CN108484620A - A kind of water-soluble rhodamine base Cu2+Fluorescence probe and its synthetic method - Google Patents
A kind of water-soluble rhodamine base Cu2+Fluorescence probe and its synthetic method Download PDFInfo
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- CN108484620A CN108484620A CN201810388438.XA CN201810388438A CN108484620A CN 108484620 A CN108484620 A CN 108484620A CN 201810388438 A CN201810388438 A CN 201810388438A CN 108484620 A CN108484620 A CN 108484620A
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Abstract
The invention belongs to diagnose biological cell field, and in particular to a kind of water-soluble rhodamine base Cu2+Fluorescence probe and its synthetic method, 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 rhodamine base 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-soluble rhodamine base Cu2+Fluorescence probe can quickly detect substance in biological cell under water environment.
Description
Technical field
The invention belongs to diagnose biological cell field, and in particular to a kind of water-soluble rhodamine base Cu2+Fluorescence probe and its
Synthetic method.
Background technology
For most of organisms, copper is a kind of micro nutritious substance, in the content of human body transition metal
In occupy third position.Copper ion plays an important role various metalloenzyme as a kind of catalytic cofactor, such as superoxides
Mutase, cytochrome c oxidase and TYR enzyme.However when the content of copper ion is more than a certain amount, it will performance copper
Poisoning, leads to neurodegenerative disease (such as senile dementia and Wilson's disease), it may be due to copper ion to generate this illness
The production of active oxygen is participated in.What therefore exploitation was new there is highly selective, highly sensitive, good water solubility copper ion fluorescence to visit
Needle set is significant.
The main method of detection copper has at present：High performance liquid chromatography, mass spectrography, atomic absorption spectrography (AAS), etc. from
Daughter incudes spectroscopic methodology, atomic emission spectrometry, electrochemical sensing, colorimetric method etc., but these methods are more expensive, professional
By force, it takes and complicated for operation.
It is the novel analytical technology of representative in life using fluorescence probe recently as the continuous development of life science,
Environment, medicine etc. are widely used, and especially detect the predetermined substance of biological living.Although analysis detection biology
The other methods of body substance also continue to develop, such as high performance liquid chromatography, mass spectrography, atomic absorption spectrography (AAS), plasma
Atomic emission spectrometry, electrochemical sensing etc., but these methods are more expensive, take and complicated for operation.Fluorescence method application
Suitable probe can realize object efficient detection, lossless, while carry out qualitative and quantitative analysis to object.At present
Fluorogen with different excitations and launch wavelength is used as the signal recipient of chemical detector, such as cumarin, pyrene, 1,8-
Aphthalimide, rhodamine, flower cyanines class, BODIPY classes etc..The fluorescence probe wherein built as fluorophor using rhodamine, due to
Its excellent fluorescence property and good modifiability, have become one of fluorescence probe of greatest concern 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.TotheknowledgeoftheRhodamine[J]
.Ber.DtschChem.Ges., 1905,38,3516-3527.), hereafter rhodamine compound is just widely used in each field.
Czarnik in 1997 etc. reports the first Cu based on rhodamine lactams loop coil off-on mechanism2+Probe
(DujolsVirginieFord,FrancisCzarnik,AnthonyW.ALong-WavelengthFluorescent
ChemodosimeterSelectiveforCu(II)IoninWater[J].JournaloftheAmericanChemical
Society,1997,119(31):After 7386-7387.), design and the synthesis of Rhodamine fluorescent probe just cause vast chemistry
The attention of family.Rhodamine lactams or Inner acyl ester derivants are unstressed configurations and colourless, and will be generated when loop coil is opened strong
Strong fluorescence and red.From this rhodamine fluorescence probe according to off-on principles in cell biology, Environmental Chemistry, pharmacology
It learns, the fields such as analytical chemistry are widely used, but current rhodamine copper ion fluorescence is poor in the presence of water solubility, sensitive
The problems such as degree degree is low, and specificity is poor, poor anti jamming capability.
