CN111647401A - Orange fluorescent carbon dot and application thereof in detection of peroxynitrite ions - Google Patents
Orange fluorescent carbon dot and application thereof in detection of peroxynitrite ions Download PDFInfo
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Abstract
The invention discloses an orange fluorescent carbon dot and application thereof in detecting peroxynitrite ions, wherein the Carbon Dots (CDs) are prepared by taking rhodamine B and p-aminophenol as raw materials through a one-step hydrothermal synthesis method; the carbon dots are zero-dimensional carbon nano-materials and can emit bright orange fluorescence. The preparation method is simple and convenient, and the prepared carbon dots have good water solubility and stable fluorescence. The carbon dots are used as fluorescent probes to quickly and sensitively detect peroxynitrite ions. When peroxynitrite ions are present, the fluorescence of the carbon dots is effectively quenched by peroxynitrite.At the same time, the color of the CDs solution changed from pink to blue-black. The detection ONOO provided by the invention‑Compared with a simple fluorescence analysis method, the analysis method of the double-mode output method has more advantages in practical application, and indicates that the method discusses ONOO in cell biology‑The effect of (2) has potential application prospect.
Description
Technical Field
The invention relates to detection of a carbon nano material and peroxynitrite ions, in particular to an orange fluorescent carbon dot and a preparation method thereof, and application of the carbon dot in fluorescent and colorimetric dual-mode detection of peroxynitrite ions.
Background
Peroxynitrite (ONOO)-) Is prepared from Nitric Oxide (NO) and superoxide radical (O)2.-) Diffusion controls coupling self-reaction generation. Studies have shown that ONOO-It exists in its acid form in the protonated equilibrium (ONOOH, pKa ═ 6.8), and it can rapidly change to nitrate. It is called a "stealth" biological oxidant due to its short lifetime, relatively low steady-state concentration, and the nature of the various targets of the in vivo reaction. Due to its strong oxidative and good nucleophilicity, ONOO-Can react with different biomolecules, and, furthermore, ONOO-Are thought to be involved in the development of various diseases such as inflammatory diseases, alzheimer's disease, cardiovascular and neurodegenerative diseases, and the like. Although ONOO-Have important roles in human health and disease, but their biological functions are not well understood. One of the main reasons is the lack of reliable methods for highly sensitive and highly selective monitoring of ONOO in vivo-And (4) horizontal. Furthermore, ONOO-The extremely short lifetime of (a), and the presence of various competing endogenous molecules make its determination more challenging.
To date, there have been many methods for detecting peroxynitrite, such as Electron Paramagnetic Resonance (EPR) spectroscopy, electrochemical analysis, uv-vis absorption spectroscopy, chromatography, and the like. However, these methods have their own disadvantages. For example, complex sample pre-treatment is required, expensive instrumentation, poor sensitivity/selectivity, and unsuitability for intracellular detection, among others. Therefore, the development of an analysis technology which is simple, convenient and quick, has good selectivity and high sensitivity, and is used for detecting and identifying peroxynitrite is of great significance.
The fluorescent carbon dots serving as a novel fluorescent nano material have good application potential in the fields of biochemical sensing, biological imaging, environmental analysis and the like. Therefore, the invention develops an analysis method for detecting peroxynitrite in a fluorescent and colorimetric dual mode based on the excellent fluorescence property and biological property of the carbon dot and by combining the fluorescent analysis and colorimetric analysis with the nano material. Compared with the simple fluorescence change, the double-output mode detection method has more outstanding advantages in practical application, and indicates that the method discusses ONOO in cell biology-The effect of (2) has potential application prospect.
Disclosure of Invention
The invention aims to provide a fluorescent carbon dot with excellent structural properties and a preparation method thereof, wherein the preparation method of the carbon dot is simple and convenient; the prepared carbon dot has excellent surface chemical structure, can be applied to detecting peroxynitrite in a fluorescence and colorimetric dual mode, and shows high selectivity and sensitivity.
The invention provides a preparation method of orange fluorescent carbon dots, which comprises the following steps:
1) putting rhodamine B and p-aminophenol in a glass beaker, adding ethanol, fully stirring, and then ultrasonically dissolving for 10-15 minutes, wherein the mass ratio of the rhodamine B to the p-aminophenol is as follows: 0.01-0.05: 0.03-0.1;
2) transferring the solution into a hydrothermal reaction kettle, placing the hydrothermal reaction kettle into an oven, and reacting for 8-12 hours at 180 ℃;
3) standing the hydrothermal reaction kettle after the reaction is stopped, cooling to room temperature, filtering to remove insoluble substances, performing rotary evaporation to obtain a deep pink solution, and filtering with a 0.22 mu m filter membrane to obtain a pure carbon dot aqueous solution;
4) and freeze-drying the carbon dot solution to obtain a target product.
The mass ratio of the rhodamine B to the p-aminophenol is preferably as follows: 0.015-0.035 to 0.04-0.06.
