CN104232077B - Single fluorescence probe and synthetic method and the application of modifying based on cholesterol - Google Patents
Single fluorescence probe and synthetic method and the application of modifying based on cholesterol Download PDFInfo
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- CN104232077B CN104232077B CN201410431030.8A CN201410431030A CN104232077B CN 104232077 B CN104232077 B CN 104232077B CN 201410431030 A CN201410431030 A CN 201410431030A CN 104232077 B CN104232077 B CN 104232077B
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Abstract
The invention discloses a kind of single fluorescence probe and synthetic method and application of modifying based on cholesterol. The structural formula of this fluorescence probe is
Description
Technical field
The invention belongs to the detection technique field of protein, be specifically related to a kind of fluorescence probe and synthetic method and detection method of measuring protein in water.
Background technology
Protein is most important large biological molecule in life, it is the material base of vital movement, it is the basic substance of all tissues in organism, and in biological phenomena and life process, playing conclusive effect, it and nutrition, enzyme, virus, immunity, matter transportation, heredity, life etc. have substantial connection. Protein is carried out to quantitative analysis and specific recognition, and to inquire into life mechanism be very important, the research of its concentration and structure has extremely important meaning at aspects such as medical science and immunity, and the development in the fields such as announcement, clinical diagnosis and drug screening to life secret has great importance.
At present, in method of protein, common method comprises: AAS, Resonance Rayleigh Scattering Spectral Method, chemoluminescence method, immunization, nano particle method, plasma resonance method, transition-metal-carbonyl fragment method etc. In the detection method of numerous trace proteins, XRF because of its have highly sensitive, selectively good, the wide and condition determination of responding range more approach life entity physiological environment advantage and in protein analysis, be widely used. Fluorescent probe technique is to utilize optical physics and the photochemical properties of material, in molecular level, study the highly sensitive analytical method of Proteins In Aqueous Solutions, thereby in recent years, along with the continuous progress of technology, fluorescence probe method is as a kind of novel quantitative detection method of protein, with its disturb 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, selectively good, responding range is wide and condition determination more approaches the fluorescence probe that can be used for detecting protein of the physiological environment of life entity, and for this fluorescence probe provides a kind of synthetic method, and this fluorescence probe is detecting ovalbumin or pepsic application.
The structural formula that solves the problems of the technologies described above adopted technical scheme and be this fluorescence probe is as follows:
In formula, n is 2 or 3 or 4.
The synthetic method of above-mentioned single fluorescence probe of modifying based on cholesterol is made up of following step:
1, synthetic pyrene sulfonyl-derivatives
Under inert gas shielding and ice bath stirring condition; the chloroform soln of pyrene sulfonic acid chloride is added drop-wise to diaminourea containing in the chloroform soln of oxygen alkane; diaminourea is 10 ﹕ 1 containing the mol ratio of oxygen alkane and pyrene sulfonic acid 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 diaminourea is 1,8-diaminourea-3 containing oxygen alkane, 6-dioxy octane, 3,6,9-trioxa hendecane-1,11-diamines, 3,6,9,12-tetra-oxa-hexadecane-1, any one in 16-diamines.
2, synthetic single fluorescence probe of modifying based on cholesterol
Under inert gas shielding and ice bath stirring 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; dripping rear continuation stirs 4～5 hours; column chromatography for separation product; obtain single fluorescence probe of modifying based on cholesterol, its reaction equation is as follows:
In above-mentioned synthetic single fluorescence probe step 2 of modifying based on cholesterol, mol ratio the best of described pyrene sulfonyl-derivatives, cholesteryl chloroformate, triethylamine is 1: 1.5: 1.5.
Single fluorescence probe of modifying based on cholesterol of the present invention is in the purposes detecting in protein, and described protein is ovalbumin or pepsin, and its detection method is as follows:
1, obtain solution
DTAB, ovalbumin, pepsin are dissolved in respectively in 10mmol/LHEPES cushioning liquid, are mixed with 6mmol/L DTAB solution, 0.25mmol/L ovalbumin solution and 0.25mmol/L pepsin solution.
