CN103224654A - Silver sulfide quantum dot-chitosan nanometer complex preparation method - Google Patents
Silver sulfide quantum dot-chitosan nanometer complex preparation method Download PDFInfo
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Abstract
The present invention relates to a silver sulfide quantum dot-chitosan nanometer complex preparation method, which comprises: 1, dissolving a certain amount of chitosan or a derivative thereof in deionized water at a room temperature to prepare a chitosan aqueous solution with a concentration of 1-20 mg/mL or a chitosan derivative aqueous solution with a concentration of 1-20 mg/mL; 2, under a room temperature stirring condition, sequentially adding a chelating agent and a water soluble silver salt to the chitosan aqueous solution or the chitosan derivative aqueous solution, and carrying out a stirring reaction for 5-20 min; and 3, adding an alkali metal sulfide and a carboxyl compound to the product obtained from the step 2, carrying out a stirring reaction for 5-20 h, carrying out water dialysis and centrifugation on the obtained reaction product, washing sequentially by using absolute methanol and diethyl ether, and carrying out vacuum drying at a room temperature to obtain the silver sulfide quantum dot-chitosan nanometer complex. Compared with the nanometer complex in the prior art, the nanometer complex of the present invention has the following characteristics that: a nanometer complex with a near-infrared fluorescence imaging function is prepared by using a simple and easy-performing method, can be used for biological fluorescence imaging or as a fluorescent probe, and has characteristics of good biocompatibility, no physiological toxicity, and wide application prospects in biomedical fields.
Description
Technical field
The invention belongs to the crossing domain of chemistry, biology and material, especially relate to a kind of silver sulfide quantum dot-chitosan nano mixture and preparation method thereof with near-infrared fluorescent imaging function.
Background technology
Chitosan is the chitinous deacetylation derivative of natural biological polysaccharide, has free amino group, and physico-chemical property is very active, have have no side effect, good biocompatibility, biological degradation is controlled and characteristic such as no antigen.Therefore, chitosan all has a wide range of applications in all many-sides such as immobilization of biomedicine, organizational project, medicament slow release, cell and enzyme.In recent years, chitosan has been obtained bigger progress as the research of functionalized nano carrier, various ions, molecule and other component are loaded in the chitosan gel rubber network successively, form the chitosan nano complex systems of functional modification.The fluorescence quantum that wavelength is in near-infrared band has a lot of special advantages, such as bigger to the tissue penetration degree of depth, can overcome the visible light quantum dot and be subject to the interferential defective when carrying out the deep tissues imaging.Common near-infrared quantum dots all contains poisonous elements such as Cd, Se, Pb at present.Low toxicity even nontoxic silver sulfide (Ag with near-infrared fluorescent
2S) quantum dot has natural advantage.There are some researches show that this novel quantum dot has high fluorescence efficiency and high-biocompatibility, has a good application prospect at aspects such as living imaging, detection, diagnosis.
The present invention utilizes simple method that silver sulfide quantum dot and chitosan or derivatives thereof are fitted together, and forms the nano-complex of chitosan or derivatives thereof parcel silver sulfide quantum dot, can launch near-infrared fluorescent under certain shooting conditions.Compare with simple silver sulfide quantum dot, the biocompatibility of this nano-complex is better, and optical characteristics and fluorescence quantum yield are almost constant, can also use as nano-medicament carrier when having the near-infrared fluorescent imaging function.
Have not yet to see silver sulfide quantum dot and chitosan or the chitosan derivatives relevant patent report of nano-complex that preparation has above-mentioned functions that combines.
Summary of the invention
Purpose of the present invention is exactly to provide a kind of simple to operate for the defective that overcomes above-mentioned prior art existence, product can be launched near-infrared fluorescent, in-vivo imaging is effective, good biocompatibility has the preparation method of the silver sulfide quantum dot-chitosan nano mixture of good prospects for application at biomedicine field.
Purpose of the present invention can be achieved through the following technical solutions: the preparation method of a kind of silver sulfide quantum dot-chitosan nano mixture is characterized in that this method may further comprise the steps:
(1) at room temperature the certain amount of chitosan or derivatives thereof is dissolved in the deionized water, makes the chitosan or the chitosan derivatives aqueous solution that concentration is 1-20mg/mL;
(2) in the chitosan that step (1) makes or the chitosan derivatives aqueous solution, adding sequestrant and water soluble silver salt successively under the stirring at room condition, stirring reaction 5-20 minute, wherein the mass ratio of sequestrant and chitosan or derivatives thereof is 1: 100～1: 20, and the mass ratio of silver salt and chitosan or derivatives thereof is 1: 50～1: 5;
(3) in the product that step (2) obtains, add alkali metalsulphide and carboxylic compound, stirring reaction 5-20 hour, wherein the mol ratio of alkali metalsulphide and silver salt is 1: 1～1: 3, and the mass ratio of carboxylic compound and chitosan or derivatives thereof is 1: 100～1: 10; With reaction product water dialysis, centrifugal, with anhydrous methanol and ether washing, vacuum-drying at room temperature obtains silver sulfide quantum dot-chitosan nano mixture in succession.
