CN106674134A - Novel fluorescent probe, preparation method thereof and application of novel fluorescent probe to detection of 6-thioguanine - Google Patents
Novel fluorescent probe, preparation method thereof and application of novel fluorescent probe to detection of 6-thioguanine Download PDFInfo
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- CN106674134A CN106674134A CN201611075558.1A CN201611075558A CN106674134A CN 106674134 A CN106674134 A CN 106674134A CN 201611075558 A CN201611075558 A CN 201611075558A CN 106674134 A CN106674134 A CN 106674134A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
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- C—CHEMISTRY; METALLURGY
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/182—Metal complexes of the rare earth metals, i.e. Sc, Y or lanthanide
Abstract
The invention discloses a novel fluorescent probe, a preparation method thereof and application of the novel fluorescent probe to detection of 6-thioguanine (6-TG). The preparation method comprises the following steps: taking DTPA (Diethylene Triamine Pentoacetic Acid), acetic anhydride and pyridine, slowly stirring and heating at the temperature of 65 DEG C for 24 hours; cooling to room temperature, filtering, washing with anhydrous ether, performing suction filtration, and performing vacuum drying to obtain DTPAA (Diethylenetriaminpentacetic Acid); taking the DTPAA, triethylamine, DMF (Dimethyl Formamide) and cytosine, keeping the temperature at 100 DEG C, heating and stirring for 24 hours; cooling to the room temperature, filtering, and performing vacuum drying to obtain DTPA-bis(cytosine); taking the DTPA-bis(cytosine), dissolving the DTPA-bis(cytosine) in a Tris-HCl buffer solution of which the pH is equal to 7.4, washing Eu(NO3)3.6H2O with the solution, collecting washing liquid, and heating or standing for a long time to obtain the fluorescent probe. When the fluorescent probe is applied to the detection of the 6-TG together with a fluorescence method, a simple and novel method is provided, high efficiency is achieved, the cost is low, and environmental pollution is avoided.
Description
Technical field
The invention belongs to analytical chemistry field, more particularly to novel fluorescence probe synthesis and its to 6-thioguanine
Detection.
Background technology
6-thioguanine (6-TG) is the analog of guanine, is introduced into clinical and patient's in early 1950s
Research.Over the last couple of decades, 6-thioguanine is used as always the common drug of leukemia treating.In recent years,
It is applied to treat breast cancer.But 6-thioguanine also has certain harm to human body, it can suppress guanosint
The synthesis of glycosides.6-thioguanine can be incorporated into CpG sites, and affect what DNA methylation transferase DNMT1 and HpaI were mediated
Cytosine methylation reacts.In the detached Jurkat T cells from ALL, 6-thioguanine shows
Writing reduces overall cytosine methylation level.And, 6-thioguanine is simply plugged into mitochondrial DNA (mtDNA), and
Cause cell Mitochondria dysfunction.In except inserting DNA, 6-thioguanine can also pass through active oxygen approach (ROS)
Kill cell.ROS acts on DNA, produces potent forcefully destructive duplication and arrests DNA pathologies including interchain linkage.
Therefore detection to 6-thioguanine it is critical that.Fluorescent technique has sensitivity high because of it, easy to operate, cost
It is low, it is selective to wait many merits well, biochemical analysis has been widely used in, environmental monitoring, the side such as food analysis and clinical examination
Face, penetrates into chemistry, biological, physics, among the multidisciplinary research such as environment and medicine field.Therefore, developed using fluorescent technique
Chemical-biological probe with practical value has become the research topic for currently receiving much attention.Wherein, fluorescence probe, is increasingly becoming
The indispensable molecular tool in the field such as modern life science and medical diagnosis on disease.The design synthesis of novel fluorescence probe and its application
For current crossing research focus in forward position interdisciplinary.
The content of the invention
It is an object of the invention to designing, synthesis is a kind of to can be used for the new of the 6-thioguanine in the middle of effective detection urine
Type fluorescence probe EuIII-dtpa-bis(cytosine).Compound involved in the present invention belongs to novel fluorescence probe, is applied
Simple to operate in detection 6-thioguanine, low cost is pollution-free, and selective good.
