CN114479843B - Preparation method and application of novel fluorescent nano material with photodynamic therapy and sterilization functions - Google Patents
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Abstract
The invention relates to the technical fields of high polymer materials, biological medicines and nano materials, in particular to a preparation method and application of a novel fluorescent nano material with photodynamic therapy and sterilization functions. The preparation method comprises the following steps: dissolving aniline compound and amino acid in deionized water, adding concentrated sulfuric acid after dissolving, and stirring and mixing uniformly; and transferring the uniformly mixed solution to a polytetrafluoroethylene reaction kettle for hydrothermal reaction to obtain the novel macromolecular fluorescent nanomaterial with the spiral structure. The fluorescent nano material can immediately generate hydroxyl radical, singlet oxygen and superoxide radical after being irradiated by ultraviolet light, visible light, laser and the like, and has extremely strong oxidation characteristic; the generation of free radicals is accompanied with the conversion of body color and fluorescence, the generation of the free radicals can be judged according to the characteristics of the body color and the fluorescence, and the free radicals can be used in the fields of photodynamic therapy, photodynamic bacteriostasis and the like according to the characteristics of photosensitizers.
Description
Technical Field
The invention relates to the technical fields of high polymer materials, biological medicines and nano materials, in particular to a preparation method and application of a novel fluorescent nano material with photodynamic therapy and sterilization functions.
Background
The nanometer technology refers to the design of synthetic nanometer materials in the range of 1-100nm, and is used for functional materials, sensors, equipment and the like. Within this scale, nanomaterials generally have the characteristics of large specific surface area, high chemical reactivity, and easy absorption by living organisms. The fluorescent nano material mainly comprises carbon nano dots, carbon nano tubes and the like, and has the characteristics of low biotoxicity, good biocompatibility, small size, unique fluorescent characteristic and the like, so that the fluorescent nano material is widely applied to the fields of disease diagnosis, drug delivery, biological treatment, in-vivo imaging, tumor targeting and the like. Currently, there are few nanomaterials with light conversion properties, and most of them are mass-color conversion, and few nanomaterials with fluorescence conversion properties are reported.
Photodynamic therapy (Photodynamic Therapy, PDT) is a new tumor treatment technique, the principle being that photosensitizers produce reactive oxygen species when subjected to photochemical reactions leading to apoptosis of tumor cells. Because PDT has the advantages of higher space-time resolution, minimally invasive surgery and the like, the PDT is expected to play an important role in future tumor treatment. More and more organic Photosensitizers (PSs) have been shown to have an effect of inhibiting tumor proliferation. Photochemical reaction according to PSsThe types of active oxygen produced in the process are classified into Type I PSs and Type II PSs. Type I PSs form Type I reactive oxygen species (Reactive Oxygen Species, ROS) such as hydroxyl radicals by electron transfer after illumination · OH), superoxide anion (O) 2 ·- ) And hydrogen peroxide (H) 2 O 2 ) Causing death of cancer cells, type I ROS is the most toxic oxidant for PDT. Most Type I PSs contain metal complexes that are difficult to degrade by metabolism, easily leading to toxicity. Type II PSs are irradiated with light and transferred to oxygen (O) 2 ) Generating Type II ROS-singlet oxygen% 1 O 2 ) Thus, type II PSs have highly oxygen dependent properties. While abnormal proliferation of cancer cells results in a tumor site in a hypoxic state, which severely limits the effectiveness of Type II PSs. In addition, the disadvantages of poor water solubility, unstable structure, etc. also affect the therapeutic effect in PDT. Furthermore, during photodynamic therapy, prolonged phototherapy may lead to photodamage of normal tissues, whereas currently reported PSs require a significant amount of illumination time, typically several tens of minutes or even hours.
For example, chinese patent CN106390119B discloses a method for synthesizing copper-containing photothermal nanomaterial and application thereof, the invention uses o-phenylenediamine and L-cysteine as raw materials, adopts a hydrothermal synthesis method to prepare fluorescent carbon dots with good stability and water solubility in one step, and prepares the copper-containing nanomaterial with excellent photothermal performance by simply mixing the carbon dots with copper-containing salt solution. The invention also provides a method for improving the stability of the copper-containing photothermal nanomaterial by surface modification. The invention finally obtains the novel photo-thermal nano material with good water dispersibility, low toxicity and excellent photo-thermal property, so as to be used for photo-thermal treatment of tumors. However, the material contains metal complex Cu salt, so that the material is difficult to be degraded by metabolism, toxicity is easy to cause, and the clinical application has a certain risk.
