CN106699715A - Preparation method of water-soluble probe identifying Fe<3+> and application thereof - Google Patents
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Abstract
The invention discloses a preparation method of a water-soluble probe identifying Fe<3+>. The preparation method includes the steps that 1, 4-diethyl salicylaldehyde, diethyl malonate and pryridine are dissolved in ethyl alcohol, reflux and stirring are performed for 6-8 hours, and reduced pressure distillation is performed to remove the ethyl alcohol; then, glacial acetic acid and concentrated hydrochloric acid are added, reflux and stirring are performed for 6-8 hours, cooling is performed to reach room temperature, then ice water is added, a pH value is regulated to be 4-5, white precipitate is obtained, filtration is performed, washing is performed with water, and then methylbenzene recrystallization is performed to obtain 7-diethylamino coumarin; 2, under N2 protection, POCl3 is dropwise added to DMF, stirring is performed at the temperature of 20-50 DEG C for 30 minutes, then a 7-diethylamino coumarin-DMF solution is dropwise added to obtain a red suspension; stirring is performed at the temperature of 60 DEG C for 12-14 hours, then the suspension is poured into ice water to obtain a mixed solution; a 20% NaOH solution is added to the mixed solution to get a crude product; the crude products are recrystallized by anhydrous ethanol to obtain the probe.
Description
Technical field
The application is related to a kind of identification Fe3+Water-soluble probe synthesis, belong to technical field of organic synthesis；Again because originally
Application is related to the biologic applications of the water-soluble probe in cell, and organism metal content analysis and detection field are belonged to again.
Background technology
There is various metals, including alkaline-earth metal, alkali metal, transition metal and heavy metal element in nature, and this
A little metals are closely related with environment, biology, medical science and chemistry subject.In various trace elements, iron is most abundant and important
Transition metal, plays an important role in the life of organism.Iron is the indispensable element of human physiological activity, in blood
In there is the transport for participating in oxygen, protein delivery, synthetic DNA and RNA, and maintain the important of intracellular osmotic pressure and acid-base balance
Effect.Once iron ion lacks in body, various physiological systems will be triggered disorderly, increase disease.
But excessive iron is also in vivo harmful or even fatal.Research shows, the iron meeting of excess intake in organism
Trigger many diseases, such as heart and liver diseases, diabetes, or even cancer.Therefore, high selectivity and high sensitivity probe are to work
The detection of body cell has a very important role.
For now, the detection method of iron ion mainly has atomic absorption spectrophotometry (AAS), uv-spectrophotometric
Method, inductively coupled plasma atomic emission spectrum (ICP-AES), inductively coupled plasma mass spectrometry (ICP-MS) and electrification
Learn analytic approach.Although these methods have sensitivity very high, because they generally require the instrument of costliness, complicated place
Reason process and high cost, prolonged consumption, so being not the best method for detecting sample.
Fluorescence titrimetric method is received due to having the advantages that high selectivity, high sensitivity, simple to operate and easily operated
The extensive concern of researcher.Fluorescence probe is the molecule that the information of molecular recognition can be passed through fluorescence signal effective expression by a class,
It is widely used in the fluoroscopic examination of the analytes such as cation, anion and neutral molecule.Fluorescence probe have sensitivity it is high, choosing
Selecting property is high, detection limit is low, real-time the advantages of, in biological study, environmental contaminants and other harmful medical monitoring ions or
Small molecule recognition detection aspect is significant.
Common fluorescent chromophore has the compounds such as porphyrin fluorescence element, rhodamine, cumarin, naphthalimide, Anthraquinones.
In these fluorophors, the unique BaP pyranone structure of cumarin probe, it is high to make it have fluorescence quantum yield, Si Tuo
Gram this displacement is big, and the characteristic such as adjustable optical physics, photochemistry and photostability, be one kind in fluorescent molecular probe very well
Candidate's fluorescent ligand.
Therefore, in order to overcome the drawbacks described above in the presence of prior art, spy proposes this application.
The content of the invention
The first purpose of the application is, there is provided a kind of a kind of identification Fe of root3+Water-soluble probe preparation method.