If patent No. CN201710019765.3 discloses a kind of difunctional fluorescence probe of Rhodamine Derivatives class and application,
The fluorescence probe is containing VO2+And Cu2+Buffer solution in, can be detected respectively using fluorescence and ultraviolet-visible absorption spectroscopy
Identify VO2+And Cu2+.The probe is to VO2+And Cu2+Identification have an excellent selectivity, strong antijamming capability has preferable
Property is sensed, detection limit is low, detection sensitivity is high；It is follow-up to be added after pyrophosphate ion, pyrophosphate ion and VO2+、Cu2 +In conjunction with the Metal ion release of coordination comes out, and the hydrazides in the fluorescence probe is returned to closed loop states, and the fluorescence of system is rapid
It reduces, realizes the invertible operation of fluorescent probe molecule, it is seen that the specificity and anti-interference ability of the probe are poor.
Patent No. CN201510952259.0 discloses a kind of probe reagent and system of more metal ion simultaneous selection measurement
It is standby and application, the probe using three (2- aminoethyls) amine as parent, respectively on an amino chain connection rhodamine B, in addition
2- hydroxyl-1-naphthalene Formaldehyde groups are connected on two amino chains, rhodamine-hydroxyl naphthalene derivatives that tripod structure is prepared are visited
Needle.In Isosorbide-5-Nitrae-dioxane/water (19/1, v/v, pH=7) solution, absorbed using the ratio of different wave length, probe is examined respectively
Survey Cu2+、Co2+、Fe3+, mutual not Interference Detection；In acetonitrile/water (19/1, v/v) solution, different wave length under different pH is utilized
Fluorescent emission, probe detects Zn respectively2+、Al3+、Hg2+、Cu2+, mutual not Interference Detection；Under 365nm ultraviolet lamps, detection
Zn2+、Al3+、Hg2+It is in blue, pink, fluorescent red-orange, probe-Zn respectively2+Mix analyte detection Cu2+Blue-fluorescence is presented to disappear
It loses, the probe is 19 in acetonitrile and water volume ratio:It is carried out in 1 solution, illustrates that the water solubility of probe is poor.
Patent No. CN201710180512.4 discloses a kind of Cu containing rhodamine-pellet sulphonyl structure2+Fluorescence probe and its
Preparation method and application have studied probe in CH by ultraviolet-uisible spectrophotometer and Fluorescence Spectrometer3CH2OH-H2O(v:v
=9:1) recognition performance of metal ion, result of study are shown in solution：The present invention is to Cu2+With efficiently single-minded selection
Property, there is stronger anti-metal cation and anion interference performance, and can change by solution colour and realize to copper ion
Bore hole identifies that the probe is limited to 1.72 μM to the lowest detection of copper ion, described to show that the sensitivity of probe is not high enough and water
Dissolubility is poor.
Therefore in order to overcome expensive equipment, it is strongly professional, time-consuming and complicated for operation the problems such as and current fluorescence probe water
The problems such as dissolubility is poor, sensitivity degree is low, poor anti jamming capability, a kind of good water solubility of design synthesis, high sensitivity, anti-interference energy
The strong novel fluorescence probe of power has great importance.
Invention content
It is visited to solve the problems such as above-mentioned analytical instrument is expensive, strongly professional, time-consuming and complicated for operation and current fluorescence
The problems such as needle water solubility is poor, and sensitivity degree is low, poor anti jamming capability, a kind of water-soluble rhodamine base Cu of the present invention2+Fluorescence is visited
Needle and its synthetic method.
A kind of water-soluble rhodamine base Cu2+Fluorescence probe, structural formula are as shown in Figure 1.
Further, water-soluble rhodamine base Cu2+Group R1, R2, R3, R4 H or group R1 in fluorescence probe structural formula
It is CH with R23, 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
With R3 be H, group R4 is CH3。
Further, water-soluble rhodamine base Cu2+N is 0,2,3 in fluorescence probe structural formula ... n.
