CN104231335B - Upper conversion composite that cyclodextrin derivative is modified and preparation method thereof and purposes - Google Patents
Upper conversion composite that cyclodextrin derivative is modified and preparation method thereof and purposes Download PDFInfo
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Abstract
A kind of method preparing the modified upper conversion composite of cyclodextrin derivative, it is that the up-conversion nanoparticles (OA UCNPs) that oleic acid wraps up is added dropwise over HCl solution, can obtain the UCNPs without oleic acid ligand.UCNPs the beta cyclodextrin (CD Cit) of citric acid-modified and without oleic acid ligand obtains, after at high temperature reacting UCNPs (CD Cit UCNPs), CD Cit UCNPs Yu the RB assembling obtaining CD Cit parcel, the upper conversion composite that cyclodextrin derivative is modified.The upper conversion composite of the present invention is based on a kind of FRET process, as energy acceptor, make use of the competitive reaction between Subjective and Objective as energy donor, rhodamine B (RB) using UCNPs.Adding after cholesterol, cholesterol induction RB dissociates the cavity of beta cyclodextrin, causes FRET to weaken, and up-conversion fluorescence strengthens, and carrys out the content of cholesterol detection with this.The invention discloses its preparation method.
Description
Technical field
The present invention relates to the modified upper conversion composite of cyclodextrin derivative and preparation method thereof and it is for cholesterol in serum
Detection.
Background technology
Cholesterol plays an important role in the evolution process of numerous disease, and the detection of cholesterol in serum is biochemistry
The analysis indexes that middle application is most.The cholesterol level of equilibrium ensure that cyto-architectural durability and complete in human body
Whole property, in serum, the height of total cholesterol level is an important indicator of medical diagnosis treatment.(see: S.R.Cao, L.
Zhang,Y.Q.Chai and R.Yuan,Biosens.Bioelectron.,2013,42,532-538.)
About cholesterol detection, many method is had been developed, as fluorescence analysis, electro chemical analysis and molecular imprinting skill
Art etc..But, being limited in that of these methods is time-consuming, lack suitable internal standard, and the selectivity of many methods depends on
Cholesterol selectivity enzyme and the use of antibody, and these enzymes and the expensive and easy degeneration of antibody.It is accordingly required in particular to
Having and can substitute, simple, cheap and efficient detection method (sees: A.Mondal and N. for cholesterol detection
R.Jana,Chem.Commun.,2012,48,7316-7318.)。
Recently cholesterol detection method of based on luminescent dye molecule is had been developed, be beta-schardinger dextrin-(CD) with
Emulative host-guest interaction between dye molecule and cholesterol (see: (a) A.Mondal and N.R.Jana,
Chem.Commun.,2012,48,7316-7318.(b)N.Zhang,Y.Liu,L.Tong,K.Xu,L.Zhuo and B.
Tang,Analyst,2008,133,1176-1181.).But, the optical property of dye molecule is the most very sensitive to many conditions,
As pH value, ionic forces and organic effect of sample solution, in test process, it should be ensured that these conditions absolute
Cause.Additionally, the absorption of biomacromolecule is concentrated mainly on ultraviolet-visible district, under this energy excitation, will produce autonomous
Fluorescence, reduces signal to noise ratio, causes the sensitivity decrease of detection.