Therefore, the synthesis of the novel PSs with the characteristics of good biocompatibility, high phototoxicity, good water solubility and the like has important significance for photodynamic treatment of tumors.
Disclosure of Invention
Aiming at the defects existing in the prior art, the technical problem to be solved by the invention is to provide a novel fluorescent nano material which has the characteristics of simple synthesis mode, degradability, high phototoxicity, short required illumination time and Type I and Type II PSs based on the defects of complex synthesis path, high biotoxicity, long illumination time and the like of the existing PSs.
The invention aims to provide a preparation method of the novel fluorescent nanomaterial.
It is another object of the present invention to provide the use of the novel fluorescent nanomaterial described above in the preparation of a drug and/or material for the treatment of cancer.
Another object of the present invention is to provide the use of the novel fluorescent nanomaterial described above in the preparation of bacteriostatic products and/or formulations.
In order to solve the technical problems, the invention provides the following technical scheme:
in one aspect, the present invention claims a method for preparing a novel fluorescent nanomaterial with photodynamic therapy and bactericidal functions, the method comprising the steps of:
s1, dissolving an aniline compound and amino acid with deionized water, adding concentrated sulfuric acid after dissolving, and stirring and uniformly mixing;
s2, transferring the uniformly mixed solution to a polytetrafluoroethylene reaction kettle, and performing hydrothermal reaction to obtain the nano-crystalline polytetrafluoroethylene composite material.
Preferably, the molar ratio of the aniline compound to the amino acid is (1-4): (2-4).
Preferably, the volume ratio of the deionized water to the concentrated sulfuric acid is (6-30): 1.
preferably, the heating temperature of the hydrothermal reaction is 160-220 ℃ and the heating time is 3-10h.
In a specific embodiment, the preparation method comprises the following steps:
0.2 to 0.5g of aniline compound and 0.3 to 0.5g of amino acid are added with 30mL of ultrapure water, 98wt% of concentrated sulfuric acid is added after uniform stirring, the solution is transferred to a 100mL polytetrafluoroethylene reaction kettle after clear and transparent stirring, and the solution is placed in an oven, wherein the temperature of the oven is 160 to 220 ℃ and the reaction time is 3 to 10 hours. The prepared fluorescent nano material is a dark green or blue nano material solution.
The fluorescent nano material prepared by the preparation method is of a hollow spiral structure; lattice spacing is 0.35nm; the spiral height is 10-20 nm, and the diameter is mainly distributed at 10-30 nm; the body color is dark green or blue at high concentration, and light green/blue at low concentration; after the light treatment of the low-concentration aqueous solution or the ethanol solution, the body color is changed from light blue/green into brown; the excitation wavelength before the light treatment is 275-365 nm; the fluorescence emission spectrum is distributed at 380-400 nm, and the fluorescence emission spectrum after illumination treatment is converted into 500-550 nm; the color conversion induced by illumination is accompanied by the conversion of the ultraviolet absorption spectrum from 200-400 nm to 200-500 nm; the light which can be adopted for the illumination treatment of the fluorescent nano material is 275-365 nm ultraviolet light, visible light and laser. The extent to which the material is oxidized is related to the light intensity and the time of illumination. The fluorescent nanomaterial can generate ROS by irradiation of the light source in an aqueous solution and an absolute ethyl alcohol solution, so that cancer cells (such as Hela cells) die. In addition, the invention also verifies the antibacterial effect of the novel fluorescent nano material, and the result shows that compared with a material-free group, after the fluorescent nano material and the xenon lamp are used for illumination treatment, growth of bacterial wilt, escherichia coli, staphylococcus aureus, bacillus subtilis and pseudomonas aeruginosa is inhibited after the illumination treatment, and the material has good photodynamic antibacterial effect.
Therefore, on the other hand, the invention claims the application of the novel fluorescent nano material prepared by the preparation method in the therapeutic drugs and/or materials for treating cancers/tumors.
In still another aspect, the invention further claims the application of the novel fluorescent nanomaterial prepared by the preparation method in preparation of antibacterial products and/or preparations.
Preferably, the bacteriostatic products and/or formulations may inhibit bacteria including, but not limited to, bacterial wilt, staphylococcus aureus, bacillus subtilis, escherichia coli and/or pseudomonas aeruginosa, and other photodynamically killed bacteria and fungi, and the like.
Compared with the prior art, the invention has the following beneficial effects:
(1) The photosensitizer characteristic fluorescent nanomaterial prepared by the invention is synthesized by a one-step hydrothermal method, and the synthesis process is simple and easy to operate.
