CN111647400A - Preparation method of fluorescent organic silicon nano particles - Google Patents
Preparation method of fluorescent organic silicon nano particles Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 239000002105 nanoparticle Substances 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 9
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- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 6
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- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical group CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 claims description 3
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- 238000001035 drying Methods 0.000 claims description 2
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- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 claims description 2
- NHBRUUFBSBSTHM-UHFFFAOYSA-N n'-[2-(3-trimethoxysilylpropylamino)ethyl]ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCNCCN NHBRUUFBSBSTHM-UHFFFAOYSA-N 0.000 claims description 2
- 210000001082 somatic cell Anatomy 0.000 claims description 2
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- 229910021642 ultra pure water Inorganic materials 0.000 claims description 2
- 239000012498 ultrapure water Substances 0.000 claims description 2
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- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 1
- 240000006365 Vitis vinifera Species 0.000 claims 1
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- 201000006845 reticulosarcoma Diseases 0.000 claims 1
- 208000029922 reticulum cell sarcoma Diseases 0.000 claims 1
- 238000012984 biological imaging Methods 0.000 abstract description 8
- 239000002086 nanomaterial Substances 0.000 abstract description 8
- 238000005265 energy consumption Methods 0.000 abstract description 4
- 239000003086 colorant Substances 0.000 abstract description 3
- 231100000053 low toxicity Toxicity 0.000 abstract description 3
- 238000004020 luminiscence type Methods 0.000 abstract description 3
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- 239000000243 solution Substances 0.000 description 8
- 230000005284 excitation Effects 0.000 description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
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- 229910052710 silicon Inorganic materials 0.000 description 4
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- 206010008342 Cervix carcinoma Diseases 0.000 description 3
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 3
- NJSVDVPGINTNGX-UHFFFAOYSA-N [dimethoxy(propyl)silyl]oxymethanamine Chemical compound CCC[Si](OC)(OC)OCN NJSVDVPGINTNGX-UHFFFAOYSA-N 0.000 description 3
- 201000010881 cervical cancer Diseases 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
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- 238000002284 excitation--emission spectrum Methods 0.000 description 2
- 238000000799 fluorescence microscopy Methods 0.000 description 2
- 238000001027 hydrothermal synthesis Methods 0.000 description 2
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- 238000000643 oven drying Methods 0.000 description 2
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- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- HXMVNCMPQGPRLN-UHFFFAOYSA-N 2-hydroxyputrescine Chemical compound NCCC(O)CN HXMVNCMPQGPRLN-UHFFFAOYSA-N 0.000 description 1
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 235000017784 Mespilus germanica Nutrition 0.000 description 1
- 244000182216 Mimusops elengi Species 0.000 description 1
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- 235000007837 Vangueria infausta Nutrition 0.000 description 1
- 241000219095 Vitis Species 0.000 description 1
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- 238000005516 engineering process Methods 0.000 description 1
- 238000002073 fluorescence micrograph Methods 0.000 description 1
- 108091006047 fluorescent proteins Proteins 0.000 description 1
- 102000034287 fluorescent proteins Human genes 0.000 description 1
- 229940087559 grape seed Drugs 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000002173 high-resolution transmission electron microscopy Methods 0.000 description 1
- 210000003701 histiocyte Anatomy 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
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- 238000007794 visualization technique Methods 0.000 description 1
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
- C09K11/07—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials having chemically interreactive components, e.g. reactive chemiluminescent compositions
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
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- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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Abstract
The invention discloses a preparation method of fluorescent organic silicon nano particles, belongs to the field of fluorescent nano materials and biological imaging nano materials, and specifically comprises the steps of extracting effective components of plants, reacting the extracted components with an amino-containing organic silane coupling agent, dialyzing, purifying and the like. The method has the advantages of simple steps, easily obtained raw materials, low cost, mild reaction conditions and low energy consumption, and the obtained organic silicon nano particles have the advantages of rich fluorescence colors, stable luminescence, photobleaching resistance, good biological compatibility, low toxicity and the like. The prepared fluorescent nanoparticles have good application value in the field of biological imaging.
Description
Technical Field
The invention belongs to the field of fluorescent nano materials and biological imaging nano materials, and particularly relates to a preparation method of a fluorescent organic silicon nano material and application of the fluorescent organic silicon nano material in the field of biological imaging.
Background
Fluorescence bioimaging is one of the most widely used and powerful visualization techniques in biological research and clinical diagnostics, with selectivity, visibility and adjustability. In order to better label and track the multilevel structure of molecules, cells and tissues, it is necessary to introduce fluorescent probes with strong fluorescence, good water dispersibility, good biocompatibility, low toxicity, and especially anti-photobleaching properties. To date, organic dyes and fluorescent proteins are the most widely used probes in fluorescence imaging. However, the biggest problem of the fluorescent dye and the protein in application is that the fluorescent dye and the protein are subjected to a photooxidation bleaching process under long-time illumination, and then fluorescence quenching occurs. This problem limits their use for long-term observation of biodynamic behavior. The synthesis of the fluorescent material with stable luminescence and photobleaching resistance is of great significance.
