CN108640925A - A kind of water solubility Hg2+Fluorescence probe and preparation method thereof - Google Patents
A kind of water solubility Hg2+Fluorescence probe and preparation method thereof Download PDFInfo
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- CN108640925A CN108640925A CN201810388448.3A CN201810388448A CN108640925A CN 108640925 A CN108640925 A CN 108640925A CN 201810388448 A CN201810388448 A CN 201810388448A CN 108640925 A CN108640925 A CN 108640925A
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Abstract
The invention belongs to field of biological detection, and in particular to a kind of water solubility Hg2+Fluorescence probe and preparation method thereof, its structural formula is as shown in the figure, rhodamine fluorogen including high sensitivity, good light stability, fluorescence quantum yield height, wavelength length, the glucose of good water solubility, a certain amount of rhodamine lactams obtains water-soluble fluorescent probe with glucose generation condensation reaction under certain condition, this building-up process raw material is simple and easy to get, reaction condition is mild, easy to operate, while gained water solubility Hg2+Fluorescence probe can quickly detect substance in biological cell under water environment.
Description
Technical field
The invention belongs to field of biological detection, and in particular to a kind of water solubility Hg2+Fluorescence probe and preparation method thereof.
Background technology
Mercury is a kind of typical heavy metal ion, has extremely strong toxicity, can cause the permanent damage of biological nervous system
Wound.Mercury in environment is oxidized to water-soluble dimercurion in air, and mercury ion once enters water environment, will be thin
Mushroom microorganism conversion be organic methyl mercury, and in vivo (such as fish) Rapid Accumulation hence into food chain.Methyl
Mercury destroys the nervous system of people, causes brain damage, cognition and dyskinesias etc., world-shaking " minamata disease " is exactly organic mercury
One type of poisoning.Therefore quick, simple, the sensitive detection method of mercury ion can be detected in aqueous environment by finding,
It is of great significance to the detection of heavy metal in water body environment.
The main method of detection mercury element has at present：High performance liquid chromatography, mass spectrography, atomic absorption spectrography (AAS), wait from
Daughter incudes spectroscopic methodology, atomic emission spectrometry, electrochemical sensing, dithizone colorimetric method etc., but these methods are more expensive,
It is strongly professional, it takes and complicated for operation.Fluorescence method can realize that efficient, " bore hole " is examined using suitable probe to object
It surveys, it is lossless, while qualitative and quantitative analysis is carried out to object.There is the fluorogen quilt of different excitations and launch wavelength at present
Signal recipient as chemical detector, such as cumarin, pyrene, 1,8- aphthalimide, rhodamine, flower cyanines class, BODIPY
Class etc..The fluorescence probe wherein built as fluorophor using rhodamine due to its excellent fluorescence property and good is modified
Property, one of fluorescence probe of greatest concern is had become at present.
Rhodamine is a kind of fluorescent dye for belonging to xanthene class, and structure such as figure A is oxygen anthracene heterocycle structure, and B is rhodamine
Dyestuff.Since it is with superior Photophysics, such as high molar extinction coefficient, good light stability, fluorescence quantum yield is high, hair
The advantages that ejected wave length is long so that it is widely used.Conjunction was reported for the first time from Noelting and Dziewonsky in 1905
At rhodamine compound (Noelting, E.；Dziewonski,K.To the knowledge of the Rhodamine
[J] .Ber.Dtsch Chem.Ges., 1905,38,3516-3527.), hereafter rhodamine compound is just widely used in respectively
Field.
The first Cu based on rhodamine lactams loop coil off-on mechanism is reported from Czarnik in 1997 etc.2+Probe
(Dujols Virginie Ford,Francis Czarnik,Anthony W.A Long-Wavelength Fluorescent
Chemodosimeter Selective for Cu(II)Ion in Water[J].Journal of the American
Chemical Society,1997,119(31):After 7386-7387.), design and the synthesis of Rhodamine fluorescent probe just cause
The attention of numerous chemists.Rhodamine lactams or Inner acyl ester derivants are unstressed configurations and colourless, and when loop coil is opened
Strong fluorescence and red will be generated.From this rhodamine fluorescence probe according to off-on principles in cell biology, environment
Chemistry, pharmacology, the fields such as analytical chemistry are widely used.Current most of rhodamine mercury ion fluorescence probes are set
Meter is to be based on rhodamine lactams loop coil off-on mechanism, but it is usually poor in the presence of water solubility, i.e., biocompatibility is poor,
It is unfavorable for being applied to imaging biological cells.