(2) The photosensitizer characteristic fluorescent nanomaterial prepared by the invention can simultaneously generate multiple ROS of Type I and Type II at the moment of illumination, has the advantage of high phototoxicity, and compared with the existing photosensitizer, the photosensitizer can instantly generate ROS, shortens the illumination time and avoids photodamage of photodynamic therapy to surrounding normal tissues.
(3) The photosensitizer characteristic fluorescent nanomaterial prepared by the invention has a special structure, is a spiral fluorescent nanomaterial, has the characteristics of visible light and fluorescence conversion, can visualize the generation of free radicals, and can be used in the fields of photodynamic therapy, photodynamic bacteriostasis and the like.
(4) The photosensitizer characteristic fluorescent nano material prepared by the invention has the advantages of good water solubility and degradability. After the light treatment, the spiral structure of the material is changed into a segment structure, which proves that the light of the material can damage the spiral structure and lead to the degradation of the material.
(5) The photosensitizer characteristic fluorescent nanomaterial prepared by the invention can generate free radicals under visible light, laser and/or ultraviolet light.
Drawings
FIG. 1 is an excitation spectrum of the fluorescent nanomaterial prepared in example 1 prior to color conversion.
Fig. 2 is an emission spectrum of the fluorescent nanomaterial prepared in example 1 before color conversion.
FIG. 3 is an excitation spectrum of the fluorescent nanomaterial prepared in example 1 after color conversion.
Fig. 4 is an emission spectrum of the fluorescent nanomaterial prepared in example 1 after color conversion.
FIG. 5 is an ultraviolet absorption spectrum before and after color inversion of the fluorescent nanomaterial prepared in example 1 by light induction.
Fig. 6 is a morphology diagram of the fluorescent nanomaterial prepared in example 1 under a transmission electron microscope.
Fig. 7 is a high resolution transmission electron microscope image of the fluorescent nanomaterial prepared in example 1 after color conversion.
Fig. 8 is a morphology picture of the fluorescent nanomaterial prepared in example 1 under an atomic force microscope.
Fig. 9 is an atomic force microscope picture of the fluorescent nanomaterial prepared in example 1 after color conversion.
FIG. 10 is an ESR signal of ROS collected at various illumination times for an aqueous solution of fluorescent nanomaterial prepared in example 1.
FIG. 11 shows the effect of the fluorescent nanomaterial prepared in example 1 in cancer cell therapy.
Fig. 12 shows the bacteriostatic effect of the fluorescent nanomaterial prepared in example 1.
Detailed Description
The present invention will be described in further detail with reference to the following examples, which are not intended to limit the present invention, but are merely illustrative of the present invention. The experimental methods used in the following examples are not specifically described, but the experimental methods in which specific conditions are not specified in the examples are generally carried out under conventional conditions, and the materials, reagents, etc. used in the following examples are commercially available unless otherwise specified.
Example 1
A preparation method of a novel fluorescent nano material with photodynamic therapy and sterilization functions comprises the following steps:
0.5g of o-phenylenediamine and 0.4. 0.4g L-cysteine or D-cysteine are added with 30mL of ultrapure water, after being stirred uniformly, 1mL of 98wt% concentrated sulfuric acid is added, after being stirred until the solution is clear and transparent, the solution is transferred to a 100mL polytetrafluoroethylene reaction kettle and placed in an oven, the temperature of the oven is 200 ℃, and the reaction time is 3 hours.
The prepared fluorescent nano material is a dark green solution.
Example 2
The preparation was similar to example 1, except that the volume of sulfuric acid added was 2mL.
Example 3
A preparation method of a novel fluorescent nano material with photodynamic therapy and sterilization functions comprises the following steps:
0.5g of o-phenylenediamine and 0.4. 0.4g L-cysteine or D-cysteine are added with 30mL of ultrapure water, 4mL of 98wt% concentrated sulfuric acid is added after uniform stirring, and the solution is transferred to a 100mL polytetrafluoroethylene reaction kettle after being stirred until the solution is clear and transparent, and the solution is placed in an oven, wherein the temperature of the oven is 160 ℃, and the reaction time is 3 hours.
Example 4
A preparation method of a novel fluorescent nano material with photodynamic therapy and sterilization functions comprises the following steps:
0.2g of o-phenylenediamine and 0.3. 0.3g L-cysteine or D-cysteine are added with 30mL of ultrapure water, 4mL of 98wt% concentrated sulfuric acid is added after uniform stirring, and after the solution is clear and transparent, the 100mL polytetrafluoroethylene reaction kettle is transferred and placed in an oven, wherein the temperature of the oven is 200 ℃, and the reaction time is 3 hours.
