CN108250197A - The fluorescence probe and its synthetic method of a kind of biological sulfhydryl compound of highly sensitive detection and application - Google Patents
The fluorescence probe and its synthetic method of a kind of biological sulfhydryl compound of highly sensitive detection and application Download PDFInfo
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- CN108250197A CN108250197A CN201810228592.0A CN201810228592A CN108250197A CN 108250197 A CN108250197 A CN 108250197A CN 201810228592 A CN201810228592 A CN 201810228592A CN 108250197 A CN108250197 A CN 108250197A
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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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
- G01N21/6402—Atomic fluorescence; Laser induced fluorescence
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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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
Abstract
The invention discloses a kind of novel probe molecule, preparation method and its applications for fluoroscopic examination biology sulfhydryl compound, belong to chemical analysis detection technique field.Its molecular structural formula is as follows：The fluorogen of this probe is imidazoles [1,5 A] pyridine skeleton structure, and the response group to sulfhydryl compound is maleimide.Individual probe is in the solution almost without fluorescent emission.After being reacted with sulfhydryl compound, probe has strong fluorescent emission in ~ 477 nm.The probe molecule has sulfhydryl compound high selectivity and sensitivity, and detection range is 0-1 μm of olL‑1, detect and be limited to 0.028 μm of olL‑1.The probe can be used for the image checking of sulfhydryl compound in living cells.
Description
Technical field
The invention belongs to chemical analysis detection technique fields, and in particular to a kind of Fluorometric assay biology sulfhydryl compound
Molecular probe and preparation method thereof and the application in terms of the biological sulfhydryl compound of detection.
Background technology
Biological sulfhydryl compound (including cysteine, homocysteine, glutathione etc.) and organism much important lifes
Reason or pathologic process are all closely related, if cysteine is the necessary amino acid that a kind of human body protein synthesizes, homocysteine energy
Antioxidation is played, glutathione is the necessary molecule for maintaining function of immune system.The exception of biological sulfhydryl compound content
Also it is one of inducement of some important diseases, such as cancer, Ah Ci sea Gadamer disease.Therefore, highly sensitive, high selection detection biology is developed
The method of sulfhydryl compound is very necessary to the development of human health status and relevant disease.Traditional biological sulfhydryl compound
Method has colorimetric method, capillary electrophoresis, high performance liquid chromatography etc..But these method general operations are cumbersome, and are difficult to reality
The in situ detection of existing bioactivity sample.And utilize molecular probe Fluorometric assay biology sulfhydryl compound have it is easy to operate,
Measuring speed is fast, can realize the advantages that detection in real time in situ, is developed and utilizes in recent years.But that develops at present is used to examine
There are some defects for the probe molecule of the biological sulfhydryl compound of survey, and if sensitivity is low, synthesis is cumbersome, and manufacturing cost is high, biofacies
The low grade of capacitive (document Wei M.Chem Commun, 2013,49,4640, Chen S.RSC Adv, 2013,3,11543；Liu
X.J.RSC Adv,2015,5,18177；Chen H.Dalton Trans,2012,41,13292.).It is it would therefore be highly desirable to explorative
The excellent biological sulfhydryl compound detection probe of energy goes to overcome the existing above problem.
Invention content
For the above situation, it is an object of the present invention to provide the highly sensitive detection lifes that a kind of new easily prepared, performance are stablized
The fluorescence probe of object sulfhydryl compound, and the synthetic method of the probe is provided, also go out in this foundational development to biological sulfydryl chemical combination
Object carries out highly selective and highly sensitive detection method.
Purpose to realize the present invention, one aspect of the present invention have stronger nucleophilic addition energy using biological sulfhydryl compound
Specific addition reaction can occur with maleimide amine unit for power；On the other hand have using imidazoles [1,5-A] pyridine skeleton structure
There is excellent spectral characteristic, after the amino conversion maleimide structure that phenyl ring aligns, fluorescence can be quenched effectively, and be given birth to
After object sulfhydryl compound and maleimide addition, and the transmitting of its hyperfluorescence can be restored.Based on this, a kind of maleimide is devised
Amine is responds group, the fluorescence that is used to detect biological sulfhydryl compound of imidazoles [1,5-A] the pyridine skeleton structure as illuminophore
Molecular probe.