To achieve these goals, the application is adopted the following technical scheme that：
One kind identification Fe3+Water-soluble probe preparation method, it is characterised in that the identification Fe3+Water-soluble probe
It is 7- lignocaine -3- formaldehyde cumarins, its preparation method is as follows：
(1) by the dissolving of 4- diethylaminos salicylide, diethyl malonate and piperidines in ethanol, it is warming up to 70-90 DEG C
6-8h is refluxed, vacuum distillation removes ethanol；Glacial acetic acid and concentrated hydrochloric acid are added afterwards, 6-8h is refluxed, and are cooled to room temperature,
Frozen water is subsequently adding, then adjusts pH value to 4-5, after stirring, obtain white precipitate, filtered, washed with water, dried, then through toluene
Recrystallization, obtains 7- lignocaine cumarins；Its reaction equation is：
2) by N2Under protection, POCl is added dropwise in DMF3, 30min is stirred at 20-50 DEG C, 7- lignocaines are then added dropwise
Cumarin-DMF solution, obtains red suspension；The red suspension is stirred into 12-14h at 50-60 DEG C, is subsequently poured into
In frozen water, mixed solution is obtained；By mass percent concentration for 20%NaOH solution is added in mixed solution, thick producing is obtained
Thing；The crude product is recrystallized through absolute ethyl alcohol, described 7- lignocaine -3- formaldehyde cumarins are obtained；Its reaction equation is：
。
Preferably, in step (1), the 4- diethylaminos salicylide, diethyl malonate and piperidines mol ratio are 1:
2:1。
Preferably, in step (1), the volume ratio of piperidines, ethanol, glacial acetic acid and concentrated hydrochloric acid is 1:30:20:20.
Preferably, in step (2), the concentration of the 7- lignocaines cumarin-DMF solution is 0.69mmol/L.
Preferably, in step (2), POCl3, DMF, 7- lignocaine cumarin-DMF solution volume ratio be 1:1:5.
Preferably, the one kind in ammoniacal liquor, NaOH solution, KOH solution is used during regulation pH value 4-5 in step (1)；It is preferred that
Use quality percent concentration is 40% NaOH solution.
Preferably, step (1) is specifically included：
By 1.93g4- lignocaine salicylides, 3.2g diethyl malonates and 1mL piperidines are added in 30mL ethanol, are returned
Ethanol is removed in stream stirring 6h, vacuum distillation；20mL glacial acetic acid and 20mL concentrated hydrochloric acids are added afterwards, 6h is refluxed, and are cooled to room temperature,
It is subsequently poured into 100mL frozen water；The NaOH solution for being added dropwise over 40% adjusts solution ph to 5, stirs 30min, obtains white heavy
Form sediment；Filtering, washes with water, dries, then obtain 7- lignocaine cumarins through re crystallization from toluene.
Preferably, step (2) is specifically included：
N2Under protection, 2mL POCl are added dropwise toward 2mL DMF3, 30min is stirred at 20-50 DEG C；Then by 7- diethylaminos
Butylcoumariii-DMF solution is added dropwise over, and obtains red suspension；Red suspension is stirred into 12h at 60 DEG C, is subsequently poured into
Mixed solution is obtained in 100mL frozen water；20%NaOH solution is added in mixed solution and obtains crude product；By the crude product
Through absolute ethyl alcohol filtering, washing, dry and crystallization, obtain described 7- lignocaine -3- formaldehyde cumarins.
The another object of the application is, there is provided one kind identification Fe3+Water-soluble probe application.
To achieve these goals, the application is adopted the following technical scheme that：
One kind identification Fe3+Water-soluble probe application, it is characterised in that by the probe application in Fe3+In detection.
Preferably, by the Fe of the probe application to lympha tumour cell3+In detection.
In the application, concentrated hydrochloric acid refers to the hydrochloric acid that mass percent concentration is 37%.
In the application, the identification Fe3+Water-soluble probe be 7- lignocaine -3- formaldehyde cumarins, also referred to as probe L.
The beneficial effect of the application is：It is water-soluble glimmering in 5 to 6.5 gentle pH value ranges this application provides one
Light probe, to Fe in the interference of other metal ions3+Inspection there is quick response and high selectivity.Provided herein
Preparation method is workable, prepared water-soluble fluorescent probe high income, and preparation process time is shortened, and reduces
Production preparation cost.
