CN105198910A - Turn-on-type BODIPY fluorescent sensor and its preparation method and use - Google Patents
Turn-on-type BODIPY fluorescent sensor and its preparation method and use Download PDFInfo
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Abstract
The invention relates to a turn-on-type BODIPY fluorescent sensor and its preparation method and use. The turn-on-type BODIPY fluorescent probe can be used as a CN<-> fluorescent sensor and has the advantages of simple synthesis, high selectivity CN<-> naked eye identification detection and easy cell CN<-> trace detection by cell permeation. Through use of CN<->, the original conjugate result of the system is changed into an unconjugated structure, intramolecular charge transfer is changed and luminescence change comprising solution color change from pink into light green is produced at macro level so that CN<-> naked eye detection is realized.
Description
Technical field
The present invention relates to a kind of open hole detection CN-Turn-on type BODIPY fluorescent optical sensors and preparation method thereof, further relate to such turn-on types fluorescent optical sensor CN in live body stomach cancer cell-The application of detection.
Background technology
Anion is in fields such as biology, environment, medicine, chemical industry using widely.Cyanogen root (CN-) ion be severe toxicity anion, belong to six grades of poisonous substances, atomic to the lethal dose of people, half lethal dose in human body is l.0mg/Kg, cyanide solution is 100mg/kg in the half lethal dose of human skin.Cyanide is widely used in industry productions such as mining, metallurgy, plating, dyestuff, synthetic fibers, resins, is the indispensable raw material of industry, but at the same time also brings very serious environmental problem.So, the fluorescent optical sensor identification of design synthesis high selectivity and detection CN-Important topic as research fields such as present analysis chemistry, Environmental Chemistry and biochemistries.The signal of detection is converted into perceived information by fluorescent optical sensor, the species and concentration to judge target such as front and rear change of intensity or wavelength by fluorescence of conversion etc. relevant parameter.
In recent years, fluorescence method and colorimetric method be in terms of ion detection, and the reason such as be easy to get due to simple to operate, instrument, be swift in response is gained great popularity (Lin, Q.；Fu,Y.-P.etc.Chem.Rev.2013,113,192).BODIPY dyestuffs are because of its higher fluorescence quantum yield and molar extinction coefficient, good photostability；It is easily accessible cell；Non-toxic the advantages of, this kind of dyestuff is set to be widely used in the design of fluorescent molecular probe.The Akkaya seminars successful design of Turkey has synthesized BODIPY probes (Ekmekci, the Z. of a kind of high selectivity and high-sensitivity detection cyanogen root；Yilmaz,M.D.；Akkaya,E.U.Org.Lett.2008,10,461).
The BODIPY fluorescence probes of most of report are all so-called " turn-off " types, i.e. fluorescent weakening or fluorescent quenching occurs in probe molecule after being combined with cyanogen root.Consider from biochemical application angle, and from the application in cell imaging field, design new turn-on type BODIPY fluorescence probes, realize that high selectivity detection cyanogen root is that have very much application prospect.Being capable of high selectivity open hole detection CN therefore, it is necessary to design and develop one kind-Turn-on type BODIPY fluorescent optical sensors.
The content of the invention
Based on the Selective recognition CN for lacking commercialization at present-BODIPY class fluorescent optical sensors, it is an object of the invention to provide a kind of turn-on types BODIPY fluorescent optical sensors and its production and use, make up the deficiency of prior art.
Concrete technical scheme is as follows：
A kind of turn-on types BODIPY fluorescent optical sensors, further, its general structure is：
Further, R is-CH3,-COOR1, or COOH etc..
Further, the fluorescent optical sensor is fluorescence probe.
