CN106674134B - A kind of novel fluorescence probe and preparation method thereof and the application in detection 6-thioguanine - Google Patents
A kind of novel fluorescence probe and preparation method thereof and the application in detection 6-thioguanine Download PDFInfo
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- CN106674134B CN106674134B CN201611075558.1A CN201611075558A CN106674134B CN 106674134 B CN106674134 B CN 106674134B CN 201611075558 A CN201611075558 A CN 201611075558A CN 106674134 B CN106674134 B CN 106674134B
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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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- 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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- 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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- 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 kind of novel fluorescence probes and preparation method thereof and the application in detection 6-thioguanine.Dtpa, acetic anhydride are taken, pyridine is slowly stirred heating for 24 hours at 65 DEG C.It is cooled to room temperature, filters, anhydrous ether washing filters, and vacuum drying obtains dtpaa.Dtpaa is taken, triethylamine, DMF, cytimidine, 100 DEG C of heating stirrings of constant temperature are for 24 hours.It is cooled to room temperature, is filtered, vacuum drying obtains dtpa-bis (cytosine).It takes dtpa-bis (cytosine) to be dissolved in the Tris-HCl buffer solution of pH=7.4, and washs Eu (NO with this solution3)3·6H2O, collects cleaning solution, and heating or for a long time placement obtain fluorescence probe.Fluorescence probe combination fluorescent method of the invention detects 6-TG, and method is simple and novel, high-efficient and at low cost, not will cause environmental pollution.
Description
Technical field
The invention belongs to the synthesis of analytical chemistry field more particularly to novel fluorescence probe and its to 6-thioguanine
Detection.
Background technique
6-thioguanine (6-TG) is the analog of guanine, is just introduced into the 1950s clinical and patient
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 treatment breast cancer.But 6-thioguanine also has certain harm to human body, it can inhibit guanosint
The synthesis of glycosides.6-thioguanine can be integrated into the site CpG, and influence DNA methylation transferase DNMT1 and HpaI mediation
Cytosine methylation reaction.From the Jurkat T cell separated in acute lymphoblastic leukemia, 6-thioguanine is aobvious
Writing reduces whole cytosine methylation level.Moreover, 6-thioguanine is simply plugged into mitochondrial DNA (mtDNA), and
Cause cell Mitochondria dysfunction.In addition in insertion DNA, 6-thioguanine can also pass through active oxygen approach (ROS)
Kill cell.ROS acts on DNA, and generating potent forcefully destructive duplication and arresting DNA lesion includes interchain linkage.
It therefore is vital to the detection of 6-thioguanine.Fluorescent technique is because it is with high sensitivity, easy to operate, cost
Low, selectivity waits well many merits, has been widely used in biochemical analysis, environmental monitoring, the side such as food analysis and clinical examination
Face penetrates into chemistry, biology, physics, among the multidisciplinary researches such as environment and medicine field.Therefore, it is developed using fluorescent technique
Chemical-biological probe with practical value has become the research topic currently to receive much attention.Wherein, fluorescence probe has become
The indispensable molecular tool in the fields such as modern life science and medical diagnosis on disease.The design of novel fluorescence probe synthesizes and its application
For current crossing research hot spot in forward position interdisciplinary.
Summary of the invention
It is an object of the invention to design synthesize it is a kind of can be used for effectively detect urine in 6-thioguanine it is new
Type fluorescence probe EuIII-dtpa-bis(cytosine).Compound involved in the present invention belongs to novel fluorescence probe, is applied
It is easy to operate in detection 6-thioguanine, it is at low cost, it is pollution-free, and selectivity is good.
The technical solution adopted by the present invention is that: a kind of novel fluorescence probe, the novel fluorescence probe is EuIII-
dtpa-bis(cytosine)。
The preparation method of above-mentioned novel fluorescence probe, the method is as follows:
1) diethylenetriamine pentaacetic acid (dtpa), acetic anhydride and pyridine are taken, is uniformly mixed, at 60-70 DEG C, agitating and heating
22-25h is cooled to room temperature, filtering, and anhydrous ether washing filters, dry, obtains diethylenetriamine pentaacetic acid dianhydride (dtpaa)；
2) diethylenetriamine pentaacetic acid dianhydride (dtpaa), triethylamine, anhydrous dimethyl formamide (DMF) and cytimidine are taken
(cytosine), it is uniformly mixed, at 95-105 DEG C, agitating and heating 22-25h stands, is cooled to room temperature, filters, and vacuum is dry
It is dry, obtain diethylenetriamine pentaacetic acid-bis- (cytimidines) (dtpa-bis (cytosine))；
3) diethylenetriamine pentaacetic acid-bis- (cytimidines) is dissolved with the Tris-HCl buffer solution of pH=7.4, obtains dtpa-
Bis (cytosine) solution washs Eu (NO with dtpa-bis (cytosine) solution3)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, and Eu is obtainedIII-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-is bis-, and (born of the same parents are phonetic
Pyridine): Eu (NO3)3·6H2O=40:1.