2, drawing standard curve
In 6mmol/L DTAB solution, add single fluorescence probe of modifying based on cholesterol, be mixed with single fluorescence probe solution that 0.5 μ mol/L modifies based on cholesterol, get this solution of 2.5mL in cuvette, add 0.25mmol/L ovalbumin solution, after mixing, the concentration that makes ovalbumin in gained mixed liquor is 0～1.4 μ mol/L, with luminoscope be 353nm at maximum excitation wavelength, emission wavelength is that fluorescence intensity is measured at 498nm place, excitation-emission slit is 2nm, fluorescence intensity when recording solution reaches balance, draw fluorescence intensity with I under the fluorescence spectrum figure of ovalbumin change in concentration and identical wavelengthM/IEValue is with the calibration curve of ovalbumin change in concentration.
Test as stated above and draw fluorescence intensity with pepsin concn change fluorescence spectrum figure and identical wavelength under IM/IEThe calibration curve that value changes with pepsin concn.
3, detect testing sample
Single fluorescence probe solution from cholesterol to 2.5mL0.5 μ mol/L that modify based on adds the testing protein quality sample of different volumes, measures the fluorescence intensity of testing protein quality sample, according to the I of testing protein quality sample with luminoscopeM/IEValue and concentration, the linear equation of combined standard curve can be determined ovalbumin or pepsin.
The present invention is based on that the chemical stability of single fluorescence probe that cholesterol modifies is good, fast response time, highly sensitive, selectively good, can directly detect with fluorescent instrument, as the single photon counting time resolution fluorescence spectral instrument of FLS920 model or other similar optical detecting instruments, realize ovalbumin or pepsic high sensitivity, low detection limit are detected.
Brief description of the drawings
Fig. 1 is the fluorescence intensity change curve map that prepared by the embodiment 1 single fluorescence probe of modifying based on cholesterol detects 0～0.19 μ mol/L pepsin solution.
Fig. 2 is concentration-I that prepared by the embodiment 1 single fluorescence probe of modifying based on cholesterol detects 0～0.19 μ mol/L pepsin solutionM/IELinear diagram.
Fig. 3 is the fluorescence intensity change curve map that prepared by the embodiment 1 single fluorescence probe of modifying based on cholesterol detects 0.2～1.4 μ mol/L pepsin solution.
Fig. 4 is concentration-I that prepared by the embodiment 1 single fluorescence probe of modifying based on cholesterol detects 0.2～1.4 μ mol/L pepsin solutionM/IELinear diagram.
Fig. 5 is the fluorescence intensity change curve map that prepared by the embodiment 1 single fluorescence probe of modifying based on cholesterol detects ovalbumin solution.
Fig. 6 is concentration-I that prepared by the embodiment 1 single fluorescence probe of modifying based on cholesterol detects ovalbumin solutionM/IELinear diagram.
Fig. 7 be embodiment 1 prepare based on cholesterol modify single fluorescence probe to ovalbumin and pepsic component-bar chart in 7 kinds of protein.
Detailed description of the invention
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 embodiment.
