CN109180744A - A kind of fluorescence probe detecting beta galactosidase - Google Patents
A kind of fluorescence probe detecting beta galactosidase Download PDFInfo
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- CN109180744A CN109180744A CN201811098563.3A CN201811098563A CN109180744A CN 109180744 A CN109180744 A CN 109180744A CN 201811098563 A CN201811098563 A CN 201811098563A CN 109180744 A CN109180744 A CN 109180744A
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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
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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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- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
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- 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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- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
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- 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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Abstract
The present invention provides a kind of fluorescence probe for detecting beta galactosidase, structural formulas are as follows:.Above-mentioned beta galactosidase probe can be applied to the content sensing detection of beta galactosidase in cell.As display aqueous solution in and intracellular beta galactosidase existing for specificity indicator.The present invention is that one kind is simple, and quickly, sensitive beta galactosidase specific detection agents have broad application prospects in biomolecule detection field.
Description
Technical field
The invention belongs to small-molecule fluorescent probe analysis detection fields, and in particular to a kind of quickly detection beta galactosidase
Fluorescence probe.
Background technique
Beta galactosidase (β-gal) is a kind of enzyme that beta galactose glycosides can be hydrolyzed into galactolipin and glucosides.With
Science and technology fast development, beta galactosidase environment, biology, medicine, chemistry, etc. fields using more and more.?
Field of food industry can hydrolyze the property of lactose using beta galactosidase to reduce the lactose content in dairy products.In life
Object field, beta galactosidase are a kind of genetic marker enzymes being widely used, and can be used to the transcriptional control for studying gene and base
Because of expression etc..Beta-galactosidase gene is most common reporter gene in genetic engineering, utilizes its expression product beta galactose
Glycosides enzyme carrys out the expression regulation of research purpose gene.The aging of the document discovery beta galactosidase and zooblast reported recently has
Close relationship.Therefore, medical research, gene diagnosis, in terms of, detectionofβ-galactosidaseactivity seems ten
Divide important.
Summary of the invention
Aiming at the problems existing in the prior art, the present invention provides a kind of fluorescence probe for detecting beta galactosidase, with
GCTPOC sloughs galactolipin group selectively as fluorogen, by beta galactosidase to realize to the glimmering of beta galactosidase
Light detection.
To achieve the above object, the present invention adopts the following technical scheme that.
A kind of fluorescence probe detecting beta galactosidase, referred to as R-GAL, structural formula are as shown in the formula (I):
Formula (I).
A kind of preparation method of above-mentioned fluorescence probe, comprising the following steps:
(1) 4- triamido ketone acid and 1,6- dihydroxy naphthlene is in trifluoroacetic acid, heating reflux reaction, and solvent is evaporated off and obtains compound 1:
；
(2) β-D- galactolipin pentaacetate and HBr are reacted at room temperature in acetic acid, and product isolates and purifies to obtain compound 2:
；
(3) compound 1 and compound 2 are in Na2SO4And Cs2CO3In the presence of in acetonitrile heat reaction, product isolate and purify to obtain change
Close object 3:
；
(4) compound 3 reacts at room temperature in methyl alcohol with sodium methoxide, and product isolates and purifies to obtain fluorescence probe:
。
In step (1), reaction temperature is 75 DEG C, reaction time 12h.
The reaction time is 1h in step (2).
In step (2), purification procedures are as follows: isometric methylene chloride and ice is added in product, and water phase is with two after layering
Chloromethanes extraction, organic layer is with NaHCO3It is washed respectively with saturated salt solution, then dry with anhydrous sodium sulfate, solvent is evaporated off.
In step (3), reaction temperature is 60 DEG C, and the reaction time is for 24 hours.
In step (3), purification procedures are as follows: product is evaporated off solvent and obtains crude product, then is separated with silicagel column, silica gel
Granular size is 200-300 mesh, and eluant, eluent is ethyl acetate/petroleum ether=1:2(v/v).
In step (4), reaction time 4h.
