CN104177453A - Synthesis method of nanoparticle surface modifier - Google Patents
Synthesis method of nanoparticle surface modifier Download PDFInfo
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- CN104177453A CN104177453A CN201410346448.9A CN201410346448A CN104177453A CN 104177453 A CN104177453 A CN 104177453A CN 201410346448 A CN201410346448 A CN 201410346448A CN 104177453 A CN104177453 A CN 104177453A
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- mannitose
- seminose
- solution
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- auag
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Abstract
The invention provides a synthesis method of a nanoparticle surface modifier. A chemical synthesis method is utilized to combine water-soluble dithiodiols with mannitose to obtain dithiodiol mannitose derivatives. The products can be used for carrying out functionalization modification on Au, Ag, Cd and other metals and semiconductor material surfaces under the covalent combination action of the sulfhydryl group, and the bare mannitose structure on the other end can be specifically combined with canavaline (ConA). The mannitose derivative modified/silver nanoparticle process and the specific recognition process of ConA and mannitose can be characterized by obvious changes (generally red shift) of the SPR image color of the mono nanoparticles in real time under a dark field microscope (DFM). The saccharide-nanoparticles obtained by surface modification of the functional molecule are low in toxicity and stable in the solution, and have the advantages of favorable biocompatibility, favorable stability and efficient targeted recognition capability for trace canavaline.
Description
Technical field
The present invention is specifically related to a kind of synthetic method of nano grain surface modifier, belongs to field of nanometer material technology.
Background technology
The reaction of albumen-sugar becomes about the basis of (comprising cell adhesion, transmission and immune response), a lot of aspects of cell recognition.These specific reactions are by glycoprotein, and glycolipid, and cell surface saccharan and phytohemagglutinin, have the protein generation of sugared binding site.Phytohemagglutinin has the combination room of very weak sudden and violent leakage in solvent conventionally.Therefore the reaction between sugar and protein is generally all more weak.For the specificity of response intensity and reaction is provided, a lot of protein capable and sugared combination is the oligopolymer by a plurality of similar or identical monomer compositions, and each monomer can be in conjunction with a glycan molecule.For participating in multivalence bond, close or form a plurality of simultaneous association reaction phytohemagglutinins, provide one significantly in conjunction with (functional bonding force) ability, and will greatly be better than the summation of the binding ability of single reaction.
Method for the reaction of study-protein-sugar is necessary for obtaining biological function and these reactions in the vital role of pathology initial stage generation.Ordinary linkage protein in solution-glycan molecule is in conjunction with being often to belong to the more weak reaction of bonding force, make like this to use as those before usually Study on Protein or nucleic acid reaction classical take solution and as basic analytical procedure, analyze association reaction and become very difficult.Take surface can be used for promoting phytohemagglutinin identification as basic sugared array, and these will become a valuable instrument in blood sugar field.In array format, the appearance of sugar provides a method of simultaneously observing binding events between a plurality of fixing sugar and the protein in solution.In addition, being fixed on surperficial sugar is that multivalence key form occurs.Phytohemagglutinin is stronger and higher specific in conjunction with the association reaction of multivalence key array contrast ordinary linkage component.Therefore, the fixedly array of group helps phytohemagglutinin binding analysis and exists site to be correlated with for cell surface.
So far, for sugar, lack strong, common and can control array assembling type, realizing the report of glycan molecule array arrangement.In addition for the making of sugared array, in conjunction with the protein of sugared array, do not use fluorescence, radioelement, or enzyme transmission group analyzes requirement, avoids using the second binding constituents while also requiring observation; In the face of defect and the deficiency in current various analysis, just need us attempting use Applications of surface plasmon resonance, a kind of incident light that can resonate with the generation of plasma nano material surface conduction band electron be studied the reaction of sugar-protein in a kind of optical phenomena of nano grain surface and electronics generation resonance initiation electromagnetic wave field effect.The present invention comes hydrophilic two sulphur glycols compounds glycan molecule and nano particle combination, obtain soaking cultivation together with nano particle that glycan molecule medium chain can be coated with CTAC, the nano particle that base exchange reacts to form the modification of glycan molecule capped derivatives so just can occur.Sugar-the nano particle obtaining by this process is water miscible, nontoxicity and stable in solution.