Embodiment 1
Single fluorescence probe of modifying based on cholesterol that composite structure formula is following:
Its synthetic method is as follows:
1, synthetic pyrene sulfonyl-derivatives
0.3g (0.997mmol) pyrene sulfonic acid chloride is dissolved in 50mL chloroform, under the condition of nitrogen gas that is 0.6～0.8mL/s at flow velocity and ice bath stirring condition, used constant pressure funnel to splash into and fill 50mL chloroform and 1.47mL (9.97mmol) 1 with the speed of 3～4 seconds/, 8-diaminourea-3, in the three-neck flask of 6-dioxy octane, stirring at room temperature 1 hour again after dripping, stop reaction, be neutral with saturated aqueous common salt by organic phase continuous washing to water, collect organic phase, and with anhydrous sodium sulfate drying, steam and desolventize, mixed solution taking the volume ratio of methyl alcohol and carrene as 1 ﹕ 30 is as eluant, eluent column chromatographic isolation and purification product, obtain the pyrene sulfonyl-derivatives shown in formula II, its yield is 55%, reaction equation is as follows:
2, synthetic single fluorescence probe of modifying based on cholesterol
0.3694g (0.82mmol) cholesteryl chloroformate is dissolved in the dissolving of 5mL carrene, then under the argon gas condition that is 0.6～0.8mL/s at flow velocity and ice bath stirring condition, used constant pressure funnel to splash into and fill 5mL carrene with the speed of 3～4 seconds/, in the three-neck flask of 114 μ L (0.82mmol) triethylamines and 0.2260g (0.55mmol) pyrene sulfonyl-derivatives, dripping rear continuation stirs 4～5 hours, stop reaction, mixed solution taking the volume ratio of ethyl acetate and benzinum as 1 ﹕ 1.5 is as eluant, eluent column chromatographic isolation and purification product, obtain single fluorescence probe of modifying based on cholesterol, its yield is 33%, its reaction equation is as follows:
The nuclear magnetic data of single fluorescence probe of modifying based on cholesterol that the present embodiment synthesizes is:1HNMR(400MHz，CDCl3)δppm：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
Single fluorescence probe of modifying based on cholesterol that composite structure formula is following:
In the synthetic pyrene sulfonyl-derivatives step 1 of embodiment 1, used 1,8-diaminourea-3,6-dioxy octane is with equimolar 3,6,9-trioxa hendecane-1,11-diamines is replaced, and other step of this step is identical with embodiment 1. Other step is identical with embodiment 1, obtains single fluorescence probe of modifying based on cholesterol.
Embodiment 3
Single fluorescence probe of modifying based on cholesterol that composite structure formula is following:
In the synthetic pyrene sulfonyl-derivatives step 1 of embodiment 1, used 1,8-diaminourea-3,6-dioxy octane is with equimolar 3,6,9,12-tetra-oxa-hexadecane-1,16-diamines is replaced, and other step of this step is identical with embodiment 1. Other step is identical with embodiment 1, obtains single fluorescence probe of modifying based on cholesterol.
Embodiment 4
Single fluorescence probe of modifying based on cholesterol that embodiment 1 synthesizes is in the purposes detecting in pepsin, and its detection method is as follows:
1, obtain solution
DTAB, pepsin are dissolved in respectively in 10mmol/LHEPES cushioning liquid, are mixed with 6mmol/L DTAB solution and 0.25mmol/L pepsin solution.
2, drawing standard curve
In 6mmol/L DTAB solution, add single fluorescence probe of modifying based on cholesterol, be mixed with single fluorescence probe solution that 0.5 μ mol/L modifies based on cholesterol, get this solution of 2.5mL in cuvette, add 0.25mmol/L pepsin solution, after mixing, make pepsic concentration in gained mixed liquor be respectively 0.02, 0.04, 0.06, 0.1, 0.12, 0.16, 0.19 μ mol/L, with luminoscope be 353nm at maximum excitation wavelength, emission wavelength is that fluorescence intensity is measured at 498nm place, excitation-emission slit is 2nm, fluorescence intensity when recording solution reaches balance, draw the fluorescence spectrum figure that fluorescence intensity changes with pepsin concn, see Fig. 1, and draw I under identical wavelengthM/IEThe calibration curve that value changes with pepsin concn, the results are shown in Figure 2.
As seen from Figure 1, concentration be the fluorescence probe of the 0.5 μ mol/L fluorescence intensity in 6mmol/L DTAB solution along with system in the increase of pepsin concn change clearly, illustrate that prepared fluorescence probe is very high to pepsic detection sensitivity. As seen from Figure 2, in the time that pepsin concn is 0.02～0.19 μ mol/L, IM/IEValue is linear with pepsin concn, and linear equation is:
y＝2.20+21.89x
In formula, y is IM/IEValue, x is pepsin concn, correlation coefficient r is 0.990, from coefficient correlation, IM/IEValue is fine with the linear relationship of pepsin concn. After tested, this fluorescence probe is limited to 202nmol/L to pepsic detecting.
3, detect testing sample
Single fluorescence probe solution from cholesterol to 2.5mL0.5 μ mol/L that modify based on adds the testing protein quality sample of different volumes, measures the fluorescence intensity of testing protein quality sample, according to the I of testing protein quality sample with luminoscopeM/IEValue and concentration, the linear equation of combined standard curve can be determined pepsin.