The technical solution used in the present invention is：A kind of novel fluorescence probe, described novel fluorescence probe is EuIII-
dtpa-bis(cytosine)。
The preparation method of above-mentioned novel fluorescence probe, method is as follows：
1) diethylenetriamine pentaacetic acid (dtpa), acetic anhydride and pyridine are taken, is well mixed, at 60-70 DEG C, agitating heating
22-25h, is cooled to room temperature, filters, and absolute ether washing, suction filtration is dried, and obtains diethylenetriamine pentaacetic acid dianhydride (dtpaa)；
2) diethylenetriamine pentaacetic acid dianhydride (dtpaa), triethylamine, anhydrous dimethyl formamide (DMF) and cytimidine are taken
(cytosine), it is well mixed, at 95-105 DEG C, agitating heating 22-25h stands, and is cooled to room temperature, filters, and vacuum is done
It is dry, obtain diethylenetriamine pentaacetic acid-bis- (cytimidines) (dtpa-bis (cytosine))；
3) diethylenetriamine pentaacetic acid-bis- (cytimidines) the Tris-HCl cushioning liquid of pH=7.4 is dissolved, obtains dtpa-
Bis (cytosine) solution, with dtpa-bis (cytosine) solution Eu (NO are washed3)3·6H2O, collects cleaning solution, cleaning solution
20-30min is heated at 70-80 DEG C or is placed 1-2 days at room temperature, obtain EuIII-dtpa-bis(cytosine)。
Preferably, the preparation method of above-mentioned novel fluorescence probe, in molar ratio, diethylenetriamine pentaacetic acid:Acetic anhydride:Pyrrole
Pyridine=1:4:6.
Preferably, the preparation method of above-mentioned novel fluorescence probe, in molar ratio, diethylenetriamine pentaacetic acid dianhydride:Three second
Amine:Cytimidine=1:3:3.
Preferably, the preparation method of above-mentioned novel fluorescence probe, in mass ratio, diethylenetriamine pentaacetic acid-bis- (born of the same parents are phonetic
Pyridine):Eu(NO3)3·6H2O=40:1.
The novel fluorescence probe of the present invention can be applied in detection 6-thioguanine.Method is as follows：The thio birds of 6- is fast
The purine Tris-HCl cushioning liquid of pH=7.4 dissolves.The pH=7.4's that addition is configured by Tris-HCl cushioning liquid is new glimmering
Light probe EuIII- dtpa-bis (cytosine), observes the change of fluorescence spectrum under the excitation wavelength of 288nm.
The invention has the beneficial effects as follows：
1. of the invention, dtpa is modified, cytimidine is connected at dtpa two ends, due to the similitude of structure, pass through
The effect crawl object of hydrogen bond and pi-pi accumulation and coordinate bond, so as to reach the purpose of detection 6-thioguanine.
2. the present invention devises a kind of new fluorescence probe for the design feature of 6-thioguanine.By this
Bright method, the probe can carry out specific detection to 6-thioguanine.With the fluorescence of other detection 6-thioguanines
Probe is compared, with simple, quickly, the features such as low cost.
Description of the drawings
Fig. 1 is fluorescence probe EuIIIThe flow chart of the synthetic reaction of-dtpa-bis (cytosine).
Fig. 2 a are dtpa-bis (cytosine) Fourier transform infrared spectroscopy (FT-IR) figures (DC-dtpa).
Fig. 2 b are Fourier transform infrared spectroscopy (FT-IR) figures of cytimidine.
Fig. 2 c are Fourier transform infrared spectroscopy (FT-IR) figures of dtpa.
Fig. 3 is Eu3+, dtpa-bis (cytosine) (dtpa-DC), EuIIIThe ultraviolet suction of-dtpa-bis (cytosine)
Receive spectrogram.
Fig. 4 a are that fluorescence probe adds different material fluorescence spectrum comparison diagram.
Fig. 4 b are fluorescence probes to different material fluorescence spectrum comparison diagram (575nm).
Fig. 4 c are fluorescence probes to different material fluorescence spectrum comparison diagram (525nm).
Fig. 5 is fluorescence probe and 6-thioguanine interaction mechanism figure.
Fig. 6 a are the interference fluorescence spectrum comparison diagrams that fluorescence probe mixes respectively to 6-thioguanine with different material.