Described chitosan or derivatives thereof is that deacetylation is one or more in the water-soluble chitosan, cm-chitosan, chitosan quaternary ammonium salt of 40%-95%, and viscosity-average molecular weight is 2-40 ten thousand.
Described sequestrant is ethylenediamine tetraacetic acid (EDTA), ethylene diamine tetra methylene phosphonic acid, 1-Hydroxy Ethylidene-1,1-Diphosphonic Acid or Amino Trimethylene Phosphonic Acid.
Described water soluble silver salt is Silver Nitrate or silver fluoride.
Described alkali metalsulphide is sodium sulphite or potassium sulphide.
Described carboxylic compound is mercaptan carboxylic acid or bovine serum albumins such as Thiovanic acid, thiohydracrylic acid, sulfydryl butyric acid.
Compared with prior art, the present invention has the following advantages and effect:
1. employed raw material is easy to obtain;
2. Zhi Bei silver sulfide quantum dot-chitosan nano mixture has the function of near-infrared fluorescent imaging, good biocompatibility, and stability is high under physiological environment;
3. the fluorescence efficiency height is strong to the penetrance of tissue and organ, and fluorescence imaging is effective in the body;
4. the preparation method is simple, and cost is lower.
Description of drawings
Fig. 1 is the transmission electron microscope photo of silver sulfide quantum dot-chitosan nano mixture.
Embodiment
The present invention is described in detail below in conjunction with the drawings and specific embodiments.
Embodiment 1
At room temperature be 100,000 with molecular weight, deacetylation is that 60% chitosan is dissolved in the deionized water, makes the chitosan aqueous solution that concentration is 5mg/ml; Adding ethylenediamine tetraacetic acid (EDTA) and Silver Nitrate under the stirring at room condition in this chitosan aqueous solution successively, the mass ratio of ethylenediamine tetraacetic acid (EDTA) and chitosan is 1: 50, and the mass ratio of Silver Nitrate and chitosan is 1: 20.Behind the stirring reaction 10 minutes, add potassium sulphide and thiohydracrylic acid, stirring reaction 8 hours, wherein the mol ratio of potassium sulphide and Silver Nitrate is 1: 2.2, the mass ratio of thiohydracrylic acid and chitosan is 1: 30; With reaction product water dialysis, centrifugal, with anhydrous methanol and ether washing, vacuum-drying at room temperature obtains silver sulfide quantum dot-chitosan nano mixture in succession.The transmission electron microscope photo of this nano-complex as shown in Figure 1.
Embodiment 2
At room temperature be 80,000 with molecular weight, deacetylation is that 50% cm-chitosan is dissolved in the deionized water, makes the chitosan aqueous solution that concentration is 7mg/ml; Adding ethylenediamine tetraacetic acid (EDTA) and silver fluoride successively under the stirring at room condition in this carboxymethyl chitosan sugar aqueous solution, the mass ratio of ethylenediamine tetraacetic acid (EDTA) and cm-chitosan is 1: 40, and the mass ratio of silver fluoride and chitosan is 1: 18.Behind the stirring reaction 15 minutes, add potassium sulphide and Thiovanic acid, stirring reaction 8 hours, wherein the mol ratio of potassium sulphide and silver fluoride is 1: 2.1, the mass ratio of Thiovanic acid and chitosan is 1: 30; With reaction product water dialysis, centrifugal, with anhydrous methanol and ether washing, vacuum-drying at room temperature obtains silver sulfide quantum dot-cm-chitosan nano-complex in succession.
Embodiment 3
At room temperature be 120,000 with molecular weight, deacetylation is that 80% chitosan is dissolved in the deionized water, makes the chitosan aqueous solution that concentration is 6mg/ml; Adding ethylene diamine tetra methylene phosphonic acid and Silver Nitrate under the stirring at room condition in this chitosan aqueous solution successively, the mass ratio of ethylene diamine tetra methylene phosphonic acid and chitosan is 1: 45, and the mass ratio of Silver Nitrate and chitosan is 1: 20.Behind the stirring reaction 15 minutes, add sodium sulphite and bovine serum albumin, stirring reaction 10 hours, wherein the mol ratio of sodium sulphite and Silver Nitrate is 1: 2.5, the mass ratio of bovine serum albumin and chitosan is 1: 20; With reaction product water dialysis, centrifugal, with anhydrous methanol and ether washing, vacuum-drying at room temperature obtains silver sulfide quantum dot-chitosan nano mixture in succession.