Up-conversion nanoparticles (UCNPs) is the fluorogen of a class doping with rare-earth ions, by multiphoton absorption process, energy
Enough low-energy light is transformed into high-energy and launches light, and then launch visible or near infrared light.They have strong fluorescence
Intensity, high quantum yield, narrow launch site, good chemical stability and light stability.Use low-yield near infrared light
(typically 980nm) excites, can avoid from biomacromolecule autonomous fluorescence disturb (see: Y.H.Wang,
Z.J.Wu and Z.H.Liu,Anal.Chem.,2013,85,258-264.).All these advantages show, UCNPs exists
Biological have huge potentiality in Analysis of environmental samples.In various lanthanide doped up-conversion, hexagonal phase
NaYF4: Yb, Er are acknowledged as maximally effective up-conversion luminescent material, the Yb wherein adulterated3+It is responsible for absorption many
Individual near-infrared photon, and Er3+It is responsible for launching visible ray.It is true that UCNPs is based on FRET (fluorescence resonance energy transfer) (FRET)
In analysis, it it is considered as optimal donor always.Up to now, some photochemistry is had been developed with UCNPs to pass
Sensor, is respectively intended to detect CN-、Hg2+(see: (a) R.Chen, V.D.Ta, F.Xiao, Q.Y. with temperature etc.
Zhang and H.D.Sun,Small,2013,9,1052-1057.L.Yao,J.Zhou,J.Liu,W.Feng and F.Li,
Adv.Funct.Mater.,2012,22,2667-2672.(b)Q.Liu,J.J.Peng,L.N.Sun and F.Y.Li,ACS
Nano,2011,5,8040-8048.(c)N.N.Tu and L.Y.Wang,Chem.Commun.,2013,49,
6319-6321.(d)C.L.Zhang,Y.X.Yuan,S.M.Zhang,Y.H.Wang and Z.H.Liu,Angew.
Chem.Int.Edit.,2011,50,6851-6854.).Regrettably, as far as we know, about the cholesterol of UCNPs
Selectivity fluorescent probe unmanned report always.Therefore, we have developed a kind of cholesterol sensor based on FRET, use
The content of cholesterol in detection human serum.
Summary of the invention
It is an object of the invention to provide the modified upper conversion composite of a kind of cyclodextrin derivative and preparation method thereof and detection gallbladder
The application of sterin.
Technical scheme is as follows:
A kind of method preparing the modified upper conversion composite of cyclodextrin derivative, it is made up of the following step:
Step 1. is with 1mmol RECl3(0.78mmol YCl3,0.2mmol YbCl3,0.02mmol ErCl3) for reacting
Monomer, adds 7.5mL oleic acid and 17.5mL1-vaccenic acid, stirs, and solution is heated to 160 DEG C, keeps 30min.
It is cooled to room temperature, is separately added into 1.6-4.0mmol NH4The methanol solution of F and 2.5mmol NaOH is added thereto, stirring
30min, evaporates methanol, and solution is heated to 280-300 DEG C under argon shield, reacts 1h, is cooled to room temperature, instead
Solution is answered to add ethanol precipitation, centrifugal, by water and washing with alcohol, obtain OA-UCNPs；
100mg OA-UCNPs is dispersed in 10mL aqueous solution by step 2., is added dropwise over the hydrochloric acid solution of 0.1M,
Until pH=3-5, stirring at normal temperature 4h, centrifugal, wash with ethanol water, obtain the UCNPs without part；
3.0g beta-schardinger dextrin-(CD) is joined in the 1.8mL aqueous solution containing 1.02g citric acid (Cit) by step 3., so
After, mixture solution to be poured in a small beaker, is placed in baking oven, 105 DEG C, react 3h, the product obtained is with different
Propanol recrystallization, product is dried 24h in the baking oven of 60 DEG C, obtains CD-Cit；
Step 4. is by 15mL diethylene glycol (DEG) and the aqueous solution of 2mL CD-Cit (3.0g), being dispersed in 5mL
UCNPs (10mg) in aqueous solution is added thereto, and mixture is heated to 100 DEG C under argon shield, reacts 30min,
Then evaporation removes water, and solution, at 160 DEG C, reacts 1-12h, is cooled to room temperature, centrifugal (16000rpm, 10min),
Wash with ethanol water, vacuum drying, obtain CD-Cit-UCNPs stand-by；
30mg CD-Cit-UCNPs is dispersed in bis-water of 5mL by step 5, the 2mL of 10mg rhodamine B (RB)
Aqueous solution is slowly added in above-mentioned secondary water, stirs 24h, centrifugal (18000rpm, 10min), wash with water under room temperature
Wash, obtain the upper conversion composite that RB-CD-Cit-UCNPs composite, i.e. cyclodextrin derivative are modified.
