CN105384789A - Amphiphilicity guanosine derivative, and preparation method therefor and application thereof in cytidine triphosphate sensing and recognition - Google Patents
Amphiphilicity guanosine derivative, and preparation method therefor and application thereof in cytidine triphosphate sensing and recognition Download PDFInfo
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Abstract
The present invention discloses an amphiphilicity guanosine derivative, a preparation method therefor and an application thereof in cytidine triphosphate sensing and recognition. The amphiphilicity guanosine derivative takes a hexadecyl chain as a tail group and a guanosine derivative as a head group, and has the features of biocompatibility and nontoxicity; the amphiphilicity guanosine derivative can be assembled with an amphiphilicity Tb (III) complex to form a vesicle type nano interface; characteristic fluorescence of the Tb (III) complex is greatly sensitized by an energy transfer process between a guanosine construction unit assembled on the interface and the Tb (III) complex; and when cytidine triphosphate which can be in complementary pairing with guanosine is added in the system, the energy transfer process between the guanosine derivative and the Tb (III) complex can be blocked drastically, thereby quenching the characteristic fluorescence of the Tb (III) complex and achieving selective recognition for the cytidine triphosphate. The amphiphilicity guanosine derivative provided by the present invention is simple in preparation method and mild in reaction condition, and can be used for cytidine triphosphate detection.
Description
Technical field
The invention belongs to supramolecule sensing material technical field, be specifically related to a kind of amphipathic guanosine derivative and preparation method thereof, and the application of vesicle type fluorescence supramolecule sensor in sensing identification cytidine adopting this amphipathic guanosine derivative to prepare.
Background technology
Biological negatively charged ion plays requisite effect in the normal operation of life entity, therefore has very important significance to their identification and detection.In life cells, most vital process has the participation of phosphate anion and derivative thereof.Such as: the reversible phosphorylation reaction of protein can be used as the activity that molecular switch carrys out Function protein matter, the Serine in protein structure, and Threonine and tyrosine phosphorylation process are the bases of protein transmission of information; Triphosaden (ATP) is the energy carrier in viable cell, extensively be present in nucleus, in plastosome, chloroplast(id) and cytoplsma matrix, and constantly mutual conversion forms Triphosaden system with adenosine diphosphate (ADP) (ADP), a large amount of energy can be discharged after phosphoric acid ester bond rupture in ATP molecule, these energy can in active cell thousands of react and drive cell movement; GTP (guanosine triphosphate) (GTP) take part in synthesis and the Chinese catalpa lemon acid circulation of RNA; Cytidine (CTP) can repair brain cell and neurocyte, helps treatment some disease neural, can promote the transport of cholesterol and fat, and play a significant role in the synthesis of nucleic acid and protein.In view of the vital role of phosphoric acid derivatives in vital movement, the efficient sensing of initiative energy also identifies that the sensing system of phosphate anion greatly will promote the understanding to molecular recognition process a lot of in life entity.And a lot of molecular recognition process all occurs on interface in life entity, such as: cell recognition process, enzyme catalysis process, outside stimulus signal transmission etc.Therefore, constructing function nano-interface, realize bioelectric interface function, differentiate the mechanism of action on interface and understand vital process and to simulate biological function most important to deep.
Be generally used for detection negatively charged ion and can use hydrogen bond action, electrostatic interaction and coordination.The sensor majority based on hydrogen bond action and electrostatic interaction reported at present only can work in organic solvent, and can not work under physiological environment, therefore greatly limit the practical application of the chemical sensor based on hydrogen bond action and electrostatic interaction.Compare with electrostatic interaction with hydrogen bond action, the outstanding advantages of coordination is to work under physiological environment based on the chemical sensor of coordination.Because coordinate bond has high bond energy, the interference of hydration can be overcome, and metal complexes has the sterie configuration of relative rigidity, be conducive to Selective recognition negatively charged ion.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of amphipathic guanosine derivative and preparation method thereof and the application in the identification of cytidine sensing.