As patent No. CN201510892168.2 disclose it is a kind of based on the Hg containing double carbon-sulfur bond structure rhodamines2+Fluorescence is visited
Needle and the preparation method and application thereof.Probe is had studied by ultraviolet-visible spectrophotometer and sepectrophotofluorometer to exist
CH3OH-H2In O solution with the evident characteristics of metal ion.The result shows that：Probe is to Hg2+With efficiently single-minded selectivity, tool
There are stronger anti-metal cation and anion interference performance, and the bore hole knowledge realized to mercury ion can be changed by solution colour
Not, but the probe application CH3The aqueous solution of OH is detected analysis, and methanol has toxicity to biological cell, therefore it is given birth to
Object compatibility is poor.
Patent No. CN201310409868.2 discloses a kind of Novel rhodamine fluorescence probe, and the probe is with rhodamine
B (RhB) is raw material, and rhodamine lactams is prepared with diamine modification RhB, so with maleic anhydride (MAH) and adamantane
Amine reacts, and rhodamine fluorescence probe is prepared, contains the multiple amido work(that can be had an effect with metal ion in structure
Energy is rolled into a ball and can be with Hg2+The carbon-carbon double bond of effect.Helical form rhodamine lactam compound with heavy metal particles after being combined, interior acyl
The protonation of amine nitrogen atom will cause nitrogen-atoms charge density to reduce, and to cause the cracking of spiral center C-N keys, generate fluorescence
Variation and color change, but gained probe all has preferable recognition capability, detection to mercury ion in aqueous solution and iron ion
When easily cause interference, do not have specificity.
Therefore, in order to overcome standby instrument more expensive, strongly professional, time-consuming and complicated for operation the problems such as and fluorescence probe
Biocompatibility is poor, specificity is poor, sensitivity is low, easily by other metal ion disturbances the problems such as, design synthesis is a kind of water-soluble
Property Hg2+Fluorescence probe has great importance.
Invention content
In order to solve fluorescence probe there are poor selectivity, biocompatibility is poor, specificity is poor the problems such as, the present invention provide
A kind of water solubility Hg2+Fluorescence probe and preparation method thereof.
A kind of water solubility Hg2+Fluorescence probe, reaction equation are as shown in Figure 1.
Further, water-soluble Hg2+Group R1, R2, R3, R4 H or group R1 and R2 are in fluorescence probe structural formula
CH3, group R3 and R4 are H or group R1 and R2 are C2H5, group R3 and R4 are H or group R1 is C2H5, group R2 and R3 be
H, group R4 is CH3。
Further, water-soluble Hg2+N is 0,2,3 in fluorescence probe structural formula ... n.
Further, above-mentioned water solubility Hg is prepared2+Fluorescence probe, synthetic method are as follows：
Step 1：The bright lactam intermediate of synthesizing rhodamine, weighs 2-3g rhodamines, is dissolved in organic solvent, connect
It and thiamines class compound solution is added dropwise in rhodamine solution, be heated to 50-60 DEG C, after back flow reaction 2-7h
To rhodamine lactam intermediate；
Step 2：Synthesizing water-solubility Hg2+Fluorescence probe weighs sulphamide in 1-2mmol rhodamines, is dissolved in organic molten
Glucose solution is then added dropwise in rhodamine in sulfonyl amine aqueous solution by agent, is heated to 60-85 DEG C, is flowed back, thin-layer chromatography
It tracks to reaction to terminate, water-soluble fluorescent probe is obtained by column chromatographic isolation and purification after reaction.
Further, organic solvent is methanol, ethyl alcohol, acetonitrile.
Further, the molar ratio of rhodamine lactams and glucose is 1:1.0-2.0.
