CN108148573A - A kind of fluorescence probe for detecting lysosomal pH and its synthetic method and application - Google Patents
A kind of fluorescence probe for detecting lysosomal pH and its synthetic method and application Download PDFInfo
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- CN108148573A CN108148573A CN201810099765.3A CN201810099765A CN108148573A CN 108148573 A CN108148573 A CN 108148573A CN 201810099765 A CN201810099765 A CN 201810099765A CN 108148573 A CN108148573 A CN 108148573A
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Abstract
The present invention provides a kind of fluorescence probes for detecting detection lysosomal pH, contain morpholine group and piperazine group；The fluorescence probe can be under different pH environment, by the protonation of naphthalimide part morpholine group and piperazine group, form of the generation with different fluorescent emission abilities passes through the pH for detecting the fluorescence intensity of different shape to measure in living cells lysosome, it is specific high, it is anti-interference；The probe synthesis technology is simple and practicable, and raw material is cheap and easy to get, and manufacturing cost is low, easy to spread.
Description
Technical field
The invention belongs to organic molecule fluorescence probe fields, and in particular to a kind of detection based on naphthalimide derivative
PH two-photon fluorescence probes and its synthetic method in cytase body.
Background technology
Intracellular ph value as metabolism an important parameter, cell cycle regulating, cell proliferation with withering
Die, played in ion transport, enzymatic activity, calcium regulation and control, the regulation and control of the cell physiologicals such as contraction of muscle and pathologic process it is very important
Effect.Meanwhile the endocytosis of cell and the internalization of receptors ligand are similarly influenced by internal pH.Internal pH
Exception can cause the physiological dysfunction, enzyme and protein active of organism inner cell and histoorgan to be suppressed, human body
Immunity degradation finally causes the diseases such as inflammation, cancer and Alzheimer's disease.Research shows that at Apoptosis initial stage, cancer
Cell would generally generate intracellular acidification, therefore intracellular acidification has become an important early stage of Apoptosis
Feature.In addition, internal pH variation is closely related with Apoptosis simultaneously.Therefore, internal pH is carried out accurately carrying out former
Position monitoring in real time helps to study the physiology and pathologic process of cell from cellular level.
Lysosome (lysosomes) is a kind of organelle in eukaryocyte, usually has the coated cryptomere knot of monofilm
Structure, mostly spherical, about 0.025-0.8 microns of size.Lysosome inner protein enzyme, nuclease, lipase and sulfuric acid lipase etc. are permitted
Multienzyme is the macromolecular substances such as intracellular digestive organs, the various protein of decomposable asymmetric choice net, has the function of to dissolve or digest.It is molten
Degrading enzyme in enzyme body is under mildly acidic conditions（PH is about 5）Play optimum activity, but when the pH exceptions in lysosome by
It changes in the activity of various degrading enzymes, dissolving digestive function can be influenced to different extents, and then leads to rheumatoid
The generation of the diseases such as arthritis, tumour.Therefore, the pH value for quickly and accurately detecting intracellular lysosome can be research relevant physiological
And the relevant diseases such as pathologic process and prevention arthritis, cancer provide important information.
Fluorescence imaging analysis method is with high sensitivity, selectivity is good, response is rapid, simple operation and other advantages, and to thin
Born of the same parents do not damage substantially, are widely used for the detection of various biological micromolecules.It is presently used for the fluorescence of detection intracellular ph value
Probe is also rapidly developed, some of commercializations.But lysosomal pH report at present and commercialization
Fluorescence probe does not have lysosome targeting mostly, generally has accordingly to all cells.Therefore develop it is new have it is highly selective,
Highly sensitive, photostability and permeable membrane are good, and the pH fluorescence probes with lysosome targeting have great importance.
Invention content
For problems of the prior art, it is molten that the present invention provides a kind of detection cell based on naphthalimide derivative
PH two-photon fluorescence probes in enzyme body, the probe is selectively good, high sensitivity.
It is a further object of the present invention to provide a kind of synthetic methods of above-mentioned fluorescence probe, and raw material is easy to get, synthesis step letter
Single, high income.
To achieve the above object, the present invention adopts the following technical scheme that.