Example 5
A preparation method of a novel fluorescent nano material with photodynamic therapy and sterilization functions comprises the following steps:
0.5g of o-phenylenediamine and 0.3. 0.3g L-cysteine or D-cysteine are added with 30mL of ultrapure water, 3mL of 98wt% concentrated sulfuric acid is added after uniform stirring, the solution is stirred until the solution is clear and transparent, then the solution is transferred to a 100mL polytetrafluoroethylene reaction kettle and placed in an oven, the temperature of the oven is 160 ℃, and the reaction time is 6 hours.
Example 6
A preparation method of a novel fluorescent nano material with photodynamic therapy and sterilization functions comprises the following steps:
0.4g of o-phenylenediamine and 0.3. 0.3g L-cysteine or D-cysteine are added with 30mL of ultrapure water, 5mL of 98wt% concentrated sulfuric acid is added after uniform stirring, the solution is stirred until the solution is clear and transparent, then the solution is transferred to a 100mL polytetrafluoroethylene reaction kettle and placed in an oven, the temperature of the oven is 200 ℃, and the reaction time is 3 hours.
Example 7
A preparation method of a novel fluorescent nano material with photodynamic therapy and sterilization functions comprises the following steps:
0.3g of o-phenylenediamine and 0.3. 0.3g L-cysteine or D-cysteine are added with 30mL of ultrapure water, 5mL of 98wt% concentrated sulfuric acid is added after uniform stirring, the solution is stirred until the solution is clear and transparent, then the solution is transferred to a 100mL polytetrafluoroethylene reaction kettle and placed in an oven, the temperature of the oven is 170 ℃, and the reaction time is 4 hours.
Example 8
A preparation method of a novel fluorescent nano material with photodynamic therapy and sterilization functions comprises the following steps:
0.4g of o-phenylenediamine and 0.3. 0.3g L-cysteine or D-cysteine are added with 30mL of ultrapure water, 2mL of 98wt% concentrated sulfuric acid is added after uniform stirring, the solution is stirred until the solution is clear and transparent, then the solution is transferred to a 100mL polytetrafluoroethylene reaction kettle and placed in an oven, the temperature of the oven is 160 ℃, and the reaction time is 10 hours.
Example 9
The preparation was similar to example 8, except that the hydrothermal reaction was carried out at 220℃for 3 hours.
Performance testing
The following performance tests were performed using the fluorescent nanomaterial solution prepared in example 1:
the fluorescence spectrum was measured, and the results are shown in FIG. 1 and FIG. 2. Fig. 1 shows excitation spectra of the fluorescent nanomaterial solution obtained in example 1 diluted 100 times with absolute ethanol, and fig. 2 shows emission spectra.
The fluorescent nanomaterial solution obtained in example 1 was diluted 100 times with absolute ethanol, and the excitation pattern and emission pattern after irradiation with ultraviolet light having a wavelength of 365nm were shown in fig. 3 and 4. The ultraviolet irradiation makes the fluorescence emission spectrum shift from 380-400 nm to 500-550 nm.
FIG. 5 is an ultraviolet absorbance spectrum before and after light-induced color shift. The ultraviolet absorption spectrum before illumination is mainly distributed at 200-400 nm, and the absorption spectrum range after color conversion is converted into 200-500 nm. And the absorption spectrum intensity around 450nm gradually increases.
FIG. 6 is a graph showing the morphology of the fluorescent nanomaterial solution obtained in example 1 under a high-resolution transmission electron microscope, wherein the fluorescent nanomaterial solution has a twisted, spiral, ring-shaped structure of nanoribbons, and the lattice spacing is 0.35nm; the diameter of the ring structure is mainly distributed between 10 and 20nm.
FIG. 7 is a high-resolution transmission electron microscope image obtained by diluting the fluorescent nanomaterial solution obtained in example 1 with ethanol 100 times, and irradiating with ultraviolet light (365 nm) for 15min, wherein the cyclic structure of the material is reduced, even eliminated, and is mostly irregular fragments after the irradiation with ultraviolet light. Indicating that the ultraviolet irradiation breaks the structure of the material, breaking into irregular fragments from the ring structure.
Fig. 8 is a graph of the morphology of the fluorescent nanomaterial solution obtained in example 1 under an atomic force microscope, in which a hollow helical structure is clearly observed, and the height is 10 to 20nm.
