CN107714724B - Carbon dots as antitumor drug and preparation method and application thereof - Google Patents
Carbon dots as antitumor drug and preparation method and application thereof Download PDFInfo
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- 125000002059 L-arginyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H] 0.000 description 1
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
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- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
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Abstract
The invention relates to a carbon dot serving as an anti-tumor medicine, and a preparation method and application thereof. Arginine is used as a carbon source, water is used for completely dissolving the arginine, a proper amount of ethylenediamine is added, ultrasonic dissolution is carried out, and microwave heating is carried out to obtain the target product carbon dots. The carbon dots prepared by the invention can be used for treating cancer because hydrogen peroxide exists in cancer cells in organisms. The fluorescent imaging method not only can be used for fluorescent imaging, but also has the characteristics of good biocompatibility, high NO release amount, long action cycle time, good drug stability, low price, easiness in obtaining and the like.
Description
Technical Field
The invention belongs to the fields of fluorescent nano materials and biomedicine, and particularly relates to a carbon dot capable of being used as an anti-tumor medicament, and a preparation method and application thereof.
Background
NO is an extremely unstable biological free radical, has small molecules, simple structure, is gas at normal temperature, is slightly soluble in water, has fat solubility, is widely distributed in various tissues in organisms, and is a novel biological messenger molecule. And has very important biological effects in the aspects of cardiovascular and cerebrovascular regulation, nerve regulation, immune regulation and the like. Therefore, the method is generally regarded by people. It can rapidly diffuse through biological membrane without any intermediary mechanism to transmit the information generated by a cell to the cells around it, and the research on the biological action and action mechanism of NO is in the spotlight, and its discovery marks the research prospect of inorganic molecules in the medical field.
In modern biomedicine, studies have found the presence of hydrogen peroxide in tumor cells. It is therefore envisaged that the production of NO in tumour cells could be achieved if the cells were killed by addition of arginine thereto. However, although arginine reacts with hydrogen peroxide to release NO, the release amount is not very large, and arginine is a biological macromolecule and can only enter cells to play a role in vivo through osmosis, so that the efficiency is not high, and the practical application of arginine is limited to a certain extent.
Disclosure of Invention
The invention aims to improve the defects of the existing technology for generating NO by arginine reaction, and arginine is made into carbon dots, so that the carbon dots are endowed with the fluorescence property, and the fluorescence imaging can be carried out. Moreover, the yield of NO is larger after improvement, and the efficiency is improved by directly entering cells through endocytosis.
In order to achieve the purpose, the invention adopts the technical scheme that: a carbon dot used as an antitumor drug is prepared by the following steps: arginine is used as a carbon source, water is used for completely dissolving the arginine, a proper amount of ethylenediamine is added, ultrasonic dissolution is carried out, and microwave heating is carried out to obtain the target product carbon dots.
The carbon dot serving as the antitumor drug is characterized in that arginine is L-arginine.
The carbon dots serving as the antitumor drug comprise (1:2) - (1:4) of ethylenediamine-arginine according to molar ratio; preferably, the ethylenediamine-arginine ratio is 1: 2.
The carbon dots serving as the antitumor drug are heated for 4min at the microwave power of 750W.
The carbon dots are used singly or mixed with other antitumor drugs to prepare the antitumor drugs.
The carbon dots prepared by the invention can generate NO through the action with hydrogen peroxide in cancer cells so as to kill the cancer cells. The carbon dots are spherical-like nanoparticles with a carbon atom as a skeleton structure, the size of the carbon dots is less than 20nm, and the carbon dots have fluorescence performance. The invention provides a carbon dot which can react with hydrogen peroxide to generate NO and can be used as an anti-tumor medicament. The drug is a carbon dot that has not been passivated or modified. The fluorescent carbon dots can be used as a cancer treatment drug because they can react with hydrogen peroxide in cancer cells to generate NO, and can kill cancer cells when the content of NO in cancer cells is higher than 1 μ M. In addition, the carbon dots have fluorescence property, so that the diagnosis and treatment of cancer can be integrated.
The invention has the beneficial effects that:
1. the carbon dots prepared by the method have the particle size of 1-5nm, are uniformly distributed spherical particles, have NO passivation or modification on the surfaces, and have NO toxicity, so that the carbon dots can be used in the field of biomedicine, and can effectively treat cancers by releasing NO through the action of the carbon dots and hydrogen peroxide in cancer cells.