Upper conversion composite according to the cyclodextrin derivative modification that above-mentioned composite preparation method prepares.
The application in cholesterol detection of the above-mentioned composite.
The OA-UCNPs of the present invention is through X-ray diffraction analysis (XRD), and result shows each diffraction of the material of preparation
The crystal face at peak is all the most corresponding with normal data, does not has miscellaneous peak to occur, is the NaYF of pure hexagonal phase4Nano material (see
Accompanying drawing 1).
The OA-UCNPs of the present invention is dispersed in cyclohexane solution, through transmission electron microscope (TEM) and high-resolution-ration transmission electric-lens
(HRTEM) analyzing, result shows that the material of preparation is uniform nanoparticle, and this nanoparticle has obvious lattice
Striped, illustrates the highly crystalline (see accompanying drawing 2a and 2b) of this material.Remove the UCNPs after oleic acid and be dispersed in aqueous solution
In, analyze through TEM and HRTEM, it can be seen that the size of nanoparticle and pattern all do not have significant change, at water
Solution has good dispersibility, illustrates that oleic acid molecular is removed totally (see accompanying drawing 2c) the most substantially, in (110) face still
Lattice fringe clearly can be seen, illustrate that its highly crystalline person's character is not changed (see accompanying drawing 2d).
The CD-Cit of the present invention analyzes through mass spectrum (MS), and result shows end carboxyl and the hydroxyl on cyclodextrin existing on citric acid
After base formation ester, the peak of compound, illustrates beta-schardinger dextrin-, citric acid-modified success (see accompanying drawing 3).
OA-UCNPs, UCNPs, CD-Cit and CD-Cit-UCNPs of the present invention are fourier transformed infrared spectrum
(FT-IR) analyzing, result shows that, in OA-UCNPs spectrum, two at 2921cm-1And 2854cm-1Peak can divide
Do not belong to the asymmetric of methylene and symmetrical stretching vibration, at 1554cm-1And 1462cm-1The peak at place is respectively belonging to
Asymmetric and the symmetrical stretching vibration of carboxyl, thus may certify that and has wrapped up one layer of oleic acid molecular outside up-conversion.
The infrared spectrum of UCNPs, it can be seen that the peak of methylene and carboxyl almost disappears, only exists 1640cm-1The peak of water, says
The removal ratio of bright oleic acid more thoroughly, so its aqueous solution has good dispersibility in TEM figure.CD-Cit's is infrared
In spectrogram, 1732cm-1And 1202cm-1The existence at two peaks, illustrates to have been formed between cyclodextrin and citric acid esters
Compound.And CD-Cit-UCNPs is after washing through water and the ethanol degree of depth, at 1726cm-1And 1202cm-1Place also divides
Do not occur in that the characteristic peak in CD-Cit, illustrate that CD-Cit the most successfully wraps up on up-conversion (see accompanying drawing 4).
The RB-CD-Cit-UCNPs composite of the present invention is analyzed through x-ray photoelectron spectroscopy (XPS), and result shows
Can simultaneously observe N, Na, Y, F, Yb, Er, C and O, illustrate RB with UCNPs already integrated in together with (see
Accompanying drawing 5).
The composite of present invention synthesis is applied to cholesterol detection, after adding cholesterol, and cholesterol induction rhodamine B (RB)
Dissociate the cavity of beta-schardinger dextrin-(CD), causes FRET to weaken, and up-conversion fluorescence strengthens, and carrys out cholesterol detection with this
Content.
The composite of present invention synthesis is applied to cholesterol detection, it is not necessary to use cholesterol selectivity enzyme or antibody,
Use 980nm light as excitation source simultaneously, eliminate the background fluorescence interference of biological sample, improve signal to noise ratio,
Sensitivity can be greatly increased.