Further, above-mentioned water-soluble rhodamine base Cu 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 aminated compounds solution is added dropwise in rhodamine solution, be heated to 50-60 DEG C, obtained after back flow reaction 2-7h
Rhodamine lactam intermediate；
Step 2：Synthesizing water-solubility rhodamine base Cu2+Fluorescence probe weighs 1-2mmol rhodamine lactams, is dissolved in
Glucose solution is then added dropwise in rhodamine lactams solution by organic solvent, is heated to 60-85 DEG C, is flowed back, thin layer
Chromatography, which tracks to reaction, to be terminated, and obtains water-soluble rhodamine base fluorescent probe by column chromatographic isolation and purification after reaction.
Further, organic solvent is methanol, ethyl alcohol, acetonitrile.
Further, the reaction temperature of the bright lactam intermediate of synthesizing rhodamine is 60 DEG C, reaction time 6h.
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 dichloromethane and ethyl alcohol.
Further, column chromatographic isolation and purification etoh solvent and methylene chloride volume ratio are 1:150-230.
Have preferable water-soluble the present invention is based on rhodamine and glucose, designs a kind of the water-soluble of special construction
Property rhodamine base Cu2+Fluorescence probe.A certain amount of rhodamine lactams occurs condensation reaction with glucose and obtains under certain condition
To water-soluble rhodamine base Cu2+Fluorescence probe, building-up process raw material is simple and easy to get, reaction condition is mild, easy to operate, while institute
Obtain water-soluble rhodamine base Cu2+Fluorescence probe can quickly detect substance in biological cell under water environment.
Description of the drawings
Fig. 1 is water-soluble rhodamine base Cu2+The structural formula of fluorescence probe；
Fig. 2 is water-soluble rhodamine base Cu2+Fluorescence emission spectrogram of compound of the fluorescence probe to metalloform-selective；
Fig. 3 is water-soluble rhodamine base Cu2+Fluorescence emission spectrogram of compound of the fluorescence probe to different copper ion concentrations；
Fig. 4 is water-soluble rhodamine base Cu2+The fluorescence range of linearity of fluorescence probe.
Specific implementation mode
As shown in Figure 1, a kind of water-soluble rhodamine base Cu2+Fluorescence probe, specific embodiment are as follows：
Embodiment one
A kind of rhodamine 110Cu2+Fluorescence probe, group R1, R2, R3, R4 H, the rhodamine 110Cu that n is 22+Fluorescence is visited
Needle.
A kind of rhodamine 110Cu2+The synthetic method of fluorescence probe prepares above-mentioned rhodamine 110Cu2+Fluorescence probe,
Synthetic method is as follows：
Bright 110 lactam intermediate of synthesizing rhodamine：110 dyestuff of 2g rhodamines is weighed, alcohol solvent is dissolved in, then will
Ethylenediamine solution is added dropwise in 110 solution of rhodamine, is heated to 50 DEG C, back flow reaction 6h, and solution is by jujube in reaction process
Red becomes orange-yellow, obtains 110 lactam intermediate of rhodamine；
The bright 110Cu of synthesizing rhodamine2+Fluorescence probe：110 lactams of 1mmol rhodamines is taken, is dissolved in alcohol solvent, then
1.2mmol glucose solutions are added dropwise in 110 lactams solution of rhodamine, are heated to 80 DEG C, reflux, thin-layer chromatography with
Track to reaction terminates, and obtains rhodamine 110Cu by column chromatographic isolation and purification after reaction2+Fluorescence probe, column chromatography for separation
Purification solvent ethyl alcohol is 1 with methylene chloride volume ratio:200.
Embodiment two
A kind of tetramethylrhodamine Cu2+Fluorescence probe, group R1 and R2 are CH3, group R3 and R4 be H, n be 2 tetramethyl
Base rhodamine Cu2+Fluorescence probe.