Fig. 6 b are the interference fluorescence spectrum comparison diagrams that fluorescence probe mixes respectively to 6-thioguanine with different material
(575nm)。
Fig. 6 c are the interference fluorescence spectrum comparison diagrams that fluorescence probe mixes respectively to 6-thioguanine with different material
(525nm)。
Specific embodiment
The novel fluorescence probe Eu of embodiment 1III-dtpa-bis(cytosine)
(1) preparation method
1st, the preparation of diethylenetriamine pentaacetic acid dianhydride (dtpaa)
Weigh dtpa 7.8100g (0.02mmol), acetic anhydride 16.0mL (0.08mmol), pyridine 10.0mL
(0.12mmol) it is placed in three neck round bottom, heating 24h is slowly stirred at 65 DEG C.Room temperature is cooled to, by reactant mixture
Filter, and washed twice with a small amount of absolute ether, use vavuum pump suction filtration, gains to be vacuum dried for 80 DEG C in vacuum drying chamber,
Obtain final product dtpaa.
2nd, the preparation of the double cytimidines (dtpa-bis (cytosine)) of diethylenetriamine pentaacetic acid
Take dtpaa (55mmol), the triethylamine of 8.0mL (165mmol), the dry DMF of 50mL and the 1.83g of 1.9610g
(165mmol) cytimidine (cytosine), in three neck round bottom.100 DEG C of heating of constant temperature, quickly stir 24h.Reaction is complete
After stand, after being cooled to room temperature, obtain white solid matter, filter, 50 DEG C vacuum drying, obtain final product dtpa-bis (cytosine).
3rd, fluorescence probe EuIIIThe preparation of-dtpa-bis (cytosine)
The dtpa-bis (cytosine) of 0.0724g is weighed in the Tris-HCl cushioning liquid of the pH=7.4 of 200.0mL
Dissolving, obtains dtpa-bis (cytosine) solution.Weigh the Eu (NO of 0.0018g3)3·6H2O is placed in beaker.Then with above
Dtpa-bis (cytosine) solution of preparation is washed three times, and cleaning solution is moved into successively in 250mL volumetric flasks, constant volume.Capacity
Solution in bottle heats 20-30min at 70-80 DEG C, forms EuIII- dtpa-bis (cytosine), now concentration be 5.0 ×
10-4Mol/L, it is standby as storing solution.Building-up process is as shown in Figure 1.
(2) detect
1. cytimidine, the FT-IR of dtpa, dtpa-bis (cytosine) is schemed as shown in Fig. 2 a, Fig. 2 b and 2c.By FT-
IR contrasts find that dtpa-bis (cytosine) in fig. 2 a, the characteristic diffraction peak for not only occurring in that cytimidine have also appeared
Dtpa is not only existed in the characteristic diffraction peak of dtpa, i.e. dtpa-bis (cytosine) also while there is cytimidine.It is found that
The v (C-N) of dtpa-bis (cytosine) occurs in 906cm in Fig. 2 a-1Place, the 982cm with cytimidine in Fig. 2 b-1Compare
One 76cm-1Red shift.The v of dtpa-bis (cytosine) in Fig. 2 as(COO) 1372cm is occurred in-1, with dtpa in Fig. 2 c
1399cm-127cm is compared-1Red shift.Additionally, the v of dtpa-bis (cytosine)as(COO) 1726cm is occurred in-1Place, and
The v of dtpaas(COO) 1734cm is occurred in-1, there is a 8cm-1Red shift.The v of dtpa-bis (cytosine)as(CONH) occur
In 1648cm-13378cm is occurred in the absworption peak of hydroxyl feature-1.These change confirmations, have synthesized dtpa-bis
(cytosine)。
2. rare earth Eu3+, dtpa-bis (cytosine) (dtpa-DC), EuIII-dtpa-bis(cytosine)(Eu3+-
Dtpa-DC) uv absorption spectra is as shown in Figure 3.By ultra-violet absorption spectrum as can be seen that Eu3+Solution have one maximum to inhale
Peak is received at 220nm wavelength, dtpa-bis (cytosine) solution shows very weak absworption peak at 205nm.Form EuIII-
Also there is maximum absorption band at 220nm after dtpa-bis (cytosine), but and Eu3+Solution than substantially becoming strong.Additionally,
EuIII- dtpa-bis (cytosine) has a new absworption peak to occur in 288nm.This shows that dtpa-bis (cytosine) can
Eu is made with the ligand field for forming new3+Electronic structure changes.This shows EuIII- dtpa-bis (cytosine) has as glimmering
Light probe detects the potential ability of 6-thioguanine.