Solving the problems of the technologies described above adopted technical scheme is that the structural formula of this amphipathic guanosine derivative is as follows:
The preparation method of above-mentioned amphipathic guanosine derivative is made up of following step:
1, syntheticcompoundofformulaⅰ
Take acetone as solvent, be 1:1 ~ 3:23 ~ 25 in molar ratio by guanosine and p-methyl benzenesulfonic acid, 2,2-methoxy propanes, stirring at normal temperature reacts 24 hours, and separation and purification product, obtains type I compound.
2, synthesis type II compound
With DMF (DMF) for solvent, under nitrogen protection; be 1:0.2 ~ 0.6:1 ~ 2 in molar ratio by type I compound, DMAP, palmitic anhydride; normal-temperature reaction 24 ~ 48 hours, separation and purification product, obtains formula II compound.
3, synthesis type III compound
It is in the aqueous formic acid of 50% that formula II compound is dissolved in massfraction, and the mol ratio of formula II compound and formic acid is 1:1.5 ~ 3, and 60 ~ 70 DEG C of heated and stirred 2 ~ 3 hours, add NaOH aqueous solution neutralization reaction liquid, separation and purification product, obtain formula III compound.
4, synthesizing amphipathic guanosine derivative
Take DMF as solvent, under nitrogen protection, be 1:3 ~ 5:0.2 ~ 0.6 in molar ratio by formula III compound, Succinic anhydried, DMAP, normal-temperature reaction 24 ~ 48 hours, separation and purification product, obtains amphipathic guanosine derivative.
In above-mentioned steps 2, the mol ratio of preferred type I compound and DMAP, palmitic anhydride is 1:0.5:1.
In above-mentioned steps 3, the mol ratio of preferred formula II compound and formic acid is 1:2.
In above-mentioned steps 4, the mol ratio of preferred formula III compound and Succinic anhydried, DMAP is 1:4:0.5.
The purposes of the amphipathic guanosine derivative of the present invention in sensing identification cytidine, concrete grammar is as follows:
1, amphipathic Tb (III) title complex being added 10mmol/LpH value is in the 4-hydroxyethyl piperazine ethanesulfonic acid buffered soln of 7.4,1 ~ 3 hour is incubated at 50 ~ 60 DEG C, naturally cool to normal temperature, normal temperature leaves standstill 8 ~ 12 hours, obtains the 100 μm of amphipathic Tb of ol/L (III) complex solutions.
The structural formula of above-mentioned amphipathic Tb (III) title complex is as follows:
2, amphipathic guanosine derivative being added 10mmol/LpH value is in the 4-hydroxyethyl piperazine ethanesulfonic acid buffered soln of 7.4,1 ~ 3 hour is incubated at 50 ~ 60 DEG C, naturally cool to normal temperature, normal temperature leaves standstill 8 ~ 12 hours, obtains 200 μm of amphipathic guanosine derivative solution of ol/L.
3, the amphipathic guanosine derivative solution of 200 μm of ol/L that the 100 μm of amphipathic Tb of ol/L (III) complex solutions step 1 obtained and step 2 obtain is 2:1 mixing by volume, 60 DEG C are incubated 1 ~ 3 hour, naturally cool to normal temperature, dynamically mixed vesica aggregate.
4, in the dynamic mixing vesica aggregate of step 3, add cytidine standard model, measure the fluorescence intensity of the corresponding system of different concns cytidine by fluorescence spectrophotometer, draw 1-I/I
0be worth the typical curve with cytidine change in concentration.
5, the fluorescence intensity of testing sample is measured, according to testing sample 1-I/I according to the method for step 4 by fluorescence spectrophotometer
0value, the linear equation of combined standard curve can highly selective identification cytidine determine the concentration of cytidine in testing sample.
