CN104232077A - Monopyrene fluorescent probe based on cholesterol modification, and synthesis method and application thereof - Google Patents
Monopyrene fluorescent probe based on cholesterol modification, and synthesis method and application thereof Download PDFInfo
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- CN104232077A CN104232077A CN201410431030.8A CN201410431030A CN104232077A CN 104232077 A CN104232077 A CN 104232077A CN 201410431030 A CN201410431030 A CN 201410431030A CN 104232077 A CN104232077 A CN 104232077A
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Abstract
The invention discloses a monopyrene fluorescent probe based on cholesterol modification, and a synthesis method and application thereof. The structural formula of the fluorescent probe is disclosed in the specification, wherein n is 2 or 3 or 4; and the fluorescent probe is prepared by mediated combination of a hydrophilic connecting arm oligomerized ethoxy and secondary amine group with cholesterol group. The fluorescent probe has the advantages of high chemical stability, high response speed, high sensitivity, wide response range and the like, and can implement continuous real-time on-line determination of pepsin and ovalbumin in proteins; and the detection limit can respectively reach 202 nmol/L and 131 nmol/L.
Description
Technical field
The invention belongs to the detection technique field of protein, be specifically related to a kind of in water, measure protein fluorescent probe and synthetic method and detection method.
Background technology
Protein is most important biomacromolecule in life, it is the basic substance of vital movement, it is the basic substance of all tissues in organism, and conclusive effect is played in biological phenomena and vital process, it and nutrition, enzyme, virus, immunity, matter transportation, heredity, life etc. have substantial connection.Carrying out quantitative analysis and specific recognition to protein, to inquire into life mechanism be very important, the research of its concentration and structure has extremely important meaning in medical science and immunity etc., has great importance to the announcement of life secret, the development in the field such as clinical diagnosis and drug screening.
At present, for detecting in method of protein, common method comprises: spectrophotometry, Resonance Rayleigh Scattering Spectral Method, chemoluminescence method, immunization, nanoparticle method, plasmon resonance, transition-metal carbonyl fragment method etc.In the detection method of numerous trace proteins, fluorometry has highly sensitive because of it, and selectivity is good, and the wide and condition determination of responding range is widely used in protein analysis closer to the advantage of the physiological environment of life entity.Fluorescent probe technique is the optical physics and the photochemical properties that utilize material, molecular level is studied the highly sensitive analytical procedure of Proteins In Aqueous Solutions, thus in recent years, along with the continuous progress of technology, fluorescence probe method as a kind of method of novel quantitative detection of protein, with its interference less, quick, highly sensitive, accurate, practicality and receiving much concern.
Summary of the invention
Technical problem to be solved by this invention be to provide a kind of highly sensitive, selectivity good, responding range is wide and condition determination closer to the fluorescent probe that can be used for detecting protein of the physiological environment of life entity, and provide a kind of synthetic method for this fluorescent probe, and this fluorescent probe is in detection ovalbumin or pepsic application.
Solving the problems of the technologies described above adopted technical scheme is that the structural formula of this fluorescent probe is as follows:
In formula, n is 2 or 3 or 4.
The synthetic method of above-mentioned single fluorescence probe based on cholesterol modification is made up of following step:
1, pyrene sulfonyl-derivatives is synthesized
Under protection of inert gas and ice bath agitation condition; the chloroform soln of pyrene SULPHURYL CHLORIDE is added drop-wise to diamino containing in the chloroform soln of oxygen alkane; diamino is 10 ﹕ 1 containing the mol ratio of oxygen alkane and pyrene SULPHURYL CHLORIDE; drip rear stirring at room temperature 1 hour; separation and purification product; obtain the pyrene sulfonyl-derivatives shown in formula I, its reaction equation is as follows:
Above-mentioned diamino is any one in 1,8-diamino-3,6-dioxy octane, 3,6,9-trioxaundecane-1,11-diamines, 3,6,9,12-tetra-oxa-n-Hexadecane-1,16-diamines containing oxygen alkane.