Summary of the invention
By chemical synthesis process by water miscible 2; 2 '-bis-sulphur di-alcohol and full acetylated seminose combination; become after the product deprotection obtaining can with 2 of canavaline specific recognition; 2 '-bis-sulphur di-alcohol mannose derivatives; then with this compound, nano particle AuAg is carried out to physiologically acceptable sex modification; 2; 2 '-bis-sulphur di-alcohol seminoses carry out biocompatibility modification to nano particle AuAg and can descend the variation of the SPR spectrum of single particle AuAg nucleocapsid structure to characterize out by dark-field microscope (DFM), and concrete steps are as follows:
Under step 1. room temperature, Powdered seminose (MW180.16) is dissolved in NaSO
4in the pyridine being dried, add excessive acetic acid acid anhydride, after stirring certain time length (being greater than 2h), revolve steaming, with pyridine in the system of removing; Be extracted with ethyl acetate saturated NaHCO
3solution, after saturated aqueous common salt cleans, constant temperature revolves steaming, vacuum-drying; Obtain full acetylated seminose:
Step 2. is by BF
3et
2o dropwise joins 0 ℃, does not stop the cystine linkage glycols carbohydrate of stirring and the CH of the full acetylated seminose that step 1 obtains
2cl
2in solution (drying processing), then mixed solution can at room temperature react and be greater than 12h (not stopping to stir); Use CH
2cl
2extraction, washed twice then, then use NaSO
4dry; Use again ethyl acetate: sherwood oil carries out purifying according to a certain ratio, obtain the mannose derivative of acetylize protection:
The purified product that step 3. obtains step 2 in a round-bottomed flask is dissolved in methyl alcohol, adds NaOMe at room temperature to stir, and solvent is steamed and carry out according to a certain ratio purifying with EtOAc:MeOH, obtains two sulphur glycols mannose derivative products:
The treating processes of step 4.ITO substrate.With washing composition, acetone, ethanol, ultrapure water soaks ITO egative film successively, and immersion egative film is positioned in ultrasonic apparatus processes 1-2h, changes solution at every turn and with ultrapure water, rinses afterwards; After 4h, with nitrogen, dry up preservation;
Step 5. is fixed on by AuAg core-shell nanocube the ITO surface that step 4 was processed, the aqueous solution soaking of the product obtaining by step 3 is the ITO substrate of AuAg NC fixedly, AuAg NC is carried out to finishing, obtain surface exposure mannose group nano particle, can be used as the bioprobe that detects canavaline.With different concns (10
-8-10
-2m) seminose carries out surface to the fixing ITO substrate of AuAg core-shell nanocube and soaks and modify.
Beneficial effect
The present invention obtain one can with 2 of canavaline specific recognition, 2 '-bis-sulphur di-alcohol mannose derivatives, then with this compound, nano particle AuAg is carried out to physiologically acceptable sex modification, AuAg NC just becomes surface exposure mannose group nano particle through modifying, surface exposure mannose group just can carry out specific detection to the micro-canavaline (ConA) existing in solution, just becomes a specific biological probe that can detect canavaline (ConA).Sugar-the nano particle obtaining by this process is water miscible, nontoxicity and stable in solution.
Accompanying drawing explanation
Fig. 1 is the H of the full acetylated seminose of product of step 1 in the present invention
1nMR spectrogram.
Fig. 2 is the H of the full acetylated seminose of product 2,2 '-bis-sulphur di-alcohol of step 2 in the present invention
1nMR spectrogram.
Fig. 3 is the H of product 2,2 '-bis-sulphur di-alcohol seminose of step 3 in the present invention
1nMR spectrogram.
Fig. 4 is that in the present invention, 2,2 '-bis-sulphur di-alcohol seminoses of step 4 are modified the process of different time to nano particle AuAg, by dark-field microscope (DFM) result that the variation of the SPR spectrum of single particle AuAg nucleocapsid structure characterizes out down.
