CN104845607B - A kind of aggregation-induced emission namo fluorescence probe and preparation method thereof - Google Patents
A kind of aggregation-induced emission namo fluorescence probe and preparation method thereof Download PDFInfo
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- CN104845607B CN104845607B CN201510123300.3A CN201510123300A CN104845607B CN 104845607 B CN104845607 B CN 104845607B CN 201510123300 A CN201510123300 A CN 201510123300A CN 104845607 B CN104845607 B CN 104845607B
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- 230000002776 aggregation Effects 0.000 title claims abstract description 29
- 238000004220 aggregation Methods 0.000 title claims abstract description 29
- 239000000523 sample Substances 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims description 7
- 229910052588 hydroxylapatite Inorganic materials 0.000 claims abstract description 35
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 claims abstract description 35
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 25
- 239000002105 nanoparticle Substances 0.000 claims abstract description 23
- 229920001661 Chitosan Polymers 0.000 claims abstract description 15
- 239000011248 coating agent Substances 0.000 claims abstract description 3
- 238000000576 coating method Methods 0.000 claims abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 39
- 229960000583 acetic acid Drugs 0.000 claims description 22
- 239000012153 distilled water Substances 0.000 claims description 20
- 238000001215 fluorescent labelling Methods 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 15
- 239000002243 precursor Substances 0.000 claims description 10
- 239000006228 supernatant Substances 0.000 claims description 10
- 239000012362 glacial acetic acid Substances 0.000 claims description 7
- STDOKXGTOHCKPX-UHFFFAOYSA-N O.[Na].[Na].[Na].C(CC(O)(C(=O)O)CC(=O)O)(=O)O Chemical compound O.[Na].[Na].[Na].C(CC(O)(C(=O)O)CC(=O)O)(=O)O STDOKXGTOHCKPX-UHFFFAOYSA-N 0.000 claims description 6
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 5
- 238000013019 agitation Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910000403 monosodium phosphate Inorganic materials 0.000 claims description 5
- 235000019799 monosodium phosphate Nutrition 0.000 claims description 5
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 238000003384 imaging method Methods 0.000 abstract description 4
- 238000001514 detection method Methods 0.000 abstract description 3
- 238000002189 fluorescence spectrum Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 238000000975 co-precipitation Methods 0.000 abstract description 2
- 238000004458 analytical method Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000013049 sediment Substances 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 229920001109 fluorescent polymer Polymers 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000012202 endocytosis Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003147 molecular marker Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
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- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
Aggregation-induced emission namo fluorescence probe disclosed by the invention has the chitosan fluorescence molecule of aggregation-induced emission characteristic at hydroxyapatite nano particle Surface coating, and the structural formula of chitosan fluorescence molecule is as the formula (1).Chemical coprecipitation analysis method is used to prepare.This aggregation-induced emission namo fluorescence probe size is at about 110 nm, stably dispersing, surface positively charged, and there is aggregation-induced emission characteristic, compared with conventional fluorescent probe, have highly sensitive, good light stability, without cancellation during high concentration, the advantage such as fluorescence spectrum not drift, it is expected to be applied to the field such as bio-imaging, fluorescent tracing detection.
Description
Technical field
The present invention relates to the preparation method of a kind of fluorescent probe, especially there is the preparation method of the hydroxyapatite/chitosan namo fluorescence probe of aggregation-induced emission characteristic.
Background technology
Probe be a kind of can and certain specific target molecules interact, it is achieved the molecule that target molecule is detected, and inspected object do not produced after requiring to interact or only produce insignificant interference.Fluorescent probe is exactly using fluorescent material as indicator, and makes indicator produce fluorescence under the exciting of certain wavelength light, is realized the qualitative of tested substance or quantitative analysis by the produced fluorescence of detection.In past 20 years, fluorescent probe causes the extensive concern of chemist and biologist for the biological process detecting living cells or animal, multiple fluorescent bio-probes is had been developed, such as: small molecule fluorescent spy, inorganic nano-particle pin and fluorescent polymer etc..Traditional small-molecule fluorescent probe has aggregation inducing cancellation (ACQ) phenomenon, and i.e. in weak solution, fluorescence is relatively strong and fluorescent weakening is even without fluorescence during state of aggregation, this greatly limits its application and development.Use inorganic-quantum-dot (QDs) that ACQ phenomenon can be avoided, but it must be carried out surface hydrophilic modification, to reduce toxicity.Another method improving tradition small-molecule fluorescent probe ACQ effect is to be marked on macromolecular chain, forms fluorescent polymer.The segment of macromolecular chain can intercept fluorogen, alleviates the gathering of fluorogen, if but the amount of labelling is relatively big, or concentration is higher, and fluorogen has hydrophobic aromatic proton, still tends to assemble.
