CN104860957B - A kind of preparation and application of near-infrared mercury ion fluorescence probe - Google Patents
A kind of preparation and application of near-infrared mercury ion fluorescence probe Download PDFInfo
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Abstract
The invention discloses a kind of near-infrared mercury ion fluorescence probes based on switch ring to detect mercury ion, and the present invention has highly sensitive, highly selective identification mercury ion to the detection of mercury ion.The probe absorbs with after mercury ion response and launch wavelength is near infrared region, be conducive to the interference for avoiding biological sample background fluorescence, and it is in significant change to respond front and back color, can be used for Visual retrieval mercury ion.The fluorescence probe of preparation has the spectral characteristic of classical rhodamine, can be based on the mercury ion in Fluorescence Increasing or coloration enhancing detection chemical example, biological sample or medical sample, and is suitble to fluorescence imaging.
Description
Technical field
The invention belongs to fluorescence probe fields, specifically design a kind of near-infrared mercury that there is similar rhodamine to switch ring response
The preparation method and application of ion fluorescence probe.
Background technology
Mercury is a kind of metal ion to the great physiological-toxicity of human body.Mercury ion poisoning can lead to a variety of diseases, including
Defect, exaltation and the arrhythmia cordis cardiomyopathy and kidney damage of Central nervous system.
Fluorescence probe is exactly using fluorescent material as indicator, and it is glimmering to generate indicator under the excitation of certain wavelength light
Light is realized by the variation of fluorescence intensity caused by detection or the variation of wavelength to the qualitative of tested substance or quantitative point
Analysis.The advantages that fluorescence analysis method has high sensitivity, and selectivity is good, and sample size is small, and the response time is fast, it is special in analytical chemistry
It is not to have wide application in the fields such as molecular biochemistry, biology and medicine.
Compared with visible light, near infrared light has unique advantage, is close red since it sends out when carrying out bio-imaging
Outer light in biosystem can minimum level light injury of the reduction to biological sample, and with stronger penetrating power and with
The background fluorescence of molecule itself has smaller interference in organism.
Invention content
The purpose of the present invention is to provide the systems of a kind of near-infrared mercury ion probe aimed detection mercury ion and the probe
Preparation Method and purposes, to quick and precisely, delicately detect chemical example, biological sample or the mercury ion in medical sample are determined
Amount and qualitative analysis and fluorescence imaging.
The present invention adopts the following technical scheme that achieve the goals above：
A kind of near-infrared mercury ion fluorescence probe for mercury ion detecting, which is characterized in that the fluorescence probe
Structural formula is：
The near infrared fluorescent probe has the fluorescent switch Response Mechanism as traditional rhodamine, and has
There is the advantages of absorption and launch wavelength of near-infrared.
The preparation method of the near-infrared mercury ion fluorescence probe, it is characterised in that include the following steps：
It is 1 to weigh molar ratio:Potassium hydroxide, is first dissolved in distilled water by 20 rhodamine B and potassium hydroxide, is cooled to room
Temperature, the rhodamine B first weighed is dissolved in wherein, is heated to 105 DEG C of 8 h of heated at constant temperature under stirring conditions, and cooling adds
A small amount of water dilutes and HCl solution neutralization reaction liquid is slowly added dropwise, and solution colour shoals, and yellow flocculent deposit occurs, and filtering is being filtered
A small amount of dilute hydrochloric acid is added dropwise in liquid again, until not generating flocculent deposit, filters, when adding suitable hydrochloric acid solution in solution
The crystal for having sheet is precipitated, this crystal is also intermediate product 1.
The concentrated sulfuric acid is added in the round-bottomed flask of 250ml and stirs, is cooled to 0 °C, then cyclohexanone is added dropwise, then exists
It is vigorously stirred disposable addition compound 1.Later, it heats the mixture to 90 DEG C, keeps temperature the reaction was continued 1-1.5 h.
Stop reaction, reaction mixture is cooled to room temperature, under stiring pours into reaction mixture in the beaker for filling ice water, immediately
Perchloric acid is added, generates a large amount of red precipitates immediately.It filters, washs solid with ice water, red solid chemical combination is obtained after dry
Object 2.
Product is directly used in and reacts in next step without being further purified.Compound 2 and Fei Sheershi aldehyde are dissolved in acetic acid
In acid anhydride, it is heated to 50 DEG C.After mixture is kept temperature the reaction was continued 30 min, into reaction mixture addition water quenching go out instead
It answers, solvent, which is evaporated off, under decompression obtains crude product, and green solid compound 3 is obtained by column chromatography gradient separations.
By compound 3, NHS and DCC are dissolved in CH2Cl2（50 ml）In, reaction mixture is protected from light is stirred to react at room temperature
0.5 h depressurizes lower rotation solvent evaporated and obtains the solid chemical compound of green with pillar layer separation.Intermediate is re-dissolved
CH2Cl2In, 4- phenyl -3- thiosemicarbazides and triethylamine is added, 10 h of reaction are stirred at room temperature in reaction mixture under nitrogen protection.