In step (4), purification procedures are as follows: product is evaporated off solvent and obtains crude product, then is separated with silicagel column, silica gel
Granular size is 200-300 mesh, and eluant, eluent is methylene chloride/methanol=10:1(v/v).
A kind of purposes of above-mentioned beta galactosidase probe, the fluorescence probe can be applied to β-half in solution or living cells
The detection of lactoside enzyme content.
The invention has the following advantages that
The synthesis of fluorescence probe of the invention only needs several steps that can complete, and last handling process is relatively easy；The probe can
To realize that the selectivity of beta galactosidase molecular probe quickly detects, and it is selective good, resist other molecule interference performances strong.
In addition, in the UV lamp it can be observed that fluorescence color enhancing, is a kind of fluorescence probe with the sensing function that adds lustre to.Based on it
Specific and significant color change, the reagent can be used as in display aqueous solution and existing for beta galactosidase in biological cell
Specificity indicator.So the present invention is that one kind is simple, quickly, sensitive beta galactosidase specific detection agents, in life
Object Molecular Detection field has broad application prospects.
Detailed description of the invention
Fig. 1 is 1 middle probe of embodiment1H NMR spectra；
Fig. 2 is the variation diagram that probe increases fluorogram with beta galactosidase concentration；
Fig. 3 is selective fluorogram of the probe to different ions and molecule；
Fig. 4 is selective histogram of the probe to different ions and molecule；
Fig. 5 is probe solution colour comparison diagram before and after beta galactosidase addition；
Fig. 6 is the fluorescence imaging figure of probe application beta galactosidase in cell.
Specific embodiment
Below with reference to embodiment and attached drawing, the present invention will be further described, but the present invention is not by the limit of following embodiments
System.
The synthesis of 1 fluorescence probe of embodiment
(1) synthesis of compound 1:
4- triamido ketone acid (1 eq), 1,6- dihydroxy naphthlene (1 eq) are dissolved in trifluoroacetic acid, and 75 DEG C are heated to reflux 12 h, decompression
It is spin-dried for solvent and obtains compound 1, yield 92%；
(2) synthesis of compound 2:
β-D- galactolipin pentaacetate (1 eq, 3.90 g), is dissolved in HBr(45%, 10mL), AcOH(5 mL) in, it is stirred at room temperature
1h.Methylene chloride (20 mL) and ice (20 g), layering is added, water phase is extracted with dichloromethane, NaHCO3(30 mL), saturation food
Salt water (30 mL) washing, anhydrous sodium sulfate is dry, and decompression is spin-dried for solvent and obtains compound 2, yield 95%；
(3) synthesis of compound 3:
Compound 1(1 eq), Na2SO4(2.5 eq), Cs2CO3(5 eq) is dissolved in ACN, and compound 2(1.5 eq) is slowly added
Enter in above-mentioned reaction solution, 60 DEG C are reacted 24 hours, and decompression is spin-dried for solvent and obtains crude product, and is separated with silicagel column, silica gel
Grain size is 200-300 mesh, and eluant, eluent proportion is ethyl acetate/petroleum ether=1:2, obtains compound 3, yield 55%；
(4) synthesis of probe R-GAL:
Compound 3(1 eq) it is dissolved in methanol, the sodium methoxide (3 eq) for being dissolved in methanol is added, reacts at room temperature 4 hours, decompression is spin-dried for
Solvent obtains crude product, and is separated with silicagel column, silica gel particle size be 200-300 mesh, eluant, eluent proportion be methylene chloride/
Methanol=10:1, obtains fluorescence probe, yield 75%,1HNMR spectrogram is as shown in Figure 1.
2 fluorescence probe of embodiment increases the variation of fluorogram with beta galactosidase concentration
Fluorescence probe prepared by Example 1 is dissolved in dimethyl sulfoxide (DMSO), and 1 mmol/L stock solution is made.From stock solution
20 μ L of middle taking-up are added in the centrifuge tube of 5 mL, and the beta galactosidase standard solution of not commensurate (0-14 U) is added
(80 U/mL) is diluted to 2 mL with PBS buffer solution (0.1 mol/L, pH=7.4) solution, measures its photoluminescent property (excitation wave
A length of 540nm).Fluorescence spectrum is as shown in Figure 2.From Figure 2 it can be seen that the increase fluorescence with beta galactosidase additional amount gradually increases
By force.