Embodiment
Embodiment 1
1. under room temperature, 2.5g, under room temperature, 2.5g, the Powdered seminose of 0.0139mol (1eq) (MW180.16) is dissolved in 20mL NaSO
4in the pyridine being dried, add 10mL, 0.083mol (1.5eq) diacetyl oxide, after stirring 16h, 70 ℃ revolve steaming, are extracted with ethyl acetate the saturated NaHCO of 2 * 100mL
3solution, 2 * 100mL saturated aqueous common salt cleans latter 40 ℃ and revolves steaming, vacuum-drying; Obtain full acetylated seminose.
2.6.4mL BF
3.Et
2o (7.2g, 5eq, 51.2mmol) dropwise joins 0 ℃, does not stop the CH of the cystine linkage di-alcohol 1.09g (1.4eq, 7mmol) of stirring and the product (4g, 1eq, 10.2mmol) of step 1
2cl
2in solution (20mL, dry), then mixed solution can at room temperature react 24h (not stopping to stir).Use 30mL CH
2cl
2extraction, 20mL NaHCO
3washed twice, Na
2sO
4dry.Thick product can carry out separation with ethyl acetate: sherwood oil=1:1, obtains the product of purifying.
3. in a round-bottomed flask, the product of (0.2g, 0.37mmol) step 2 is dissolved in 5mL methyl alcohol, adds (0.03g, 0.55mmol) NaOMe at room temperature to stir 30min and solvent is steamed and purify with EtOAc:MeOH=10:0.2.Obtain 2,2 '-bis-sulphur di-alcohol seminoses.
The treating processes of 4.ITO substrate.With washing composition, acetone, ethanol, ultrapure water soaks ITO egative film successively, and immersion egative film is positioned in ultrasonic apparatus processes 1-2h, changes solution at every turn and with ultrapure water, rinses afterwards; After 4h, with nitrogen, dry up preservation.
5. AuAg core-shell nanocube is fixed on to the ITO surface that step 4 was processed, the ITO substrate that fixedly step 4 of AuAg NC was processed of the aqueous solution soaking of the product obtaining by step 3, with 10
-2m carries out finishing to AuAg NC, and modification is as follows: the AuAg NC solution soaking ITO substrate of crossing with purifying, makes AuAg be absorbed and fixed at ITO surface; Then be fixed on dark-field microscope (DFM) Stage microscope, adjusting focal length, obtains the colored CCD picture of AuAg NC clearly; Choose at random several single particle AuAg NC, then in substrate, add 200uL10
-2the product of the step 3 of M, carries out real-time monitored 0.5h to the modification of selected particle surface.Can see that 2,2 '-bis-sulphur di-alcohol mannose derivatives are adsorbed on AuAg NC surface process, will there is red shift in the SPR spectrum of AuAg NC.As the square dotted line of Fig. 4.
Embodiment 2
1. under room temperature, 2.5g, under room temperature, 2.5g, the Powdered seminose of 0.0139mol (1eq) (MW180.16) is dissolved in 20mL NaSO
4in the pyridine being dried, add 10mL, 0.083mol (1.5eq) diacetyl oxide, after stirring 16h, 70 ℃ revolve steaming, are extracted with ethyl acetate the saturated NaHCO of 2 * 100mL
3solution, 2 * 100mL saturated aqueous common salt cleans latter 40 ℃ and revolves steaming, and vacuum-drying, obtains full acetylated seminose.
2.6.4mL BF
3.Et
2o (7.2g, 5eq, 51.2mmol) dropwise joins 0 ℃, does not stop the CH of the cystine linkage di-alcohol 1.09g (1.4eq, 7mmol) of stirring and the product (4g, 1eq, 10.2mmol) of step 1
2cl
2in solution (20mL, dry), then mixed solution can at room temperature react 24h (not stopping to stir).Use 30mL CH
2cl
2extraction, 20mL NaHCO
3washed twice, Na
2sO
4dry.Thick product can carry out separation with ethyl acetate: sherwood oil=1:1, obtains the product of purifying.