Accompanying drawing explanation
Fig. 1 is the x-ray diffraction pattern (XRD) of the pressed powder OA-UCNPs (OA-NaYF4:Yb, Er) of the present invention,
The rectilinear of bottom is hexagonal phase NaYF4Normal data figure (JCPDS28-1192).
Fig. 2 is the TEM (a) that is dispersed in cyclohexane solution of the pressed powder OA-UCNPs of the present invention and HRTEM
(b) figure and remove TEM (c) and HRTEM (d) figure of UCNPs aqueous solution of oleic acid.
Fig. 3 is the mass spectral characteristi figure (MS) of the CD-Cit aqueous solution of the present invention.
Fig. 4 is in Fu of pressed powder OA-UCNPs, UCNPs, CD-Cit-UCNPs and CD-Cit of the present invention
Leaf transformation infrared spectrogram (FT-IR).
Fig. 5 is the x-ray photoelectron spectroscopy figure (XPS) of the RB-CD-Cit-UCNPs of the present invention.
Fig. 6 is uv-visible absorption spectra (UV-vis, dotted line) and the OA-UCNPs of the RB aqueous solution of the present invention
The up-conversion fluorescence spectrum (UCL, solid line) of cyclohexane solution.
Fig. 7 is the Tris-HCl buffer solution (concentration 0.5mg/mL, pH=7.4) of the pressed powder of the present invention, adds
Up-conversion fluorescence spectrum after 0-200 μM of cholesterol (Cho).Illustration is GRR (the green glow integration of 515-565nm
The ratio of the HONGGUANG integrated intensity of intensity and 640-685nm) with the curve chart of cholesterol level change.
Fig. 8 is the Tris-HCl buffer solution (concentration 0.5mg/mL, pH=7.4) of the pressed powder of the present invention, adds
80 μMs of cholesterol, and up-conversion fluorescence Strength Changes when being not added with or add the interfering material of other 7 class 4mM
(this 7 class chaff interference is 1.NaCl respectively, KCl, MgCl2,CaCl2,ZnCl2；2. glycine and glucose；3. gluathione
Peptide and lecithin；4. vitamin C；5. boric acid and sucrose；6. bilirubin, sorbose and mannitol；7. tryptophan).
Fig. 9 is the Tris-HCl buffer solution (concentration 0.5mg/mL, pH=7.4) of the pressed powder of the present invention, not
GRR when adding and add the interfering material of 80 μMs of cholesterol or other 7 class 4mM (does not 1. have additive；2.
Cholesterol；3.NaCl,KCl,MgCl2,CaCl2,ZnCl2；4. glycine and glucose；5. glutathion and lecithin；
6. vitamin C；7. boric acid and sucrose；8. bilirubin, sorbose and mannitol；9. tryptophan).
Detailed description of the invention
The preparation of the upper conversion composite that embodiment 1. cyclodextrin derivative is modified
Step 1. is with 1mmol RECl3(0.78mmol YCl3,0.2mmol YbCl3,0.02mmol ErCl3) for reacting
Raw material, adds 7.5mL oleic acid and 17.5mL1-vaccenic acid, stirs, and solution is heated to 160 DEG C, keeps 30min.
It is cooled to room temperature, is separately added into 4mmol NH4The methanol solution of F and 2.5mmol NaOH, stirs 30min.Evaporate
Methanol, solution is heated to 300 DEG C under argon shield, reacts 1h, is cooled to room temperature.Reaction solution adds ethanol precipitation,
Centrifugal, wash several times with water and ethanol, obtain white precipitate, be i.e. OA-UCNPs；
100mg OA-UCNPs is dispersed in 10mL aqueous solution by step 2., is added dropwise over the hydrochloric acid solution of 0.1M,
Until pH=4, stirring at normal temperature 4h.Centrifugal, with ethanol aqueous wash several times, obtain the UCNPs without part；
3.0g beta-schardinger dextrin-(CD) is joined in the 1.8mL aqueous solution containing 1.02g citric acid (Cit) by step 3..
