CN108548799B - Organic fluorescent polydopamine nanoparticle solution and preparation method and application thereof - Google Patents

Organic fluorescent polydopamine nanoparticle solution and preparation method and application thereof Download PDF

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CN108548799B
CN108548799B CN201810190235.XA CN201810190235A CN108548799B CN 108548799 B CN108548799 B CN 108548799B CN 201810190235 A CN201810190235 A CN 201810190235A CN 108548799 B CN108548799 B CN 108548799B
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dopamine
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熊华玉
王升富
张修华
文为
王鑫
许佳青
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Abstract

The invention relates to a preparation method of an organic fluorescent polydopamine nanoparticle solution, which comprises the following steps of S1, dissolving dopamine in an acid-base buffer solution with the pH value of 2-7 to obtain a polydopamine solution; s2, adding an aqueous solution of an inorganic oxidant into the dopamine solution and mixing to obtain a reaction solution; s3, reacting the reaction liquid at 20-80 ℃ for 2-6h, filling the reaction liquid into a dialysis bag with the molecular weight cutoff of 100-500Da, and dialyzing for 36-48h to obtain the product. The preparation method has the beneficial effects that the invention provides a brand-new method for preparing the organic fluorescent poly-dopamine nanoparticle solution, and the organic fluorescent poly-polyamine nanoparticles can be prepared by one step by selecting a proper inorganic oxidant aqueous solution to be mixed with the dopamine solution, so that the preparation method is simple; the organic fluorescent polydopamine nanoparticle solution prepared by the invention can be used for detecting the concentration of ferrous ions in the solution and indicating the pH value of the solution.