Selectivity of 3 fluorescence probe of embodiment to different molecular or ion
It is added in the centrifuge tube of 5 mL from 20 μ L are taken out in embodiment 2 in fluorescence probe stock solution, is separately added into competition point
Substandard solution (100 eq), it is one of that beta galactosidase solution (4 U) is added, the fluorescence hair of solution is detected after 10 min
Spectrum change is penetrated, by Fig. 3 and Fig. 4 it can be found that the fluorescence of other ion pair probes R-Gal has little effect, and β-gala
The addition of glucosides enzyme solutions significantly increases the fluorescence of probe R-Gal.
Visual retrieval of 4 fluorescence probe of embodiment to beta galactosidase
It is added in the sample cell of 5mL from 30 μ L are taken out in embodiment 2 in fluorescence probe stock solution, beta galactose glycosides is added
Enzyme standard solution (40 U), beta galactosidase can make the aqueous solution of fluorescence probe that apparent color change, solution face occur
Discoloration is deep (Fig. 5).Along with the beta galactosidase inducing solution color change of macroscopic under ultraviolet lamp, explanation is a kind of tool
There is the fluorescence probe for the sensing function that adds lustre to.
Fluorescence imaging of 5 fluorescence probe of embodiment to endogenous cellular beta galactosidase
The probe application obtained in embodiment 1 carries out endogenic beta galactosidase in OVCAR-3 and HeLa cell
Fluorescence imaging, specific steps are as follows: 20 μM of probe DMSO solutions are added to give birth to HeLa cell and OVCAR-3
It is imaged after cultivating 50 min in cell culture fluid in carbon dioxide incubator with Laser Scanning Confocal Microscope, as shown in fig. 6, its
In, be a) concentration and probe concentration it is that 1 mM is added 20 μM and cultivates light field figure after 50 min, b into OVCAR-3 cell) for concentration and probe concentration
The stacking chart for being a and b for 20 μM of the 1 mM addition fluorescence imaging figures into OVCAR-3 cell after culture 50min, c).It d) is spy
Needle concentration be 1 mM be added 20 μM of light field figures cultivated into HeLa cell after 50 min, e) be concentration and probe concentration be 1 mM addition
20 μM into HeLa cell cultivate 50min after fluorescence imaging figure, f) be d and e stacking chart.It will be appreciated from fig. 6 that being with 561nm
Exciting light, almost without red fluorescence in HeLa cell, and OVCAR-3 cell is observed that strong red fluorescence, explanation
This fluorescence probe can carry out fluorescence imaging to endogenic beta galactosidase.
Claims (7)
1. a kind of fluorescence probe for detecting beta galactosidase, structural formula are as shown in the formula (I):
Formula (I).
2. a kind of preparation method of fluorescence probe as described in claim 1, which comprises the following steps:
(1) 4- triamido ketone acid and 1,6- dihydroxy naphthlene is in trifluoroacetic acid, heating reflux reaction, and solvent is evaporated off and obtains compound 1:
；
(2) β-D- galactolipin pentaacetate and HBr are reacted at room temperature in acetic acid, and product isolates and purifies to obtain compound 2:
；
(3) compound 1 and compound 2 are in Na2SO4And Cs2CO3In the presence of in acetonitrile heat reaction, product isolate and purify to obtain change
Close object 3:
；
(4) compound 3 reacts at room temperature in methyl alcohol with sodium methoxide, and product isolates and purifies to obtain fluorescence probe:
。
3. preparation method according to claim 2, which is characterized in that in step (1), reaction temperature is 75 DEG C, when reaction
Between be 12h；The reaction time is 1h in step (2)；In step (3), reaction temperature is 60 DEG C, and the reaction time is for 24 hours；Step (4)
In, reaction time 4h.