3. in a round-bottomed flask, the product of (0.2g, 0.37mmol) step 2 is dissolved in 5mL methyl alcohol, adds (0.03g, 0.55mmol) NaOMe at room temperature to stir 30min and solvent is steamed and purify with EtOAc:MeOH=10:0.2.Obtain 2,2 '-bis-sulphur di-alcohol seminoses.
The treating processes of 4.ITO substrate.With washing composition, acetone, ethanol, ultrapure water soaks ITO egative film successively, and immersion egative film is positioned in ultrasonic apparatus processes 1-2h, changes solution at every turn and with ultrapure water, rinses afterwards; After 4h, with nitrogen, dry up preservation.
5. AuAg core-shell nanocube is fixed on to the ITO surface that step 4 was processed, the ITO substrate that fixedly step 4 of AuAg NC was processed of the aqueous solution soaking of the product obtaining by step 3, with 10
-2m carries out finishing to AuAg NC, and modification is as follows: the AuAg NC solution soaking ITO substrate of crossing with purifying, makes AuAg be absorbed and fixed at ITO surface; Then be fixed on dark-field microscope (DFM) Stage microscope, adjusting focal length, obtains the colored CCD picture of AuAg NC clearly; Choose at random several single particle AuAg NC, then in substrate, add 200uL10
-2the product of the step 3 of M, carries out real-time monitored 1.0h to the modification of selected particle surface.Can see that 2,2 '-bis-sulphur di-alcohol mannose derivatives are adsorbed on AuAg NC surface process, will there is red shift in the SPR spectrum of AuAg NC.As the ball dotted line of Fig. 4.
Embodiment 3
1. under room temperature, 2.5g, under room temperature, 2.5g, the Powdered seminose of 0.0139mol (1eq) (MW180.16) is dissolved in 20mL NaSO
4in the pyridine being dried, add 10mL, 0.083mol (1.5eq) diacetyl oxide, after stirring 16h, 70 ℃ revolve steaming, are extracted with ethyl acetate the saturated NaHCO of 2 * 100mL
3solution, 2 * 100mL saturated aqueous common salt cleans latter 40 ℃ and revolves steaming, vacuum-drying; Obtain full acetylated seminose.
2.6.4mL BF
3.Et
2o (7.2g, 5eq, 51.2mmol) dropwise joins 0 ℃, does not stop the CH of the cystine linkage di-alcohol 1.09g (1.4eq, 7mmol) of stirring and the product (4g, 1eq, 10.2mmol) of step 1
2cl
2in solution (20mL, dry), then mixed solution can at room temperature react 24h (not stopping to stir).Use 30mL CH
2cl
2extraction, 20mL NaHCO
3washed twice, Na
2sO
4dry.Thick product can carry out separation with ethyl acetate: sherwood oil=1:1, obtains the product of purifying.
3. in a round-bottomed flask, the product of (0.2g, 0.37mmol) step 2 is dissolved in 5mL methyl alcohol, adds (0.03g, 0.55mmol) NaOMe at room temperature to stir 30min and solvent is steamed and purify with EtOAc:MeOH=10:0.2.Obtain 2,2 '-bis-sulphur di-alcohol seminoses.
The treating processes of 4.ITO substrate.With washing composition, acetone, ethanol, ultrapure water soaks ITO egative film successively, and immersion egative film is positioned in ultrasonic apparatus processes 1-2h, changes solution at every turn and with ultrapure water, rinses afterwards; After 4h, with nitrogen, dry up preservation.
