CN1331979C - Method for preparing water-soluble quantum point of biological functionalized sugar - Google Patents
Method for preparing water-soluble quantum point of biological functionalized sugar Download PDFInfo
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- CN1331979C CN1331979C CNB2005100182335A CN200510018233A CN1331979C CN 1331979 C CN1331979 C CN 1331979C CN B2005100182335 A CNB2005100182335 A CN B2005100182335A CN 200510018233 A CN200510018233 A CN 200510018233A CN 1331979 C CN1331979 C CN 1331979C
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- quantum dots
- soluble quantum
- sugar
- quantum dot
- organic solvent
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- 238000000034 method Methods 0.000 title claims abstract description 15
- 239000002096 quantum dot Substances 0.000 claims abstract description 62
- 230000008827 biological function Effects 0.000 claims abstract description 5
- 150000001720 carbohydrates Chemical class 0.000 claims abstract 4
- 238000007306 functionalization reaction Methods 0.000 claims abstract 3
- 230000009920 chelation Effects 0.000 claims abstract 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 39
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 claims description 12
- 239000004570 mortar (masonry) Substances 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 11
- 229920001661 Chitosan Polymers 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 229920000936 Agarose Polymers 0.000 claims description 2
- 229920002101 Chitin Polymers 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000003517 fume Substances 0.000 claims 3
- 239000012454 non-polar solvent Substances 0.000 claims 3
- 239000002244 precipitate Substances 0.000 claims 2
- 235000014633 carbohydrates Nutrition 0.000 claims 1
- 238000004140 cleaning Methods 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 150000004676 glycans Chemical class 0.000 abstract description 8
- 229920001282 polysaccharide Polymers 0.000 abstract description 7
- 239000005017 polysaccharide Substances 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 238000011953 bioanalysis Methods 0.000 abstract description 2
- 238000003384 imaging method Methods 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 238000002372 labelling Methods 0.000 abstract 1
- 230000009471 action Effects 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000695 excitation spectrum Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000002073 fluorescence micrograph Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000000163 radioactive labelling Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The present invention discloses a method for preparing water-soluble quantum dots with saccharide biological functionalization. In the method, saccharide materials with chelation and biological function are used as modifying reagents; saccharide biological functionalization is realized when quantum dots are transferred from oil solubility into water solubility by grinding. The method has the characteristics of simple application, strong operability, good repeatability and low cost of the modifying reagents. The obtained products can be widely used in the bioanalysis field of biologic labeling, cell imaging, etc. The present invention can also be used for the field of material science, etc. by utilizing the characteristic that high polysaccharide is easy to form a film.
Description
Technical field
The present invention relates to a kind of preparation method of water-soluble quantum dot of biological functionalized sugar, belong to biochemistry and material science.
Background technology
In recent years, quantum dot has been brought into play vital role as a kind of novel inorganic nano material at biological radioactive labelling and cell imaging field.Quantum dot has very excellent photoluminescent property, and fluorescence is strong, fluorescence emission peak is narrow and symmetrical, fluorescence color is continuous bands of a spectrum, is easy to realize that the unit excites polynary emission etc. based on composition and controllable size, excitation spectrum.But all by the preparation of organic phase high-temperature cracking method, product is an oil soluble to present high-quality quantum dot, and all living things systems all are that polarity is water miscible, and quantum dot only carries out just having using value behind the biological functional.So, by the surface chemistry method quantum dot surface is modified, realize that water-solubleization and the biological functional of oil soluble quantum dot is the key of quantum dot in the biomedical sector widespread use.
Again since glucide as the indispensable part of life entity, it is closely related with increasing biological phenomena, thereby caused numerous scientific workers' interest, but glucide is of a great variety, complex structure causes people that the understanding of sugar also just is in the preliminary stage, therefore, people press for and understand the vital role of sugar in biological phenomena, and this just need understand its biomechanism by suitable technology.But quantum dot is as a kind of fluorescent marker of excellent performance at present, and its effect is confined to and couplings such as DNA, protein, biological micromolecule more, and quantum dot is not also playing a role aspect the understanding glucide.