2, the single fluorescence probe modified based on cholesterol is synthesized
Under protection of inert gas and ice bath agitation condition; the dichloromethane solution of cholesteryl chloroformate is added drop-wise in the dichloromethane solution of pyrene sulfonyl-derivatives and triethylamine; the mol ratio of pyrene sulfonyl-derivatives, cholesteryl chloroformate, triethylamine is 1: 1.3 ~ 1.5: 1.3 ~ 2.0; drip rear continuation stirring 4 ~ 5 hours; column chromatography for separation product; obtain the single fluorescence probe modified based on cholesterol, its reaction equation is as follows:
In single fluorescence probe step 2 that above-mentioned synthesis is modified based on cholesterol, mol ratio the best of described pyrene sulfonyl-derivatives, cholesteryl chloroformate, triethylamine is 1: 1.5: 1.5.
The single fluorescence probe modified based on cholesterol of the present invention is detecting the purposes in protein, and described protein is ovalbumin or stomach en-, and its detection method is as follows:
1, obtain solution
Trimethyllaurylammonium bromide, ovalbumin, stomach en-are dissolved in respectively in 10mmol/L HEPES buffered soln, are mixed with 6mmol/L Trimethyllaurylammonium bromide solution, 0.25mmol/L ovalbumin solution and 0.25mmol/L pepsin solution.
2, drawing standard curve
The single fluorescence probe modified based on cholesterol is added in 6mmol/L Trimethyllaurylammonium bromide solution, be mixed with single fluorescence probe solution that 0.5 μm of ol/L modifies based on cholesterol, get this solution of 2.5mL in cuvette, add 0.25mmol/L ovalbumin solution, after mixing, the concentration of ovalbumin in gained mixed solution is made to be 0 ~ 1.4 μm of ol/L, be 353nm with luminoscope at maximum excitation wavelength, emission wavelength is that fluorescence intensity is measured at 498nm place, excitation-emission slit is 2nm, recording solution reaches fluorescence intensity during balance, draw fluorescence intensity with I under the fluorescence spectrum figure of ovalbumin change in concentration and phase co-wavelength
m/ I
ebe worth the typical curve with ovalbumin change in concentration.
Test as stated above and I under drawing the fluorescence spectrum figure and phase co-wavelength that fluorescence intensity changes with pepsin concn
m/ I
ebe worth the typical curve with pepsin concn change.
3, testing sample is detected
Add the testing protein quality sample of different volumes to 2.5mL 0.5 μm of ol/L based on single fluorescence probe solution that cholesterol is modified, measure the fluorescence intensity of testing protein quality sample with luminoscope, according to the I of testing protein quality sample
m/ I
evalue and concentration, the linear equation of combined standard curve can determine ovalbumin or stomach en-.
The present invention is based on that the chemical stability of single fluorescence probe that cholesterol modifies is good, fast response time, highly sensitive, selectivity good, can detect by direct fluorescent instrument, as single photon counting time resolution fluorescence spectral instrument or other similar optical detecting instruments of FLS920 model, realize detecting ovalbumin or pepsic highly sensitive, low detection limit.
Accompanying drawing explanation
Fig. 1 is the fluorescence intensity change graphic representation of single fluorescence probe detection 0 ~ 0.19 μm of ol/L pepsin solution based on cholesterol modification prepared by embodiment 1.
Fig. 2 is the concentration-I of single fluorescence probe detection 0 ~ 0.19 μm of ol/L pepsin solution based on cholesterol modification prepared by embodiment 1
m/ I
elinear diagram.
Fig. 3 is the fluorescence intensity change graphic representation of single fluorescence probe detection 0.2 ~ 1.4 μm of ol/L pepsin solution based on cholesterol modification prepared by embodiment 1.
Fig. 4 is the concentration-I of single fluorescence probe detection 0.2 ~ 1.4 μm of ol/L pepsin solution based on cholesterol modification prepared by embodiment 1
m/ I
elinear diagram.
Fig. 5 is the fluorescence intensity change graphic representation of the single fluorescence probe detection ovalbumin solution based on cholesterol modification prepared by embodiment 1.
Fig. 6 is the concentration-I of the single fluorescence probe detection ovalbumin solution based on cholesterol modification prepared by embodiment 1
m/ I
elinear diagram.