Specific embodiment
With reference to embodiment in detail the application is described in detail, but the application is not limited to these embodiments.
Unless otherwise instructed, the raw material in embodiments herein is bought by commercial sources.
Embodiment 1
The present embodiment is related to the preparation of water-soluble probe：
(1) synthesis (1) of 7- lignocaines cumarin
By (1.93g, 10mmol) 4- lignocaine salicylides, (3.2g, 20mmol) diethyl malonate and 1mL piperidines add
Enter in 30mL ethanol, 6h is refluxed at 90 DEG C, solvent is removed in vacuum distillation.Backward mixture in add 20mL glacial acetic acid and
20mL concentrated hydrochloric acids, are refluxed 6h, are cooled to room temperature, are subsequently poured into 100mL frozen water.It is added dropwise over 40% NaOH solution regulation
Solution ph stirs 30min to 5, obtains white precipitate.Filtering, washes with water, dries, then obtain 7- diethyls through re crystallization from toluene
The synthesis (1.74g, 8mmol) of aminocoumarin, yield is 80.1%.
(2) synthesis (L) of 7- lignocaines -3- formaldehyde cumarins
N2Under protection, 2mL POCl are added dropwise toward the 2mL DMF of new distillation3, stirring 30min obtains red molten at 20-50 DEG C
Liquid.Then 1 (1.50g, 6.91mmol are dissolved in 10mL DMF) is added dropwise in above-mentioned solution, produces red suspension
Liquid.Mixture is stirred into 12h at 60 DEG C, is subsequently poured into 100mL frozen water.20%NaOH solution is added in mixture and is obtained
Obtain and largely precipitate.Crude product is filtered through absolute ethyl alcohol, washes, dries and crystallized, and obtains 7- lignocaine -3- formaldehyde cumarins
Synthesis (1.20g, 4.89mmol), yield is 70.8%.1H NMR(400MHz,CDCl3) δ=12.35 (s, 1H), 8.62 (s,
1H), 7.44 (d, J=9.0,1H), 6.69 (d, J=2.2,1H), 6.51 (s, 1H), 3.49 (q, J=7.0,4H), 1.26 (t, J
=7.1,6H)13C NMR(101MHz,CDCl3)δ(ppm):165.55,164.46,158.04,153.80,150.23,
131.96,110.96,108.53,105.46,96.81,77.38,77.06,76.74,45.36,12.39；ESI-MS m/z([M
+H]+):Calcd 245；found:244.5.
Embodiment 2
The present embodiment is related to recognize Fe3+Water-soluble probe application
First, preliminary test
Respectively with ethanol, acetonitrile, methyl alcohol, tetrahydrofuran, dichloromethane, water etc. prepares 5,10,20 μM for solvent respectively
Probe observes its fluorescence under 365nm uviol lamps, is then separately added into the Pb of 10 equivalents2+,Ni2+,Mg2+,Cd2+,Co2+,Cu2+,
Ni2+,Fe2+,Zn2+,K+,Li+,Na+,Al3+,Fe3+,Cr3+Deng metal ion, find only have Fe3+It is quenched.Comprehensive consideration, with
Distilled water is prepared 10 μM of probes and is tested as solvent.
2nd, spectrum test
In order to explore the metal selective of fluorescence probe, its fluorescence spectrum is obtained by adding different metal ions, its
Include Pb2+,Ni2+,Mg2+,Cd2+,Co2+,Cu2+,Ni2+,Fe2+,Zn2+,K+,Li+,Na+,Al3+,Fe3+,Cr3+Deng during experiment
To adding 10 equivalents of metal ion in 10 μM of probes.
We can clearly be observed that in 200nm-350nm wave-length coverages the intensity that iron ion absorbs ultraviolet is bright
Aobvious is higher than other ions or blank probe.Additionally, experiment finds, Cu2+And Cr3+Addition can cause maximum absorption band occur it is red
Move phenomenon.
Impact analysis by different metal ions to the fluorescence spectrum of fluorescence probe, it can be found that Fe3+Addition lead
Fluorescence probe quenching is caused, and removes copper ion, chromium ion slightly influences on the fluorescence intensity of probe, and other metal ions are to probe
Fluorescence intensity has little to no effect.Thus illustrate, probe is to Fe3+With good selectivity.