Compared with prior art, the beneficial effect that has of the present invention is as follows:
1, the amphipathic guanosine derivative of the present invention has the feature of nontoxicity, biocompatibility, and it can form the vesicle type supramolecule sensing interface of Stability Analysis of Structures, size uniformity with the self-assembly in aqueous phase of amphipathic Tb (III) title complex.By the theory of Supramolecular Assembling, realize energy trasfer therebetween, avoid complicated tediously long synthesis.Using this supramolecule sensing interface as sensing platform, the supramolecule sensing interface of high-sequential is utilized to have molecular conecentration on pre-organized structure, interface far above body phase, be conducive to the feature that collaborative complexing has the negatively charged ion of multiple binding site, be expected to obtain application in raising sensor over-all properties.
2, the present invention utilizes cytidine series of nucleotides different from amphipathic guanosine derivative hydrogen bond formation ability, makes the Tb on its surface
3+ion fluorescence quencher degree is different, when add in system can cytidine with guanosine complementary pairing time, then significantly can block the energy transfer process of guanosine derivative and Tb (III) title complex, thus the characteristic fluorescence of quencher Tb (III) title complex, thus achieve the Selective recognition to cytidine.
3, the preparation method of the amphipathic guanosine derivative of the present invention is simple, and reaction conditions is gentle.
Accompanying drawing explanation
Fig. 1 is the grain size distribution that amphipathic guanosine derivative and amphipathic Tb (III) title complex are total to assembly system.
Fig. 2 is the transmission electron microscope figure that amphipathic guanosine derivative and amphipathic Tb (III) title complex are total to assembly system.
Fig. 3 is the fluorescence spectrum figure of fluorescence intensity with cytidine change in concentration that amphipathic guanosine derivative and amphipathic Tb (III) title complex are total to assembly system.
Fig. 4 is the linear diagram of relative intensity of fluorescence with cytidine change in concentration that amphipathic guanosine derivative and amphipathic Tb (III) title complex are total to assembly system.
Fig. 5 is amphipathic guanosine derivative and amphipathic Tb (III) the title complex relative intensity of fluorescence comparison diagram of assembly system in different anions system altogether.
Embodiment
Below in conjunction with drawings and Examples, the present invention is described in more detail, but protection scope of the present invention is not limited only to these embodiments.
Embodiment 1
1, syntheticcompoundofformulaⅰ
3.5g (12mmol) guanosine is dissolved in 140mL acetone, then 2.34g (12mmol) p-methyl benzenesulfonic acid (TsOH), 35mL (284mmol) 2 is added, 2-methoxy propane, stirring at normal temperature reacts 24 hours, remove acetone under reduced pressure after reaction terminates, add 25mL distilled water and stir and add 1.038gNaHCO in batches
3solid, stirring at normal temperature 2 hours, more dropwise add the saturated NaHCO of 25mL
3the aqueous solution stirs 2 hours, suction filtration, then washes, and after repeating 2 ~ 3 times, the vacuum-drying of gained solid matter is obtained white powdery solids, i.e. type I compound, reaction equation is as follows:
The structural characterization data of gained type I compound are:
1h-NMR (600MHz, DMSO, Me
4si): 10.69 (1H, NH), 7.92 (1H, CHN), 6.52 (2H, NH
2), 5.93 (1H, CHN), 5.18 (1H, OCHCH
2oH), 5.04 (1H, CHCHO), 4.97 (1H, CHCHO), 4.11 (2H, CHCH
2oH), 1.51 (3H, CH
3), 1.32 (3H, CH
3).
2, synthesis type II compound
Under nitrogen protection, 1.214g (3.75mmol) type I compound is dissolved in 70mLDMF, then 0.092g (0.75mmol) DMAP (DMAP) is added, 1.856g (3.75mmol) palmitic anhydride, stirring at normal temperature reacts 48 hours, remove DMF under reduced pressure, 30mL sherwood oil reflux is added 1 hour in thick product, suction filtration, pillar layer separation (eluent is the volume ratio of methylene dichloride and methyl alcohol is the mixed solution of 1:1), evaporate to dryness, the vacuum-drying of gained solid matter is obtained white powdery solids, i.e. formula II compound, reaction equation is as follows:
The structural characterization data of gained formula II compound are:
1h-NMR (600MHz, DMSO, Me
4si): 10.76 (1H, NH), 7.86 (1H, CHN), 6.58 (2H, NH
2), 6.02 (1H, CHN), 5.25 (1H, OCHCH
2o), 5.13 (1H, OCHCHO), 4.25 (2H, OCH
2cH), 4.12 (1H, COCHCH), 2.26 (2H, OCCH
2), 1.51 (2H, CH
2), 1.22 (24H, (CH
2)
12), 0.85 (3H, CH
3).