The ACQ effect faced for fluorescent probe technique and cytotoxicity two large problems, the discovery of aggregation-induced emission (AIE) fluorescence molecule provides splendid resolving ideas undoubtedly.AIE effect makes fluorescent probe easy of use, and AIE system does not has toxicity to cell, does not interferes with cytophysiology and cell proliferation.AIE molecular marker can be effectively improved on macromolecular chain biocompatibility and avoid dyestuff to reveal.The macromole being used for fixing dyestuff should have good biocompatibility and relatively high reaction activity and hydrophilic.Chitosan, as a kind of natural polysaccharide rich in amino, becomes excellent choosing naturally.And hydroxyapatite has good application prospect with biocompatibility (similar with natural bone composition) and unique needle-like crystal structure of its excellence at the aspect such as bio-imaging, medicine controlled releasing.
Summary of the invention
It is an object of the invention to provide a kind of highly sensitive, good light stability, without cancellation during high concentration, the preparation method of the aggregation-induced emission namo fluorescence probe that fluorescence spectrum is not drifted about.
The aggregation-induced emission namo fluorescence probe of the present invention, has the chitosan fluorescence molecule of aggregation-induced emission characteristic at hydroxyapatite nano particle Surface coating, the structural formula of chitosan fluorescence molecule as the formula (1),
Formula (1)
In formula: m, x, y are respectively number of repeat unit.
The preparation method of the aggregation-induced emission namo fluorescence probe of the present invention, step is as follows:
1) anhydrous calcium chloride, sodium dihydrogen phosphate and citric acid monohydrate trisodium being pressed the ratio 5:5:1 mixing of the amount of material, adds tri-distilled water, drip glacial acetic acid and dissolve under magnetic agitation, the consumption of glacial acetic acid is the 2% of mixeding liquid volume, and making concentration is 5
Mg/mL hydroxyapatite precursor solution；
2) the hydroxyapatite precursor solution tri-distilled water that step 1) prepares is diluted to 1 mg/mL, regulates pH=10 with aqueous slkali under stirring, continue to be stirred overnight, prepare hydroxyapatite nano particle solution；
3) it is 0.1 by mark rate
It is in 2% aqueous acetic acid that the AIE fluorescent labeling chitosan of mol%-20 mol% is dissolved in volumetric concentration, and compound concentration is the AIE fluorescent labeling chitosan-acetic acid solution of 0.1-5 mg/mL；
4) by step 2) prepare hydroxyapatite nano particle solution centrifugal abandoning supernatant, clean with tri-distilled water, be centrifuged again, precipitation is joined step 3) prepare AIE fluorescent labeling chitosan-acetic acid solution in, stirring at least 1 h, centrifugal abandoning supernatant, adds tri-distilled water and makes hydroxyapatite nano particle concentration be 1
Mg/mL, stirring, obtain aggregation-induced emission namo fluorescence probe.
The present invention passes through chemical coprecipitation, prepare, for dispersant, the hydroxyapatite nano particle that surface is electronegative with citric acid monohydrate trisodium, and be coated with the chitosan of one layer of aggregation-induced emission fluorescence molecule labelling thereon by electrostatic adsorption, thus prepare the namo fluorescence probe with aggregation-induced emission characteristic.
It is an advantage of the current invention that:
1) namo fluorescence probe a size of about 110nm, is shaped as needle-like, and surface is positively charged, it is easy to interact with cell membrane, and then enter cell interior by endocytosis, it is achieved the purpose of cell imaging.
2) fluorescent probe has aggregation-induced emission characteristic, compared with conventional fluorescent probe, has highly sensitive, good light stability, without cancellation during high concentration, and the advantage such as fluorescence spectrum not drift, it is expected to be applied to the field such as bio-imaging, fluorescent tracing detection.
3) material (chitosan, hydroxyapatite) used in the present invention is respectively provided with good biocompatibility.
Accompanying drawing explanation
Fig. 1 is the transmission electron microscope photo of aggregation-induced emission namo fluorescence probe.
Detailed description of the invention
The present invention is further illustrated below in conjunction with example.