2. The carbon dot-based antitumor drug disclosed by the invention not only can be subjected to fluorescence imaging, but also has the characteristics of good biocompatibility, high NO release amount, long action cycle time, good drug stability and the like. For example in biological imaging: the fluorescent carbon dots can be used as antitumor drugs and can be used for fluorescence imaging in organisms so as to realize the diagnosis and treatment integration of cancers. In addition, the medicine can enter cells through endocytosis to play a role, so that the treatment effect is better; the preparation method has the advantages of simple process, easy operation, low preparation cost and easy popularization.
3. According to the invention, arginine is made into carbon dots, so that intracellular fluorescence imaging can be realized, the amount of generated NO is larger, and the method is more favorable for killing tumor cells. In addition, the endocytosis at the carbon point in the biological cell is more efficient than the osmosis of arginine, which is more beneficial to the exertion of the drug effect. The carbon dots prepared by the method can be used as antitumor drugs in biomedicine.
Drawings
FIG. 1 is a transmission electron microscopy image of L-arginine carbon dots.
FIG. 2 is a fluorescence spectrum of the L-arginine carbon dot at an optimum excitation wavelength of 370 nm.
FIG. 3 is a NO release curve of L-arginine carbon point and arginine at 24 hours.
FIG. 4 shows the results of cell experiments with L-arginine carbon dots.
Detailed Description
The invention is illustrated in further detail below by way of non-limiting examples.
Example 1
Respectively weighing 11.5mmol L-arginine, respectively adding 5.7mmol urea and 5.7mmol ethylenediamine, dissolving in 15mL ultrapure water, completely dissolving, heating in a microwave oven at 750W for 4min, and taking out to obtain L-arginine urea carbon dot (URCD) and L-arginine ethylenediamine carbon dot (LACD).
The URCD and LACD were dissolved by adding each to 90mL of PBS buffer solution with pH 6.5. 80mL of the above-dissolved solution was taken, and 100. mu. L H was added to each solution2O2. And respectively measuring the release condition of NO in the solution of the two systems after reacting for 15 hours by using a Griess reagent. The results are shown in Table 5.
TABLE 5
| NO release (μ M) after 15 hours of reaction | |
| LACD | 6.5 |
| URCD | 6.3 |
TABLE 5 LACD and URCD with H, respectively2O2Statistical results of NO release at 15 hours of reaction. It can be seen from table 5 that LACD releases more NO than URCD. The amount of NO released by LACD was 6.5. mu.M and the amount of NO released by URCD was 6.3. mu.M, measured at 15 hours of release. Therefore, ethylenediamine is preferred in the present invention.
Example 2
Weighing 2g L-arginine and 0.173g, 0.230g, 0.345g, 0.690g and 1.38g of ethylenediamine respectively, dissolving the ethylenediamine and the L-arginine in 15mL of ultrapure water (the mass ratio of the ethylenediamine to the L-arginine is 1:4,1:3,1:2,1:1 and 2:1 respectively), heating for 4 minutes in a microwave oven at 750W, and taking out to obtain L-arginine carbon dots (LACD) with different ratios.
Dissolving the five LACDs in 40mL PBS buffer solution with pH of 6.5, respectively, collecting 20mL solutions, and adding 200 μ L H2O2The reaction was carried out for 12 hours. The NO release amount was measured by Griess reagent for 12 hours of reaction, and the results are shown in Table 6.
TABLE 6
| The weight ratio of the ethylenediamine to the L-arginine | NO release (μ M) after 12 hours of reaction |
| 1:4 | 24.68 |
| 1:3 | 23.46 |
| 1:2 | 28.44 |
| 1:1 | 6.74 |
| 2:1 | 8.28 |
As can be seen from Table 6, the amount of NO released was the largest at a 1:2 ratio of ethylenediamine to L-arginine species, and the amount released was 28.44. mu.M.
Example 3L-arginine carbon Point
2g (11.5mmol) of L-arginine and 0.345g (5.7mmol) were weighed out and dissolved in 15mL of ultrapure water, and after complete dissolution, the solution was heated for 4 minutes in a microwave oven at 750W to obtain an L-arginine carbon dot (LACD).