Fig. 7 is that the single fluorescence probe based on cholesterol modification of embodiment 1 preparation is to ovalbumin and pepsic component-bar chart in 7 kinds of protein.
Embodiment
Below in conjunction with accompanying drawing and example, the present invention is described in more detail, but protection scope of the present invention is not limited only to these embodiments.
Embodiment 1
The single fluorescence probe modified based on cholesterol that composite structure formula is following:
Its synthetic method is as follows:
1, pyrene sulfonyl-derivatives is synthesized
0.3g (0.997mmol) pyrene SULPHURYL CHLORIDE is dissolved in 50mL trichloromethane, under flow velocity is the condition of nitrogen gas of 0.6 ~ 0.8mL/s and ice bath agitation condition, constant pressure funnel is used to fill 50mL trichloromethane and 1.47mL (9.97mmol) 1 with the speed of 3 ~ 4 seconds/instillation, 8-diamino-3, in the three-necked flask of 6-dioxy octane, stirring at room temperature 1 hour again after dripping, stopped reaction, be neutral by organic phase continuous washing to aqueous phase with saturated aqueous common salt, collect organic phase, and with anhydrous sodium sulfate drying, steam except desolventizing, be that the mixing solutions of 1 ﹕ 30 is for eluent column chromatographic isolation and purification product with the volume ratio of methyl alcohol and methylene dichloride, obtain the pyrene sulfonyl-derivatives shown in formula II, its yield is 55%, reaction equation is as follows:
2, the single fluorescence probe modified based on cholesterol is synthesized
0.3694g (0.82mmol) cholesteryl chloroformate is dissolved in the dissolving of 5mL methylene dichloride, then under flow velocity is the argon gas condition of 0.6 ~ 0.8mL/s and ice bath agitation condition, constant pressure funnel is used to fill 5mL methylene dichloride with the speed of 3 ~ 4 seconds/instillation, in the three-necked flask of 114 μ L (0.82mmol) triethylamines and 0.2260g (0.55mmol) pyrene sulfonyl-derivatives, drip rear continuation stirring 4 ~ 5 hours, stopped reaction, be that the mixing solutions of 1 ﹕ 1.5 is for eluent column chromatographic isolation and purification product with the volume ratio of ethyl acetate and sherwood oil, obtain the single fluorescence probe modified based on cholesterol, its yield is 33%, its reaction equation is as follows:
The nuclear magnetic data of the single fluorescence probe based on cholesterol modification of the present embodiment synthesis is:
1h NMR (400MHz, CDCl
3) δ ppm:9.00 (1H), 8.71 (1H), 8.34-8.11 (7H), 5.64 (1H), 5.29 (1H), 5.12 (1H), 4.46 (1H), 3.43-3.17 (12H).
Embodiment 2
The single fluorescence probe modified based on cholesterol that composite structure formula is following:
In the synthesis pyrene sulfonyl-derivatives step 1 of embodiment 1, equimolar 3,6,9-trioxaundecane-1, the 11-diamines of 1,8-diamino-3,6-dioxy octane used are replaced, and other step of this step is identical with embodiment 1.Other step is identical with embodiment 1, obtains the single fluorescence probe modified based on cholesterol.
Embodiment 3
The single fluorescence probe modified based on cholesterol that composite structure formula is following:
In the synthesis pyrene sulfonyl-derivatives step 1 of embodiment 1, equimolar 3,6,9,12-tetra-oxa-n-Hexadecane-1, the 16-diamines of 1,8-diamino-3,6-dioxy octane used are replaced, and other step of this step is identical with embodiment 1.Other step is identical with embodiment 1, obtains the single fluorescence probe modified based on cholesterol.
Embodiment 4
The purposes of single fluorescence probe in detection stomach en-of modifying based on cholesterol that embodiment 1 is synthesized, its detection method is as follows:
1, obtain solution
Trimethyllaurylammonium bromide, stomach en-are dissolved in respectively in 10mmol/L HEPES buffered soln, are mixed with 6mmol/L Trimethyllaurylammonium bromide solution and 0.25mmol/L pepsin solution.
