CN106243244B - A kind of carboxyl chitosan namo fluorescence probe and preparation method thereof with aggregation-induced emission characteristic - Google Patents
A kind of carboxyl chitosan namo fluorescence probe and preparation method thereof with aggregation-induced emission characteristic Download PDFInfo
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- CN106243244B CN106243244B CN201610632880.3A CN201610632880A CN106243244B CN 106243244 B CN106243244 B CN 106243244B CN 201610632880 A CN201610632880 A CN 201610632880A CN 106243244 B CN106243244 B CN 106243244B
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Abstract
A kind of carboxyl chitosan namo fluorescence probe with aggregation-induced emission characteristic disclosed by the invention, preparation method key step include: that tetraphenylethylene fluorescent molecule (TPE) is tagged to the TPE-NCS on carboxyl chitosan chain (NCS) obtained having aggregation-induced emission (AIE) characteristic；TPE-NCS nanoparticle is made by ionic cross-linking using sodium polyphosphate.Namo fluorescence probe produced by the present invention has good dispersibility in aqueous solution, and there is aggregation-induced emission characteristic, compared with conventional fluorescent probe, have many advantages, such as that high sensitivity, good light stability, fluorescence spectrum are not drifted about, nano-particles size stable uniform, easily stored.Further, since carboxyl chitosan inherent characteristic, which has good biocompatibility, and good dispersibility within the scope of the long anelasticity of body-internal-circulation and wide pH value is expected to be used for the fields such as long period Cellular tracking, pathological monitoring, drug metabolism detection.
Description
Technical field
The present invention relates to a kind of with the carboxyl chitosan namo fluorescence probe of aggregation-induced emission characteristic and its preparation side
Method.
Background technique
Fluorescence probe is using fluorescent material as indicator, and it is glimmering to generate indicator under the excitation of certain wavelength light
Light, by detecting qualitative or quantitative analysis of the generated fluorescence realization to tested substance.Currently, fluorescence probe is mainly answered
For fields such as biology, medicine and environmental monitorings, for different demands, corresponding probe is largely probed into, overall next
It says, can be divided into three classes: traditional fluorescence probe, inorganic-quantum-dot probe, novel fluorescence probe.Wherein, traditional fluorescence
Probe has the defects of photo-labile, photobleaching and aggregation inducing quenching effect, and inorganic-quantum-dot probe contains weight because of it
Metal and there is very important cytotoxicity problem, therefore novel fluorescence probe is shown one's talent.And there is aggregation-induced emission
(AIE) probe of characteristic is concerned because of its brilliant fluorescence property.Carboxyl chitosan (NCS) is chitosan part saccharide ring by carboxylic
Product after change, within the scope of excellent biocompatibility, bioactivity, nontoxicity, the long anelasticity of body-internal-circulation, wide pH value
Can be water-soluble etc. performances, in field of biomedicine by favor.Accordingly, it is considered to till now to cell long period in biomedical research
Tracer (development, diagnosis, treatment as studied cancer；Immune response and transfer after stem cell gene integrality, increment, divide
Change etc.) and wide pH value in use (such as cancer patient's external pHeBetween 5.7 to 7.8) fluorescence probe compel
It is essential and asks, preparing can be water-soluble within the scope of a kind of wide pH value and have important with the fluorescence probe of long period Cellular tracking performance
Scientific meaning and good application prospect.
Summary of the invention
In view of the above-mentioned deficiencies in the prior art, it is an object of the present invention to which can be water-soluble within the scope of a kind of wide pH value and length be had by providing
The carboxyl chitosan namo fluorescence probe and preparation method thereof with aggregation-induced emission characteristic of cycling cells tracer performance.
The preparation method of carboxyl chitosan namo fluorescence probe with aggregation-induced emission characteristic of the invention, including such as
Lower step:
It 1) is 10,000-100 ten thousand by viscosity average molecular weigh, the carboxyl chitosan of acetyl degree 5%-20%, carboxylation degree 20%-60%
It is scattered in DMSO, 12-48h is swollen at 50-65 DEG C, then the TPE containing isothiocyanate functionality points are added into the solution
The molar ratio of amino is 1%-20% in sub (TPEITC), TPEITC and chitosan, reacts 24-48h, obtains solution A；
2) be added tetrahydrofuran into solution A, the volume ratio of tetrahydrofuran and solution A is 10, stand after mixing evenly to
Solution layering removes supernatant, centrifugation, and the appropriate dehydrated alcohol ultrasonic disperse 20min of gained sediment is centrifuged, and precipitating is used
Tri-distilled water dissolution, obtains solution B；
3) solution B is fitted into be placed in tri-distilled water in the bag filter that molecular cut off is 3500 and is dialysed 4-5 days, is lyophilized,
Obtain the carboxyl chitosan (TPE-NCS) of fluorescent marker；
4) the fluorescent marker carboxyl chitosan of step 3) is dissolved in the acetum that volume fraction is 1%, obtains fluorescence
Mark carboxyl chitosan solution C；
5) the polyphosphoric acids sodium solution that mass fraction is 1-40% is prepared, is with Solute mass ratio by polyphosphoric acids sodium solution
The ratio of 1:5 is added dropwise to solution C, it may be assumed that so that sodium polyphosphate and TPE-NCS mass ratio are 1:5, it is vigorously stirred 0.5-1h, from
The heart removes supernatant, and appropriate tri-distilled water is added, and obtaining, there is the carboxyl chitosan nano fluorescent of aggregation-induced emission characteristic to visit
Needle.