Then, mixture solution is poured in a small beaker, is placed in baking oven, 105 DEG C, react 3h.The product obtained is used
Recrystallisation from isopropanol, product is dried 24h in the baking oven of 60 DEG C, obtains CD-Cit；
Step 4. is by 15mL diethylene glycol (DEG) and the aqueous solution of 2mL CD-Cit (3.0g), being dispersed in 5mL
UCNPs (10mg) in aqueous solution is added thereto.Mixture is heated to 100 DEG C under argon shield, reacts 30min,
Then evaporation removes water, and solution, at 160 DEG C, reacts 1h, is cooled to room temperature, centrifugal (16000rpm, 10min),
With ethanol aqueous wash 3 times, vacuum drying, stand-by；
30mg CD-Cit-UCNPs is dispersed in bis-water of 5mL by step 5, the 2mL of 10mg rhodamine B (RB)
Aqueous solution is slowly added thereto.Stir 24h, centrifugal (18000rpm, 10min) under room temperature, wash 3 times, obtain ring
The upper conversion composite that dextrin derivative is modified.
The preparation of the upper conversion composite that embodiment 2. cyclodextrin derivative is modified
The upper conversion composite that cyclodextrin derivative is modified is prepared by the step of embodiment 1, but NH4The amount of the material of F is divided
Not being 1.6 and 2.8mmol, other steps are identical.Result is with embodiment 1.
The preparation of the upper conversion composite that embodiment 3. cyclodextrin derivative is modified
Prepare, by the step of embodiment 1, the upper conversion composite that cyclodextrin derivative is modified, but in step 1, solution is at argon
Being heated to 280 DEG C under protection, other steps are identical.Result is with embodiment 1.
The preparation of the upper conversion composite that embodiment 4. cyclodextrin derivative is modified
Prepare, by the step of embodiment 1, the upper conversion composite that cyclodextrin derivative is modified, but in step 1, solution is at argon
Being heated to 290 DEG C under protection, other steps are identical.Result is with embodiment 1.
The preparation of the upper conversion composite that embodiment 5. cyclodextrin derivative is modified
The upper conversion composite that cyclodextrin derivative is modified is prepared by the step of embodiment 1, but salt acid for adjusting pH in step 2
=3, other steps are identical.Result is with embodiment 1.
The preparation of the upper conversion composite that embodiment 6. cyclodextrin derivative is modified
The upper conversion composite that cyclodextrin derivative is modified is prepared by the step of embodiment 1, but salt acid for adjusting pH in step 2
=5, other steps are identical.Result is with embodiment 1.
The preparation of the upper conversion composite that embodiment 7. cyclodextrin derivative is modified
Preparing, by the step of embodiment 1, the upper conversion composite that cyclodextrin derivative is modified, in step 4, solution is at 160 DEG C
Under, react 6h, other steps are identical.Result is with embodiment 1.
The preparation of the upper conversion composite that embodiment 8. cyclodextrin derivative is modified
Preparing, by the step of embodiment 1, the upper conversion composite that cyclodextrin derivative is modified, in step 4, solution is at 160 DEG C
Under, react 12h, other steps are identical.Result is with embodiment 1.
The fluoroscopic examination of embodiment 9. cholesterol
The RB-CD-Cit-UCNPs (1mg) of preparation is dissolved in 2mL water, and dilutes with Tris-HCl (pH7.4),
Take the ethanol solution mixing of 90 these solution of μ L and 10 μ L variable concentrations cholesterol (final concentration 0-200 μM), stand 40
Carrying out up-conversion fluorescence mensuration after min, result is shown in Fig. 7.