Embodiment 5
Single fluorescence probe of modifying based on cholesterol that embodiment 1 synthesizes is in the purposes detecting in pepsin, and its detection method is as follows:
1, obtain solution
DTAB, pepsin are dissolved in respectively in 10mmol/LHEPES cushioning liquid, are mixed with 6mmol/L DTAB solution and 0.25mmol/L pepsin solution.
2, drawing standard curve
In 6mmol/L DTAB solution, add single fluorescence probe of modifying based on cholesterol, be mixed with single fluorescence probe solution that 0.5 μ mol/L modifies based on cholesterol, get this solution of 2.5mL in cuvette, add 0.25mmol/L pepsin solution, after mixing, make pepsic concentration in gained mixed liquor be respectively 0.2, 0.4, 0.6, 0.8, 1.0, 1.2, 1.4 μ mol/L, with luminoscope be 353nm at maximum excitation wavelength, emission wavelength is that fluorescence intensity is measured at 498nm place, excitation-emission slit is 2nm, fluorescence intensity when recording solution reaches balance, draw the fluorescence spectrum figure that fluorescence intensity changes with pepsin concn, see Fig. 3, and draw I under identical wavelengthM/IEThe calibration curve that value changes with pepsin concn, the results are shown in Figure 4.
As seen from Figure 3, concentration be the fluorescence probe of the 0.5 μ mol/L fluorescence intensity in 6mmol/L DTAB solution along with system in the increase of pepsin concn change clearly, illustrate that prepared fluorescence probe is very high to pepsic detection sensitivity. As seen from Figure 4, in the time that pepsin concn is 0.2～1.4 μ mol/L, IM/IEValue is linear with pepsin concn, and linear equation is:
y＝6.65+18.15x
In formula, y is IM/IEValue, x is pepsin concn, correlation coefficient r is 0.990, from coefficient correlation, IM/IEValue is fine with the linear relationship of pepsin concn.
3, detect testing sample
Single fluorescence probe solution from cholesterol to 2.5mL0.5 μ mol/L that modify based on adds the testing protein quality sample of different volumes, measures the fluorescence intensity of testing protein quality sample, according to the I of testing protein quality sample with luminoscopeM/IEValue and concentration, the linear equation of combined standard curve can be determined pepsin.
Embodiment 6
Single fluorescence probe of modifying based on cholesterol that embodiment 1 synthesizes is in the purposes detecting in ovalbumin, and its detection method is as follows:
1, obtain solution
DTAB, ovalbumin are dissolved in respectively in 10mmol/LHEPES cushioning liquid, are mixed with 6mmol/L DTAB solution and 0.25mmol/L ovalbumin solution.
2, drawing standard curve
In 6mmol/L DTAB solution, add single fluorescence probe of modifying based on cholesterol, be mixed with single fluorescence probe solution that 0.5 μ mol/L modifies based on cholesterol, get this solution of 2.5mL in cuvette, add 0.25mmol/L ovalbumin solution, after mixing, make the concentration of ovalbumin in gained mixed liquor be respectively 0.1, 0.2, 0.4, 0.6, 0.8, 1.0, 1.2, 1.4 μ mol/L, with luminoscope be 353nm at maximum excitation wavelength, emission wavelength is that fluorescence intensity is measured at 498nm place, excitation-emission slit is 2nm, fluorescence intensity when recording solution reaches balance, draw the fluorescence spectrum figure of fluorescence intensity with ovalbumin change in concentration, see Fig. 5, and draw I under identical wavelengthM/IEValue, with the calibration curve of ovalbumin change in concentration, the results are shown in Figure 6.
As seen from Figure 5, concentration be the fluorescence probe of the 0.5 μ mol/L fluorescence intensity in 6mmol/L DTAB solution along with system in the increase of ovalbumin concentration change clearly, illustrate that prepared fluorescence probe is very high to the detection sensitivity of ovalbumin. As seen from Figure 6, in the time that ovalbumin concentration is 0.1～1.4 μ mol/L, IM/IEValue is linear with ovalbumin concentration, and linear equation is:
y＝1.03+2.82x
In formula, y is IM/IEValue, x is ovalbumin concentration, correlation coefficient r is 0.996, from coefficient correlation, IM/IEValue is fine with the linear relationship of ovalbumin concentration. After tested, this fluorescence probe is limited to 131nmol/L to detecting of ovalbumin.