The present invention is obtained by the way that tetraphenylethylene (TPE) fluorescent molecule to be tagged on carboxyl chitosan chain with AIE spy
Property TPE-NCS, recycle sodium polyphosphate that TPE-NCS carried out ionomer, so that being made has aggregation-induced emission special
Finely dispersed namo fluorescence probe (TPE-NCS NP in property and aqueous solutions).The TPE-NCS molecular formula that the present invention obtains is as schemed
Shown in 1, polyphosphate radical structural formula is as shown in Fig. 2, product TPE-NCS NPsTEM it is as shown in Figure 3.
TPE group on product is labeled assigns its aggregation-induced emission characteristic, with conventional fluorescent probe and inorganic quantum
The advantages that point probe is compared, and has high sensitivity, good light stability, and fluorescence spectrum does not drift about, good biocompatibility.And carboxylation shell
Glycan is amphipathic molecule, can in dilute acid soln, neutral aqueous solution and dilute alkaline soln when carboxylation degree is between 20%-60%
It is molten, and because being rich in amino, carboxylic group, with good bioactivity, it can be achieved that the function that long circulating, length are detained in organism
Effect.In addition, the TPE-NCS NP after ionomersNano-particles size is uniform, is easy to cell endocytosis, and convenient for storage.In short,
The TPE-NCS NP of this method preparationsNamo fluorescence probe have wide pH value it is solvable, can long circulating tracer and aggregation-induced emission
Equal good characteristics are expected to be applied to the fields such as the tracer of cell long period, drug metabolism detection, pathological monitoring.
Detailed description of the invention
Fig. 1 is carboxyl chitosan base aggregation-induced emission fluorescent molecular structure formula.
Fig. 2 is crosslinking agent polyphosphate radical molecular structural formula.
Fig. 3 is carboxyl chitosan base aggregation-induced emission namo fluorescence probe TEM figure.
Specific embodiment
The present invention is further illustrated below in conjunction with drawings and concrete examples.
Embodiment 1:
1) it weighs 1g carboxyl chitosan (viscosity average molecular weigh is 10,000, and acetyl degree is 20%, carboxylation degree 20%) and is added to eggplant shape
In bottle, it is scattered in 10mL DMSO, 12h is swollen at 50 DEG C, be then added TPEITC into eggplant-shape bottle, in TPEITC and chitosan
The molar ratio of amino is 1%, and reaction for 24 hours, obtains solution A and is poured into 250mL beaker；
2) 100mL tetrahydrofuran is added into solution A, is stood after mixing evenly to solution and is layered, removes supernatant, from
The heart, gained sediment is dissolved with 20mL dehydrated alcohol and ultrasonic disperse 20min, centrifugation, and precipitating 5mL tri-distilled water is dissolved, is obtained
To solution B；
3) solution B is fitted into be placed in tri-distilled water in the bag filter that molecular cut off is 3500 and is dialysed 4 days, be lyophilized, obtain
Obtain the carboxyl chitosan TPE-NCS of fluorescent marker；4) weigh 0.5g TPE-NCS be dissolved in 10mL volume fraction be 1% acetic acid it is molten
Liquid obtains the fluorescent marker carboxyl chitosan solution C of 50mg/mL；
5) the polyphosphoric acids sodium solution that mass fraction is 1% is prepared, by polyphosphoric acids sodium solution with Solute mass ratio for 1:5
Ratio be added dropwise in solution C, be vigorously stirred 0.5h, be centrifuged, remove supernatant, be added 10mL tri-distilled water obtain have aggregation lures
Lead the carboxyl chitosan namo fluorescence probe of the characteristics of luminescence.
TPE-NCS fluorescence probe TPE mark rate made from this example is 0.71%.