Summary of the invention
For water-solubleization that realize the oil soluble quantum dot and quantum dot-based in the biological functional of glucide, the invention provides a kind of derivative and quantum dot combination with sugar, polysaccharide and polysaccharide, giving quantum dot the water miscible while, given on the glucide mark quantum dot conversely again, provide fluorescently-labeled method for understanding the relevant biological phenomena of glucide.
The technical solution used in the present invention is to prepare the water-soluble quantum dot of biological functionalized sugar as follows:
(1) with ordinary method that CdSe, CdSe/ZnS, CdSe/CdS type oil soluble quantum dot surface washing is clean, then it is dissolved in the organic solvent, making concentration is the solution that contains quantum dot of 0.5～4mg/ml;
(2) take by weighing glucose, agarose, chitosan, cm-chitosan, the carboxymethyl chitin class glucide that has sequestering action and biological function in right amount, place mortar, add the solution contain quantum dot, fully grind, be positioned over again in the stink cupboard to organic solvent and volatilize fully;
(3) add an amount of organic solvent in mortar, fully grind, be positioned over again in the stink cupboard to organic solvent and volatilize 3～5 times so repeatedly fully;
(4) mortar was placed in the stink cupboard after 3～10 minutes, promptly obtained the water-soluble quantum dot of biological functionalized sugar.The organic solvent that wherein dissolves quantum dot can be selected normal hexane, toluene, chloroform for use.
The present invention has the derivative of oil soluble quantum dot and sugar, polysaccharide and polysaccharide etc. the glucide of sequestering action and biological function, only just can realize the water-solubleization while biological functionalized sugar of oil soluble quantum dot by polishing, product after the modification has excellent photoluminescent property, compare with existing other water-solubleization of quantum dot modifying method, have tangible advantage.Can make selectivity of product ground have different glucides and different functional groups after the glucide that the derivative of sugar, polysaccharide and polysaccharide etc. has sequestering action and a biological function is modified quantum dot, this just studies the biological activity of different glucides for us and connects different biomolecules provides possible.In addition, utilize the easy film forming characteristic of high glycan, also can with quantum dot and sugar the compound system film forming, thereby a kind of novel fluorescent screen material is provided.Therefore, the present invention can make quantum dot be applied even more extensively in bioanalysis field and material science.
And present method is easy to operation, cost is low, good reproducibility, all can finish at general chemistry and Biochemistry Experiment chamber.
Description of drawings
Fig. 1 is the fluorescence micrograph of the sugar-modified quantum dot of carboxymethyl chitosan that makes with the present invention;
Fig. 2 is the transmission electron microscope photo of the sugar-modified quantum dot of carboxymethyl chitosan that makes with the present invention;
Fig. 3 for the fluorescence spectrum of quantum dot in sugar-modified quantum dot of the carboxymethyl chitosan that makes with the present invention and the oil phase relatively.
Embodiment
Below by embodiment the preparation method of the water-soluble quantum dot of biological functionalized sugar is done detailed explanation.
Embodiment 1
(1) CdSe oil soluble quantum dot is dissolved in the normal hexane, making concentration is the hexane solution of the oil soluble quantum dot of 1mg/mL, CdSe oil soluble quantum dot can adopt the method for 02 1 No. 39152.1 patent disclosures of ZL, but does not need to prepare under the situation of sulfide storing solution.
(2) get the hexane solution of the above-mentioned oil soluble quantum dot of 0.5mL, add the ethanol sedimentation oil soluble quantum dot of 3 times of normal hexane volumes, with normal hexane throw out is dissolved into the solution of 0.5mL then again
(3) do twice again according to the method for (2), finally become the solution for later use of 2mL with n-hexane dissolution.
(4) take by weighing cm-chitosan 20mg and be put in the agate mortar,, ground 2～3 minutes, be positioned over and treat the normal hexane volatilization in the stink cupboard fully the quantum dot hexane solution adding of above-mentioned 2mL.
(5) add about 2mL normal hexane again in mortar, ground 2～3 minutes, be positioned over and treat the normal hexane volatilization in the stink cupboard fully, 3～5 times so repeatedly.
(6) mortar is placed in the stink cupboard after 10 minutes, is the CdSe quantum dot of water miscible biological functionalized sugar.