5. AuAg core-shell nanocube is fixed on to the ITO surface that step 4 was processed, the ITO substrate that fixedly step 4 of AuAg NC was processed of the aqueous solution soaking of the product obtaining by step 3, with 10
-2m carries out finishing to AuAg NC, and modification is as follows: the AuAg NC solution soaking ITO substrate of crossing with purifying, makes AuAg be absorbed and fixed at ITO surface; Then be fixed on dark-field microscope (DFM) Stage microscope, adjusting focal length, obtains the colored CCD picture of AuAg NC clearly; Choose at random several single particle AuAg NC, then in substrate, add 200uL10
-2the product of the step 3 of M, carries out real-time monitored 2.0h to the modification of selected particle surface.Can see that 2,2 '-bis-sulphur di-alcohol mannose derivatives are adsorbed on AuAg NC surface process, will there is red shift in the SPR spectrum of AuAg NC.As the inverted triangle dotted line of Fig. 4.
Claims (3)
1. the synthetic method based on nano grain surface modifier, is characterized in that, takes following steps to synthesize two sulphur glycols mannose derivatives:
Synthesizing of the full acetylated seminose of step 1.:
Under room temperature, Powdered seminose (MW180.16) is dissolved in NaSO
4in the pyridine being dried, add excessive acetic acid acid anhydride, stir after duration is greater than 2h and revolve steaming, with pyridine in the system of removing; Be extracted with ethyl acetate saturated NaHCO
3solution, after saturated aqueous common salt cleans, constant temperature revolves steaming, vacuum-drying; Obtain full acetylated seminose;
Step 2. is by BF
3et
2o dropwise joins 0 ℃, does not stop the cystine linkage glycols carbohydrate of stirring and the CH of the full acetylated seminose that step 1 obtains
2cl
2in solution, then mixed solution can at room temperature react and be greater than 12h; Use CH
2cl
2extraction, washed twice then, then use NaSO
4dry; Use again ethyl acetate: sherwood oil carries out purifying according to a certain ratio, obtain the mannose derivative of acetylize protection;
Step 3. preparation two sulphur glycols mannose derivatives:
The purified product in a round-bottomed flask, step 2 being obtained is dissolved in methyl alcohol, adds NaOMe at room temperature to stir, and solvent is steamed and carry out according to a certain ratio purifying with EtOAc:MeOH, obtains product;
Step 4. is fixed on conductive glass surface by the nano particle of Au, Ag, Cd metal or its semiconductor material, the aqueous solution soaking of the product obtaining by step 3 is the conductive glass substrate of the nano particle of Au, Ag, Cd metal or its semiconductor material fixedly, the nano particle of Au, Ag, Cd metal or its semiconductor material is carried out to finishing, obtain surface exposure mannose group nano particle.
2. a kind of synthetic method based on nano grain surface modifier according to claim 1, it is characterized in that, in above-mentioned steps 2, cystine linkage glycols carbohydrate is symmetry or the asymmetric carbon hydrate with cystine linkage and two hydroxyls of a series of different chain length.
3. a kind of synthetic method based on nano grain surface modifier according to claim 1, it is characterized in that conductive glass is a series of transparent conducting glass that comprise ITO, FTO or TCO, combination can be adsorbed with the nano particle of Au, Ag, Cd metal or its semiconductor material through processing in surface.
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Cited By (2)
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| CN107698629A (en) * | 2017-10-19 | 2018-02-16 | 上海科技大学 | Disulfide bond bridging detergent and its application in memebrane protein research |
| CN116448637A (en) * | 2023-06-14 | 2023-07-18 | 北京建工环境修复股份有限公司 | Method for detecting nano plastic by modified gold particle marked dark field microscopic imaging |
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| CN107698629A (en) * | 2017-10-19 | 2018-02-16 | 上海科技大学 | Disulfide bond bridging detergent and its application in memebrane protein research |
| CN107698629B (en) * | 2017-10-19 | 2021-01-19 | 上海科技大学 | Disulfide bond bridging detergent and application thereof in membrane protein research |
| CN116448637A (en) * | 2023-06-14 | 2023-07-18 | 北京建工环境修复股份有限公司 | Method for detecting nano plastic by modified gold particle marked dark field microscopic imaging |
| CN116448637B (en) * | 2023-06-14 | 2023-09-08 | 北京建工环境修复股份有限公司 | Method for detecting nano plastic by modified gold particle marked dark field microscopic imaging |
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