Further, R1=H, C1-12Alkyl, CH=CH-CH=CH, cycloalkyl, phenyl, naphthyl, F, Cl, Br, I, OR2、NR2R3, CN, (CH=CH2)(C6H4)R2、(CH2)mO(CH2)nH、(CH2)nCOOM、(CH2)mCOM or (CH2)mSO3M。
Further, R therein2、R3For identical or different H, C1-12Straight chain or branched alkyl, C1-12Cycloalkyl, (CH2)mO(CH2)nH、(CH2)mCOOM、(CH2) mCOM or (CH2)mSO3M；N, m=0-15；M=H, Li, Na, K, NH4。
The preparation method of above-mentioned turn-on types BODIPY fluorescent optical sensors, comprises the following steps：
(1)BODIPY3THF/H2O, DDQ are dissolved in THF；
(2) it is added drop-wise to dropwise in reaction bulb；
(3) room temperature magnetic agitation, reacts certain time and is quenched reaction；
(4) extract, dry, filtering is concentrated under reduced pressure, and purifies；
(5) BODIPY4 is obtained
(6) hydroformylation dyestuff BODIPY4 and the third two eyeballs are dissolved in toluene；
(7) piperidines is added in the mixed solution of step (6)；
(8) reaction is stirred at room temperature, extracts, dries, filtering is concentrated under reduced pressure, and purifies；
(9) BODIPY1, i.e. BODIPY fluorescent optical sensors are obtained.
Further, step (2) is added drop-wise in reaction bulb dropwise under the conditions of ice-water bath.
Further, reaction adds water and is quenched reaction for 12 hours in step (3), and/or, silica gel column chromatography separating-purifying is used in step (4) and (8).
The purposes of above-mentioned turn-on types BODIPY fluorescent optical sensors, further, for open hole detection CN-。
Further, for detecting CN in live body stomach cancer cell-。
Compared with currently available technology, the present invention is due to CN-Addition so that original conjugation result is changed into non-conjugated structure in system, causes Intramolecular electron transfer to change, and macroscopically shows as luminous change, i.e., original solution colour becomes light green color by pink, and then realizes bore hole to CN-Detection.
In addition, based on such fluorescent optical sensor preferably water-soluble, biocompatibility and hypotoxicity, we have studied detection limits of the BODIPY1 to cyanide ion, result of calculation is as follows:
Linear regression coeffficient:R=0.99154,
Detectable limit：DL=3 σbi/ m=3*98.2178*10-5/ 10292.48622=2.8*10-7M (S/N=3).
We have also investigated BODIPY1 in living cells CN-Detection.With the aquicultural stomach cancer cells of BODIPY1, CN is added-Afterwards, observed under fluorescence inverted microscope, there is obvious green fluorescence.And for reference group, i.e., only use the aquicultural stomach cancer cells of BODIPY1, then almost without fluorescence.Light field observation is it can be seen that good cell state, it was demonstrated that cytoactive is good in whole process.Cell imaging experiment shows, BODIPY1 can penetration cell film well, thereby increases and it is possible to CN-Useful effect is realized to CN in active somatic cell-Trace detection.This suffers from great meaning for fields such as biochemistry, cell biology and clinical medicine.
Specifically：
1) BODIPY1 of the invention, it is prepared and separation process is simple, and yield is preferable；
2) BODIPY1 of the invention, is used as CN-Fluorescent optical sensor, may be used as to CN-High sensitivity, high selectivity open hole detection.
3) CN of the invention-Fluorescent optical sensor, has preferable water-soluble, biocompatibility and hypotoxicity, can realize to CN-High selectivity open hole detection, the CN in active somatic cell can be also realized certainly-Trace detection.
Brief description of the drawings
Fig. 1 a are ultraviolet spectrograms of the BODIPY1 in different solvents；
Fig. 1 b are fluorescence spectras (Ex=490nm) of the BODIPY1 in different solvents；
Fig. 2 a are the ultraviolet curve that BODIPY1 is titrated to cyanide ion；
Fig. 2 b are the fluorescence curve that BODIPY1 is titrated to cyanide ion；
Fig. 3 is BODIPY1 in THF-H2O(v/v,1:1) to the ultraviolet response curve of various anion in
0:blank,1:F-,2:SCN-,3:NO3 -,4:Br-,5:HSO4 -,6:HPO4 2-,7:H2PO4 -,8:Cl-,9:ClO4 -10:AcO-,11:HSO3 -；
Fig. 4 a are the fluorescence spectrum situation that BODIPY fluorescent optical sensors 1 are acted on various anion；
Fig. 4 b are BODIPY1 in THF-H2O(v/v,1:1) to CN in-Selectivity and competitive scheme；
0:blank,1:F-,2:SCN-,3:NO3 -,4:Br-,5:HSO4 -,6:HPO4 2-,7:H2PO4 -,8:Cl-,9:ClO4 -10:AcO-,11:HSO3 -.