Description

Organic fluorescent polydopamine nanoparticle solution and preparation method and application thereof
Technical Field
The invention belongs to the technical field of chemistry and bioscience, and particularly relates to an organic fluorescent polydopamine nanoparticle solution as well as a preparation method and application thereof.
Background
The organic fluorescent nano material has outstanding advantages in the aspects of biodegradation, biocompatibility, light stability and the like. Dopamine is a nerve-conducting substance, a chemical substance used to help cells deliver impulses, and widely exists in the human body. Dopamine is a small molecule which is easy to generate self-polymerization under the condition of oxygen, and the dopamine is a material with attractive force and application prospect when used for preparing an organic fluorescent nano material.
So far, there are relatively few reports on the synthesis of fluorescent polydopamine nanomaterials. The reported literature generally uses a two-step synthesis. The first step is as follows: dopamine is oxidized into large polydopamine nanoparticles by oxygen in water under alkaline conditions; the second step is that: adding a large amount of H2O2Etching large polydopamine nanoparticles into small fluorescent polydopamine nanoparticles [ X.Zhang, S.Wang, L.xu, L.Feng, Y.Ji, L.Tao, S.Li and Y.Wei, Nanoscale,2012,4,5581-]. The disadvantage is that the degree of polymerization is difficult to control when dopamine is oxidatively polymerized by oxygen, so the fluorescent polydopamine nano-materials synthesized in the prior art are all mixtures composed of different polymerization degrees [ A.YIldirim and M.Baylindrir, anal.chem.,2014,86,5508-]. Furthermore, H2O2Is a strong oxidant, large amount of H2O2The existence of the (B) can cause certain influence on the purification treatment and the subsequent analysis application, and in addition, a large amount of H is used2O2The resulting security threat is also not negligible.
Disclosure of Invention
The invention provides an organic fluorescent polydopamine nanoparticle solution and a preparation method and application thereof, overcomes the technical defects caused by two steps of oxygen oxidation and hydrogen peroxide oxidation and the use of oxygen and hydrogen peroxide in the prior art when preparing the fluorescent polydopamine nanoparticle solution, and aims to provide a novel preparation method of the organic fluorescent polydopamine nanoparticle solution which is simpler, more convenient and more environment-friendly and expand the application of the organic fluorescent polydopamine nanoparticles.
The technical scheme for solving the technical problems is as follows: a preparation method of an organic fluorescent polydopamine nanoparticle solution comprises the following steps:
s1, dissolving dopamine in an acid-base buffer solution with the pH value of 2-7 to obtain a dopamine solution;
s2, adding an aqueous solution of an inorganic oxidant into the dopamine solution and mixing to obtain a reaction solution, wherein the mass ratio of the dopamine to the inorganic salt oxidant is 20-65: 1-5;
s3, reacting the reaction liquid at 20-80 ℃ for 2-6h, filling the reaction liquid into a dialysis bag with the molecular weight cutoff of 100-500Da, and dialyzing for 36-48h to obtain the product.
On the basis of the technical scheme, the invention can also make the following further specific selection or optimal selection.
Specifically, the concentration of the dopamine solution in S1 is 20-65 mM.
Specifically, the acid-base buffer solution in S1 is Tris-HCl buffer solution.
Specifically, the inorganic oxidizing agent in S2 is ammonium persulfate, sodium persulfate or potassium persulfate, and the concentration of the aqueous solution of the inorganic oxidizing agent is 40-60 mM.
Most preferably, when the inorganic oxidizing agent is a persulfate, the reaction temperature in S3 is 65 ℃.
Specifically, the inorganic oxidant in S2 is copper sulfate or copper chloride, the concentration of the aqueous solution of the inorganic oxidant is 40-60mM,
most preferably, when the inorganic oxidizing agent is a cupric salt, the reaction temperature in S3 is 37 to 80 ℃.
The invention also provides an organic fluorescent polydopamine nanoparticle solution, which is prepared by the method.
The invention also provides application of the organic fluorescent polydopamine nanoparticle solution, and particularly relates to application of the organic fluorescent polydopamine nanoparticle solution in detection of Fe in the solution2+The concentration of (c).
The invention also provides an application of the organic fluorescent polydopamine nanoparticle solution, and particularly relates to an application of the organic fluorescent polydopamine nanoparticle solution in indicating the pH value of the solution.
Compared with the prior art, the invention has the beneficial effects that:
the invention provides a brand-new method for preparing organic fluorescent poly-dopamine nanoparticle solution, which selects proper inorganic oxidant aqueous solution (aqueous solution of cupric salt or persulfate) to mix with dopamine solution, and can prepare organic fluorescent poly-polyamine nanoparticles by one step, the preparation method is simple, and the defects of low efficiency, difficult control of polymerization degree, hydrogen peroxide environmental protection, poor safety and the like in the traditional two-step method of preparing by using oxygen and hydrogen peroxide are overcome; the organic fluorescent polydopamine nanoparticle solution prepared by the invention can be used for detecting the concentration of ferrous ions in the solution and indicating the pH value of the solution.
Drawings
Fig. 1 is an excitation diagram and an emission diagram of a raw material and a prepared polydopamine nanoparticle solution used in example 1 of the present invention, where a is the excitation diagram (ex. ═ 300nm) of the polydopamine nanoparticle solution, b is the emission diagram (Em. ═ 430nm) of the polydopamine nanoparticle solution, and c is the emission diagram at 300nm after the raw material dopamine solution (i.e., a solution obtained by dissolving dopamine in S1 in an acid-base buffer) is left to stand at room temperature for 2 hours;
FIG. 2 is a transmission electron microscope image of polydopamine nanoparticle solution obtained in example 1 of the present invention;
FIG. 3 shows the fluorescence response of polydopamine nanoparticle solution obtained in example 1 of the present invention to different metal ions (the concentration of each metal ion is the same and 50 μ M);
FIG. 4 shows that the polydopamine nanoparticle solution obtained in example 1 of the present invention is used as a fluorescent probe to measure Fe2+Fluorescence intensity and Fe2+The variation relation of the concentration;
fig. 5 is an excitation diagram and an emission diagram of the raw material and the prepared polydopamine nanoparticle solution in example 4 of the present invention, where a is the excitation diagram (ex. ═ 452nm) of the polydopamine nanoparticle solution, b is the emission diagram (Em. ═ 514nm) of the polydopamine nanoparticle solution, and c is the emission diagram at 452nm after the raw material dopamine solution (i.e., the solution obtained by dissolving dopamine in S1 in an acid-base buffer) is left to stand at room temperature for 2 hours;
FIG. 6 shows the response of fluorescence intensity of the raw material and the polydopamine nanoparticle solution according to the present invention in example 4, as a function of pH.
Detailed Description