Further, the reaction temperature of synthesising target compound is 80 DEG C.
Further, column chromatographic isolation and purification solvent is ethyl alcohol and dichloromethane, volume ratio 1：150-200.
Have preferable water-soluble the present invention is based on rhodamine and glucose, designs a kind of the water-soluble of special construction
Property Hg2+Fluorescence probe.A certain amount of rhodamine lactams occurs condensation reaction with glucose and obtains water solubility under certain condition
Hg2+Fluorescence probe, building-up process raw material is simple and easy to get, reaction condition is mild, easy to operate, while gained water solubility Hg2+Fluorescence
Probe can quickly detect substance in biological cell under water environment.
Description of the drawings
Fig. 1 is water solubility Hg2+The structural formula of fluorescence probe；
Fig. 2 is water solubility Hg2+Fluorescence emission spectrogram of compound of the fluorescence probe to metalloform-selective；
Fig. 3 is water solubility Hg2+Ultraviolet-visible absorption spectroscopy figure of the fluorescence probe in different aqueous solvents；
Fig. 4 is water solubility Hg2+Fluorescence emission spectrogram of compound of the fluorescence probe to different ion concentration of mercury；
Fig. 5 is water solubility Hg2+The fluorescence range of linearity of fluorescence probe.
Specific implementation mode
As shown in Figure 1, a kind of water solubility Hg2+Fluorescence probe, specific embodiment are as follows：
Embodiment one
A kind of rhodamine 110Hg2+Fluorescence probe, group R1, R2, R3, R4 H, the rhodamine 110Hg that n is 22+Fluorescence is visited
Needle.
A kind of rhodamine 110Hg2++The synthetic method of fluorescence probe prepares above-mentioned rhodamine 110Hg2++Fluorescence probe,
Its synthetic method is as follows：
Sulphamide intermediate in synthesizing rhodamine bright 110：110 dyestuff of 2g rhodamines is weighed, is dissolved in alcohol solvent, then
Second thiamines solution is added dropwise in 110 solution of rhodamine, is heated to 50 DEG C, back flow reaction 6h, in reaction process solution by
Purplish red becomes orange-yellow, obtains sulphamide intermediate in rhodamine 110；
The bright 110Hg of synthesizing rhodamine2+Fluorescence probe：Sulphamide in 1mmol rhodamines 110 is taken, alcohol solvent is dissolved in, is connect
It and 1.2mmol glucose solutions is added dropwise in rhodamine 110 in sulfonyl amine aqueous solution, be heated to 80 DEG C, flow back, thin layer
Analysis tracks to reaction and terminates, and obtains rhodamine 110Hg by column chromatographic isolation and purification after reaction2+Fluorescence probe, column chromatography
It is 1 that etoh solvent, which is isolated and purified, with methylene chloride volume ratio:200.
Embodiment two
A kind of tetramethylrhodamine Hg2+Fluorescence probe, group R1 and R2 are CH3, group R3 and R4 be H, n be 2 tetramethyl
Base rhodamine Hg2+Fluorescence probe.
A kind of synthetic method of water solubility tetramethylrhodamine fluorescence probe, prepares above-mentioned tetramethylrhodamine Hg2+It is glimmering
Light probe, synthetic method are as follows：
Synthesize sulphamide intermediate in tetramethylrhodamine：2g tetramethylrhodaminedye dyes are weighed, it is molten to be dissolved in ethyl alcohol
Second thiamines solution is then added dropwise in tetramethylrhodamine solution by agent, is heated to 50 DEG C, and back flow reaction 6h reacted
Solution becomes orange-yellow by purplish red in journey, obtains sulphamide intermediate in tetramethylrhodamine；
Synthesize tetramethylrhodamine Hg2+Fluorescence probe：Sulphamide in 1mmol tetramethylrhodamines is taken, ethyl alcohol is dissolved in
1.2mmol glucose solutions are then added dropwise in tetramethylrhodamine in sulfonyl amine aqueous solution, are heated to 80 DEG C by solvent,
Reflux, thin-layer chromatography, which tracks to reaction, to be terminated, and obtains tetramethylrhodamine Hg by column chromatographic isolation and purification after reaction2+It is glimmering
Light probe, column chromatographic isolation and purification etoh solvent are 1 with methylene chloride volume ratio:200.