A kind of fluorescence probe for detecting lysosomal pH, structural formula such as formula（I）It is shown：
Formula（I）.
A kind of preparation method of the fluorescence probe of above-mentioned detection lysosomal pH, includes the following steps：
Compound 1 and hydroxyethyl piperazine are dissolved in glycol monoethyl ether, reaction is heated in the presence of potassium carbonate, is divided after reaction
From product is purified to obtain, that is, detect the fluorescence probe of lysosomal pH：
Compound 1.
The compound 1 and the molar ratio of hydroxyethyl piperazine are 1:1-1.2.
The reaction temperature is 120 DEG C, reaction time 4-6h.
The purification procedures are：Reaction solution obtains solid except solvent, then with dichloromethane:Methanol=30:1 it is mixed
Bonding solvent carries out column chromatography purifying for eluent.
The preparation method of the compound 1 is as follows：
Bromo- 1, the 8- naphthalic anhydrides of 4- and aminoethyl morpholine make solvent with ethyl alcohol, in 80 DEG C of reflux；Then by reaction solution cooling chamber
Precipitation is precipitated in temperature, filters, drying, column chromatography is crossed by eluent of dichloromethane：
。
Application of the above-mentioned fluorescence probe in Cytolysosome pH is detected.
Fluorescence probe of the present invention can pass through naphthalimide part morpholine group and piperazine collection under different pH environment
The protonation of group, form of the generation with different fluorescent emission abilities, work is measured by detecting the fluorescence intensity of different shape
PH in Cytolysosome.
Beneficial effects of the present invention are：
The two-photon fluorescence probe of pH can be obtained through chemical synthesis in detection biological cell and lysosome of the present invention, be synthesized
Simple for process, raw material is cheap and easy to get, and manufacturing cost is low, easy to spread.
It is of the present invention detection biological cell and lysosome in pH two-photon fluorescence probe have high specific, into
It is not interfered by other components in the corresponding pH detection process of row, is detected available for pH in lysosome in living cells, had wide
Application prospect.
The fluorescence probe high sensitivity of the intracellular lysosomal pH of detection of the present invention, has good fluorescence emission
Spectral property（400-500 nm）, intracellular lysosomal pH measure is carried out by drawing standard curve, can be realized in cell
The purpose that pH is quick and precisely detected.
Description of the drawings
Fig. 1 is fluorescence probe1H NMR spectras；
Fig. 2 is fluorescence spectrum of the fluorescence probe under condition of different pH；
Fig. 3 is fluorescence probe to the fluorescence intensity of different pH and linear relationship range；
Fig. 4 is the fluorescence spectrum after fluorescence probe is reacted with different material；
Fig. 5 is that fluorescence probe is imaged with common locations of the Lyso-Tracker Red in living cells；
Fig. 6 is the imaging of fluorescence probe living cells under condition of different pH.
Specific embodiment
With reference to embodiment and attached drawing, the present invention will be further described, but the present invention is not limited by following embodiments
System.
The synthesis of 1 fluorescence probe of embodiment
（1）By the bromo- 1,8- naphthalic anhydrides of 4-（1 mmol）And aminoethyl morpholine（1 mmol）Solvent is done with ethyl alcohol, is returned in 80 DEG C
Stream 2 hours；Then reaction solution is cooled down into room temperature, after precipitation is precipitated, filters, drying, chromatographic column is crossed by eluent of dichloromethane
Purifying, obtains compound 1；
（2）By compound 1（1 mmol）, hydroxyethyl piperazine（1 mmol）, potassium carbonate（0.2 mmol）And glycol monoethyl ether（10
mL）It is added in 50 mL single-necked flasks, is stirred 4 hours at 120 DEG C, the reaction was complete, is spin-dried for obtained solid after solvent with dichloro
Methane:Methanol=30:1 mixed solvent carries out column chromatography purifying for eluent, obtains 215 mg pale red products, as this hair
The bright detection organism and internal pH fluorescence probe, 49 % of yield,1H NMR spectras are shown in Fig. 1.