A kind of synthetic method of water solubility tetramethylrhodamine fluorescence probe, prepares above-mentioned tetramethylrhodamine Cu2+It is glimmering
Light probe, synthetic method are as follows：
Synthesize tetramethylrhodamine lactam intermediate：2g tetramethylrhodaminedye dyes are weighed, alcohol solvent is dissolved in,
Then ethylenediamine solution is added dropwise in tetramethylrhodamine solution, is heated to 50 DEG C, back flow reaction 6h, in reaction process
Solution becomes orange-yellow by purplish red, obtains tetramethylrhodamine lactam intermediate；
Synthesize tetramethylrhodamine Cu2+Fluorescence probe：1mmol tetramethylrhodamine lactams is taken, it is molten to be dissolved in ethyl alcohol
1.2mmol glucose solutions are then added dropwise in tetramethylrhodamine lactams solution by agent, are heated to 80 DEG C, are flowed back,
Thin-layer chromatography, which tracks to reaction, to be terminated, and obtains tetramethylrhodamine Cu by column chromatographic isolation and purification after reaction2+Fluorescence is visited
Needle, column chromatographic isolation and purification etoh solvent are 1 with methylene chloride volume ratio:200.
Embodiment three
A kind of rhodamine B Cu2+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 BCu2+The synthetic method of fluorescence probe prepares above-mentioned rhodamine B fluorescence probe, closes
It is as follows at method：
The bright B lactam intermediates of synthesizing rhodamine：2g rhdamine Bs are weighed, alcohol solvent is dissolved in, then by second two
Amine aqueous solution is added dropwise in rhodamine B solution, is heated to 50 DEG C, back flow reaction 6h, and solution is by purplish red discoloration in reaction process
At orange-yellow, rhodamine B lactam intermediate is obtained；
The bright BCu of synthesizing rhodamine2+Fluorescence probe：1mmol rhodamine B lactams 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 Cu 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 6GCu2+Fluorescence probe, group R1 are C2H5, group R2 and R3 be H, group R4 is CH3, n
For 2 water-soluble rhodamine 6GCu2+Fluorescence probe.
A kind of water-soluble rhodamine 6GCu2+The synthetic method of fluorescence probe prepares above-mentioned rhodamine 6G Cu2+Fluorescence is visited
Needle, synthetic method are as follows：
The bright 6G lactam intermediates of synthesizing rhodamine：2g rhodamine 6G dyestuffs are weighed, alcohol solvent is dissolved in, then by second
Diamine 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
Become orange-yellow, obtains rhodamine 6G lactam intermediate；
The bright 6GCu of synthesizing rhodamine2+Fluorescence probe：1mmol rhodamine 6G lactams is taken, alcohol solvent is dissolved in, then will
1.2mmol glucose solutions are added dropwise in rhodamine 6G lactams solution, are heated to 80 DEG C, reflux, thin-layer chromatography tracks
Terminate to reaction, rhodamine 6G Cu is obtained by column chromatographic isolation and purification after reaction2+Fluorescence probe, column chromatographic isolation and purification
Etoh solvent is 1 with 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+、Pb2+When ion, probe solution is colourless, and fluorescence intensity does not also change at 580nm, it is seen that probe keeps former
The structure come, can be stable in the presence of in these solution systems.When Cu is added in probe solution2+Afterwards, solution becomes red from colourless
Color, fluorescence intensity is remarkably reinforced at 580nm, a strong emission peak occurs.This is because Cu2+With probe reaction so that Luo Dan
Bright loop coil is opened, and fluorescent emission is generated.