Embodiment 4
At room temperature be 90,000 with molecular weight, deacetylation is that 60% chitosan quaternary ammonium salt is dissolved in the deionized water, making concentration is the chitosan quaternary ammonium salt brine solution of 8mg/ml; Adding ethylene diamine tetra methylene phosphonic acid and Silver Nitrate successively under the stirring at room condition in this chitosan quaternary ammonium salt brine solution, the mass ratio of ethylene diamine tetra methylene phosphonic acid and chitosan quaternary ammonium salt is 1: 50, and the mass ratio of Silver Nitrate and chitosan quaternary ammonium salt is 1: 25.Behind the stirring reaction 15 minutes, add sodium sulphite and bovine serum albumin, stirring reaction 9 hours, wherein the mol ratio of sodium sulphite and Silver Nitrate is 1: 2.2, the mass ratio of bovine serum albumin and chitosan quaternary ammonium salt is 1: 25; With reaction product water dialysis, centrifugal, with anhydrous methanol and ether washing, vacuum-drying at room temperature obtains silver sulfide quantum dot-chitosan quaternary ammonium salt nano-complex in succession.
Embodiment 5
Organic fluorescence molecule-chitosan nano mixture nitric oxide donors and preparation method thereof may further comprise the steps:
(1) at room temperature certain amount of chitosan is dissolved in the deionized water, makes the chitosan aqueous solution that concentration is 12mg/mL;
(2) in the chitosan aqueous solution that step (1) makes, adding ethylenediamine tetraacetic acid (EDTA) and Silver Nitrate successively under the stirring at room condition, stirring reaction 12 minutes, wherein the mass ratio of ethylenediamine tetraacetic acid (EDTA) and chitosan is 1: 30, and the mass ratio of Silver Nitrate and chitosan is 1: 25;
(3) in the product that step (2) obtains, add potassium sulphide and thiohydracrylic acid, stirring reaction 12 hours, wherein the mol ratio of potassium sulphide and Silver Nitrate is 1: 2.3, the mass ratio of thiohydracrylic acid and chitosan is 1: 60; With reaction product water dialysis, centrifugal, with anhydrous methanol and ether washing, vacuum-drying at room temperature obtains silver sulfide quantum dot-chitosan nano mixture in succession.
Embodiment 6
The preparation method of a kind of silver sulfide quantum dot-chitosan nano mixture, this method may further comprise the steps:
(1) at room temperature molecular weight is 20,000, deacetylation is that 95% chitosan is dissolved in the deionized water, makes the chitosan aqueous solution that concentration is 1mg/mL;
(2) in the chitosan aqueous solution that step (1) makes, adding ethylenediamine tetraacetic acid (EDTA) and Silver Nitrate successively under the stirring at room condition, stirring reaction 5 minutes, wherein the mass ratio of ethylenediamine tetraacetic acid (EDTA) and chitosan is 1: 100, and the mass ratio of Silver Nitrate and chitosan is 1: 50;
(3) in the product that step (2) obtains, add sodium sulphite and Thiovanic acid, stirring reaction 5 hours, wherein the mol ratio of sodium sulphite and Silver Nitrate is 1: 1, the mass ratio of Thiovanic acid and chitosan is 1: 100; With reaction product water dialysis, centrifugal, with anhydrous methanol and ether washing, vacuum-drying at room temperature obtains silver sulfide quantum dot-chitosan nano mixture in succession.
Embodiment 7
The preparation method of a kind of silver sulfide quantum dot-chitosan nano mixture, this method may further comprise the steps:
(1) at room temperature molecular weight is 400,000, deacetylation is that 40% chitosan is dissolved in the deionized water, makes the chitosan aqueous solution that concentration is 20mg/mL;
(2) in the chitosan aqueous solution that step (1) makes, adding Amino Trimethylene Phosphonic Acid and silver fluoride successively under the stirring at room condition, stirring reaction 20 minutes, wherein the mass ratio of Amino Trimethylene Phosphonic Acid and chitosan is 1: 20, and the mass ratio of silver fluoride and chitosan is 1: 5;
(3) in the product that step (2) obtains, add potassium sulphide and bovine serum albumin, stirring reaction 20 hours, wherein the mol ratio of sodium sulphite potassium and silver fluoride is 1: 3, the mass ratio of bovine serum albumin and chitosan is 1: 10; With reaction product water dialysis, centrifugal, with anhydrous methanol and ether washing, vacuum-drying at room temperature obtains silver sulfide quantum dot-chitosan nano mixture in succession.