Novel fluorescence probe of the invention can be applied in detection 6-thioguanine.Method is as follows: the thio bird of 6- is fast
The purine Tris-HCl buffer solution of pH=7.4 dissolves.The novel glimmering of the pH=7.4 configured by Tris-HCl buffer solution is added
Light probe EuIII- dtpa-bis (cytosine) observes the variation of fluorescence spectrum under the excitation wavelength of 288nm.
The beneficial effects of the present invention are:
1. the present invention, modifies dtpa, connects cytimidine at the both ends dtpa, due to the similitude of structure, pass through
The effect of hydrogen bond and pi-pi accumulation and coordinate bond grabs object, to achieve the purpose that detect 6-thioguanine.
2. the present invention is directed to the design feature of 6-thioguanine, a kind of novel fluorescence probe is devised.By this hair
Bright method, the probe can carry out specific detection to 6-thioguanine.With the fluorescence of other detection 6-thioguanines
Probe is compared, have it is simple, quickly, it is at low cost the features such as.
Detailed description of the invention
Fig. 1 is fluorescence probe EuIIIThe flow chart of the synthetic reaction of-dtpa-bis (cytosine).
Fig. 2 a is Fourier transform infrared spectroscopy (FT-IR) figure of dtpa-bis (cytosine) (DC-dtpa).
Fig. 2 b is Fourier transform infrared spectroscopy (FT-IR) figure of cytimidine.
Fig. 2 c is Fourier transform infrared spectroscopy (FT-IR) figure of dtpa.
Fig. 3 is Eu3+, dtpa-bis (cytosine) (dtpa-DC), EuIIIThe ultraviolet suction of-dtpa-bis (cytosine)
Receive spectrogram.
Fig. 4 a is that different material fluorescence spectrum comparison diagram is added in fluorescence probe.
Fig. 4 b is fluorescence probe to different material fluorescence spectrum comparison diagram (575nm).
Fig. 4 c is fluorescence probe to different material fluorescence spectrum comparison diagram (525nm).
Fig. 5 is fluorescence probe and 6-thioguanine interaction mechanism figure.
Fig. 6 a is the interference fluorescence spectrum comparison diagram that fluorescence probe mixes 6-thioguanine with different material respectively.
Fig. 6 b is the interference fluorescence spectrum comparison diagram that fluorescence probe mixes 6-thioguanine with different material respectively
(575nm)。
Fig. 6 c is the interference fluorescence spectrum comparison diagram that fluorescence probe mixes 6-thioguanine with different material respectively
(525nm)。
Specific embodiment
1 novel fluorescence probe Eu of embodimentIII-dtpa-bis(cytosine)
(1) preparation method
1, the preparation of diethylenetriamine pentaacetic acid dianhydride (dtpaa)
It weighs dtpa 7.8100g (0.02mmol), acetic anhydride 16.0mL (0.08mmol), pyridine 10.0mL
(0.12mmol) is placed in three neck round bottom, and heating is slowly stirred at 65 DEG C for 24 hours.It is cooled to room temperature, by reaction mixture
Filtering, and washed twice with a small amount of anhydrous ether, it is filtered with vacuum pump, gains 80 DEG C of vacuum drying in a vacuum drying oven,
Up to dtpaa.
2, the preparation of the double cytimidines (dtpa-bis (cytosine)) of diethylenetriamine pentaacetic acid
Take the anhydrous DMF and 1.83g of the dtpaa (55mmol) of 1.9610g, the triethylamine of 8.0mL (165mmol), 50mL
The cytimidine (cytosine) of (165mmol), in three neck round bottom.100 DEG C of constant temperature heating are quickly stirred for 24 hours.Fully reacting
After stand, after being cooled to room temperature, obtain white solid matter, filter, 50 DEG C vacuum drying to get dtpa-bis (cytosine).