FIG. 9 is an atomic force microscope image of the fluorescent nanomaterial obtained in example 1 after 100-fold dilution with absolute ethanol and irradiation with ultraviolet light (365 nm) for 15min, and it can be seen that the regular spiral structure disappears before irradiation, the morphology is irregular, and the height is 10 to 20nm. The result of combining an electron microscope shows that the material can be photolyzed and has degradable property.
Fig. 10 is an ESR signal of ROS collected under different illumination times after diluting the aqueous solution of fluorescent nanomaterial obtained in example 1 with ultrapure water by 100 times, and it is understood that the fluorescent nanomaterial generates ROS under illumination and the ROS content increases as the illumination time is prolonged.
Fig. 11 shows the effect of the fluorescent nanomaterial obtained in example 1 on cancer cell therapy, in which Hela cells normally survive after the fluorescent nanomaterial is used alone, but all cancer cells are killed after ultraviolet light (365 nm) is applied to the fluorescent nanomaterial, so that the fluorescent nanomaterial shows extremely strong phototoxicity.
Fig. 12 shows the bacteriostatic effect of the fluorescent nanomaterial obtained in example 1, and shows that the growth of bacterial wilt (Pseudomonas solanacearum, p. Solanacearum), bacillus subtilis (Bacillus subtilis, b. Subtilis), staphylococcus aureus (Staphylococcus aureus, s. Aureus), escherichia coli (e.coli) and pseudomonas aeruginosa (Pseudomonas aeruginosa, p. Aeromonas) was inhibited after the light treatment, compared with the non-material group.
Finally, it should be noted that the above description is only for illustrating the technical solution of the present invention, and not for limiting the scope of the present invention, and that the simple modification and equivalent substitution of the technical solution of the present invention can be made by those skilled in the art without departing from the spirit and scope of the technical solution of the present invention.
Claims (3)
1. A preparation method of a fluorescent nanomaterial with photodynamic therapy and sterilization functions, which is characterized by comprising the following steps:
s1, dissolving an aniline compound and amino acid with deionized water, adding concentrated sulfuric acid after dissolving, and stirring and uniformly mixing; the molar ratio of the aniline compound to the amino acid is (1-4): (2-4); the volume ratio of the deionized water to the concentrated sulfuric acid is (6-30): 1, a step of;
s2, transferring the uniformly mixed solution to a polytetrafluoroethylene reaction kettle, and performing hydrothermal reaction to obtain the catalyst; the heating temperature of the hydrothermal reaction is 160-220 ℃ and the heating time is 3-10h; the aniline compound is o-phenylenediamine; the amino acid is L-cysteine or D-cysteine.
2. The fluorescent nanomaterial prepared by the preparation method of claim 1 is applied to preparation of cancer therapeutic drugs and/or materials.
3. The fluorescent nanomaterial prepared by the preparation method of claim 1 is applied to preparation of antibacterial products and/or preparations.
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| WO2014023097A1 (en) * | 2012-08-06 | 2014-02-13 | 中国科学院理化技术研究所 | Preparation method of heteroatom doped multifunctional carbon quantum dot and application thereof |
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Patent Citations (3)
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| CN106390119A (en) * | 2016-09-13 | 2017-02-15 | 东南大学 | Application and synthesis method of copper-containing photo-thermal nano material |
| CN111518552A (en) * | 2019-09-10 | 2020-08-11 | 安徽大学 | Preparation of fluorine-containing graphene quantum dots and application of fluorine-containing graphene quantum dots as photodynamic therapy photosensitizer |
| CN111943170A (en) * | 2020-08-17 | 2020-11-17 | 中国科学院苏州生物医学工程技术研究所 | Carbon dots with antibacterial effect, preparation method thereof, composition and application thereof |
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| Tao Liang et al..Morphology Control of Luminescent Carbon Nanomaterials: From Dots to Rolls and Belts.《ACS Nano》.2020,第15卷第1579−1586页. * |
| Xian-Wu Hua et al..Fluorescent Carbon Quantum Dots with Intrinsic Nucleolus- Targeting Capability for Nucleolus Imaging and Enhanced Cytosolic and Nuclear Drug Delivery.ACS Appl. Mater. Interfaces.2018,第10卷第10554-10677页. * |
| Yulong Bai et al..Carbon Dots with Absorption Red-Shifting for Two-Photon Fluorescence Imaging of Tumor Tissue pH and Synergistic Phototherapy.《ACS Appl. Mater. Interfaces》.2021,第13卷第35365-35375页. * |
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