Response of 2 fluorescence probe of embodiment to pH
The probe compound obtained in embodiment 1 is dissolved with ethyl alcohol, it is molten that addition PBS buffer solution is configured to 5 μM of B-F probes bufferings
Liquid（Containing 5% ethyl alcohol）, it is respectively 2.0,2.5,3.0,3.5,4.0,4.5,5.0,5.5,6.0,6.5,7.0,7.5,8.0 to make pH,
8.5,9.0,9.5,10.0, totally 17；Then fluoroscopic examination is carried out（λEx = 450 nm）, calculate fluorescence intensity in each system；It is logical
The relationship of the fluorescence intensity intensity and pH at 531 nm of analysis is crossed, assesses response performance of the probe to pH（See Fig. 2 and Fig. 3）.
Fig. 2 shows the increase with hydroxy lamine concentration, and the fluorescence intensity at 531 nm of solution gradually enhances, and the fluorescence at 637nm is strong
Degree gradually weakens.Fig. 3 shows analytical solution pH in the range of 5.5-8.0, the linear relationship of fluorescence intensity and pH at 531nm,
Formula Y=336.3- 41.1X can be used（R = 0 .991）It represents, Y is fluorescence intensity, and X is pH value.
3 fluorescence probe of embodiment analyzes the specificity of pH
It is containing 5% ethyl alcohol, pH=7.4 and 5% ethyl alcohol, 5 μM of the probe B-F of each 21 parts of 5mL in pH=5.0 respectively to prepare two kinds
Then buffer solution sequentially adds Hcys, Na of a concentration of 10 mM of 50 μ L into the system respectively2S、Na2SO3、NO、H2O2、
HClO4、Cys、GSH、NaNO2, the analyte of interest such as Vc buffer solution.Then fluoroscopic examination is carried out（λEx = 450 nm）Each body
Fluorescence intensity in system；Assess interference of the different material to fluorescence probe solution（See Fig. 4）.As seen in Figure 4, molten
When liquid pH is 5.0 or 7.4, when adding in different metal ions and other small molecules, the fluorescence intensity of solution is basically unchanged, this expression
Testing result is not influenced substantially by other interfering substances.
Imaging of 4 fluorescence probe of embodiment in living cells
4.1 intracellular common locations
HeLa cells are placed on culture medium（DMEM culture mediums containing 10%BAS）In, condition is positioned over as 37 DEG C, 5% CO2With 20%
O2Incubator in cultivate 24-48h.With the fluorescence probe solution obtained in microsyringe extraction embodiment 1（10 μM）With
In culture medium of the lysosome location reagent Lyso-Tracker Red injections containing HeLa cells, continuation cultivates 30 in the incubator
min.PBS is used later（Phosphate buffer solution）Rinse culture cell 3 times, fluorescence probe λEx =561 nm, Lyso-Tracker
The λ of RedEx =647 nm carry out fluorescence imaging, as a result see Fig. 5.Under pH=7.4, the imaging of difference light field, probe（10 μM）
Green channel imaging, Lyso-Tracker Red are in red channel imaging and the superposition picture of three.The chart is bright, and both are glimmering
Light has good degree of overlapping, and probe of the invention is targeted with lysosome.
4.2 pairs of intracellular difference pH responses
HeLa cells are placed on culture medium（DMEM culture mediums containing 10%BAS）In, condition is positioned over as 37 DEG C, 5% CO2With 20%
O2Incubator in cultivate 24-48h.With the fluorescence probe solution obtained in microsyringe extraction embodiment 1（10 μM）Note
Enter in the culture medium containing HeLa cells, 30 min are cultivated in continuation in the incubator.Culture medium is blotted, it is each to add in 1 ml pH
For 4.5,5.5,6.5,7.5 B-F buffer solutions, 30 min are cultivated in continuation in the incubator.In λEx =561 nm carry out fluorescence
Imaging, detects green channel, as a result sees Fig. 6：With the increase of pH, cell fluorescence intensity continuously decreases, and shows that the probe can be used
PH in detection lysosome.
Claims (6)
1. a kind of fluorescence probe for detecting lysosomal pH, structural formula such as formula（I）It is shown：
Formula（I）.