The fluorescence probe Eu of embodiment 2IIIApplications of-the dtpa-bis (cytosine) in detection 6-thioguanine
1. fluorescence spectrum of the fluorescence probe to different material
Experiment condition：Take 6-thioguanine, guanine, adenine, uric acid, xanthine, hypoxanthine, cytimidine, urine
Pyrimidine, the thymidine Tris-HCl buffer solutions of pH=7.4 are configured to respectively concentration for 5.0 × 10-4The solution of mol/L, makees
For storing solution.5.0mL is taken respectively in 50mL volumetric flasks, then is separately added into the fluorescence probe of the 5.0mL of the preparation of embodiment 1
EuIII- dtpa-bis (cytosine) storing solution, constant volume.Now probe and each detection material concentration are all 5.0 × 10-5mol/L。
The change of fluorescence spectrum is observed under the excitation wavelength of 288nm.As a result as shown in Fig. 4 a, Fig. 4 b and Fig. 4 c.As shown in Figure 4 b, exist
At 575nm, fluorescence probe is more notable to the fluorescence intensity of 6-thioguanine.And there is fluorescence peak simultaneously at 525nm,
And other materials at 525nm without obvious characteristic peak.By Fig. 4 b and Fig. 4 c, fluorescence intensity can be more intuitively observed
In the change of 575nm and 525nm.As can be seen here, fluorescence probe EuIII- dtpa-bis (cytosine) can be in combined with fluorescent method
6-thioguanine is detected.
2. fluorescence probe EuIIIThe detection mechanism of-dtpa-bis (cytosine) to 6-thioguanine
Based on testing result of the fluorescence probe to 6-thioguanine, the present invention proposes fluorescence probe and detected material 6-
The mechanism of thioguanine reaction, as shown in Figure 5.It is well known that Eu ions are nine coordinations, in EuIII-dtpa-bis
(cytosine) water for having a molecule in is coordinated therewith.Dtpa after modification, upper and lower ends formed two " arm ", two
Only " arm " is that cytimidine has certain similitude with the structure of 6-thioguanine, can by hydrogen bond and pi-pi accumulation and
Coordinate bond captures detected material, so as to form a new complex.After forming new complex, the coordination of Eu becomes
Change, so there is fluorescence peak at the 575nm of fluorescence spectrum.6-thioguanine is continuously added, due to binding site and combination
The change of mode, i.e. 6-thioguanine are combined in the outside of two " arm ", and fluorescence peak is now occurred in that at 525nm.By
It is similar to guanine in the structure of 6-thioguanine, so guanine is added in fluorescence probe, but the detection is not
Have at 525nm and fluorescence peak occur, it can be seen that, fluorescence probe EuIII- dtpa-bis (cytosine) can be to the thio birds of 6-
Purine selective enumeration method.
3.6- thioguanines mix to fluorescence probe Eu with different testing sampleIII- dtpa-bis (cytosine) detections
Affect
Experiment condition：Guanine, adenine, uric acid, xanthine, hypoxanthine, cytimidine, uracil, thymus gland are taken respectively
Pyrimidine storing solution 5.0mL is separately added into the 6-thioguanine storing solution of 5.0mL in 50mL volumetric flasks, then is separately added into
The fluorescence probe storing solution of 5.0mL, constant volume is configured to probe, and 6-thioguanine, each detection material concentration is all 5.0 × 10- 5The solution of mol/L.The change of fluorescence spectrum is observed under the excitation wavelength of 288nm.As a result as shown in Fig. 6 a, Fig. 6 b and Fig. 6 c.
Detection of other detectable substances on fluorescence probe at 575nm has certain impact, but very little is affected at 525nm.This phenomenon is in figure
It is more directly perceived in 6b and Fig. 6 c.As can be seen here, fluorescence probe is in the case where there is other materials to disturb, to 6-thioguanine according to
So there is specificity.