The technical solution of the present invention for solving the problems, such as to take is a kind of fluoroscopic examination biology sulfhydryl compound fluorescence probe,
Molecular structural formula is,
The synthetic route of the fluorescence probe is as follows,
Specific preparation method includes the following steps：1) 2- benzoylpyridines and 4- nitrobenzaldehydes are dissolved in acetic acid, added
After entering ammonium acetate, heat temperature raising, back flow reaction.After reaction, reaction solution is poured into cold water, through extraction, revolving, decompression rotation
It is dry, obtain target product 1 through chromatographing column separating purification.2) upper step product 1 and stannous chloride are dispersed in ethyl acetate, slowly added
Enter concentrated hydrochloric acid solution.After being added dropwise, temperature control back flow reaction filters after having reacted, and Washing of Filter Cake collects filtrate, and decompression is spin-dried for
Obtain target product 2.3) upper step product 2 with maleic anhydride is mixed and be dissolved in acetic acid, temperature control back flow reaction.Reaction terminates, and stops
It only heats, depressurizes and be spin-dried for after reaction solution cooling, obtained crude product obtains probe molecule through chromatographing post separation.
Fluorescent molecular probe application method of the present invention is as follows：Probe molecule is dissolved in containing 30% first of mass percentage
In alcohol, the phosphate buffer solution that pH is 7.4, tested at room temperature.After biological sulfhydryl compound is added in, since it can be with
Addition reaction occurs for maleimide base group, and fluorescence is enable to restore.Probe molecule and biological sulfhydryl compound action principle are such as
Under,
The specific features of biology sulfhydryl compound fluorescence probe of the invention are as follows：Probe molecule without apparent fluorescent emission, but
After being acted on biological sulfhydryl compound, there is apparent emission peak at 477nm in probe molecule, fluorescence intensity enhance 25 times with
On.
Probe molecule synthesis of the present invention is simple, and cost is relatively low, good to the selectivity of biological sulfhydryl compound, anti-dry
Disturb that ability is strong, fast response time (response time is 30 seconds).(probe solution can stablize storage three to stable optical performance indoors
Month or more, spectral quality remains unchanged), detection limits low (0.028 μM), and therefore, the type probe can be used for water body and biology
The detection of biological sulfhydryl compound in system.Therefore the fluorescence probe has practical application in biochemistry detects and is imaged
Value.
Description of the drawings
Fig. 1 is the nuclear magnetic resonance spectroscopy of molecular probe that the present invention synthesizes.
After Fig. 2 is adds in various concentration cysteine, 10 μm of olL of the present invention-1The fluorescence emission spectrogram of compound of molecular probe,
From a to q, semicystinol concentration is respectively 0,0.2,0.4,0.6,0.8,1,2,3,4,5,6,7,8,9,10,20,50 μm of olL-1, abscissa is wavelength, and ordinate is fluorescence intensity.Solution system is water and the mixing buffer solution (H of methanol2O/CH3OH=
7/3,v/v,10mM PBS,pH 7.4)。
Concentration standard curve figures of the Fig. 3 for cysteine, i.e. 10 μm of olL-1Molecular probe of the present invention, reaction it is front and rear
Fluorescent emission intensity and the linear relationship of semicystinol concentration at 477nm；Abscissa is the concentration of cysteine, and ordinate is glimmering
Light emitting intensity value.
Concentration standard curve figures of the Fig. 4 for homocysteine, i.e. 10 μm of olL-1Molecular probe of the present invention, reaction it is front and rear
Fluorescent emission intensity and the linear relationship of homocysteine at 477nm；Abscissa is the concentration of homocysteine, and ordinate is glimmering
Light emitting intensity value.
Concentration standard curve figures of the Fig. 5 for glutathione, i.e. 10 μm of olL-1Molecular probe of the present invention, reaction it is front and rear
Fluorescent emission intensity and the linear relationship of glutathione concentrations at 477nm；Abscissa is the concentration of glutathione, and ordinate is glimmering
Light emitting intensity value.
Fig. 6 is selectivity of the molecular probe of the present invention to biological sulfhydryl compound；That is 10 μM of molecular probes of the present invention add in
20μmol·L-1Interfering substance or biological sulfhydryl compound (are followed successively by from a to w：Glycine, alanine, valine, leucine,
Isoleucine, phenylalanine, proline, tryptophan, serine, tyrosine, methionine, asparagine, glutamine, Soviet Union's ammonia
Acid, aspartic acid, glutamic acid, lysine, arginine, histidine, cysteine, homocysteine, glutathione) after,
Fluorescent emission intensity value at 477nm；Abscissa is the substance of test, and ordinate is fluorescent emission intensity value.
Fig. 7 is the imaging picture that molecular probe of the present invention detects human lung carcinoma cell (A549) cysteine.(A, B) is respectively
Fluorescence probe (10 μm of olL of the present invention-1) culture the light field picture of A549 and fluorescence picture；(C, D) is that the present invention is glimmering respectively
Light probe (10 μm of olL-1) and cysteine (20 μm of olL-1) culture the light field picture of A549 cells and fluorescence picture.
Scale：50μm.
Specific embodiment
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention..