The fluorescent organic silicon nano particle has wide prospect in the field of biological imaging as a novel fluorescent nano material. The organic silicon fluorescent nano particle has the advantages of high luminous quantum yield, photobleaching resistance, small size, low biological toxicity and the like. At present, the novel material has single luminescent color, high energy consumption of a synthesis method and high material cost. For example, Chen group synthesizes the green fluorescent organosilicon nanoparticles by a hydrothermal method, the energy consumption of the hydrothermal method is high, and the synthesized particles only emit light in a green area, which cannot meet the requirements of biological imaging on multicolor fluorescent probes.
Disclosure of Invention
The invention aims to overcome the defects in the background technology and provide a preparation method of a fluorescence imaging organic silicon nano material, which has the advantages of simple process, cheap and easily-obtained raw materials, high material light-emitting stability and rich fluorescence colors.
The technical scheme adopted by the invention is as follows:
a preparation method of fluorescent organic silicon nano particles comprises the following steps:
(1) extracting effective plant components, wherein the extraction process comprises the steps of chopping, grinding, extracting, filtering and drying plant raw materials, and the effective plant components are anthocyanin, procyanidine or phenolic substances;
(2) preparing the plant extract extracted in the step (1) into a water solution with the concentration of 10-1000 mg/mL, and reacting the water solution with an organosilane coupling agent with amino at 50-100 ℃ for 2-10 hours to obtain a fluorescent organic silicon nanoparticle solution;
(3) and (3) dialyzing the organic silicon nano particle solution obtained in the step (2) in a dialysis bag to obtain pure fluorescent organic silicon nano particles.
More specifically, in the step (1), the plant raw materials are fully cut and ground, fully extracted by ethanol for 3-5 times, filtered for 3-5 times, and vacuum-dried for 12-24 hours at the temperature of 60-80 ℃, and the plant raw materials can be grape seeds, rose petals, black medlar, blueberry epidermis and the like.
In the step (2), the organosilane coupling agent may be (3-aminopropyl) trimethoxysilane (APTMS), (3-aminopropyl) triethoxysilane (APTES), N- [3- (trimethoxysilyl) propyl ] ethylenediamine (DAMO), diethylenetriaminopropyltrimethoxysilane (AEEA), or the like.
In the step (3), ultrapure water is used during dialysis, the molecular weight cut-off of a dialysis bag is 500-5000, the dialysis time is 10-30 hours, and water is changed every 4-8 hours.
The invention also aims to provide an application of a product based on the preparation method in biological cell fluorescence labeling, and the specific technical scheme is as follows:
a biological cell fluorescence labeling method comprises the steps of (1) to (3) preparing fluorescent organic silicon nano particles, incubating the prepared fluorescent organic silicon nano particles and biological cells to be labeled together to obtain cells labeled by the fluorescent organic silicon nano particles, and observing the cell morphology under a microscope; the concentration of the organic silicon nano particles is 10-1000 mu g/mL, the biological cells are mammalian somatic cells or cancer cells, and more specifically, the biological cells can be mouse adrenal cortex cells, human thyroid duct cancer cells, human histiocyte lymphoma cells, cervical cancer cells and the like.
Has the advantages that:
the method of the invention adopts the organic silane coupling agent and the plant extract to heat at lower temperature to obtain the fluorescent nano particles, so the method has simple steps, easily obtained raw materials, low cost, mild reaction conditions and low energy consumption. The obtained organic silicon nano particles have the advantages of rich fluorescence colors (with multicolor such as red, orange, blue, green and the like), stable luminescence, photobleaching resistance, good biological compatibility, low toxicity and the like. The fluorescent nanoparticles can be used for observing static cell morphology and observing cell dynamics behaviors for a long time, and have wide value in the field of biological imaging.
Drawings
FIG. 1 shows fluorescence excitation spectrum and emission spectrum of red fluorescent organosilicon nanoparticles obtained by reacting Lycium ruthenicum Murr extract with APTMS in example 1.
FIG. 2 is a high-resolution TEM image and a particle size distribution histogram of the red fluorescent organosilicon nanoparticles of example 1.
FIG. 3 shows fluorescence excitation spectrum and emission spectrum of blue-green fluorescence-tunable organosilicon nanoparticles obtained by reacting grape seed extract with APTES in example 2.
Fig. 4 is a fluorescent photograph of cervical cancer cells labeled with red fluorescent silicone nanoparticles in example 3 at different excitation times.
Detailed Description
The present invention will be described in detail with reference to examples.
Example 1: preparation process of red fluorescent organic silicon nano particle
Pulverizing 100g Lycium ruthenicum Murr, grinding into powder with mortar, dissolving in 100mL ethanol, extracting for 2 hr, filtering to remove residue to obtain Lycium ruthenicum Murr extract solution, repeating the extraction process for three times, and oven drying the obtained solution in vacuum drying oven for 24 hr to obtain Lycium ruthenicum Murr extract (mainly containing anthocyanin). 5mL of Lycium ruthenicum Murr extract with the concentration of 50mg/mL is mixed with 1mL of (3-aminopropyl) trimethoxy silane (APTMS), the mixture is stirred and reacted for 5 hours at the temperature of 50 ℃, and then the mixed solution is dialyzed for 18 hours in a dialysis bag with the molecular weight cutoff of 1000, so that the red fluorescent organic silicon nanoparticles are obtained. The particle has an emission peak at 620nm and an optimal excitation wavelength of 540nm, as shown in FIG. 1. The morphology and size of the particles are shown in FIG. 2, with the size at 3.5. + -. 0.5 nm.