Claims (7)
1. a kind of novel fluorescence probe, it is characterised in that described fluorescence probe is EuIII-dtpa-bis(cytosine)。
2. the preparation method of the novel fluorescence probe described in claim 1, it is characterised in that method is as follows：
1) diethylenetriamine pentaacetic acid, acetic anhydride and pyridine are taken, is well mixed, at 60-70 DEG C, agitating heating 22-25h, cooling
To room temperature, filter, absolute ether washing, suction filtration is dried, and obtains diethylenetriamine pentaacetic acid dianhydride (dtpaa)；
2) diethylenetriamine pentaacetic acid dianhydride (dtpaa), triethylamine, dry DMF and cytimidine are taken, is well mixed, in 95-105 DEG C
Under, agitating heating 22-25h stands, and is cooled to room temperature, filters, and vacuum drying obtains diethylenetriamine pentaacetic acid-bis- (cytimidines)
(dtpa-bis(cytosine))；
3) diethylenetriamine pentaacetic acid-bis- (cytimidines) the Tris-HCl cushioning liquid of pH=7.4 is dissolved, obtains dtpa-bis
(cytosine) solution, with dtpa-bis (cytosine) solution Eu (NO are washed3)3·6H2O, collect cleaning solution, cleaning solution in
20-30min is heated at 70-80 DEG C or is placed 1-2 days at room temperature, obtain EuIII-dtpa-bis(cytosine)。
3. the preparation method of novel fluorescence probe as claimed in claim 2, it is characterised in that：In molar ratio, Diethylenetriamine five
Acetic acid:Acetic anhydride:Pyridine=1:4:6.
4. the preparation method of novel fluorescence probe as claimed in claim 2, it is characterised in that：In molar ratio, Diethylenetriamine five
Acetic acid dianhydride:Triethylamine:Cytimidine=1:3:3.
5. the preparation method of novel fluorescence probe as claimed in claim 2, it is characterised in that：In mass ratio, Diethylenetriamine five
Acetic acid-bis- (cytimidine):Eu(NO3)3·6H2O=40:1.
6. application of the novel fluorescence probe described in claim 1 in detection 6-thioguanine.
7. application as claimed in claim 6, it is characterised in that method is as follows：By 6-thioguanine with pH=7.4's
Tris-HCl cushioning liquid dissolves, and adds new described in the claim 1 of the pH=7.4 configured by Tris-HCl cushioning liquid
Fluorescence probe EuIII- dtpa-bis (cytosine), observes the change of fluorescence spectrum under the excitation wavelength of 288nm.
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| CN109180707A (en) * | 2018-10-08 | 2019-01-11 | 辽宁大学 | Fluorescence probe and its preparation method and application for detecting xanthine |
| CN110183474A (en) * | 2019-06-13 | 2019-08-30 | 辽宁大学 | A kind of novel fluorescence probe and preparation method thereof and in detection urine " clenbuterol hydrochloride " clenbuterol application |
| CN110540838A (en) * | 2019-10-10 | 2019-12-06 | 辽宁大学 | Novel fluorescent probe, preparation method thereof and application of novel fluorescent probe in detection of basic orange in bean product |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109180707A (en) * | 2018-10-08 | 2019-01-11 | 辽宁大学 | Fluorescence probe and its preparation method and application for detecting xanthine |
| CN109180707B (en) * | 2018-10-08 | 2020-05-12 | 辽宁大学 | Fluorescent probe for detecting xanthine and preparation method and application thereof |
| CN110183474A (en) * | 2019-06-13 | 2019-08-30 | 辽宁大学 | A kind of novel fluorescence probe and preparation method thereof and in detection urine " clenbuterol hydrochloride " clenbuterol application |
| CN110183474B (en) * | 2019-06-13 | 2021-06-25 | 辽宁大学 | Novel fluorescent probe, preparation method thereof and application of novel fluorescent probe in detection of clenbuterol |
| CN110540838A (en) * | 2019-10-10 | 2019-12-06 | 辽宁大学 | Novel fluorescent probe, preparation method thereof and application of novel fluorescent probe in detection of basic orange in bean product |
| CN110540838B (en) * | 2019-10-10 | 2022-08-30 | 辽宁大学 | Fluorescent probe, preparation method thereof and application of fluorescent probe in detection of basic orange in bean product |
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