3, detect testing sample
Single fluorescence probe solution from cholesterol to 2.5mL0.5 μ mol/L that modify based on adds the testing protein quality sample of different volumes, measures the fluorescence intensity of testing protein quality sample, according to the I of testing protein quality sample with luminoscopeM/IEValue and concentration, the linear equation of combined standard curve can be determined ovalbumin.
In order to prove beneficial effect of the present invention, inventor is according to the method for embodiment 4, the ovalbumin, beta lactoglobulin, cromoci, pepsin, trypsase, lysozyme, the bovine serum albumin(BSA) that are 5 μ mol/L to concentration detect respectively, and 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 pepsin that obvious quencher can occur, and there is not significant change in other protein fluorescence intensity, illustrate that fluorescence probe of the present invention is in the HEPES of 6mmol/L DTAB cushioning liquid (concentration of cushioning liquid is 10mmol/L), be can well selective discrimination ovalbumin or pepsin under 0.5 μ mol/L in concentration and probe concentration, then further according to I corresponding under variable concentrationsM/IEValue, can determine ovalbumin and pepsin in conjunction with the linear equation of ovalbumin or pepsin calibration curve.
Claims (4)
1. a single fluorescence probe of modifying based on cholesterol, the structural formula that it is characterized in that this fluorescence probe asShown in lower:
In formula, the value of n is 2.
2. a synthetic method for single fluorescence probe of modifying based on cholesterol of claim 1, its feature existsFormed by following step in it:
(1) synthetic pyrene sulfonyl-derivatives
Under inert gas shielding and ice bath stirring condition, the chloroform soln of pyrene sulfonic acid chloride is added drop-wise to diaminoBase is containing in the chloroform soln of oxygen alkane, and diaminourea is 10 ﹕ 1 containing the mol ratio of oxygen alkane and pyrene sulfonic acid chloride,Drip rear stirring at room temperature 1 hour, separation and purification product, obtains structural formula pyrene sulfonyl as follows derivativeThing;
Above-mentioned diaminourea is 1,8-diaminourea-3 containing oxygen alkane, 6-dioxy octane;
(2) synthetic single fluorescence probe of modifying based on cholesterol
Under inert gas shielding and ice bath stirring condition, the dichloromethane solution of cholesteryl chloroformate is drippedIn the dichloromethane solution of pyrene sulfonyl-derivatives and triethylamine, pyrene sulfonyl-derivatives, chloro-carbonic acid cholesterolThe mol ratio of ester, triethylamine is 1: 1.3～1.5: 1.3～2.0, drips rear continuation and stirs 4～5 hours, postChromatography product, obtains single fluorescence probe of modifying based on cholesterol.
3. the synthetic method of single fluorescence probe of modifying based on cholesterol according to claim 2, its spyLevy and be: in synthetic single fluorescence probe step (2) of modifying based on cholesterol, described pyrene sulfonyl spreads outThe mol ratio of biology, cholesteryl chloroformate, triethylamine is 1: 1.5: 1.5.
4. the purposes of single fluorescence probe of modifying based on cholesterol claimed in claim 1 in detection protein,Described protein is ovalbumin or pepsin.
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| 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 |
| 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 |
| CN108373922B (en) * | 2018-01-30 | 2021-03-30 | 山西大学 | Pyrene-containing chiral luminescent liquid crystal compound and preparation method thereof |
| 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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| JP5004234B2 (en) * | 2006-11-10 | 2012-08-22 | 独立行政法人産業技術総合研究所 | Sensitive molecular probe for membrane microdomain or cholesterol recognition protein detection |
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| Fluorescence and electrochemistry studies of pyrene-functionalized surface adlayers to probe the microenvironment formed by cholesterol;Liping Ding等;《Electrochimica Acta》;20081231;第53卷;6704–6713 * |
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