Example 2: preparation process of organosilicon nanoparticles with adjustable blue-green fluorescence
Grinding 50g grape seed into powder, dissolving in 50mL ethanol, extracting for 5 hr, filtering to remove residue to obtain grape seed extract solution, repeating the extraction process for five times, and oven drying the obtained solution in vacuum oven for 20 hr to obtain grape seed extract (mainly containing phenolic substances). 10mL of grape seed extract with the concentration of 80mg/mL is mixed with 1mL of (3-aminopropyl) triethoxysilane (APTES), the mixture is stirred and reacted for 3 hours at the temperature of 60 ℃, and then the mixed solution is dialyzed for 24 hours in a dialysis bag with the molecular weight cutoff of 2000, so that the organosilicon nanoparticles with adjustable fluorescence from blue to green are obtained. The emission peak position of the particle changes along with the change of the excitation wavelength, when the excitation wavelength is 360-420nm, the fluorescence color is blue (450-480nm), and when the excitation wavelength is 440-500nm, the fluorescence color is green (500-560 nm). The optimum excitation wavelength for an emission wavelength of 460nm is 400 nm. As shown in fig. 3.
Example 3: use of red fluorescent silicone nanoparticles for biological imaging
First, cervical cancer cells (HeLa cells) were seeded in 12-well plates at 37 ℃ with 5% CO2Incubate in culture under conditions for 12 hours. The cells were washed three times with PBS buffer (0.1M) to remove the culture medium. Cells were incubated with 100. mu.g/mL of red fluorescent silicone nanoparticles for 30 minutes. Excess red fluorescent probe was removed by washing the cells three times with PBS buffer (0.1M). Then, the cell sample was observed under a fluorescence microscope. A1000 w mercury lamp was used as the excitation light source to excite the fluorescent probe with a band pass filter BP510-550 (green light) to observe the fluorescence image of the cells. The emission channels used bandpass filters BA575-625 (red). After 30min of irradiation, the red probe in the cells still emitted light, and the fluorescence photographs of the cells at different times are shown in FIG. 4.
Claims (6)
1. A preparation method of fluorescent organic silicon nano particles comprises the following steps:
(1) extracting effective plant components, wherein the extraction process comprises the steps of chopping, grinding, extracting, filtering and drying plant raw materials, and the effective plant components are anthocyanin, procyanidine or phenolic substances;
(2) preparing the plant extract extracted in the step (1) into a water solution with the concentration of 10-1000 mg/mL, and reacting the water solution with an organosilane coupling agent with amino at 50-100 ℃ for 2-10 hours to obtain a fluorescent organic silicon nanoparticle solution;
(3) and (3) dialyzing the organic silicon nano particle solution obtained in the step (2) in a dialysis bag to obtain pure fluorescent organic silicon nano particles.
2. The preparation method of the fluorescent organosilicon nanoparticles according to claim 1, wherein the step (1) is carried out by sufficiently chopping and grinding the plant raw materials, sufficiently extracting with ethanol for 3-5 times, filtering for 3-5 times, and vacuum drying at 60-80 ℃ for 12-24 hours, wherein the plant raw materials are grape seeds, rose petals, lycium ruthenicum or blueberry epidermis.
3. The method of claim 1, wherein in step (2), the organosilane coupling agent is (3-aminopropyl) trimethoxysilane, (3-aminopropyl) triethoxysilane, N- [3- (trimethoxysilyl) propyl ] ethylenediamine or diethylenetriaminopropyltrimethoxysilane.
4. The method for preparing fluorescent organosilicon nanoparticles according to claim 1, wherein ultrapure water is used in the dialysis in the step (3), the cut-off molecular weight of a dialysis bag is 500-5000, the dialysis time is 10-30 hours, and the water is changed every 4-8 hours.
5. A biological cell fluorescence labeling method, preparing fluorescence organosilicon nanometer particle according to the steps (1) - (3) of claim 1, incubating the prepared fluorescence organosilicon nanometer particle and biological cell needing to be labeled, obtaining the cell labeled by the fluorescence organosilicon nanometer particle, and observing the cell shape under a microscope; the concentration of the organic silicon nano particles is 10-1000 mu g/mL, and the biological cells are mammalian somatic cells or cancer cells.
6. The fluorescence labeling method of claim 5, wherein the biological cell is mouse adrenal cortex cell, human thyroid duct carcinoma cell, human histiocytic lymphoma cell or cervical carcinoma cell.
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2020
- 2020-06-11 CN CN202010528969.1A patent/CN111647400A/en active Pending
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Application publication date: 20200911 |