The technical solutions provided by the present invention are further described in detail with reference to the accompanying drawings and specific embodiments, which are only used for explaining the present invention and are not used for limiting the scope of the present invention.
The pharmaceutical products used in the following examples are all commercially available products unless otherwise specified, and the methods used are all conventional methods used by those skilled in the art without further specification.
Example 1
An organic fluorescent polydopamine nanoparticle solution is prepared by the following steps:
s1, dissolving dopamine in a Tris-HCl buffer solution with the pH value of 5 to obtain a dopamine solution, wherein the concentration of the dopamine aqueous solution is 0.01g/mL, namely 64 mM;
s2, adding 40 mu L of ammonium persulfate aqueous solution with the concentration of 50mM into 1000 mu L of dopamine aqueous solution, and fully mixing to obtain reaction liquid, wherein dopamine, ammonium persulfate and H in the reaction liquid2O2The ratio of the amounts of substances of (a) is about 64: 2;
s3, reacting the reaction liquid at 65 ℃ for 3h, then filling the reaction liquid into a dialysis bag with the molecular weight cutoff of 100-500Da, and dialyzing for 40h to obtain the product.
Example 2
An organic fluorescent polydopamine nanoparticle solution is prepared by the following steps:
s1, dissolving dopamine in a Tris-HCl buffer solution with the pH value of 2 to obtain a dopamine solution, wherein the concentration of the dopamine aqueous solution is 0.005g/mL, namely 32 mM;
s2, adding 20 mu L of 60mM sodium persulfate aqueous solution into 1000 mu L of dopamine aqueous solution, and fully mixing to obtain reaction liquid, wherein dopamine, sodium persulfate and H are contained in the reaction liquid2O2Is about 32: 1.2;
s3, reacting the reaction liquid at 20 ℃ for 6h, then filling the reaction liquid into a dialysis bag with the molecular weight cutoff of 100-500Da, and dialyzing for 48h to obtain the product.
Example 3
An organic fluorescent polydopamine nanoparticle solution is prepared by the following steps:
s1, dissolving dopamine in a Tris-HCl buffer solution with the pH value of 7 to obtain a dopamine solution, wherein the concentration of the dopamine aqueous solution is 0.003g/mL, namely about 20 mM;
s2, adding 125 mu L of 40mM potassium persulfate aqueous solution into 1000 mu L of dopamine aqueous solution, and fully mixing to obtain reaction liquid, wherein dopamine, potassium persulfate and H are contained in the reaction liquid2O2About 20: 5;
s3, reacting the reaction liquid at 80 ℃ for 2h, then filling the reaction liquid into a dialysis bag with the molecular weight cutoff of 100-500Da, and dialyzing for 36h to obtain the product.
Example 4
An organic fluorescent polydopamine nanoparticle solution is prepared by the following steps:
s1, dissolving dopamine in a Tris-HCl buffer solution with the pH value of 5 to obtain a dopamine solution, wherein the concentration of the dopamine aqueous solution is 0.005g/mL, namely 32 mM;
s2, adding 40 mu L of copper sulfate aqueous solution with the concentration of 50mM into 1000 mu L of dopamine aqueous solution, and fully mixing to obtain reaction liquid, wherein dopamine, copper sulfate and H are contained in the reaction liquid2O2Is about 32: 2;
s3, reacting the reaction liquid at 50 ℃ for 4h, then filling the reaction liquid into a dialysis bag with the molecular weight cutoff of 100-500Da, and dialyzing for 40h to obtain the product.
Example 5
An organic fluorescent polydopamine nanoparticle solution is prepared by the following steps:
s1, dissolving dopamine in a Tris-HCl buffer solution with the pH value of 5 to obtain a dopamine solution, wherein the concentration of the dopamine aqueous solution is 0.01g/mL, namely 64 mM;
s2, adding 80 mu L of copper sulfate aqueous solution with the concentration of 60mM into 1000 mu L of dopamine aqueous solution, and fully mixing to obtain reaction liquid, wherein dopamine, copper sulfate and H are contained in the reaction liquid2O2The ratio of the amounts of substances of (a) is about 64: 4.8;
s3, reacting the reaction liquid at 37 ℃ for 6h, then filling the reaction liquid into a dialysis bag with the molecular weight cutoff of 100-500Da, and dialyzing for 48h to obtain the product.
Example 6
An organic fluorescent polydopamine nanoparticle solution is prepared by the following steps:
s1, dissolving dopamine in a Tris-HCl buffer solution with the pH value of 5 to obtain a dopamine solution, wherein the concentration of the dopamine aqueous solution is 0.003g/mL, namely about 20 mM;
s2, adding 25 mu L of 40mM copper sulfate aqueous solution into 1000 mu L of dopamine aqueous solution, and fully mixing to obtain a reaction solution, wherein dopamine, copper sulfate and H are contained in the reaction solution2O2About 20: 1;
s3, reacting the reaction liquid at 80 ℃ for 3h, then filling the reaction liquid into a dialysis bag with the molecular weight cutoff of 100-500Da, and dialyzing for 36h to obtain the product.
The organic fluorescent poly-dopamine nanoparticle solutions prepared in the embodiments 1 to 6 are respectively used as test samples, and each sample has an obvious fluorescent effect through detection, can be used for detecting ferrous ions in the solution, and the fluorescent intensity of the solution changes along with the change of pH. Taking the organic fluorescent polydopamine nanoparticle solution prepared in example 1 as a representative, the fluorescence effect of the organic fluorescent polydopamine nanoparticle solution is tested and shown in fig. 1, and it can be known from fig. 1 that the polydopamine nanoparticle is successfully synthesized by the invention and has the fluorescence effect (a and b have obvious excitation peaks and emission peaks, and c as a comparison has no emission peak); as can be seen from fig. 2, the polydopamine nanoparticle sample prepared in example 1 of the present invention has a nano size and relatively uniform size; as can be seen from fig. 3, when the ion concentrations are all 50 μ M, the enhancement effect of the ferrous ions on the fluorescence intensity of the polydopamine nanoparticle solution prepared in example 1 of the present invention is significantly smaller than that of the other metal ions, and the solution containing only ferrous ions can be selectively identified by using this characteristic (it should be noted that the identification here is suitable for identifying a plurality of bottles of solutions containing only a single metal ion, and is particularly suitable for the case where the metal ion concentration is low and is difficult to identify by other methods); as can be seen from fig. 4, when the concentrations of ferrous ions and ferric ions are relatively low, the fluorescence intensity of the poly-dopamine nanoparticle solution during detection is obviously enhanced along with the increase of the corresponding ferrous ion concentration, and the correlation is good, so that the quantitative detection of the ferrous ions with very low concentrations can be considered according to the characteristic. As can be seen from fig. 5, example 4 using copper sulfate as oxidant can also successfully synthesize polydopamine nanoparticles and have fluorescence effect (a and b have distinct excitation peak and emission peak, and c as comparison has no emission peak); as can be seen from fig. 6, the polydopamine nanoparticle solution synthesized in example 4 using copper sulfate as an oxidant has a better response to pH change, and this property can be used to indicate the pH of the solution.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.