Embodiment 1：The synthesis of compound 1
2- benzoylpyridines (1.6g, 8.74mmol) and 4- nitrobenzaldehydes (1.8g, 13.1mmol) are dissolved in acetic acid
(50mL, after adding in ammonium acetate (3.4g, 43.7mmol), heat temperature raising, 120 DEG C of temperature controls reflux 12h.After reaction, it will react
Liquid is poured into cold water, is extracted with dichloromethane, and revolving, decompression is spin-dried for, through chromatograph column separating purification obtain target product 1 (2.38g,
Yield：86.6%).Compound 1 is characterized as below：1H NMR(600MHz,DMSO-d6) δ 8.69 (d, J=7.2Hz, 1H), 8.38
(d, J=8.8Hz, 2H), 8.23 (d, J=8.8Hz, 2H), 8.08 (d, J=9.2Hz, 1H), 7.97 (d, J=7.4Hz, 2H),
7.50 (t, J=7.7Hz, 2H), 7.34 (t, J=7.4Hz, 1H), 7.09 (dd, J=9.1,6.5Hz, 1H), 6.93 (t, J=
6.7Hz,1H).13C NMR(150MHz,DMSO-d6)δ146.85,136.29,135.63,134.64,133.80,132.43,
131.65,129.31,128.69,127.51,127.21,125.73,124.01,123.22,122.60,120.57,119.26,
117.35,115.29.HRMS(EI)m/z calcd for[C19H13N3O2+H]+:316.1086,Found:316.1090.
Embodiment 2：The synthesis of compound 2
Compound 1 (0.5g, 1.6mmol) obtained by upper step is dispersed in ethyl acetate with stannous chloride (0.3g, 1.6mmol)
In (40mL), it is slowly added to concentrated hydrochloric acid solution (2mL).After being added dropwise, 80 DEG C of back flow reaction 8h of temperature control are filtered after having reacted,
Filter cake is washed with ethyl acetate, collects filtrate, and decompression is spin-dried for that target product 2 (0.42g, yield 92.1%) can be obtained.Chemical combination
Object 2 is characterized as below：1H NMR(600MHz,DMSO-d6) δ 8.70 (d, J=7.2Hz, 1H), 8.41 (d, J=8.8Hz, 2H),
8.24 (d, J=8.8Hz, 2H), 8.11 (d, J=9.2Hz, 1H), 7.97 (d, J=7.3Hz, 2H), 7.52 (t, J=7.7Hz,
2H), 7.36 (t, J=7.4Hz, 1H), 7.13 (dd, J=9.2,6.4Hz, 1H), 6.97 (dd, J=10.0,3.5Hz, 1H)13C
NMR(150MHz,DMSO-d6)δ147.05,135.59,135.36,133.91,129.30,128.89,127.41,126.88,
124.66,123.50,122.91,119.32,115.75.HRMS(EI)m/z calcd for[C19H15N3+H]+:286.1344,
Found:286.1349.
Embodiment 3：The synthesis of probe molecule
Upper step products therefrom 2 (0.285g, 1mmol) and maleic anhydride (0.98g, 10mmol) are mixed and are dissolved in acetic acid
In (10mL), 120 DEG C of back flow reaction 8h of temperature control.Stop heating, depressurize and be spin-dried for after reaction solution cooling, obtained crude product is through chromatography
Post separation can obtain probe molecule (0.306g, yield 83.8%).Probe molecule is characterized as below：1H NMR(600MHz,
DMSO-d6) δ 8.54 (d, J=7.1Hz, 1H), 8.02 (d, J=8.5Hz, 3H), 7.96 (d, J=7.6Hz, 2H), 7.57 (d, J
=8.2Hz, 2H), 7.49 (t, J=7.5Hz, 2H), 7.31 (t, J=7.2Hz, 1H), 7.24 (s, 2H), 7.03-6.95 (m,
1H), 6.81 (t, J=6.6Hz, 1H)13C NMR(150MHz,DMSO-d6)δ170.32,137.09,135.28,135.08,
132.14,131.11,129.39,129.25,128.77,128.06,127.54,126.82,126.53,123.10,121.57,
119.09,114.43.HRMS(EI)m/z calcd for[C23H15N3O2+H]+:366.1243,Found:366.1246.
