide ions and synthetic method and application thereof |
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