3, synthesis type III compound
It is in the aqueous formic acid of 50% that 1.5g (2.6mmol) formula II compound is dissolved in 90mL massfraction, 70 DEG C of heated and stirred 2 hours, suction filtration, in thick product, add 30mL distilled water, stirring at normal temperature 1 hour, then add the pH value to 7 that the 1mmol/LNaOH aqueous solution regulates reaction solution, suction filtration, the vacuum-drying of gained solid matter is obtained white powdery solids, i.e. formula III compound, reaction equation is as follows:
The structural characterization data of gained formula III compound are:
1h-NMR (600MHz, DMSO, Me
4si) 10.65 (1H, NH), 7.85 (1H, CHN), 6.48 (2H, NH
2), 5.71 (1H, CHN), 5.53 (1H, OCHCH
2o), 5.30 (1H, CHOH), 4.43 (1H, CHOH), 4.27 (1H, OH), 4.15 (2H, CHCH
2o), 4.01 (1H, OH), 2.30 (2H, CH
2cO), 1.48 (2H, CH
2)), 1.22 (24H, (CH
2)
12), 0.86 (3H, CH
3).
4, synthesizing amphipathic guanosine derivative
Under nitrogen protection, 1.0g (1.9mmol) formula III compound is dissolved in 90mLDMF, adds 0.76g (7.6mmol) Succinic anhydried, 0.046g (0.38mmol) DMAP, normal-temperature reaction 48 hours.DMF is removed under reduced pressure after reaction terminates, add 25mL tetracol phenixin stirring at normal temperature after 2 hours, suction filtration, pillar layer separation (eluent is the volume ratio of methylene dichloride and methyl alcohol is the mixed solution of 1:5), evaporate to dryness, the vacuum-drying of gained solid matter is obtained white powdery solids, i.e. amphipathic guanosine derivative, reaction equation is as follows:
The structural characterization data of the amphipathic guanosine derivative of gained are:
1h-NMR (600MHz, CDCl
3, Me
4si): 10.78 (1H, NH), 7.84 (1H, CHN), 6.57 (2H, NH
2), 6.01 (1H, OCHN), 5.26 (1H, OCHCH
2), 5.08 (1H, OCHCHO), 4.19 (2H, CHCH
2o), 4.05 (1H, OCHCHO), 3.30 (4H, CH
2cH
2cOOH), 2.26 (4H, CH
2cH
2cOOH), 2.21 (2H, CH
2cO), 1.32 (2H, CH
2), 1.23 (24H, (CH
2)
12), 0.85 (3H, CH
3).
Embodiment 2
The purposes of amphipathic guanosine derivative in sensing identification cytidine of embodiment 1, concrete grammar is as follows:
1, amphipathic Tb (III) title complex being added 10mmol/LpH value is in the 4-hydroxyethyl piperazine ethanesulfonic acid buffered soln of 7.4,1 ~ 3 hour is incubated at 50 ~ 60 DEG C, naturally cool to normal temperature, normal temperature leaves standstill 8 ~ 12 hours, obtains the 100 μm of amphipathic Tb of ol/L (III) complex solutions.
The structural formula of above-mentioned amphipathic Tb (III) title complex is as follows:
2, amphipathic guanosine derivative being added 10mmol/LpH value is in the 4-hydroxyethyl piperazine ethanesulfonic acid buffered soln of 7.4,1 ~ 3 hour is incubated at 50 ~ 60 DEG C, naturally cool to normal temperature, normal temperature leaves standstill 8 ~ 12 hours, obtains 200 μm of amphipathic guanosine derivative solution of ol/L.