4. preparation method according to claim 2, which is characterized in that in step (2), purification procedures are as follows: product adds
Enter isometric methylene chloride and ice, water phase is extracted with dichloromethane after layering, and organic layer is with NaHCO3With saturated common salt moisture
It does not wash, then dry with anhydrous sodium sulfate, solvent is evaporated off.
5. preparation method according to claim 2, which is characterized in that in step (3), purification procedures are as follows: product steams
It except solvent obtains crude product, then is separated with silicagel column, silica gel particle size is 200-300 mesh, and eluant, eluent is ethyl acetate/stone
Oily ether=1:2(v/v).
6. preparation method according to claim 2, which is characterized in that in step (4), purification procedures are as follows: product steams
It except solvent obtains crude product, then is separated with silicagel column, silica gel particle size is 200-300 mesh, and eluant, eluent is methylene chloride/first
Alcohol=10:1(v/v).
7. the application of beta galactosidase in a kind of fluorescence probe detection solution as described in claim 1 or living cells.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110256513A (en) * | 2019-06-12 | 2019-09-20 | 济南大学 | A kind of FRET-ICT type beta galactosidase fluorescence probe and the preparation method and application thereof |
| CN110845556A (en) * | 2019-11-27 | 2020-02-28 | 济南大学 | Target tumor β -galactosidase near-infrared fluorescent probe and preparation method thereof |
| CN111690403A (en) * | 2020-06-03 | 2020-09-22 | 济南大学 | Fluorescent probe for detecting beta-galactosidase and preparation method and application thereof |
| CN111778014A (en) * | 2019-04-04 | 2020-10-16 | 复旦大学 | Beta-galactosidase near-infrared fluorescent probe and preparation method and application thereof |
| CN113234111A (en) * | 2021-02-22 | 2021-08-10 | 西北大学 | Fluorescent probe for simultaneously detecting beta-galactosidase and lysosome pH, and preparation method and application thereof |
| CN114605343A (en) * | 2022-03-14 | 2022-06-10 | 吉林大学 | Fluorescent group LAN-OH, fluorescent sensor LAN-beta gal, preparation method and application thereof |
| WO2023166801A1 (en) * | 2022-03-02 | 2023-09-07 | 国立大学法人 東京大学 | Novel time-resolved fluorescence imaging probe |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111778014A (en) * | 2019-04-04 | 2020-10-16 | 复旦大学 | Beta-galactosidase near-infrared fluorescent probe and preparation method and application thereof |
| CN111778014B (en) * | 2019-04-04 | 2024-01-02 | 复旦大学 | Near infrared fluorescent probe of beta-galactosidase, preparation method and application thereof |
| CN110256513A (en) * | 2019-06-12 | 2019-09-20 | 济南大学 | A kind of FRET-ICT type beta galactosidase fluorescence probe and the preparation method and application thereof |
| CN110845556A (en) * | 2019-11-27 | 2020-02-28 | 济南大学 | Target tumor β -galactosidase near-infrared fluorescent probe and preparation method thereof |
| CN111690403A (en) * | 2020-06-03 | 2020-09-22 | 济南大学 | Fluorescent probe for detecting beta-galactosidase and preparation method and application thereof |
| CN111690403B (en) * | 2020-06-03 | 2021-09-24 | 济南大学 | Fluorescent probe for detecting beta-galactosidase and preparation method and application thereof |
| CN113234111A (en) * | 2021-02-22 | 2021-08-10 | 西北大学 | Fluorescent probe for simultaneously detecting beta-galactosidase and lysosome pH, and preparation method and application thereof |
| WO2023166801A1 (en) * | 2022-03-02 | 2023-09-07 | 国立大学法人 東京大学 | Novel time-resolved fluorescence imaging probe |
| CN114605343A (en) * | 2022-03-14 | 2022-06-10 | 吉林大学 | Fluorescent group LAN-OH, fluorescent sensor LAN-beta gal, preparation method and application thereof |
| CN114605343B (en) * | 2022-03-14 | 2022-11-18 | 吉林大学 | Fluorescent group LAN-OH, fluorescent sensor LAN-beta gal, preparation method and application thereof |
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