3, fluorescence probe EuIIIThe preparation of-dtpa-bis (cytosine)
The dtpa-bis (cytosine) of 0.0724g is weighed in the Tris-HCl buffer solution of the pH=7.4 of 200.0mL
Dissolution, obtains dtpa-bis (cytosine) solution.Weigh the Eu (NO of 0.0018g3)3·6H2O is placed in a beaker.Then with above
Three times, cleaning solution successively moves into 250mL volumetric flask, constant volume for dtpa-bis (cytosine) the solution washing of preparation.Capacity
Solution in bottle heats 20-30min at 70-80 DEG C, forms EuIII- dtpa-bis (cytosine), at this time concentration be 5.0 ×
10-4Mol/L, it is spare as stock solution.Synthesis process is as shown in Figure 1.
(2) it detects
1. the FT-IR of cytimidine, dtpa, dtpa-bis (cytosine) schemes as shown in Fig. 2 a, Fig. 2 b and 2c.Pass through FT-
IR comparison discovery, dtpa-bis (cytosine) in fig. 2 a, the characteristic diffraction peak for cytimidine not only occur have also appeared
There is only dtpa also to exist simultaneously cytimidine in the characteristic diffraction peak of dtpa, i.e. dtpa-bis (cytosine).It can be found that
The v (C-N) of dtpa-bis (cytosine) appears in 906cm in Fig. 2 a-1Place, the 982cm with cytimidine in Fig. 2 b-1Compared to having
One 76cm-1Red shift.The v of dtpa-bis (cytosine) in Fig. 2 as(COO) 1372cm is appeared in-1, with dtpa in Fig. 2 c
1399cm-1Compared to there is 27cm-1Red shift.In addition, the v of dtpa-bis (cytosine)as(COO) 1726cm is appeared in-1Place, and
The v of dtpaas(COO) 1734cm is appeared in-1, there is a 8cm-1Red shift.The v of dtpa-bis (cytosine)as(CONH) occur
In 1648cm-13378cm is appeared in the absorption peak of hydroxyl feature-1.These variations confirm, 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.The Eu it can be seen from ultra-violet absorption spectrum3+Solution there is one maximum to inhale
Peak is received at 220nm wavelength, dtpa-bis (cytosine) solution shows very weak absorption peak at 205nm.Form EuIII-
Also there is maximum absorption band at 220nm after dtpa-bis (cytosine), but and Eu3+Solution become strong compared to obvious.In addition,
EuIII- dtpa-bis (cytosine) has a new absorption peak to appear in 288nm.This shows that dtpa-bis (cytosine) can
Make Eu with the ligand field for forming new3+Electronic structure changes.This shows EuIII- dtpa-bis (cytosine) has as glimmering
The potential ability of light probe detection 6-thioguanine.
2 fluorescence probe Eu of embodimentIIIApplication of-the dtpa-bis (cytosine) in detection 6-thioguanine
1. fluorescence probe is to the fluorescence spectrum of different material
Experiment condition: 6-thioguanine, guanine, adenine, uric acid, xanthine, hypoxanthine, cytimidine, urine are taken
Pyrimidine, it is 5.0 × 10 that thymidine is configured to concentration with the Tris-HCl buffer of pH=7.4 respectively-4The solution of mol/L is made
For stock solution.It takes 5.0mL in 50mL volumetric flask respectively, then is separately added into the fluorescence probe of the 5.0mL of the preparation of embodiment 1
EuIII- dtpa-bis (cytosine) stock solution, constant volume.Probe and each detection material concentration are all 5.0 × 10 at this time-5mol/L。
The variation 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 significant to the fluorescence intensity of 6-thioguanine.And there is fluorescence peak simultaneously at 525nm,
And other substances at 525nm without obvious characteristic peak.By Fig. 4 b and Fig. 4 c, more intuitive fluorescence intensity can be observed
In the variation of 575nm and 525nm.It can be seen that fluorescence probe EuIII- dtpa-bis (cytosine) can combine fluorescent method
6-thioguanine is detected.