3, the amphipathic guanosine derivative solution of 200 μm of ol/L that the 100 μm of amphipathic Tb of ol/L (III) complex solutions step 1 obtained and step 2 obtain is 2:1 mixing by volume, 60 DEG C are incubated 1 ~ 3 hour, naturally cool to normal temperature, dynamically mixed vesica aggregate.Adopt dynamic light scattering, transmission electron microscopy Electronic Speculum to characterize the vesica pattern formed respectively, the results are shown in Figure 1 ~ 2.As seen from the figure, amphipathic guanosine derivative and amphipathic Tb (III) title complex form the spherical vesicles aggregate of size uniformity in buffered soln, and its mean diameter is 255nm.
4, in the dynamic mixing vesica aggregate of step 3, cytidine standard model is added, the concentration of cytidine in gained mixed solution is made to be 0,10,20,30,40,50,60 μm of ol/L respectively, adopt fluorescence spectrophotometer maximum excitation wavelength be 245nm, emission wavelength is the fluorescence intensity that different concns cytidine correspondence system is measured at 545nm place, the results are shown in Figure 3, draw 1-I/I
0be worth the typical curve with cytidine change in concentration, the results are shown in Figure 4.
As seen from Figure 4, the fluorescence intensity of this system along with cytidine concentration in system increase change clearly, illustrate amphipathic Tb (III) title complex and amphipathic guanosine derivative doping system very high to the detection sensitivity of cytidine.Wherein, cytidine when concentration is 0 ~ 60 μm of ol/L, 1-I/I
0value is linear with cytidine concentration, and linear equation is:
y＝0.0006+0.007x
In formula, y is 1-I/I
0value, x is cytidine concentration, and correlation coefficient r is 0.99, from relation conefficient, 1-I/I
0value is fine with the linear relationship of cytidine concentration.
5, the fluorescence intensity of testing sample is measured, according to testing sample 1-I/I according to the method for step 4 by fluorescence spectrophotometer
0value, the linear equation of combined standard curve can highly selective identification cytidine determine the concentration of cytidine in testing sample.
In order to prove beneficial effect of the present invention, contriver adopt the method for embodiment 2 respectively to concentration be the cytidine (1) of 60 μm of ol/L, cytidine diphosphate (CDP) (2), monophosphate cytidine (3), uridine triphosphate (4), thymidine triphosphate (5), trisodium phosphate (6), Tri sodium Phosphate (7) maximum excitation wavelength be 245nm, emission wavelength is that fluorescence intensity is measured at 545nm place, test result is shown in Fig. 5.As seen from Figure 5, in these 7 kinds of anion systems, obvious quencher can be there is due to hydrogen bond formation effect in cytidine series of nucleotides, and other anion fluorescent Strength Changes are more weak, the selectivity that the amphipathic guanosine derivative of the present invention is very high to cytidine nucleotide is described, and more remarkable to the responsiveness of cytidine, accordingly, achieve the Selective recognition to cytidine.
Claims (6)
1. an amphipathic guanosine derivative, is characterized in that the structural formula of this amphipathic guanosine derivative is as follows:
2. a preparation method for amphipathic guanosine derivative according to claim 1, is characterized in that it is made up of following step:
(1) syntheticcompoundofformulaⅰ
Take acetone as solvent, be 1:1 ~ 3:23 ~ 25 in molar ratio by guanosine and p-methyl benzenesulfonic acid, 2,2-methoxy propanes, stirring at normal temperature reacts 24 hours, and separation and purification product, obtains type I compound;
(2) synthesis type II compound
Taking DMF as solvent, under nitrogen protection, is 1:0.2 ~ 0.6:1 ~ 2 by type I compound, DMAP, palmitic anhydride in molar ratio, normal-temperature reaction 24 ~ 48 hours, and separation and purification product, obtains formula II compound;
(3) synthesis type III compound
It is in the aqueous formic acid of 50% that formula II compound is dissolved in massfraction, and the mol ratio of formula II compound and formic acid is 1:1.5 ~ 3, and 60 ~ 70 DEG C of heated and stirred 2 ~ 3 hours, add NaOH aqueous solution neutralization reaction liquid, separation and purification product, obtain formula III compound;
(4) synthesizing amphipathic guanosine derivative
Take DMF as solvent, under nitrogen protection, be 1:3 ~ 5:0.2 ~ 0.6 in molar ratio by formula III compound, Succinic anhydried, DMAP, normal-temperature reaction 24 ~ 48 hours, separation and purification product, obtains amphipathic guanosine derivative.