Claims (6)
1. the preparation method of silver sulfide quantum dot-chitosan nano mixture is characterized in that, this method may further comprise the steps:
(1) at room temperature the certain amount of chitosan or derivatives thereof is dissolved in the deionized water, makes the chitosan or the chitosan derivatives aqueous solution that concentration is 1-20mg/mL;
(2) in the chitosan that step (1) makes or the chitosan derivatives aqueous solution, adding sequestrant and water soluble silver salt successively under the stirring at room condition, stirring reaction 5-20 minute, wherein the mass ratio of sequestrant and chitosan or derivatives thereof is 1: 100～1: 20, and the mass ratio of silver salt and chitosan or derivatives thereof is 1: 50～1: 5;
(3) in the product that step (2) obtains, add alkali metalsulphide and carboxylic compound, stirring reaction 5-20 hour, wherein the mol ratio of alkali metalsulphide and silver salt is 1: 1～1: 3, and the mass ratio of carboxylic compound and chitosan or derivatives thereof is 1: 100～1: 10; With reaction product water dialysis, centrifugal, with anhydrous methanol and ether washing, vacuum-drying at room temperature obtains silver sulfide quantum dot-chitosan nano mixture in succession.
2. the preparation method of a kind of silver sulfide quantum dot according to claim 1-chitosan nano mixture, it is characterized in that, described chitosan or derivatives thereof is that deacetylation is one or more in the water-soluble chitosan, cm-chitosan, chitosan quaternary ammonium salt of 40%-95%, and viscosity-average molecular weight is 2-40 ten thousand.
3. the preparation method of a kind of silver sulfide quantum dot according to claim 1-chitosan nano mixture is characterized in that described sequestrant is ethylenediamine tetraacetic acid (EDTA), ethylene diamine tetra methylene phosphonic acid, 1-Hydroxy Ethylidene-1,1-Diphosphonic Acid or Amino Trimethylene Phosphonic Acid.
4. the preparation method of a kind of silver sulfide quantum dot according to claim 1-chitosan nano mixture is characterized in that described water soluble silver salt is Silver Nitrate or silver fluoride.
5. the preparation method of a kind of silver sulfide quantum dot according to claim 1-chitosan nano mixture is characterized in that described alkali metalsulphide is sodium sulphite or potassium sulphide.
6. the preparation method of a kind of silver sulfide quantum dot according to claim 1-chitosan nano mixture is characterized in that described carboxylic compound is mercaptan carboxylic acid or bovine serum albumins such as Thiovanic acid, thiohydracrylic acid, sulfydryl butyric acid.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103656668A (en) * | 2013-12-06 | 2014-03-26 | 山东省医学科学院药物研究所 | Bortezomib sustained-release preparation and preparation method thereof |
| CN105754584A (en) * | 2016-04-08 | 2016-07-13 | 苏州大学 | Preparation method and application of metal sulfur-group compound multifunctional nano probe |
| CN107253734A (en) * | 2017-06-29 | 2017-10-17 | 河南师范大学 | A kind of preparation method of the water-soluble silver sulfide quantum dot with bioactivity |
| CN107655871A (en) * | 2017-09-12 | 2018-02-02 | 重庆医科大学 | A kind of highly sensitive wide detection range fluoroscopic examination new method of Alendronate sodium |
| CN111450260A (en) * | 2020-04-17 | 2020-07-28 | 西南交通大学 | Bifidobacterium bifidum anti-tumor preparation, and preparation method, product and application thereof |
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| CN1831080A (en) * | 2006-03-29 | 2006-09-13 | 武汉大学 | Stable, water soluble chitin derivatives fluorescent quantal-points and prepn. method therefor |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103656668A (en) * | 2013-12-06 | 2014-03-26 | 山东省医学科学院药物研究所 | Bortezomib sustained-release preparation and preparation method thereof |
| CN103656668B (en) * | 2013-12-06 | 2016-08-17 | 山东省医学科学院药物研究所 | Bortezomib slow releasing preparation and preparation method thereof |
| CN105754584A (en) * | 2016-04-08 | 2016-07-13 | 苏州大学 | Preparation method and application of metal sulfur-group compound multifunctional nano probe |
| CN107253734A (en) * | 2017-06-29 | 2017-10-17 | 河南师范大学 | A kind of preparation method of the water-soluble silver sulfide quantum dot with bioactivity |
| CN107655871A (en) * | 2017-09-12 | 2018-02-02 | 重庆医科大学 | A kind of highly sensitive wide detection range fluoroscopic examination new method of Alendronate sodium |
| CN111450260A (en) * | 2020-04-17 | 2020-07-28 | 西南交通大学 | Bifidobacterium bifidum anti-tumor preparation, and preparation method, product and application thereof |
| CN111450260B (en) * | 2020-04-17 | 2021-06-25 | 西南交通大学 | Bifidobacterium bifidum anti-tumor preparation, and preparation method, product and application thereof |
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