The interference experiment of embodiment 10. cholesterol in serum detection
The Tris-HCl buffer solution (2ml) (pH=7.4) of 0.5mg/mL RB-CD-Cit-UCNPs adds 80
μM cholesterol, is not added with or adds the interfering material of other 7 class 4mM, investigates up-conversion fluorescence Strength Changes (this
7 class chaff interferences are 1.NaCl respectively, KCl, MgCl2,CaCl2,ZnCl2；2. glycine and glucose；3. glutathion and
Lecithin；4. vitamin C；5. boric acid and sucrose；6. bilirubin, sorbose and mannitol；7. tryptophan) (result is shown in figure
8 and 9).
The detection of embodiment 11. cholesterol in serum
The detection of cholesterol in serum is HAS's (being provided by attached drum tower hospital of Nanjing University).0.5mL blood
Mix with 4.5mL ethanol clearly, stand 10min, centrifugal (4000rpm, 10min), different types of serum supernatant
Liquid (10 μ L) mixes with the Tris-HCl buffer solution (pH=7.4,90 μ L) of RB-CD-Cit-UCNPs, and final concentration faces
Bed analysis result contains the cholesterol of 17.2,25.6,39.3,58.7,73.6 and 98.5 μMs respectively, after 40min, uses
The inventive method measures the content (the results are shown in Table 1) of cholesterol.
The clinical analysis of cholesterol level and the inventive method analysis result synopsis in table 1 blood serum sample
Claims (3)
1. the method preparing the modified upper conversion composite of cyclodextrin derivative, is characterized in that it includes
The following step:
Step 1. is with 0.78mmol YCl3,0.2mmol YbCl3With 0.02mmol ErCl3The 1mmol of composition
RECl3For reaction monomers, adding 7.5mL oleic acid and 17.5mL1-vaccenic acid, stir, solution is heated to
160 DEG C, keep 30min, be cooled to room temperature, add 1.6-4.0mmol NH4The first of F and 2.5mmol NaOH
Alcoholic solution is added thereto, and stirs 30min, and methanol removed by evaporation, solution is heated under argon shield
280-300 DEG C, reacting 1h, be cooled to room temperature, reaction solution adds ethanol precipitation, centrifugal, with water and ethanol
Washing, obtains OA-UCNPs；
100mg OA-UCNPs is dispersed in 10mL aqueous solution by step 2., and the hydrochloric acid being added dropwise over 0.1M is molten
Liquid, until pH=3-5, stirring at normal temperature 4h, centrifugal, wash with ethanol water, obtain the UCNPs without part；
The 1.8mL that 3.0g beta-schardinger dextrin-(CD) is joined containing 1.02g citric acid (Cit) by step 3. is water-soluble
In liquid, then, mixture solution is poured in a small beaker, is placed in baking oven, 105 DEG C, react 3h,
The product recrystallisation from isopropanol obtained, product is dried 24h in the baking oven of 60 DEG C, obtains CD-Cit；
Step 4. is by 15mL diethylene glycol (DEG) and the aqueous solution of the 3.0g CD-Cit of 2mL, dispersion
10mg UCNPs in 5mL aqueous solution is added thereto, and mixture is heated to 100 DEG C under argon shield,
Reaction 30min, then evaporation removes water, and solution, at 160 DEG C, reacts 1-12h, is cooled to room temperature, from
The heart, washs with ethanol water, and vacuum drying obtains CD-Cit-UCNPs stand-by；
30mg CD-Cit-UCNPs is dispersed in bis-water of 5mL by step 5,10mg rhodamine B (RB)
2mL aqueous solution be slowly added in above-mentioned secondary water, stir 24h under room temperature, centrifugal, wash with water, obtain
The upper conversion composite that RB-CD-Cit-UCNPs composite, i.e. cyclodextrin derivative are modified.
The upper conversion of the cyclodextrin derivative modification that composite preparation method prepares the most according to claim 1 is multiple
Condensation material.
3. the application in detection by quantitative cholesterol of the composite described in claim 2.
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