Fig. 5 is BODIPY1 fluorescence area with CN-The linear relationship of change in concentration；
The fluorescence intensity of Fig. 6 probe molecules and the graph of a relation of pH value of solution；
Fig. 7 a are the photograph via bright field of the cell arrived by OLYMPUS-IX71 type fluorescence microscopes；
Fig. 7 b are fluorescence imaging figures of the BODIPY1 in cell；
Fig. 8 a are the photograph via bright field of weaker red fluorescent cell；
Fig. 8 b are BODIPY1+CN-Fluorescence imaging in cell；
Fig. 9 is BODIPY1 mono-crystalline structures figure
Figure 10 is turn-on type BODIPY fluorescent optical sensor general structures.
Embodiment
Below according to accompanying drawing, the present invention will be described in detail, and it is a kind of preferred embodiment in numerous embodiments of the present invention.
A kind of open hole detection CN-Turn-on type BODIPY fluorescent optical sensors, its general structure is：
In formula：R1=H, C1-12Alkyl, CH=CH-CH=CH, cycloalkyl, phenyl, naphthyl, F, Cl, Br, I, OR2、NR2R3, CN, (CH=CH2)(C6H4)R2、(CH2)mO(CH2)nH、(CH2)nCOOM、(CH2)mCOM or (CH2)mSO3M；R2、R3For identical or different H, C1-12Straight chain or branched alkyl, C1-12Cycloalkyl, (CH2)mO(CH2)nH、(CH2)mCOOM、(CH2) mCOM or (CH2)mSO3M；N, m=0-15；M=H, Li, Na, K, NH4。
Eye detection CN-BODIPY fluorescent optical sensors synthetic method, be characterised by that this method uses following preparation steps：BODIPY3 in 50mL round-bottomed flasks(64mg,0.20mmol),THF/H2O (8/0.08mL), DDQ (180mg, 0.8mmol) is dissolved in 2mLTHF, it is added drop-wise to dropwise in reaction bulb under the conditions of ice-water bath, room temperature magnetic agitation, reaction 12 hours plus the quenching reaction of 20mL water, extraction, dry, filtering is concentrated under reduced pressure, silica gel column chromatography separating-purifying (300-400 mesh silica whites, n-hexane/ethyl acetate=6/1, V/V) obtain Orange red solid dyestuff powder BODIPY460.0mg, yield 90%.
Hydroformylation dyestuff BODIPY4 (166mg, 0.5mmol) 10mL toluene is dissolved in the third two eyeballs (40mg0.6mmol), then Jia one in mixed solution and drip piperidines, reaction 0.5 hour, extraction is stirred at room temperature, dry, filtering, is concentrated under reduced pressure, silica gel column chromatography separating-purifying (300-400 mesh silica whites, n-hexane/ethyl acetate=3/1, V/V) obtain aubergine solid powder dyestuff BODIPY1.Open hole detection CN-BODIPY fluorescence probes and its synthetic method, it is characterized in that：The organic solvent is selected from 1,2- dichloroethanes, toluene, chlorobenzene, ortho-xylene, paraxylene.Open hole detection CN-BODIPY fluorescence probes and its synthetic method, it is characterized in that：Described acid is selected from HOAc, CH3-C6H4-SO3H、HCOOH、HCl、HBr、CH3SO3H、CF3SO3H。
Case study on implementation 1：
BODIPY1 titration experiments are in THF-H2O(v/v,1:1) carried out in, concentration is 1.0*10-5mol/L.In titration process, the absorbent body peak at 547nm fades away, and a new peak is generated at 511nm, and gradually strengthen.1 isobestic point formed at 513nm, illustrates that the structure of the compound under cyanide ion effect, is changed, generates new compound.Solution colour becomes light green color by pink simultaneously.