The carbon point prepared by the method has stable fluorescence property, good water solubility and dispersibility, simple and effective synthesis method, cheap and easily-obtained raw materials, mild reaction conditions, environmental friendliness, capability of being completed in a common laboratory and easy popularization. In addition, the carbon dots show good selectivity, in the carbon dot solution, only peroxynitrite is added, so that the color of the solution is changed from pink to blue-black, the fluorescence of the carbon dots is quenched, and reducing agents (Cys and GSH) and oxidizing agents (H) are added2O2tBuO, HO and1O2) Some ions (Zn)2+、Mg2+、Ca2+、NO3 -、SO4 2-) The color of the solution has no obvious change, and the fluorescence intensity of the carbon dots has no obvious change.
The invention provides a method for detecting peroxynitrite ions in a fluorescent carbon dot fluorescent and colorimetric dual mode, which is characterized by comprising the following steps of:
1) preparing the carbon dot solution with the concentration of 0.1mg/mL prepared by the method;
2) adding 11.7 μ L of ONOO with different concentrations (30-1070nM) into the fluorescence cup-Dissolving to gradually quench the fluorescence of the carbon dots to obtain carbon dots/ONOO-The solution changes from pink to blue-black;
4) measuring the fluorescence intensity before and after the carbon dot reaction, and establishing a standard curve for detecting peroxynitrite ions according to the relation between the concentration of the peroxynitrite ions and the relative fluorescence intensity change value; thereby realizing the dual-mode detection of peroxynitrite ions by fluorescence and colorimetry.
The invention has the following beneficial technical effects:
(1) the carbon dot solution can be obtained by a one-step hydrothermal method, the synthesis method is simple and effective, the raw materials are cheap and easy to obtain, the reaction conditions are mild, the environment is friendly, the reaction can be completed in a common laboratory, and the method is easy to popularize. The prepared carbon quantum dots can be used as probes for detecting ONOO in aqueous solution-The linear range was 30-480 and 670-1070nmol/L, with a detection limit of 15.45 nmol/L.
(2) Compared with the traditional organic probe, the fluorescent probe based on the carbon point has simple preparation steps, does not need subsequent addition of strong acid and strong base or surface passivator for treatment, and can obtain the target carbon point by carbonizing, polymerizing and surface modifying reactants in the same system.
(3) The invention utilizes the method of combining fluorescence analysis and colorimetric analysis, compared with a single detection mode, the double-output detection mode has more superiority in detection, improves the selectivity and the sensitivity of the analysis method, and can realize accurate qualitative and quantitative analysis on the object to be detected.
Drawings
FIG. 1 shows fluorescence emission spectrum and UV absorption spectrum of carbon dots prepared in example 1;
FIG. 2 is an infrared spectrum of the carbon dots prepared in example 1, in which the abscissa is the detection wavelength and the ordinate is the transmittance;
FIG. 3 carbon dot detection ONOO prepared in example 1-A fluorescence emission spectrum;
FIG. 4 carbon dot detection ONOO prepared in example 1-Ultraviolet absorption spectrum of (1);
FIG. 5 shows carbon dots, carbon dots/ONOO-Photos of the solution system under a fluorescent lamp and an ultraviolet lamp;
FIG. 6 is a carbon dot coating ONOO prepared in example 1-Quenching laser confocal mapping, the cell is PC-12 cell.
Detailed Description
The present invention will be described in detail with reference to the following examples and the accompanying drawings, wherein the examples show detailed embodiments and specific operation procedures, but the scope of the present invention is not limited to the following examples.
Example 1
The preparation method of the carbon dots comprises the following steps:
1) placing 0.03g of rhodamine B and 0.05g of p-aminophenol in a glass beaker, adding ethanol, fully stirring, and ultrasonically dissolving for 15 minutes;
2) transferring the solution into a hydrothermal reaction kettle, placing the hydrothermal reaction kettle into an oven, and reacting for 10 hours at 180 ℃;
3) standing the hydrothermal reaction kettle after the reaction is stopped, cooling to room temperature, filtering to remove insoluble substances, performing rotary evaporation to obtain a deep pink solution, and filtering with a 0.22 mu m filter membrane to obtain a pure carbon dot aqueous solution;
4) and freeze-drying the carbon dot solution to obtain a target product.
Example 2
The fluorescent carbon dots prepared in example 1 were subjected to fluorescence excitation, emission and ultraviolet absorption spectrum characterization (see FIG. 1), and the distinct absorption peaks of the carbon dots at 221nm and 295nm can be attributed to aromatic benzene ring sp2And C-N bonds N/pi transition. The optimal excitation and emission wavelengths for CDs are 554nm and 580nm, respectively. The carbon point is characterized by infrared (as shown in figure 2), and the surface contains amino, carboxyl and hydroxyl groups.