Embodiment three
A kind of rhodamine B Hg2+Fluorescence probe, group R1 and R2 are C2H5, group R3 and R4 be H, n be 2 water-soluble sieve
Red bright B fluorescence probes.
A kind of water-soluble rhodamine B Hg2+The synthetic method of fluorescence probe prepares above-mentioned rhodamine B fluorescence probe,
Synthetic method is as follows：
Sulphamide intermediate in the bright B of synthesizing rhodamine：2g rhdamine Bs are weighed, alcohol solvent is dissolved in, then by second
Thiamines solution is added dropwise in rhodamine B solution, is heated to 50 DEG C, back flow reaction 6h, and solution is by purplish red in reaction process
Become orange-yellow, obtains sulphamide intermediate in rhodamine B；
The bright B fluorescence probes of synthesizing rhodamine：Sulphamide in 1mmol rhodamine Bs is taken, alcohol solvent is dissolved in, then will
1.2mmol glucose solutions are added dropwise in rhodamine B lactams solution, are heated to 80 DEG C, reflux, thin-layer chromatography tracks to
Reaction terminates, and obtains rhodamine B Hg by column chromatographic isolation and purification after reaction2+Fluorescence probe, column chromatographic isolation and purification are molten
Agent ethyl alcohol is 1 with methylene chloride volume ratio:200.
Example IV
A kind of water-soluble rhodamine 6G Hg2+Fluorescence probe, group R1 are C2H5, group R2 and R3 be H, group R4 is CH3,
The water-soluble rhodamine 6G Hg that n is 22+Fluorescence probe.
A kind of water-soluble rhodamine 6G Hg2+The synthetic method of fluorescence probe prepares above-mentioned rhodamine 6G Hg2+Fluorescence
Probe, synthetic method are as follows：
Sulphamide intermediate in the bright 6G of synthesizing rhodamine：2g rhodamine 6G dyestuffs are weighed, alcohol solvent is dissolved in, then will
Second thiamines solution is added dropwise in rhodamine 6G solution, is heated to 50 DEG C, back flow reaction 6h, and solution is by purplish red in reaction process
Discoloration obtains sulphamide intermediate in rhodamine 6G at orange-yellow；
The bright 6G Hg of synthesizing rhodamine2+Fluorescence probe：Sulphamide in 1mmol rhodamine 6Gs is taken, alcohol solvent is dissolved in, is connect
It and 1.2mmol glucose solutions is added dropwise in rhodamine 6G lactams solution, be heated to 80 DEG C, flow back, thin-layer chromatography
It tracks to reaction to terminate, rhodamine 6G Hg is obtained by column chromatographic isolation and purification after reaction2+Fluorescence probe, column chromatography point
It is 1 from purification solvent ethyl alcohol and methylene chloride volume ratio:200.
Embodiment five
As shown in Fig. 2, being separately added into the K of 5 times of equivalents into probe solution+、Na+、Ca2+、Mg2+、Zn2+、Cd2+、Mn2+、
Fe3+、Cu2+、Pb2+When ion, probe solution is colourless, and fluorescence intensity does not also change at 580nm, it is seen that probe is protected
Original structure is held, can be stable in the presence of in these solution systems.When Hg is added in probe solution2+Afterwards, solution is by no discoloration
For red, fluorescence intensity is remarkably reinforced at 580nm, a strong emission peak occurs.This is because Hg2+With probe reaction so that
The loop coil of rhodamine is opened, and fluorescent emission is generated.
Embodiment six
As shown in figure 3, probe is respectively in the CH of ten various different moisture contents3Ultra-violet absorption spectrum in CN dicyandiamide solutions,
Dicyandiamide solution is CH3CN:H2O(v:V)=1:0,1:1,1:2,1:3,1:4,1:5,1:6,1:7,1:8,1:9,1:10.It can by figure
Know, in this ten kinds of systems, there is the ultraviolet absorption peak of aromatic rings between 200-350 in probe, without absorption peak between 500-600,
Solution is colourless, illustrates that probe can be stabilized in these solvents, is not decomposed or the variations such as open loop.As solvent contains
The raising of water, decreased solubility of the probe in these solvents, experiment find probe CH3CN:H2O(v:V)=1:It is just opened when 9
There is turbid solution in beginning.