Embodiment 1:
1) 0.0555 is weighed
G anhydrous calcium chloride, 0.0468 g sodium dihydrogen phosphate and 0.0294 g citric acid monohydrate trisodium, in 20 mL seed bottle, add 10 mL tri-distilled waters, drip 200 μ L glacial acetic acid and dissolve, make 5 mg/mL hydroxyapatite precursor solutions under magnetic agitation；
2) the hydroxyapatite precursor solution tri-distilled water of step 1) is diluted to 1 mg/mL, the lower dropping 40 of stirring
Wt% sodium hydrate aqueous solution regulation pH value of solution=10, now hydroxyapatite nano particle separates out, and continues to be stirred overnight, and prepares hydroxyapatite nano particle solution；
3) it is 0.1 by mark rate
It is in 2% aqueous acetic acid that the AIE fluorescent labeling chitosan of mol% is dissolved in volumetric concentration, and compound concentration is the AIE fluorescent labeling chitosan-acetic acid solution of 1 mg/mL；
4) 1 is measured
ML step 2) prepare hydroxyapatite nano particle solution, abandoning supernatant after centrifugal, recentrifuge after tri-distilled water cleaning, lower sediment is joined 1 mL step 3) prepare AIE fluorescent labeling chitosan-acetic acid solution in, stir 1 h, abandoning supernatant after centrifugal, adds tri-distilled water and makes hydroxyapatite nano particle concentration be 1
Mg/mL, stirring, prepare the namo fluorescence probe with aggregation-induced emission characteristic.
Namo fluorescence probe a size of 111.9 nm that this example prepares, surface potential is 11.51
MV, its transmission electron microscope photo is shown in Fig. 1.
Embodiment 2:
1) 0.0555 is weighed
G anhydrous calcium chloride, 0.0468 g sodium dihydrogen phosphate and 0.0557 g citric acid monohydrate trisodium, in 20 mL seed bottle, add 10 mL tri-distilled waters, drip 200 μ L glacial acetic acid and dissolve, make 5 mg/mL hydroxyapatite precursor solutions under magnetic agitation；
2) the hydroxyapatite precursor solution tri-distilled water of step 1) is diluted to 1 mg/mL, the lower dropping 40 of stirring
Wt% sodium hydrate aqueous solution regulation pH value of solution=10, now hydroxyapatite nano particle separates out, and continues to be stirred overnight, and prepares hydroxyapatite nano particle solution；
3) it is 20 by mark rate
It is in 2% aqueous acetic acid that the AIE fluorescent labeling chitosan of mol% is dissolved in volumetric concentration, and compound concentration is the AIE fluorescent labeling chitosan-acetic acid solution of 3 mg/mL；
4) 1 is measured
ML step 2) prepare hydroxyapatite nano particle solution, abandoning supernatant after centrifugal, recentrifuge after tri-distilled water cleaning, lower sediment is joined 1 mL step 3) prepare AIE fluorescent labeling chitosan-acetic acid solution in, stir 1 h, abandoning supernatant after centrifugal, adds tri-distilled water and makes hydroxyapatite nano particle concentration be 1
Mg/mL, stirring, prepare the namo fluorescence probe with aggregation-induced emission characteristic.
Namo fluorescence probe a size of 105.9 nm that this example prepares, surface potential is 10.25
mV。
Embodiment 3:
1) 0.0555 is weighed
G anhydrous calcium chloride, 0.0468 g sodium dihydrogen phosphate and 0.147 g citric acid monohydrate trisodium, in 20 mL seed bottle, add 10 mL tri-distilled waters, drip 200 μ L glacial acetic acid and dissolve, make 5 mg/mL hydroxyapatite precursor solutions under magnetic agitation；
2) the hydroxyapatite precursor solution tri-distilled water of step 1) is diluted to 1 mg/mL, the lower dropping 40 of stirring
Wt% sodium hydrate aqueous solution regulation pH value of solution=10, now hydroxyapatite nano particle separates out, and continues to be stirred overnight, and prepares hydroxyapatite nano particle solution；
3) it is 10 by mark rate
It is in 2% aqueous acetic acid that the AIE fluorescent labeling chitosan of mol% is dissolved in volumetric concentration, and compound concentration is the AIE fluorescent labeling chitosan-acetic acid solution of 5 mg/mL；
4) 1 is measured
ML step 2) prepare hydroxyapatite nano particle solution, abandoning supernatant after centrifugal, recentrifuge after tri-distilled water cleaning, lower sediment is joined 1 mL step 3) prepare AIE fluorescent labeling chitosan-acetic acid solution in, stir 1 h, abandoning supernatant after centrifugal, adds tri-distilled water and makes hydroxyapatite nano particle concentration be 1
Mg/mL, stirring, prepare the namo fluorescence probe with aggregation-induced emission characteristic.