3rd, difference Fe3+Influence of the concentration to fluorescence probe intensity
In experimentation, in 0-10 equivalent weight ranges, different Fe3+Concentration has an impact to the fluorescence intensity of probe.With Fe3 +The increase of concentration, fluorescence intensity is also accordingly reduced.
The test limit of probe can be calculated according to fluorescence titration.Probe L is calculated by Stern Wallmate equation
Detection be limited to 0.025 μM.
Test limit=3 σ ÷ m=2.46 × 10-8Mol=0.025 μM
Wherein σ is the standard deviation of blank solution, and m is the slope of calibration curve, and the detection line is more most than what is reported before
The test limit of number probe will be much lower, it can be seen that probe L has sensitivity higher.
4th, Job curves are drawn
Job curves are drawn by experimental study, it is known that, when the content of probe L reaches 50%, (1-XL) maximum is reached,
This shows probe L and Fe3+Form 1:1 compound.
5th, the influence of pH
In order to study influence of the pH value to the fluorescence intensity of probe, the measuring fluorescence of the scope internal probes of pH 2~9
The change of intensity, adds Fe3+Probe its fluorescence intensity have almost no change, and do not add Fe3+Probe its fluorescence intensity exist
Sharply increased in the range of pH 4~5, when pH is more than 6, fluorescence intensity starts to reduce, draw the optimum scopes of probe L for 5~
6.5.After measured, the pH of distilled water used by laboratory is 5.8, it is possible to be directly used in experiment without the corresponding of buffer solution
Regulation.
6th, it is restorative to probe into
The invertibity of probe is a key factor in practical application.In order to explore the invertibity of probe, L- is used in experiment
Fe3+With H2PO4 -Carry out fluorescence titration experiment.As expected, as the Fe of 10 equivalents3+When being added to probe L, Ke Yiguan
An obvious fluorescent quenching is observed, as the H for adding 30 equivalents2PO4 -To in mixed solution, obvious fluorescent quenching before recovers
To probe L fluorescence intensities in itself.Therefore can draw, probe L is to Fe3+Detection be reversible.
7th, cell experiment
With the understanding to fluorescence probe Response Mechanism, and according to its obvious fluorescent characteristic, inquire into herein in live body
Fe is recognized in cell3+Possibility.At 37 DEG C, human lymphocyte tumour cell Ramos is incubated with probe L (10 μm of ol)
35min, and rinsed to remove the compound L of residual with PBS.Then appropriate Fe is added to Ramos cells3+(0,5,
10 equivalents) 0.5h is incubated afterwards, after being rinsed with PBS, the confocal fluorescent microscope imaging of cell.As a result, with not plus Fe3+
The cell of culture has very strong bright fluorescence, and those add Fe3+Cell show obvious fluorescent quenching, it is not bright
Aobvious fluorescence is found, and illustrates that sensor L is one and can be used for Fe in biosystem3+The fluorescence probe of detection.Moreover,
Carry out incubated cell 48h with the probe L (10 μm of ol, 20 μm of ol, 50 μm of ol) of various concentrations, as a result find most of Ramos cells
Maintain a good state, this shows that probe L has that toxicity is low, good biocompatibility characteristic.
The above, is only several embodiments of the application, any type of limitation is not done to the application, although this Shen
Please disclosed as above with preferred embodiment, but and be not used to limit the application, any those skilled in the art are not taking off
In the range of technical scheme, make a little variation using the technology contents of the disclosure above or modification is equal to
Effect case study on implementation, belongs in the range of technical scheme.