2, drawing standard curve
The single fluorescence probe modified based on cholesterol is added in 6mmol/L Trimethyllaurylammonium bromide solution, be mixed with single fluorescence probe solution that 0.5 μm of ol/L modifies based on cholesterol, get this solution of 2.5mL in cuvette, add 0.25mmol/L pepsin solution, after mixing, pepsic concentration in gained mixed solution is made to be respectively 0.02, 0.04, 0.06, 0.1, 0.12, 0.16, 0.19 μm of ol/L, be 353nm with luminoscope at maximum excitation wavelength, emission wavelength is that fluorescence intensity is measured at 498nm place, excitation-emission slit is 2nm, recording solution reaches fluorescence intensity during balance, draw the fluorescence spectrum figure that fluorescence intensity changes with pepsin concn, see Fig. 1, and I under drawing phase co-wavelength
m/ I
ebe worth the typical curve with pepsin concn change, the results are shown in Figure 2.
As seen from Figure 1, concentration be the fluorescent probe of the 0.5 μm of ol/L fluorescence intensity in 6mmol/L Trimethyllaurylammonium bromide solution along with system in pepsin concn increase change clearly, the fluorescent probe prepared by explanation is very high to pepsic detection sensitivity.As seen from Figure 2, when pepsin concn is 0.02 ~ 0.19 μm of ol/L, I
m/ I
evalue is linear with pepsin concn, and linear equation is:
y＝2.20+21.89x
In formula, y is I
m/ I
evalue, x is pepsin concn, and correlation coefficient r is 0.990, from relation conefficient, I
m/ I
evalue is fine with the linear relationship of pepsin concn.After tested, this fluorescent probe is limited to 202nmol/L to pepsic detecting.
3, testing sample is detected
Add the testing protein quality sample of different volumes to 2.5mL 0.5 μm of ol/L based on single fluorescence probe solution that cholesterol is modified, measure the fluorescence intensity of testing protein quality sample with luminoscope, according to the I of testing protein quality sample
m/ I
evalue and concentration, the linear equation of combined standard curve can determine stomach en-.
Embodiment 5
The purposes of single fluorescence probe in detection stomach en-of modifying based on cholesterol that embodiment 1 is synthesized, its detection method is as follows:
1, obtain solution
Trimethyllaurylammonium bromide, stomach en-are dissolved in respectively in 10mmol/L HEPES buffered soln, are mixed with 6mmol/L Trimethyllaurylammonium bromide solution and 0.25mmol/L pepsin solution.
2, drawing standard curve
The single fluorescence probe modified based on cholesterol is added in 6mmol/L Trimethyllaurylammonium bromide solution, be mixed with single fluorescence probe solution that 0.5 μm of ol/L modifies based on cholesterol, get this solution of 2.5mL in cuvette, add 0.25mmol/L pepsin solution, after mixing, pepsic concentration in gained mixed solution is made to be respectively 0.2, 0.4, 0.6, 0.8, 1.0, 1.2, 1.4 μm of ol/L, be 353nm with luminoscope at maximum excitation wavelength, emission wavelength is that fluorescence intensity is measured at 498nm place, excitation-emission slit is 2nm, recording solution reaches fluorescence intensity during balance, draw the fluorescence spectrum figure that fluorescence intensity changes with pepsin concn, see Fig. 3, and I under drawing phase co-wavelength
m/ I
ebe worth the typical curve with pepsin concn change, the results are shown in Figure 4.
As seen from Figure 3, concentration be the fluorescent probe of the 0.5 μm of ol/L fluorescence intensity in 6mmol/L Trimethyllaurylammonium bromide solution along with system in pepsin concn increase change clearly, the fluorescent probe prepared by explanation is very high to pepsic detection sensitivity.As seen from Figure 4, when pepsin concn is 0.2 ~ 1.4 μm of ol/L, I
m/ I
evalue is linear with pepsin concn, and linear equation is:
y＝6.65+18.15x
In formula, y is I
m/ I
evalue, x is pepsin concn, and correlation coefficient r is 0.990, from relation conefficient, I
m/ I
evalue is fine with the linear relationship of pepsin concn.