2. fluorescence probe EuIIIDetection mechanism of-the dtpa-bis (cytosine) to 6-thioguanine
Based on fluorescence probe to the testing result of 6-thioguanine, the invention proposes fluorescence probes and detected material 6-
The mechanism of thioguanine reaction, as shown in Figure 5.It is well known that Eu ion is nine coordinations, in EuIII-dtpa-bis
(cytosine) water of a molecule is coordinated in therewith.By modification after dtpa, upper and lower ends formed two " arm ", two
Only the structure of " arm " i.e. cytimidine and 6-thioguanine has certain similitude, can by hydrogen bond and pi-pi accumulation and
Coordinate bond grabs detected material, to form a new complex.It is formed after 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 combine in two " arm " outsides, occur fluorescence peak at 525nm at this time.By
It is similar to guanine in the structure of 6-thioguanine, so joined guanine in fluorescence probe, but the detection is not
Have and occur fluorescence peak at 525nm, it can be seen that, fluorescence probe EuIII- dtpa-bis (cytosine) can be to the thio bird of 6-
Purine selective enumeration method.
3.6- thioguanine is mixed with different testing sample to fluorescence probe EuIII- dtpa-bis (cytosine) detection
It influences
Experiment condition: guanine, adenine, uric acid, xanthine, hypoxanthine, cytimidine, uracil, thymus gland are taken respectively
Pyrimidine stock solution 5.0mL is separately added into the 6-thioguanine stock solution of 5.0mL in 50mL volumetric flask, then is separately added into
The fluorescence probe stock solution of 5.0mL, constant volume are configured to probe, and 6-thioguanine, each material concentration that detects all is 5.0 × 10- 5The solution of mol/L.The variation 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.
Other detectable substances have certain influence to the detection of fluorescence probe at 575nm, but very little is influenced at 525nm.This phenomenon is being schemed
It is more intuitive in 6b and Fig. 6 c.It can be seen that fluorescence probe have other substances interference in the case where, to 6-thioguanine according to
So there is specificity.
Claims (6)
1. a kind of novel fluorescence probe, which is characterized in that the fluorescence probe is EuIII- dtpa-bis (cytosine), tool
Have following structural formula:
2. the preparation method of novel fluorescence probe described in claim 1, which is characterized in that method is as follows:
1) diethylenetriamine pentaacetic acid, acetic anhydride and pyridine are taken, is uniformly mixed, at 60-70 DEG C, agitating and heating 22-25h is cooling
To room temperature, filtering, anhydrous ether washing is filtered, dry, obtains diethylenetriamine pentaacetic acid dianhydride (dtpaa)；
2) diethylenetriamine pentaacetic acid dianhydride (dtpaa), triethylamine, anhydrous DMF and cytimidine are taken, is uniformly mixed, in 95-105 DEG C
Under, agitating and heating 22-25h stands, is cooled to room temperature, filters, and it is bis- (cytimidine) to obtain diethylenetriamine pentaacetic acid-for vacuum drying
(dtpa-bis(cytosine))；
3) diethylenetriamine pentaacetic acid-bis- (cytimidines) is dissolved with the Tris-HCl buffer solution of pH=7.4, obtains dtpa-bis
(cytosine) solution washs Eu (NO with dtpa-bis (cytosine) solution3)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, and Eu is obtainedIII-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-is bis- (cytimidine): Eu (NO3)3·6H2O=40:1.
6. a kind of method for detecting 6-thioguanine, which is characterized in that method is as follows: by 6-thioguanine pH=7.4
The dissolution of Tris-HCl buffer solution, the described in claim 1 new of the pH=7.4 configured by Tris-HCl buffer solution is added
Type fluorescence probe EuIII- dtpa-bis (cytosine) observes the variation of fluorescence spectrum under the excitation wavelength of 288nm.
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| 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 |
| 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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| WO2007015168A2 (en) * | 2005-07-01 | 2007-02-08 | Dako Denmark A/S | Monomeric and polymeric linkers useful for conjugating biological molecules and other substances |
| CN105535991A (en) * | 2016-01-11 | 2016-05-04 | 上海交通大学 | Amphiphilic basic group conjugate nanometer particles for treating tumors and preparation method thereof |
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| WO2007015168A2 (en) * | 2005-07-01 | 2007-02-08 | Dako Denmark A/S | Monomeric and polymeric linkers useful for conjugating biological molecules and other substances |
| CN105535991A (en) * | 2016-01-11 | 2016-05-04 | 上海交通大学 | Amphiphilic basic group conjugate nanometer particles for treating tumors and preparation method thereof |
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| Title |
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| Design and synthesis of a novel lanthanide fluorescent probe (EuIII-dtpa-(bis)melamine) and application in melamine detection in milk products;Jiang X Q. et al.;《Sensors and Actuators B》;20160721;第238卷;第605-612页 |
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