Claims (10)
1. it is a kind of to recognize Fe3+Water-soluble probe preparation method, it is characterised in that the identification Fe3+Water-soluble probe be
7- lignocaine -3- formaldehyde cumarins, its preparation method is as follows：
(1) by the dissolving of 4- diethylaminos salicylide, diethyl malonate and piperidines in ethanol, 6-8h is refluxed, is depressurized
Ethanol is distilled off；Glacial acetic acid and concentrated hydrochloric acid are added afterwards, 6-8h is refluxed, room temperature is cooled to, and are subsequently adding frozen water, then adjust
Section pH value after stirring, obtains white precipitate to 4-5, filters, and washes with water, dries, then through re crystallization from toluene, obtain 7- diethyls
Aminocoumarin；Its reaction equation is：
(2) by N2Under protection, POCl is added dropwise in DMF3, 30min is stirred at 20-50 DEG C, 7- lignocaine tonka-beans are then added dropwise
Element-DMF solution, obtains red suspension；The red suspension is stirred into 12-14h at 50-60 DEG C, frozen water is subsequently poured into
In, obtain mixed solution；By mass percent concentration for 10-25%NaOH solution is added in mixed solution, crude product is obtained；
The crude product is recrystallized through absolute ethyl alcohol, described 7- lignocaine -3- formaldehyde cumarins are obtained；Its reaction equation is：
2. preparation method according to claim 1, it is characterised in that in step (1), by 4- diethylaminos salicylide,
Diethyl malonate and piperidines dissolving in ethanol, are warming up to 70-90 DEG C and are refluxed 6-8h.
3. preparation method according to claim 1, it is characterised in that in step (1), the 4- diethylaminos bigcatkin willow
Aldehyde, diethyl malonate and piperidines mol ratio are 1:2:1.
4. preparation method according to claim 1 and 2, it is characterised in that in step (1), piperidines, ethanol, glacial acetic acid and
The volume ratio of concentrated hydrochloric acid is 1:30:20:20.
5. preparation method according to claim 1, it is characterised in that in step (2), the 7- lignocaines cumarin-
The concentration of DMF solution is 0.69mmol/L.
6. preparation method according to claim 1 or 5, it is characterised in that in step (2), POCl3, DMF, 7- lignocaine
The volume ratio of cumarin-DMF solution is 1:1:5.
7. preparation method according to claim 1, it is characterised in that in step (1) during regulation pH value 4-5, using ammoniacal liquor,
One kind in NaOH solution, KOH solution；Preferably use the NaOH solution that mass percent concentration is 40%.
8. preparation method according to claim 1, it is characterised in that step (1) is specifically included：
By 1.93g4- lignocaine salicylides, 3.2g diethyl malonates and 1mL piperidines are added in 30mL ethanol, and backflow is stirred
6h is mixed, ethanol is removed in vacuum distillation；20mL glacial acetic acid and 20mL concentrated hydrochloric acids are added afterwards, 6h is refluxed, and are cooled to room temperature, then
Pour into 100mL frozen water；The NaOH solution for being added dropwise over 40% adjusts solution ph to 5, stirs 30min, obtains white precipitate；Cross
Filter, washes with water, dries, then obtain 7- lignocaine cumarins through re crystallization from toluene.
9. the preparation method according to claim 1 or 8, it is characterised in that step (2) is specifically included：
N2Under protection, 2mL POCl are added dropwise toward 2mL DMF3, 30min is stirred at 20-50 DEG C；Then by 7- diethylamino basic notes
Legumin-DMF solution is added dropwise over, and obtains red suspension；Red suspension is stirred into 12h at 60 DEG C, 100mL is subsequently poured into
Mixed solution is obtained in frozen water；20%NaOH solution is added in mixed solution and obtains crude product；By the crude product through nothing
Water-ethanol filtering, washing, dry and crystallization, obtain described 7- lignocaine -3- formaldehyde cumarins.
10. the identification Fe in a kind of claim 1-9 prepared by any one3+Water-soluble probe application, it is characterised in that will
The probe application is in Fe3+In detection, it is preferable that by the Fe of the probe application to lympha tumour cell3+In detection.
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| CN108129435A (en) * | 2018-02-06 | 2018-06-08 | 济南大学 | A kind of Novel iron ion fluorescence probe and preparation method thereof |
| CN108912084A (en) * | 2018-06-06 | 2018-11-30 | 济南大学 | A kind of carbon monoxide fluorescence probe and its preparation method and application |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108129435A (en) * | 2018-02-06 | 2018-06-08 | 济南大学 | A kind of Novel iron ion fluorescence probe and preparation method thereof |
| CN108912084A (en) * | 2018-06-06 | 2018-11-30 | 济南大学 | A kind of carbon monoxide fluorescence probe and its preparation method and application |
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