Test of 4 probe of the present invention of embodiment to sulfhydryl compound biological in solution
Above-mentioned obtained molecular probe is dissolved in the mixing buffer solution (H of water and methanol2O/CH3OH=7/3, v/v, 10mM
PBS, pH 7.4)), it is configured to 10 μm of olL-1Probe solution.10 μm of ol that 2mL is prepared are added in the cuvette of 3mL
L-1Probe solution of the present invention uniformly mixes after being then respectively adding the cysteine of various concentration, tests its fluorescence spectrum, as a result
As shown in Figure 2.With solution, fluorescent emission intensity value maps to the concentration of cysteine at 477nm, and semicystinol concentration is 0-1
μmol·L-1In the range of when, good linear relationship (Fig. 3) is presented between the two.Similar operation is to homocysteine and paddy Guang
Sweet peptide has proceeded to quantitative analysis, as a result as shown in Figure 4 and Figure 5.And response of this probe to biological sulfhydryl compound, not by
The influence of some other amino acid, such as：Glycine, alanine, valine, leucine, isoleucine, phenylalanine, proline,
Tryptophan, serine, tyrosine, methionine, asparagine, glutamine, threonine, aspartic acid, glutamic acid, lysine,
Arginine, histidine.Under the conditions of existing for above-mentioned interfering ion, probe has good selectivity biological sulfhydryl compound
With sensitivity (Fig. 5).
Test of 5 probe of the present invention of embodiment to cysteine in cell
Cultured human lung carcinoma cell (A549) is placed at 37 DEG C in the PBS solution of 10 μM of probes of the present invention and is cultivated
The cell image unstressed configuration obtained after 30min.And A549 cells are first placed at 37 DEG C in the PBS solution of 20 μM of cysteines
30min is cultivated, then is placed in the PBS solution of 10 μM of probes of the present invention at 37 DEG C and cultivates 30min, it is rinsed through PBS buffer solution
Afterwards, the fluorescence imaging of cell can be obtained.Thus illustrate, probe has good cell membrane permeability, available for biomedicine
The cell imaging analysis in field.
Claims (5)
1. a kind of fluorescent molecular probe for detecting biological sulfhydryl compound, which is characterized in that its molecular structure is as follows：
。
2. prepare the fluorescent molecular probe method of the biological sulfhydryl compound of detection as described in claim 1, which is characterized in that
It is realized by step：
(1) 2- benzoylpyridines and 4- nitrobenzaldehydes are dissolved in acetic acid, after adding in ammonium acetate, back flow reaction, reaction terminates
Afterwards, reaction solution is poured into cold water, through extraction, revolving, decompression is spin-dried for, and target product 1 is obtained through chromatographing column separating purification；
(2) product 1 and stannous chloride are dispersed in ethyl acetate, are slowly added to hydrochloric acid solution, after being added dropwise, temperature control returns
Stream reaction filters after having reacted, collects filtrate, and decompression is spin-dried for, and obtains target product 2；
(3) product 2 and maleic anhydride are dissolved in acetic acid, temperature control back flow reaction, reaction terminates, and stops heating, treats that reaction solution is cold
But decompression is spin-dried for afterwards, and obtained crude product obtains probe molecule through chromatographing post separation.
3. the application of the fluorescent molecular probe of the biological sulfhydryl compound of detection as described in claim 1, which is characterized in that utilize
The molecular probe qualitatively or quantitatively determines sulfhydryl compound biological in water body and biosystem.
4. the application of the fluorescent molecular probe of the biological sulfhydryl compound of detection as claimed in claim 3, which is characterized in that use
During fluoroscopic examination, molecular probe of the present invention is dissolved in the mixing buffer system of water and methanol, added in containing various concentration biology
Sulfhydryl compound solution tests its fluorescence intensity at 477 nm, then with solution at 477 nm fluorescent emission intensity pair
The concentration of biological sulfhydryl compound makees standard drawing, and according to standard drawing, the quantitative biological sulfhydryl compound of detection is in solution to be measured
Content.
5. the application of the fluorescent molecular probe of the biological sulfhydryl compound of detection as claimed in claim 3, which is characterized in that pass through
Cell biological sample and molecular probe of the present invention are cultivated, using the method for fluorescence imaging to the biological mercapto in cell biological sample
Based compound progress is qualitative to pick up survey.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111499629A (en) * | 2020-04-14 | 2020-08-07 | 曲阜师范大学 | Fluorescent probe for detecting phosgene, and preparation method and application thereof |
-
2018
- 2018-03-20 CN CN201810228592.0A patent/CN108250197A/en active Pending
Non-Patent Citations (2)
| Title |
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| CHEN SONG等: "A novel imidazo[1,5-alpha]pyridine-based fluorescent probe with a large Stokes shift for imaging hydrogen sulfide", 《SENSORS AND ACTUATORS B-CHEMICAL》 * |
| QU LIJUN等: "A maleimide-based thiol fluorescent probe and its application for bioimaging", 《SENSORS AND ACTUATORS B-CHEMICAL》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111499629A (en) * | 2020-04-14 | 2020-08-07 | 曲阜师范大学 | Fluorescent probe for detecting phosgene, and preparation method and application thereof |
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Application publication date: 20180706 |