Then the lower rotation solvent evaporated of decompression obtains the solid chemical compound 4 of yellow green with column chromatography gradient separations（I.e. near-infrared mercury from
Sub- fluorescence probe）.
Probe provided by the invention is the novel structure of the switch ring based on similar rhodamine, has the light of classical rhodamine
Spectral property, i.e. good light stability, higher molar extinction coefficient, higher fluorescence quantum yield and to the characteristics such as pH is insensitive,
And it absorbs and launch wavelength is near infrared region, be very suitable for determining for fluorescence microscopy detection Mercury in Biological Sample ion
Amount and qualitative analysis and fluorescence imaging.
Fluorescence probe provided by the invention can be used for quantifying for mercury ion in chemical example, biological sample or medical sample
Analysis and fluorescence imaging.
Probe provided by the invention, prominent advantage are：
Probe itself no UV absorption and fluorescent emission at long wavelength, when with Hg2+After effect, absorbed at 725 nm
It significantly increasing, while the fluorescence at 750 nm is significantly enhanced, fluorescence intensity is in a linear relationship in a certain range with concentration,
It can be used as and quantitatively detect Hg2+Foundation.
Since absorbing wavelength and launch wavelength are near infrared region, be conducive to the interference for avoiding biological sample background fluorescence.
This probe is Fluorescence Increasing type, high sensitivity.
Since the design of this probe is to be based on Hg2+Thiophilicity reaction, so high selectivity, other metal ions are nearly all
It is not responding to.
Probe itself be in very shallow ecru, when with Hg2+After response, open loop occurs for closed loop configuration, and conjugated degree increases, molten
Liquid color becomes green, and it is in significant change to respond front and back color, can be used for Visual retrieval mercury ion.
Description of the drawings
The synthetic route of Fig. 1 probes
The fluorescence spectrum of the mercury ion of Fig. 2 probes and various concentration response
The ultraviolet spectra of the mercury ion of Fig. 3 probes and various concentration response
Fig. 4 probes analyze the selectivity of mercury ion
Specific implementation mode
The following examples are only intended to that the present invention will be described in detail, do not limit the range of invention in any way.
The synthesis of embodiment probe：
Weigh KOH（5.612g, 100 mmol）In round-bottomed flask, adds distillation water dissolution, be cooled to room temperature, weigh sieve
Red bright B（2.2178 g, 5mmol）, it is added in KOH solution, is stirred and heated to 105 DEG C of 8 h of heated at constant temperature, it is cooling to add on a small quantity
Water dilutes and HCl solution neutralization reaction liquid is slowly added dropwise, and solution colour shoals, and yellow flocculent deposit occurs, filtering, in filtrate
A small amount of dilute hydrochloric acid is added dropwise again, until not generating flocculent deposit, filters, is had when adding suitable hydrochloric acid solution in solution
The crystal of sheet is precipitated, this crystal is also intermediate product 1.
The concentrated sulfuric acid (70 ml) is added in the round-bottomed flask of 250ml, stirring is opened in ice bath, is cooled to 0 °C, then by
It is added dropwise to cyclohexanone (6.6 ml, 63.7 mmol), is then added at one time compound 1 with vigorous stirring.Later, it will mix
Object is heated to 90 DEG C, keeps temperature the reaction was continued 1-1.5 h.Stop reaction, reaction mixture is cooled to room temperature, under stiring
Reaction mixture is poured into the beaker for filling 300 g ice water, 7 ml, 70% perchloric acid is added immediately, generated immediately a large amount of red
Precipitation.It filters, washs solid with the ice water of 100 ml, red solid chemical compound 2 is obtained after dry.
Product is directly used in and reacts in next step without being further purified.By compound 2（99.8 mg, 0.21 mmol）With
Fei Sheershi aldehyde（44.2 mg, 0.22 mmol）It is dissolved in 8 ml acetic anhydride, is heated to 50 DEG C.By mixture keep temperature after
After 30 min of continuous reaction, 8 ml water quenchings are added into reaction mixture and go out reaction, solvent is evaporated off under decompression and obtains crude product, passes through column
Chromatographic grade detaches to obtain green solid compound 3.
By compound 3（0.46 mmol, 302.1 mg）, NHS（0.63 mmol, 72.2 mg）And DCC（0.46 mmol,
93.5 mg）It is dissolved in CH2Cl2（50 ml）In, reaction mixture is protected from light at room temperature is stirred to react 0.5 h, depressurizes lower rotation and steams
Dry solvent obtains the solid chemical compound of green with pillar layer separation.By intermediate（0.21 mmol, 140.7 mg）It re-dissolves
CH2Cl2（25 ml）In, 4- phenyl -3- thiosemicarbazides is added（Or the 4- phenyl -3- thiosemicarbazides with substituent group）（1.46
Mmol, 244.2 mg）With 3 drop triethylamines, 10 h of reaction are stirred at room temperature in reaction mixture under nitrogen protection.Then decompression backspin
Turn solvent evaporated, with column chromatography gradient separations, obtains the solid chemical compound 4 of yellow green, as near-infrared mercury ion fluorescence probe.