3. the preparation method of amphipathic guanosine derivative according to claim 2, is characterized in that: in described step (2), and the mol ratio of type I compound and DMAP, palmitic anhydride is 1:0.5:1.
4. the preparation method of amphipathic guanosine derivative according to claim 2, is characterized in that: in described step (3), and the mol ratio of formula II compound and formic acid is 1:2.
5. amphipathic guanosine derivative preparation method according to claim 2, is characterized in that: in described step (4), and the mol ratio of formula III compound and Succinic anhydried, DMAP is 1:4:0.5.
6. the purposes of amphipathic guanosine derivative according to claim 1 in sensing identification cytidine, its recognition methods is as follows:
(1) amphipathic Tb (III) title complex being added 10mmol/LpH value is in the 4-hydroxyethyl piperazine ethanesulfonic acid buffered soln of 7.4,1 ~ 3 hour is incubated at 50 ~ 60 DEG C, naturally cool to normal temperature, normal temperature leaves standstill 8 ~ 12 hours, obtains the 100 μm of amphipathic Tb of ol/L (III) complex solutions;
The structural formula of above-mentioned amphipathic Tb (III) title complex is as follows:
(2) amphipathic guanosine derivative being added 10mmol/LpH value is in the 4-hydroxyethyl piperazine ethanesulfonic acid buffered soln of 7.4,1 ~ 3 hour is incubated at 50 ~ 60 DEG C, naturally cool to normal temperature, normal temperature leaves standstill 8 ~ 12 hours, obtains 200 μm of amphipathic guanosine derivative solution of ol/L;
(3) the amphipathic guanosine derivative solution of 200 μm of ol/L that the 100 μm of amphipathic Tb of ol/L (III) complex solutions step (1) obtained and step (2) obtain is 2:1 mixing by volume, 60 DEG C are incubated 1 ~ 3 hour, naturally cool to normal temperature, dynamically mixed vesica aggregate;
(4) in the dynamic mixing vesica aggregate of step (3), add cytidine standard model, measure the fluorescence intensity of the corresponding system of different concns cytidine by fluorescence spectrophotometer, draw 1-I/I
0be worth the typical curve with cytidine change in concentration;
(5) fluorescence intensity of testing sample is measured, according to testing sample 1-I/I according to the method for step (4) by fluorescence spectrophotometer
0value, the linear equation of combined standard curve can highly selective identification cytidine determine the concentration of cytidine in testing sample.
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| CN109632740A (en) * | 2018-12-26 | 2019-04-16 | 商丘师范学院 | Detection method, probe and the preparation method of prostate cancer marker citric acid |
| CN110016146A (en) * | 2019-05-10 | 2019-07-16 | 华东理工大学 | A kind of preparation method and application of magnetic/functionalized rare-earth fluorescent probe solution |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109632740A (en) * | 2018-12-26 | 2019-04-16 | 商丘师范学院 | Detection method, probe and the preparation method of prostate cancer marker citric acid |
| CN109632740B (en) * | 2018-12-26 | 2021-05-11 | 商丘师范学院 | Method for detecting citric acid in aqueous solution |
| CN110016146A (en) * | 2019-05-10 | 2019-07-16 | 华东理工大学 | A kind of preparation method and application of magnetic/functionalized rare-earth fluorescent probe solution |
| CN110016146B (en) * | 2019-05-10 | 2021-08-06 | 华东理工大学 | Preparation method and application of magnetic functionalized rare earth fluorescent probe solution |
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