Example 3
3mL of the aqueous fluorescent carbon dot solution (0.1mg/mL) prepared in example 1 was placed in a fluorescence cuvette, and 11.7. mu.L of ONOO with different concentrations was added dropwise to the cuvette-(30-1070nM), mixed well and scanned in a fluorescence spectrometer for emission spectra (. lamda.)ex＝554nm，λem580nm) according to ONOO-The concentration of (2) and the relative fluorescence intensity change value, and calculating the carbon point pair ONOO-The detection range and detection limit (see fig. 3).
Example 4
3mL of the aqueous fluorescent carbon dot solution (0.1mg/mL) prepared in example 1 was placed in a fluorescence cuvette, and 14. mu.L of ONOO with different concentrations was added dropwise to the cuvette-(300-1000nM), mixed well and scanned for UV absorption spectra in a UV spectrometer (see FIG. 4).
Example 5
FIG. 5 shows carbon dots, carbon dots/ONOO-Photos of the solution system under a fluorescent lamp and an ultraviolet lamp; in the figure: first, the aqueous fluorescent carbon dot solution prepared in example 1 was placed in a glass bottle in pink under a fluorescent lamp, and ONOO was added-Then becomes blue black; the second row is the picture of the first row under 365nm ultraviolet lamp, the carbon dot solution is orange fluorescence, and ONOO is added-Fluorescence quenching (see FIG. 5).
Example 6
The aqueous solution (0.1mg/mL) of the fluorescent carbon dots prepared in example 1 was used for labeling PC-12 cells, and as shown in FIG. 6, the cell morphology was good, and the carbon dots were low in cytotoxicity and useful for labeling living cells. FIG. 6 is a carbon dot coating ONOO prepared in example 1-The quenched laser confocal images, from left to right, are: dark field cytogram (orange), bright field and dark field overlay.
Claims (6)
1. A preparation method of orange fluorescent carbon dots is characterized by comprising the following steps:
1) putting rhodamine B and p-aminophenol in a glass beaker, adding ethanol, fully stirring, and then ultrasonically dissolving for 10-15 minutes, wherein the mass ratio of the rhodamine B to the p-aminophenol is as follows: 0.01-0.05: 0.03-0.1;
2) transferring the solution into a hydrothermal reaction kettle, placing the hydrothermal reaction kettle into an oven, and reacting for 8-12 hours at 180 ℃;
3) standing the hydrothermal reaction kettle after the reaction is stopped, cooling to room temperature, filtering to remove insoluble substances, performing rotary evaporation to obtain a deep pink solution, and filtering with a 0.22 mu m filter membrane to obtain a pure carbon dot aqueous solution;
4) and freeze-drying the carbon dot solution to obtain a target product.
2. The method for preparing a fluorescent carbon dot as claimed in claim 1, wherein the mass ratio of rhodamine B to p-aminophenol is: 0.015-0.035: 0.04-0.06;
3. an orange fluorescent carbon dot prepared by the method of claim 1 or 2.
4. The orange fluorescent carbon dot of claim 3 for fluorescence and colorimetric dual-mode detection of ONOO-The use of (1).
5. Use of the orange fluorescent carbon dot of claim 3 in the preparation of a reagent for cellular fluorescence imaging.
6. A method for detecting peroxynitrite ions in a fluorescent and colorimetric dual-mode is characterized by comprising the following steps:
1) preparing the carbon dot solution of claim 3 at a concentration of 0.1 mg/mL;
2) adding 11.7 mu L of ONOO with different concentrations into the fluorescent cup-A solution;
3) adding ONOO into the carbon dot solution-Gradually quenching the fluorescence of the carbon dots to obtain carbon dots/ONOO-The solution changes from pink to blue-black;
4) measuring the fluorescence intensity before and after the carbon point reaction according to ONOO-The relationship between the concentration of (D) and the relative fluorescence intensity change value establishes a standard curve for detecting peroxynitrite ions.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112730330A (en) * | 2021-01-19 | 2021-04-30 | 中南大学 | Carbon point waveguide-based benzoyl peroxide gas sensor |
| CN113416540A (en) * | 2021-06-09 | 2021-09-21 | 安徽融慧精准医学有限公司 | Carbon dots applied to reagent for detecting drug-induced deafness and preparation method thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112730330A (en) * | 2021-01-19 | 2021-04-30 | 中南大学 | Carbon point waveguide-based benzoyl peroxide gas sensor |
| CN112730330B (en) * | 2021-01-19 | 2022-11-01 | 中南大学 | Carbon point waveguide-based benzoyl peroxide gas sensor |
| CN113416540A (en) * | 2021-06-09 | 2021-09-21 | 安徽融慧精准医学有限公司 | Carbon dots applied to reagent for detecting drug-induced deafness and preparation method thereof |
| CN113416540B (en) * | 2021-06-09 | 2023-08-25 | 安徽融慧精准医学有限公司 | Carbon spot applied to detection of drug-induced deafness reagent and preparation method thereof |
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