The measurement of embodiment spectrum
0.03 mL probe mother liquors are added in test tube（5×10-4mol/L）, 0.27 mL ethyl alcohol and 2.7 mL pH value
It for 7.4 PBS buffer solutions, is uniformly mixed, the mercury ion solution of 0-6 μ L is then added, spectrum survey is carried out after reacting 1 min
It is fixed.A length of 680 nm of excitation light wave, exciting light slit width are 5.0 nm, and emission peak slit width is 5.0 nm.Fig. 2-3 can
Know, the high sensitivity to mercury ion of probe.
Various analytes are such as：Mercury chloride（HgCl2）, aluminium chloride（AlCl3·6H2O）, silver nitrate（AgNO3）, caddy
（CdCl2·1/2H2O）, copper chloride（CuCl2·2H2O）, cobalt chloride（CoCl2·6H2O）, frerrous chloride（FeCl2）, manganese sulfate
（MnSO4·H2O）, iron chloride（FeCl3）, zinc chloride（ZnCl2）, nickel chloride（NiCl2·6H2O）, palladium bichloride（PdCl2）, chlorination
Gold（AuCl3）, magnesium chloride（MgCl2）, plumbi nitras（Pb(NO3)2）, calcium chloride（CaCl2）, it is made into the aqueous solution of 5 mM, test is molten
Liquid is prepared：0.03 mL probe mother liquors, 0.27 mL ethyl alcohol and 2.7 mL pH value are added in test tube to buffer for 7.4 PBS
Solution is uniformly mixed, is then respectively adding various analyte solutions, after 1 minute, surveys their UV absorption and fluorescence spectrum.
A length of 680 nm of excitation light wave, exciting light slit width are 5.0 nm, and emission peak slit width is 5.0 nm.It is visited known to Fig. 4
There is very strong selectivity for mercury ion.
Claims (3)
1. a kind of near infrared fluorescent probe for mercury ion detecting, structure is as follows：
2. the preparation method of fluorescence probe described in claim 1, characterization step includes following steps：
(1) it is 1 to weigh molar ratio:Potassium hydroxide, is first dissolved in distilled water by 20 rhodamine B and potassium hydroxide, is cooled to room
Temperature, the rhodamine B first weighed is dissolved in wherein, is heated to 105 DEG C of heated at constant temperature 8h under stirring conditions, cooling to add less
Amount water dilutes and HCl solution neutralization reaction liquid is slowly added dropwise, and solution colour shoals, and yellow flocculent deposit occurs, filtering, in filtrate
In a small amount of dilute hydrochloric acid is added dropwise again, until not generating flocculent deposit, filter, the meeting when adding suitable hydrochloric acid solution in solution
There is the crystal of sheet to be precipitated, this crystal is also intermediate product 1；
(2) concentrated sulfuric acid is added in the round-bottomed flask of 250ml and stirs, is cooled to 0 DEG C, then cyclohexanone is added dropwise, then exists
It is vigorously stirred disposable addition compound 1；Later, it heats the mixture to 90 DEG C, keeps temperature the reaction was continued 1-1.5h；Stop
It only reacts, reaction mixture is cooled to room temperature, under stiring pour into reaction mixture in the beaker for filling ice water, add immediately
Enter perchloric acid, generates a large amount of red precipitates immediately；It filters, washs solid with ice water, red solid chemical compound is obtained after dry
2；
The structure of the compound 1 is as follows：
The structure of the compound 2 is as follows：
(3) product is directly used in and reacts in next step without being further purified；Compound 2 and Fei Sheershi aldehyde are dissolved in acetic acid
In acid anhydride, it is heated to 50 DEG C；After mixture is kept temperature the reaction was continued 30min, into reaction mixture addition water quenching go out reaction,
Solvent is evaporated off under decompression and obtains crude product, green solid compound 3 is obtained by column chromatography gradient separations；
The structure of the compound 3 is as follows：
(4) compound 3, NHS and DCC are dissolved in CH2Cl2In, reaction mixture is protected from light is stirred to react 0.5h at room temperature, subtracts
Pressure rotation solvent evaporated obtains the solid chemical compound of green with pillar layer separation；Intermediate is re-dissolved into CH2Cl2In, add
Enter 4- phenyl -3- thiosemicarbazides and triethylamine, reaction 10h is stirred at room temperature in reaction mixture under nitrogen protection；Then under decompression
Rotate solvent evaporated, with column chromatography gradient separations, obtain the solid chemical compound 4 of yellow green, the compound 4 be near-infrared mercury from
Sub- fluorescence probe.
3. quantitative analysis of the fluorescence probe described in claim 1 for mercury ion in chemical example, biological sample or medical sample
With the purposes of fluorescence imaging.
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| CN106432257B (en) * | 2016-09-14 | 2018-06-01 | 湘潭大学 | The preparation method and application of GSH water-soluble fluorescent probes based on rhodamine |
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| CN113956265B (en) * | 2021-11-17 | 2022-11-25 | 湖南大学 | Near-infrared molecular probe based on malondialdehyde response, preparation method and application thereof |
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