Embodiment seven
As shown in Figure 4 and Figure 5,5 μM of probe solutions for preparing 16 parts of 5mL, are separately added into 0-80 μM of Hg2+, carry out fluorescence
Detect (λEx=520nm), fluorescence intensity in each system is calculated, by analyzing fluorescence intensity and Hg at 580nm2+The pass of concentration
System, assessment probe is to Hg2+Response performance.Fig. 4 shows with Hg2+The fluorescence intensity of the increase of concentration, solution gradually increases,
Until maximum emission intensity is not changing.Fig. 5 shows probe in Hg2+Concentration 4 × 10-6Mol/L~6 × 10-5Within the scope of mol/L
It is in a linear relationship, linearly dependent coefficient R2=0.9614, and probe is to Hg2+Detection be limited to 3.89 × 10-7mol/L。
The preferred embodiment of the present invention is above are only, but the design concept of the present invention is not limited thereto, all profits
The change for carrying out unsubstantiality to the present invention with this design, should all belong to the behavior for invading the scope of the present invention.
Claims (8)
1. a kind of water solubility Hg2+Fluorescence probe, it is characterised in that：Water-soluble Hg2+Fluorescence probe structural formula is as follows：
2. water solubility Hg according to claim 12+Fluorescence probe, it is characterised in that：The water solubility Hg2+Fluorescence probe structure
Group R1, R2, R3, R4 H or group R1 and R2 are CH in formula3, group R3 and R4 are H or group R1 and R2 are C2H5, group
R3 and R4 is H or group R1 is C2H5, group R2 and R3 be H, group R4 is CH3。
3. water solubility Hg according to claim 12+Fluorescence probe, it is characterised in that：The water solubility Cu2+Fluorescence probe structure
N is 0,2,3 in formula ... n.
4. a kind of water solubility Hg2+The synthetic method of fluorescence probe, which is characterized in that prepare water solubility Hg described in claim 12+
Fluorescence probe, synthetic method are as follows：
Step 1：The bright interior sulphamide intermediate of synthesizing rhodamine, weighs 2-3g rhodamines, is dissolved in organic solvent, then
Thiamines class compound solution is added dropwise in rhodamine solution, 50-60 DEG C is heated to, is obtained after back flow reaction 2-7h
Sulphamide intermediate in rhodamine；
Step 2：Synthesizing water-solubility Hg2+Fluorescence probe weighs sulphamide in 1-2mmol rhodamines, is dissolved in organic solvent,
Then glucose solution is added dropwise in rhodamine in sulfonyl amine aqueous solution, is heated to 60-85 DEG C, reflux, thin-layer chromatography with
Track to reaction terminates, and obtains water-soluble fluorescent probe by column chromatographic isolation and purification after reaction.
5. water solubility Hg according to claim 42+The synthetic method of fluorescence probe, it is characterised in that：The organic solvent is
Methanol, ethyl alcohol, acetonitrile.
6. water solubility Hg according to claim 42+The synthetic method of fluorescence probe, it is characterised in that：Acyl in the rhodamine
The molar ratio of amine and glucose is 1:1.0-2.0.
7. water solubility Hg according to claim 42+The synthetic method of fluorescence probe, it is characterised in that：The synthesis targeted
The reaction temperature for closing object is 80 DEG C.
8. water solubility Hg according to claim 42+The synthetic method of fluorescence probe, it is characterised in that：The column chromatography for separation
The solvent of purifying is ethyl alcohol and dichloromethane, and the volume ratio of the ethyl alcohol and dichloromethane is 1:150-200.
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| CN105859734A (en) * | 2016-05-19 | 2016-08-17 | 苏州大学 | Compound based on Rhodamine B and thiobisethylamine as well as preparation method and application thereof |
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