2. a kind of preparation method of fluorescence probe as described in claim 1, includes the following steps：
Compound 1 and hydroxyethyl piperazine are dissolved in glycol monoethyl ether, reaction is heated in the presence of potassium carbonate, is divided after reaction
From product is purified to obtain, that is, detect the fluorescence probe of lysosomal pH：
Compound 1.
3. preparation method according to claim 2, which is characterized in that the molar ratio of compound 1 and hydroxyethyl piperazine is 1:
1-1.2。
4. preparation method according to claim 2, which is characterized in that the reaction temperature is 120 DEG C, reaction time 4-
6h。
5. preparation method according to claim 2, which is characterized in that the purification procedures are：Reaction solution removes solvent
Solid is obtained, then with dichloromethane:Methanol=30:1 mixed solvent carries out column chromatography purifying for eluent.
6. a kind of application of fluorescence probe as described in claim 1 in Cytolysosome pH is detected.
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Cited By (7)
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| CN108949161A (en) * | 2018-09-28 | 2018-12-07 | 台州学院 | A kind of Ratiometric fluorescent probe compound and application thereof for detecting hypobromous acid |
| CN109096189A (en) * | 2018-09-14 | 2018-12-28 | 济南大学 | The two-photon fluorescence probe of pH in a kind of detection endocytoplasmic reticulum |
| CN109776499A (en) * | 2019-03-19 | 2019-05-21 | 山东省医学科学院药物研究所（山东省抗衰老研究中心、山东省新技术制药研究所） | A kind of fluorescence probe for pH detection, synthetic method and its application |
| CN110143931A (en) * | 2019-06-18 | 2019-08-20 | 济南大学 | A kind of targeting lysosome detects fluorescence probe and its application of hydrogen sulfide |
| CN110372590A (en) * | 2019-07-29 | 2019-10-25 | 济南大学 | A kind of fluorescence probe and its preparation method and application detecting lysosomal pH |
| CN113429346A (en) * | 2021-06-21 | 2021-09-24 | 陕西科技大学 | Fluorescent probe for detecting polarity change of lysosome and preparation method and application thereof |
| CN114195839A (en) * | 2021-12-27 | 2022-03-18 | 济南大学 | Lysosome targeted fluorescent probe for glucuronidase detection and preparation thereof |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109096189A (en) * | 2018-09-14 | 2018-12-28 | 济南大学 | The two-photon fluorescence probe of pH in a kind of detection endocytoplasmic reticulum |
| CN108949161A (en) * | 2018-09-28 | 2018-12-07 | 台州学院 | A kind of Ratiometric fluorescent probe compound and application thereof for detecting hypobromous acid |
| CN108949161B (en) * | 2018-09-28 | 2021-03-16 | 台州学院 | Ratiometric fluorescent probe compound for detecting hypobromous acid and application thereof |
| CN109776499A (en) * | 2019-03-19 | 2019-05-21 | 山东省医学科学院药物研究所（山东省抗衰老研究中心、山东省新技术制药研究所） | A kind of fluorescence probe for pH detection, synthetic method and its application |
| CN109776499B (en) * | 2019-03-19 | 2021-06-15 | 山东省医学科学院药物研究所（山东省抗衰老研究中心、山东省新技术制药研究所） | Fluorescent probe for pH detection, and synthesis method and application thereof |
| CN110143931A (en) * | 2019-06-18 | 2019-08-20 | 济南大学 | A kind of targeting lysosome detects fluorescence probe and its application of hydrogen sulfide |
| CN110372590A (en) * | 2019-07-29 | 2019-10-25 | 济南大学 | A kind of fluorescence probe and its preparation method and application detecting lysosomal pH |
| CN110372590B (en) * | 2019-07-29 | 2021-10-26 | 济南大学 | Fluorescent probe for detecting pH of lysosome and preparation method and application thereof |
| CN113429346A (en) * | 2021-06-21 | 2021-09-24 | 陕西科技大学 | Fluorescent probe for detecting polarity change of lysosome and preparation method and application thereof |
| CN114195839A (en) * | 2021-12-27 | 2022-03-18 | 济南大学 | Lysosome targeted fluorescent probe for glucuronidase detection and preparation thereof |
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