3, testing sample is detected
Add the testing protein quality sample of different volumes to 2.5mL 0.5 μm of ol/L based on single fluorescence probe solution that cholesterol is modified, measure the fluorescence intensity of testing protein quality sample with luminoscope, according to the I of testing protein quality sample
m/ I
evalue and concentration, the linear equation of combined standard curve can determine stomach en-.
Embodiment 6
The purposes of single fluorescence probe in detection ovalbumin of modifying based on cholesterol that embodiment 1 is synthesized, its detection method is as follows:
1, obtain solution
Trimethyllaurylammonium bromide, ovalbumin are dissolved in respectively in 10mmol/L HEPES buffered soln, are mixed with 6mmol/L Trimethyllaurylammonium bromide solution and 0.25mmol/L ovalbumin solution.
2, drawing standard curve
The single fluorescence probe modified based on cholesterol is added in 6mmol/L Trimethyllaurylammonium bromide solution, be mixed with single fluorescence probe solution that 0.5 μm of ol/L modifies based on cholesterol, get this solution of 2.5mL in cuvette, add 0.25mmol/L ovalbumin solution, after mixing, the concentration of ovalbumin in gained mixed solution is made to be respectively 0.1, 0.2, 0.4, 0.6, 0.8, 1.0, 1.2, 1.4 μm of ol/L, be 353nm with luminoscope at maximum excitation wavelength, emission wavelength is that fluorescence intensity is measured at 498nm place, excitation-emission slit is 2nm, recording solution reaches fluorescence intensity during balance, draw the fluorescence spectrum figure of fluorescence intensity with ovalbumin change in concentration, see Fig. 5, and I under drawing phase co-wavelength
m/ I
ebe worth the typical curve with ovalbumin change in concentration, the results are shown in Figure 6.
As seen from Figure 5, concentration be the fluorescent probe of the 0.5 μm of ol/L fluorescence intensity in 6mmol/L Trimethyllaurylammonium bromide solution along with system in ovalbumin concentration increase change clearly, the fluorescent probe prepared by explanation is very high to the detection sensitivity of ovalbumin.As seen from Figure 6, when ovalbumin concentration is 0.1 ~ 1.4 μm of ol/L, I
m/ I
evalue is linear with ovalbumin concentration, and linear equation is:
y＝1.03+2.82x
In formula, y is I
m/ I
evalue, x is ovalbumin concentration, and correlation coefficient r is 0.996, from relation conefficient, I
m/ I
evalue is fine with the linear relationship of ovalbumin concentration.After tested, this fluorescent probe is limited to 131nmol/L to detecting of ovalbumin.
3, testing sample is detected
Add the testing protein quality sample of different volumes to 2.5mL 0.5 μm of ol/L based on single fluorescence probe solution that cholesterol is modified, measure the fluorescence intensity of testing protein quality sample with luminoscope, according to the I of testing protein quality sample
m/ I
evalue and concentration, the linear equation of combined standard curve can determine ovalbumin.
In order to prove beneficial effect of the present invention, contriver is according to the method for embodiment 4, to concentration be the ovalbumin of 5 μm of ol/L, beta-lactoglobulin, cytochrome C, stomach en-, trypsinase, N,O-Diacetylmuramidase, bovine serum albumin detect respectively, test result is shown in Fig. 7.As seen from Figure 7, under the same conditions, add 7 kinds of different protein, only have ovalbumin and stomach en-that obvious quencher can occur, and there is not considerable change in other protein fluorescence intensity, illustrate that fluorescent probe of the present invention is in the HEPES buffered soln (concentration of buffered soln is 10mmol/L) of 6mmol/L Trimethyllaurylammonium bromide, can well selective discrimination ovalbumin or stomach en-under concentration and probe concentration is 0.5 μm of ol/L, then further according to I corresponding under different concns
m/ I
evalue, the linear equation in conjunction with ovalbumin or stomach en-typical curve can determine ovalbumin and stomach en-.
Claims (4)
1., based on the single fluorescence probe that cholesterol is modified, it is characterized in that the structural formula of this fluorescent probe is as follows:
In formula, the value of n is 2 or 3 or 4.