BODIPY1 and CN-In the fluorescence spectroscopic titration of effect, excitation wavelength used is 490nm, adds CN-Concentration is 0-20 equivalents.In titration process, the emission peak at 588nm is gradually reduced, and the emission peak at 545nm gradually strengthens.Reaction system is adding the CN of 10 equivalents-After reached balance.Find out that BODIPY1 is in THF-H from figure two (B)2O(v/v,1:1) with CN in-After effect, titration curve occurs in that obvious blue shift, and fluorescence has obvious enhancing.
Case study on implementation 2：
(concentration is 1.0*10 to BODIPY1 solution-5Mol/L) a maximum absworption peak at 547nm, is separately added into the F of 20 equivalents-,SCN-,NO3 -,Br-,HSO4 -,H2PO4 -,Cl-,ClO4 -,AcO-,HSO3 -Deng anion, the change for causing absorption spectrum is there is no, as 20 equivalent HPO of addition4 2-When, the absworption peak at 547nm is somewhat reduced.After 10 equivalent cyanide ion is added, obvious decline occurs for the absworption peak at 547nm, and a new absworption peak is generated at 511nm.
Case study on implementation 3：
Under same concentrations, BODIPY1 bulk solutions are added after cyanide ion, and significant change occurs for the fluorescent intensity degree at 588nm and 545mn；Almost, the almost detection for cyanide ion is not interfered with the fluorescence intensity ratio and bulk solution added in bulk solution at other anionic ions, 588nm and 545nm.It is can be seen that from figure four (B) in the bulk solution for adding a series of other anion of 20 equivalents, after the cyanide ion for continuously adding 10 equivalents, there is obvious Fluorescence Increasing in solution originally, show on the integral area of fluorescence curve, light green color also occurs in solution, this explanation CN-Very strong competitiveness is shown relative to other anion.
Case study on implementation 4：
Under same concentrations, the solution containing BODIPY1 molecules is adding CN-With other 12 kinds of anion (0:blank,1:F-,2:SCN-,3:NO3 -,4:Br-,5:HSO4 -,6:HPO4 2-,7:H2PO4 -,8:Cl-,9:ClO4 -,10:AcO-,11:HSO3 -,12:CN-).It is aobvious red in the mixed solution of tetrahydrofuran and water, but is adding CN-Afterwards, bore hole perceived color is changed into green by red, and fluorescence is very weak under 365nm ultra violet lamps, adds CN-Launch bright green fluorescence afterwards, it is possible to achieve open hole detection (naked-eyedetection) cyanide ion.
Case study on implementation 5：
In the range of pH=2~10, the fluorescent absorption intensity of BODIPY1 solution does not have significant change, in the range of pH=3~10,1 with cyanogen root act on after solution fluorescence intensity it is also basicly stable, and when pH is less than 3 or more than 10, the fluorescence intensity of working solution is substantially reduced, and the pH of this explanation BODIPY1 working environment should be maintained in the range of 3~10.
Under argon gas protection, 180mgDDQ (0.8mmol) 2mLTHF is added dropwise in BODIPY3 (64mg, 0.2mmol) 8mLTHF/H2O (v/v=100/1), is stirred overnight at room temperature.Extraction, is dried, and is filtered, revolving.Crude product purifies to obtain orange powder BODIPY4 (60mg, 90%) by chromatographic column (silica gel).1HNMR(300MHz,CDCl3):δ10.29(s,1H),2.76(q,2H),2.72(s,3H),2.64(s,3H),2.38(q,2H),2.34(s,3H),2.27(s,3H),1.19(s,3H),1.03(s,3H).13CNMR(75MHz,CDCl3):186.1,164.0,142.2,142.1,138.9,137.6,136.7,136.6,133.5,132.1,17.9,17.8,17.3,15.1,14.8,14.5,13.5,13.2.