Namo fluorescence probe a size of 111.5 nm that this example prepares, surface potential is 13.28
mV。
Claims (2)
1. an aggregation-induced emission namo fluorescence probe, is characterized in that the chitosan fluorescence molecule at hydroxyapatite nano particle Surface coating with aggregation-induced emission characteristic, the structural formula of chitosan fluorescence molecule as the formula (1),
Formula (1)
In formula: m, x, y are respectively number of repeat unit.
2. the method for preparation aggregation-induced emission namo fluorescence probe described in claim 1, it is characterised in that step is as follows:
1) anhydrous calcium chloride, sodium dihydrogen phosphate and citric acid monohydrate trisodium are pressed the ratio 5:5:1 mixing of the amount of material, add tri-distilled water, dripping glacial acetic acid under magnetic agitation to dissolve, the consumption of glacial acetic acid is the 2% of mixeding liquid volume, and making concentration is 5 mg/mL hydroxyapatite precursor solutions；
2) the hydroxyapatite precursor solution tri-distilled water that step 1) prepares is diluted to 1 mg/mL, regulates pH=10 with aqueous slkali under stirring, continue to be stirred overnight, prepare hydroxyapatite nano particle solution；
3) it is 0.1 mol% by mark rate
It is in 2% aqueous acetic acid that the aggregation-induced emission fluorescent labeling chitosan of-20 mol% is dissolved in volumetric concentration, and compound concentration is 0.1-5
The aggregation-induced emission fluorescent labeling chitosan-acetic acid solution of mg/mL；
4) by step 2) prepare hydroxyapatite nano particle solution centrifugal abandoning supernatant, clean with tri-distilled water, be centrifuged again, precipitation is joined step 3) prepare aggregation-induced emission fluorescent labeling chitosan-acetic acid solution in, stirring at least 1 h, centrifugal abandoning supernatant, adding tri-distilled water makes hydroxyapatite nano particle concentration be 1 mg/mL, stirring, obtains aggregation-induced emission namo fluorescence probe.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106010503B (en) * | 2016-05-07 | 2018-01-30 | 浙江大学 | One kind is suitable to macrocyclic chitosan-based fluorescence probe of blood and preparation method thereof |
| CN107311957A (en) * | 2017-06-21 | 2017-11-03 | 海南大学 | One kind is based on aggregation-induced emission and excited state intramolecular proton transfer compound and its preparation method and application |
| CN107502344B (en) * | 2017-09-12 | 2019-07-19 | 中南大学 | Multi-functional organic fluorescence nano particle and preparation and application based on dione pyrrolo-pyrrole compound and tetraphenyl ethylene class compound |
| CN107828052B (en) * | 2017-10-16 | 2020-04-28 | 华南理工大学 | Conjugated polymer with aggregation-induced emission property and preparation method and application thereof |
| CN108559008B (en) * | 2018-06-25 | 2020-11-13 | 浙江大学 | Quaternized chitosan/heparin composite nano fluorescent probe with aggregation-induced emission characteristic and preparation method thereof |
| CN109810702B (en) * | 2019-02-20 | 2021-12-21 | 深圳大学 | Nano fluorescent probe with good biocompatibility and preparation method thereof |
| CN110372685A (en) * | 2019-07-30 | 2019-10-25 | 天津大学 | The pH that new A IE molecule and its synthesis step, preparation generate active oxygen responds AIE nanoparticle approach |
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|---|---|---|---|---|
| JP2006117593A (en) * | 2004-10-22 | 2006-05-11 | Osaka Prefecture | New fluorescent compound and method for producing the same |
| CN101419140A (en) * | 2008-11-18 | 2009-04-29 | 浙江理工大学 | Method for fluorescence labeling hydroxylapatite |
| CN101643645A (en) * | 2009-07-24 | 2010-02-10 | 华中科技大学 | Calcium phosphate material marked by fluorescein isothiocyanate and preparation method thereof |
| CN104356345A (en) * | 2014-12-01 | 2015-02-18 | 四川大学 | Fluorescent graft degradable block polyurethane, bone repair material and preparation method thereof |
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Patent Citations (4)
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|---|---|---|---|---|
| JP2006117593A (en) * | 2004-10-22 | 2006-05-11 | Osaka Prefecture | New fluorescent compound and method for producing the same |
| CN101419140A (en) * | 2008-11-18 | 2009-04-29 | 浙江理工大学 | Method for fluorescence labeling hydroxylapatite |
| CN101643645A (en) * | 2009-07-24 | 2010-02-10 | 华中科技大学 | Calcium phosphate material marked by fluorescein isothiocyanate and preparation method thereof |
| CN104356345A (en) * | 2014-12-01 | 2015-02-18 | 四川大学 | Fluorescent graft degradable block polyurethane, bone repair material and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
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