2. a synthetic method for the single fluorescence probe based on cholesterol modification of claim 1, is characterized in that it is made up of following step:
(1) pyrene sulfonyl-derivatives is synthesized
Under protection of inert gas and ice bath agitation condition, the chloroform soln of pyrene SULPHURYL CHLORIDE is added drop-wise to diamino containing in the chloroform soln of oxygen alkane, diamino is 10 ﹕ 1 containing the mol ratio of oxygen alkane and pyrene SULPHURYL CHLORIDE, drip rear stirring at room temperature 1 hour, separation and purification product, obtains the pyrene sulfonyl-derivatives that structural formula is as follows;
Above-mentioned diamino is any one in 1,8-diamino-3,6-dioxy octane, 3,6,9-trioxaundecane-1,11-diamines, 3,6,9,12-tetra-oxa-n-Hexadecane-1,16-diamines containing oxygen alkane;
(2) synthesis is based on single fluorescence probe of cholesterol modification
Under protection of inert gas and ice bath agitation condition; the dichloromethane solution of cholesteryl chloroformate is added drop-wise in the dichloromethane solution of pyrene sulfonyl-derivatives and triethylamine; the mol ratio of pyrene sulfonyl-derivatives, cholesteryl chloroformate, triethylamine is 1: 1.3 ~ 1.5: 1.3 ~ 2.0; drip rear continuation stirring 4 ~ 5 hours; column chromatography for separation product, obtains the single fluorescence probe modified based on cholesterol.
3. the synthetic method of the single fluorescence probe based on cholesterol modification according to claim 2; it is characterized in that: in single fluorescence probe step (2) that synthesis is modified based on cholesterol, the mol ratio of described pyrene sulfonyl-derivatives, cholesteryl chloroformate, triethylamine is 1: 1.5: 1.5.
4. the single fluorescence probe modified based on cholesterol according to claim 1 is detecting the purposes in protein, and described protein is ovalbumin or stomach en-.
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| CN106632326A (en) * | 2016-11-16 | 2017-05-10 | 陕西师范大学 | Di-pyrene modified perylene bisimide derivative fluorescent probe and synthesis method and application thereof |
| CN107098852A (en) * | 2017-06-20 | 2017-08-29 | 陕西师范大学 | The amine-modified pyrene derivatives fluorescence probe of two (2 picolines) and its synthetic method and application |
| CN108373922A (en) * | 2018-01-30 | 2018-08-07 | 山西大学 | A kind of chirality containing pyrene shines liquid-crystal compounds and preparation method thereof |
| CN108689824A (en) * | 2018-07-17 | 2018-10-23 | 郑州大学 | Application of the pyrene end group acetylenic ketone compounds as surfactant fluorescence probe |
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| CN106632326A (en) * | 2016-11-16 | 2017-05-10 | 陕西师范大学 | Di-pyrene modified perylene bisimide derivative fluorescent probe and synthesis method and application thereof |
| CN106632326B (en) * | 2016-11-16 | 2018-08-24 | 陕西师范大学 | Double pyrene modification imide derivative fluorescence probes and its synthetic method and application |
| CN107098852A (en) * | 2017-06-20 | 2017-08-29 | 陕西师范大学 | The amine-modified pyrene derivatives fluorescence probe of two (2 picolines) and its synthetic method and application |
| CN107098852B (en) * | 2017-06-20 | 2020-04-24 | 陕西师范大学 | Di (2-methylpyridine) amine modified pyrene derivative fluorescent probe and synthetic method and application thereof |
| CN108373922A (en) * | 2018-01-30 | 2018-08-07 | 山西大学 | A kind of chirality containing pyrene shines liquid-crystal compounds and preparation method thereof |
| CN108373922B (en) * | 2018-01-30 | 2021-03-30 | 山西大学 | Pyrene-containing chiral luminescent liquid crystal compound and preparation method thereof |
| CN108689824A (en) * | 2018-07-17 | 2018-10-23 | 郑州大学 | Application of the pyrene end group acetylenic ketone compounds as surfactant fluorescence probe |
| CN108689824B (en) * | 2018-07-17 | 2021-01-26 | 郑州大学 | Application of pyrene end-group alkynone compound as surfactant fluorescent probe |
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