Embodiment six
As shown in Figure 3 and Figure 4,5 μM of probe solutions for preparing 16 parts of 5mL are separately added into 0-80 μM of copper ion, carry out glimmering
Light detection (λEx=520nm), fluorescence intensity in each system is calculated, by analyzing fluorescence intensity and Cu at 580nm2+Concentration
Relationship, assessment probe is to Cu2+Response performance.Fig. 3 shows with Cu2+The fluorescence intensity of the increase of concentration, solution gradually increases
By force, until maximum emission intensity is not changing.Fig. 4 shows probe in Cu2+Concentration 4 × 10-6Mol/L~6 × 10-5Mol/L ranges
It is interior in a linear relationship, linearly dependent coefficient R2=0.9915, and probe is to Cu2+Detection be limited to 1.16 × 10-8mol/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 (10)
1. a kind of water-soluble rhodamine base Cu2+Fluorescence probe, it is characterised in that：Water-soluble rhodamine base Cu2+Fluorescence probe structure
Formula is as follows：
2. water-soluble rhodamine base Cu according to claim 12+Fluorescence probe, it is characterised in that：The rhodamine Cu2+Base is glimmering
Group R1, R2, R3, R4 H or group R1 and R2 are CH in light probe structural formula3, group R3 and R4 be H or group R1 and R2
For C2H5, group R3 and R4 are H or group R1 is C2H5, group R2 and R3 be H, group R4 is CH3。
3. water-soluble rhodamine base Cu according to claim 12+Fluorescence probe, it is characterised in that：The water-soluble rhodamine
Base Cu2+N is 0,2,3 in fluorescence probe structural formula ... n.
4. a kind of water-soluble rhodamine base Cu2+The synthetic method of fluorescence probe, which is characterized in that prepare described in claim 1
Water-soluble rhodamine base Cu2+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, then will
Aminated compounds solution is added dropwise in rhodamine solution, is heated to 50-60 DEG C, Luo Dan is obtained after back flow reaction 2-7h
Bright lactam intermediate；
Step 2：Synthesizing water-solubility rhodamine base Cu2+Fluorescence probe weighs 1-2mmol rhodamine lactams, is dissolved in organic
Glucose solution is then added dropwise in rhodamine lactams solution by solvent, is heated to 60-85 DEG C, is flowed back, thin-layer chromatography
It tracks to reaction to terminate, water-soluble rhodamine base fluorescent probe is obtained by column chromatographic isolation and purification after reaction.
5. water-soluble rhodamine base Cu according to claim 42+The synthetic method of fluorescence probe, it is characterised in that：It is described to have
Solvent is methanol, ethyl alcohol, acetonitrile.
6. water-soluble rhodamine base Cu according to claim 42+The synthetic method of fluorescence probe, it is characterised in that：The conjunction
Reaction temperature at intermediate is 60 DEG C, reaction time 6h.
7. water-soluble rhodamine base Cu according to claim 42+The synthetic method of fluorescence probe, it is characterised in that：Sieve
The molar ratio of red bright lactams and glucose is 1:1.0-2.0.
8. water-soluble rhodamine base Cu according to claim 42+The synthetic method of fluorescence probe, it is characterised in that：The conjunction
Reaction temperature at target compound is 80 DEG C.
9. water-soluble rhodamine base Cu according to claim 42+The synthetic method of fluorescence probe, it is characterised in that：The column
Chromatography purification solvent is dichloromethane and ethyl alcohol.
10. water-soluble rhodamine base Cu according to claim 92+The synthetic method of fluorescence probe, it is characterised in that：The column
Chromatography purification solvent ethyl alcohol is 1 with methylene chloride volume ratio:150-230.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014058535A1 (en) * | 2012-08-19 | 2014-04-17 | Michigan Technological University | Lysosomal targeting probes |
| CN104087285A (en) * | 2014-06-23 | 2014-10-08 | 昆山东大智汇技术咨询有限公司 | Rhodamine structure based Cu<2+> fluorescent probe and preparation method thereof |
| CN104936966A (en) * | 2012-10-29 | 2015-09-23 | 布约迪姆实验室 | New antibacterial compounds and biological applications thereof |
-
2018
- 2018-04-26 CN CN201810388438.XA patent/CN108484620A/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014058535A1 (en) * | 2012-08-19 | 2014-04-17 | Michigan Technological University | Lysosomal targeting probes |
| CN104936966A (en) * | 2012-10-29 | 2015-09-23 | 布约迪姆实验室 | New antibacterial compounds and biological applications thereof |
| CN104087285A (en) * | 2014-06-23 | 2014-10-08 | 昆山东大智汇技术咨询有限公司 | Rhodamine structure based Cu<2+> fluorescent probe and preparation method thereof |
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Application publication date: 20180904 |