Under argon gas protection, hydroformylation dyestuff BODIPY4 (166mg, 0.5mmol) and the third two eyeball (40mg; 10mL toluene 0.6mmol) is dissolved in, then Jia one in mixed solution drips piperidines, and reaction 0.5 hour is stirred at room temperature; extraction, dries, is spin-dried for; it is concentrated under reduced pressure, silica gel column chromatography separating-purifying (300-400 mesh silica whites, n-hexane/ethyl acetate=3/1; V/V aubergine solid powder dyestuff BODIPY1) is obtained; 186mg, yield 97%1HNMR(300MHz,CDCl3) δ 8.24 (s, 1H), 2.71 (s, 2H), 2.68 (s, 3H), 2.58 (s, 3H), 2.44 (d, J=7.5Hz, 2H), 2.39 (s, 3H), 2.36 (s, 3H), 1.16-1.05 (m, 6H)13CNMR(75MHz,CDCl3)δ165.1,151.1,142.6,140.6,138.1,137.1,136.8,135.6,134.5,133.1,114.5,113.4,82.6,19.2,17.6,17.1,15.0,14.5,14.2,14.2,13.5.HRMS(EI)calcd.forC21H24BF2N4[M+H]+:381.2057,found381.2053；HRMS(EI)calcd.forC21H23BFN4[M-F]+:361.1994,found361.1994.
Case study on implementation 6：
50mL, which is dried, adds BODIPY1 (76mg, 0.2mmo) in round-bottomed flask, potassium cyanide (16.3mg, 0.25mmol) is dissolved in 10mL acetonitriles, adds the K of catalytic amount2CO3, magnetic agitation reacts at room temperature 3min, and dichloromethane is extracted immediately, is dried, and is filtered, and concentration obtains darkviolet solid powder dyestuff 2,100mg through silica gel column chromatography separating-purifying (n-hexane/ethyl acetate=2/1, V/V), yield 98%,1HNMR(300MHz,CDCl3) δ 5.24 (s, H), 4.75 (s, 1H), 2.68 (s, 3H), 2.61 (m, 2H), 2.48 (s, 3H), 2.46 (m, 2H), 2.40 (s, 3H), 2.31 (s, 3H), 1.20 (t, J=7.2Hz, 3H), 1.08 (d, J=7.5Hz, 3H)；13CNMR(75MHz,CDCl3)δ161.9,142.1,138.8,135.1,134.7,132.6,131.9,130.0,114.0,110.3,109.9,31.9,29.7,27.4,17.7,17.1,14.9,14.7,14.4,14.0,13.2.
Case study on implementation 7：
Adherent method culture stomach cancer cell (Gastriccancercell-SGC7901) to proper density, PBS rinses cell three times is added containing 10 μM of BODIPY1 probe face liquid (CH3CN/ culture mediums, V/V, 1/100) 2mL, in 37 DEG C, 5%CO2Under the conditions of be placed in cell case be incubated dyeing 0.5h, then with PBS rinses cell three times, the photograph via bright field figure eight (L) of cell and weaker red fluorescence picture figure eight (R) can be observed by fluorescence microscope (OLYMPUS-IX71 types), illustrate that probe molecule is easier to realize effective dyeing to cell through cell.
Case study on implementation 8：
Adherent method culture stomach cancer cell (Gastriccancercell-SGC7901) to proper density, PBS rinses cell three times adds and contains 5mMCN-Culture medium 2mL, in 37 DEG C, 5%CO2Under the conditions of be placed in cell case be incubated dyeing 0.5h.Add containing 10 μM of BODIPY1 working solutions (CH3CN/ culture mediums, V/V, 1/100) 2mL, in 37 DEG C, 5%CO2Under the conditions of be placed in cell case be incubated dyeing 0.5h, then PBS rinses cell three times.0.5h is only then cultivated in the medium with reference to experimental group.Light field is imaged and fluorescence imaging is observed with fluorescence inverted microscope (OLYMPUS-IX71).From figure nine as can be seen that cell, which can be observed, by fluorescence microscope send out strong green fluorescence figure nine (R), (weaker red fluorescence) is compared with the spectral quality that it is above determined, illustrates that probe molecule is easier to pass through cell and may be with CN-Useful effect is realized to CN in cell-Trace detection.
Spectral quality subordinate list 1 (Table1.PhotophysicalpropertiesofBODIPY1-2indifferentsolv ents) of BODIPY1 and BODIPY2 in different solvents
The present invention is exemplarily described above in conjunction with accompanying drawing; the obvious present invention, which is implemented, to be not subject to the restrictions described above; as long as employing the various improvement that method of the present invention design and technical scheme are carried out; or it is not improved directly applying to other occasions, within protection scope of the present invention.