Embodiment 2
(1) CdSe/ZnS oil soluble quantum dot is dissolved in the normal hexane, and making concentration is the hexane solution of the oil soluble quantum dot of 1mg/mL, and CdSe/ZnS oil soluble quantum dot can adopt the method preparation of 1 No. 39152.1 patent disclosures of ZL02.
(2) get the hexane solution of the above-mentioned oil soluble quantum dot of 0.5mL, add the ethanol sedimentation oil soluble quantum dot of 3 times of normal hexane volumes, with normal hexane throw out is dissolved into the solution of 0.5mL then again
(3) do twice again according to the method for (2), finally become the solution for later use of 2mL with n-hexane dissolution.
(4) take by weighing cm-chitosan 20mg and be put in the agate mortar,, ground 2～3 minutes, be positioned over and treat the normal hexane volatilization in the stink cupboard fully the quantum dot hexane solution adding of above-mentioned 2mL.
(5) add about 2mL normal hexane again in mortar, ground 2～3 minutes, be positioned over and treat the normal hexane volatilization in the stink cupboard fully, 3～5 times so repeatedly.
(6) mortar is placed in the stink cupboard after 10 minutes, is the CdSe/ZnS quantum dot of water miscible biological functionalized sugar.
Because the toxicity of normal hexane is less, generally in implementation process, organic solvent is preferably selected normal hexane for use.
It is existing to levy by instrumentation tables such as transmission electron microscope, fluorescence inverted microscope, fluorescence spectrophotometer, see Fig. 1-Fig. 3 modify the back quantum point grain diameter still homogeneous, monodispersity is good, fluorescence quantum yield is high, fluorescence peak is narrow and symmetrical.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100182335A CN1331979C (en) | 2005-02-01 | 2005-02-01 | Method for preparing water-soluble quantum point of biological functionalized sugar |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100182335A CN1331979C (en) | 2005-02-01 | 2005-02-01 | Method for preparing water-soluble quantum point of biological functionalized sugar |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1660960A CN1660960A (en) | 2005-08-31 |
| CN1331979C true CN1331979C (en) | 2007-08-15 |
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| Application Number | Title | Priority Date | Filing Date |
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| CNB2005100182335A Expired - Fee Related CN1331979C (en) | 2005-02-01 | 2005-02-01 | Method for preparing water-soluble quantum point of biological functionalized sugar |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101962450B (en) * | 2010-10-20 | 2012-08-29 | 武汉大学 | Aqueous phase preparation method for chitosan-quantum dot fluorescent probe |
| CN103204634B (en) * | 2013-03-15 | 2014-12-17 | 北京科技大学 | Method for manufacturing semiconductor sulfide biopolymer nano-composite film |
| CN104177541B (en) * | 2014-06-11 | 2016-05-18 | 太原理工大学 | There is the preparation method of carbon point/polyacrylamide cartilage substitution material of fluorescent tracing performance |
| CN107987826A (en) * | 2018-01-02 | 2018-05-04 | 京东方科技集团股份有限公司 | Preparation method, application process and the quantum dot product of quantum dot |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6251303B1 (en) * | 1998-09-18 | 2001-06-26 | Massachusetts Institute Of Technology | Water-soluble fluorescent nanocrystals |
| CN1403379A (en) * | 2002-10-10 | 2003-03-19 | 武汉大学 | Prepn of CdSe/CdS or CdSe/ZnS core-shell quantum dot |
| CN1431070A (en) * | 2003-01-21 | 2003-07-23 | 武汉大学 | Method for preparing water-soluble nano particles |
-
2005
- 2005-02-01 CN CNB2005100182335A patent/CN1331979C/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6251303B1 (en) * | 1998-09-18 | 2001-06-26 | Massachusetts Institute Of Technology | Water-soluble fluorescent nanocrystals |
| CN1403379A (en) * | 2002-10-10 | 2003-03-19 | 武汉大学 | Prepn of CdSe/CdS or CdSe/ZnS core-shell quantum dot |
| CN1431070A (en) * | 2003-01-21 | 2003-07-23 | 武汉大学 | Method for preparing water-soluble nano particles |
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| CN1660960A (en) | 2005-08-31 |
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Granted publication date: 20070815 Termination date: 20130201 |