Claims (9)

1. A preparation method of an organic fluorescent polydopamine nanoparticle solution is characterized by comprising the following steps:
s1, dissolving dopamine in an acid-base buffer solution with the pH value of 2-7 to obtain a dopamine solution;
s2, adding an aqueous solution of an inorganic oxidant into the dopamine solution and mixing to obtain a reaction solution, wherein the mass ratio of the dopamine to the inorganic oxidant is 20-65: 1-5, wherein the inorganic oxidant is a cupric salt or a persulfate;
s3, reacting the reaction liquid at 20-80 ℃ for 2-6h, filling the reaction liquid into a dialysis bag with the molecular weight cutoff of 100-500Da, and dialyzing for 36-48h to obtain the product;
the concentration of the dopamine solution in the S1 is 20-65 mM;
the concentration of the aqueous solution of the inorganic oxidant in S2 is 40-60 mM.
2. The method for preparing an organic fluorescent polydopamine nanoparticle solution according to claim 1, wherein the acid-base buffer solution in S1 is Tris-HCl buffer solution.
3. The method for preparing an organic fluorescent polydopamine nanoparticle solution according to claim 1, wherein the inorganic oxidant in S2 is ammonium persulfate, sodium persulfate or potassium persulfate.
4. The method for preparing organic fluorescent polydopamine nanoparticle solution according to claim 3, wherein the reaction temperature in S3 is 65 ℃.
5. The method for preparing organic fluorescent polydopamine nanoparticle solution according to claim 1, wherein the inorganic oxidant in S2 is copper sulfate or copper chloride.
6. The method for preparing organic fluorescent polydopamine nanoparticle solution according to claim 5, wherein the reaction temperature in S3 is 37-80 ℃.
7. An organic fluorescent polydopamine nanoparticle solution, characterized in that it is prepared by the method according to any one of claims 1 to 6.
8. Use of the organic fluorescent polydopamine nanoparticle solution according to claim 7 for detecting Fe in solution2+The concentration of (c).
9. Use of the organic fluorescent polydopamine nanoparticle solution according to claim 7, for indicating the pH of the solution.
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