The prepared L-arginine carbon dots (LACD) were subjected to electron microscope scanning, and as shown in FIG. 1, the prepared L-arginine carbon dots (LACD) had an average particle diameter of 3nm, were uniformly distributed, and were uniformly distributed as spherical particles, as can be seen from FIG. 1.
Example 4 application of L-arginine carbon Point
The L-arginine carbon dot prepared in example 3 was diluted with water to near colorless, and the mixture was placed in a cuvette, and the carbon dot was measured by a fluorescence spectrometer to have an optimum excitation wavelength of 370nm, and then the absorbance of the carbon dot solution was adjusted to 0.1 at a wavelength of 370nm by an ultraviolet spectrophotometer. The fluorescence spectrum of the carbon dot solution at this concentration was measured at an excitation wavelength of 370nm by a fluorescence spectrophotometer, and the quinine sulfate fluorescence spectrum was measured in the same manner, and as shown in fig. 2, the quantum yield of the L-arginine carbon dots (LACD) was 6.88% by integration since the quantum yield of the quinine sulfate standard was 54%.
Example 5 carbon-point in vitro simulation of L-arginine
0.89g of each of L-arginine carbon dot (LACD) and L-arginine prepared in example 3 was added to a 80ml of PBS buffer solution having a pH of 6.5, and 100. mu. L H was added thereto2O2Stirring at constant temperature of 37 ℃. And respectively measuring the release conditions of NO in the solutions of the two systems at different times by using a Griess reagent. The results are shown in FIG. 3.
FIG. 3 is a kinetic release profile of NO produced by the reaction. It can be seen from FIG. 3 that LACD releases more NO than L-arginine. The amount of NO released by LACD was 13.38. mu.M and the amount of NO released by L-arginine was 11.12. mu.M, measured at 24 hours of in vitro release.
Example 6L-arginine carbon dot cell assay
Cell viability was measured by incubating 0.5,1,10,20,50,100,200mg/mL of the L-arginine carbon dot (LACD) prepared in example 3 and 100. mu.L of the L-arginine solution with BGC823 gastric cancer cells for 48 hours, respectively, and the results are shown in FIG. 4. It can be seen from FIG. 4 that LACD has higher lethality to cancer cells than L-arginine. At a drug concentration of 20mg/mL, LACD reduced the survival rate of cancer cells to 43.1%, whereas the carbon point of L-arginine increased the survival rate of cells to 148.6%.
In conclusion, the preparation process shows that the method has low raw material price, simple and easy operation and does not need complex reaction conditions, and the carbon dots prepared by the method can be used for treating cancers. The fluorescent imaging method not only can be used for fluorescent imaging, but also has the characteristics of good biocompatibility, high NO release amount, long action cycle time, good drug stability, low price, easiness in obtaining and the like. In view of these excellent properties, the novel carbon dots are expected to be applied to the field of cancer diagnosis and treatment integration.
Claims (3)
1. The application of the carbon dots serving as the antitumor drugs singly or mixed with other antitumor drugs in the preparation of the antitumor drugs for diagnosis and treatment is characterized in that the preparation method of the carbon dots comprises the following steps: taking L-arginine as a carbon source, completely dissolving with water, adding a proper amount of ethylenediamine, ultrasonically dissolving, wherein the microwave power is 750W, and heating for 4min by microwave to obtain a target product L-arginine carbon point; ethylenediamine-L-arginine =1:2 in molar ratio.
2. The use of claim 1, wherein the L-arginine carbon dot is present at a drug concentration of 0.5 to 100 mg/mL.
3. The use of claim 1, wherein the L-arginine carbon dot is at a drug concentration of 20 mg/mL.
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| CN113548656B (en) * | 2020-06-16 | 2023-02-21 | 哈尔滨成程生命与物质研究所 | Carbon dots with anticancer bioactivity and preparation method thereof |
| CN112546223B (en) * | 2020-12-22 | 2022-01-18 | 福州大学 | Photocatalyst for treating hypoxia tumor nitric oxide and preparation method thereof |
| CN112442362B (en) * | 2021-01-22 | 2021-08-20 | 暨南大学 | High-nitric oxide-loading fluorescent carbon dot and preparation method and application thereof |
| CN115252596A (en) * | 2022-07-27 | 2022-11-01 | 辽宁大学 | Manganese dioxide modified carbon quantum dot composite nano-microsphere and preparation method and application thereof |
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