Claims (10)
1. a kind of turn-on types BODIPY fluorescent optical sensors, it is characterised in that its general structure is：
2. turn-on types BODIPY fluorescent optical sensors as claimed in claim 1, it is characterised in that R is-CH3,-COOR1, or COOH etc..
3. turn-on types BODIPY fluorescent optical sensors as claimed in claim 1 or 2, it is characterised in that the fluorescent optical sensor is fluorescence probe.
4. the turn-on type BODIPY fluorescent optical sensors as any one of claim 1-3, it is characterised in that R1=H, C1-12Alkyl, CH=CH-CH=CH, cycloalkyl, phenyl, naphthyl, F, Cl, Br, I, OR2、NR2R3, CN, (CH=CH2)(C6H4)R2、(CH2)mO(CH2)nH、(CH2)nCOOM、(CH2)mCOM or (CH2)mSO3M。
5. turn-on types BODIPY fluorescent optical sensors as claimed in claim 4, it is characterised in that R therein2、R3For identical or different H, C1-12Straight chain or branched alkyl, C1-12Cycloalkyl, (CH2)mO(CH2)nH、(CH2)mCOOM、(CH2) mCOM or (CH2)mSO3M；N, m=0-15；M=H, Li, Na, K, NH4。
6. a kind of preparation method of the turn-on types BODIPY fluorescent optical sensors as described in claim 1-5, it is characterised in that comprise the following steps：
(1)BODIPY3THF/H2O, DDQ are dissolved in THF；
(2) it is added drop-wise to dropwise in reaction bulb；
(3) room temperature magnetic agitation, reacts certain time and is quenched reaction；
(4) extract, dry, filtering is concentrated under reduced pressure, and purifies；
(5) BODIPY4 is obtained
(6) hydroformylation dyestuff BODIPY4 and the third two eyeballs are dissolved in toluene；
(7) piperidines is added in the mixed solution of step (6)；
(8) reaction is stirred at room temperature, extracts, dries, filtering is concentrated under reduced pressure, and purifies；
(9) BODIPY1, i.e. BODIPY fluorescent optical sensors are obtained.
7. the preparation method of turn-on types BODIPY fluorescent optical sensors as claimed in claim 6, it is characterised in that step (2) is added drop-wise in reaction bulb dropwise under the conditions of ice-water bath.
8. the preparation method of turn-on type BODIPY fluorescent optical sensors as claimed in claims 6 or 7, it is characterized in that, reaction adds water for 12 hours in step (3) is quenched reaction, and/or, silica gel column chromatography separating-purifying is used in step (4) and (8).
9. a kind of purposes of the turn-on types BODIPY fluorescent optical sensors as described in claim 1-5, it is characterised in that for open hole detection CN-。
10. the purposes of turn-on types BODIPY fluorescent optical sensors as claimed in claim 9, it is characterised in that for detecting CN in live body stomach cancer cell-。
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105837492A (en) * | 2016-03-28 | 2016-08-10 | 浙江理工大学 | Cyanide ion probe, preparation and application |
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| CN107082785A (en) * | 2017-06-06 | 2017-08-22 | 江汉大学 | Application process is closed in a kind of fluorescence probe for detecting cyanide ion and its synthesis |
| CN107082785B (en) * | 2017-06-06 | 2019-01-18 | 江汉大学 | A kind of fluorescence probe and its synthesis and methods for using them of detection cyanide ion |
| CN109053778A (en) * | 2018-06-14 | 2018-12-21 | 忻州师范学院 | The reagent and its synthetic method of specific detection cyanogen root and application |
| CN110204564A (en) * | 2019-05-30 | 2019-09-06 | 上海应用技术大学 | A kind of fluorescence probe and its preparation method and application detecting cyanide ion |
| CN110204564B (en) * | 2019-05-30 | 2021-07-20 | 上海应用技术大学 | Fluorescent probe for detecting cyanide ions and preparation method and application thereof |
| 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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