Embodiment 2:
1) it weighs 1g carboxyl chitosan (viscosity average molecular weigh is 50,000, and acetyl degree is 15%, carboxylation degree 30%) and is added to eggplant shape
In bottle, it is scattered in 10mL DMSO, 12h is swollen at 50 DEG C, be then added TPEITC into eggplant-shape bottle, in TPEITC and chitosan
The molar ratio of amino is 5%, and reaction for 24 hours, obtains solution A and is poured into 250mL beaker；
2) 100mL tetrahydrofuran is added into solution A, is stood after mixing evenly to solution and is layered, removes supernatant, from
The heart, gained sediment is dissolved with 20mL dehydrated alcohol and ultrasonic disperse 20min, centrifugation, and precipitating 5mL tri-distilled water is dissolved, is obtained
To solution B；
3) solution B is fitted into be placed in tri-distilled water in the bag filter that molecular cut off is 3500 and is dialysed 4 days, be lyophilized, obtain
Obtain the carboxyl chitosan TPE-NCS of fluorescent marker；
4) it weighs 0.5g TPE-NCS and is dissolved in the acetum that 10mL volume fraction is 1%, obtain the fluorescence mark of 50mg/mL
Remember carboxyl chitosan solution C；
5) the polyphosphoric acids sodium solution that mass fraction is 5% is prepared, by polyphosphoric acids sodium solution with Solute mass ratio for 1:5
Ratio be added dropwise in solution C, be vigorously stirred 0.5h, be centrifuged, remove supernatant, be added 10mL tri-distilled water obtain have aggregation lures
Lead the carboxyl chitosan namo fluorescence probe of the characteristics of luminescence.
TPE-NCS fluorescence probe TPE mark rate made from this example is 1.35%.
Embodiment 3:
1) it weighs 1g carboxyl chitosan (viscosity average molecular weigh is 200,000, and acetyl degree is 10%, carboxylation degree 35%) and is added to eggplant
In shape bottle, it is scattered in 10mL DMSO, is swollen at 50 DEG C for 24 hours, TPEITC, TPEITC and chitosan are then added into eggplant-shape bottle
The molar ratio of middle amino is 10%, reacts 36h, obtains solution A and is poured into 250mL beaker；
2) 100mL tetrahydrofuran is added into solution A, is stood after mixing evenly to solution and is layered, removes supernatant, from
The heart, gained sediment is dissolved with 20mL dehydrated alcohol and ultrasonic disperse 20min, centrifugation, and precipitating 5mL tri-distilled water is dissolved, is obtained
To solution B；
3) solution B is fitted into be placed in tri-distilled water in the bag filter that molecular cut off is 3500 and is dialysed 4 days, be lyophilized, obtain
Obtain the carboxyl chitosan TPE-NCS of fluorescent marker；
4) it weighs 0.5g TPE-NCS and is dissolved in the acetum that 10mL volume fraction is 1%, obtain the fluorescence mark of 50mg/mL
Remember carboxyl chitosan solution C；
5) the polyphosphoric acids sodium solution that mass fraction is 10% is prepared, by polyphosphoric acids sodium solution with Solute mass ratio for 1:
5 ratio is added dropwise in solution C, is vigorously stirred 1h, and centrifugation removes supernatant, and 10mL tri-distilled water is added and obtains, and there is aggregation to lure
Lead the carboxyl chitosan namo fluorescence probe of the characteristics of luminescence.
TPE-NCS fluorescence probe TPE mark rate made from this example is 3.58%.
Embodiment 4:
1) it weighs 1g carboxyl chitosan (viscosity average molecular weigh is 500,000, and acetyl degree is 10%, carboxylation degree 40%) and is added to eggplant
In shape bottle, it is scattered in 10mL DMSO, 36h is swollen at 50 DEG C, TPEITC, TPEITC and chitosan are then added into eggplant-shape bottle
The molar ratio of middle amino is 15%, reacts 36h, obtains solution A and is poured into 250mL beaker；
2) 100mL tetrahydrofuran is added into solution A, is stood after mixing evenly to solution and is layered, removes supernatant, from
The heart, gained sediment is dissolved with 20mL dehydrated alcohol and ultrasonic disperse 20min, centrifugation, and precipitating 5mL tri-distilled water is dissolved, is obtained
To solution B；
3) solution B is fitted into be placed in tri-distilled water in the bag filter that molecular cut off is 3500 and is dialysed 5 days, be lyophilized, obtain
Obtain the carboxyl chitosan TPE-NCS of fluorescent marker；
4) it weighs 0.5g TPE-NCS and is dissolved in the acetum that 10mL volume fraction is 1%, obtain the fluorescence mark of 50mg/mL
Remember carboxyl chitosan solution C；
5) the polyphosphoric acids sodium solution that mass fraction is 20% is prepared, by polyphosphoric acids sodium solution with Solute mass ratio for 1:
5 ratio is added dropwise in solution C, is vigorously stirred 1h, and centrifugation removes supernatant, and 10mL tri-distilled water is added and obtains, and there is aggregation to lure
Lead the carboxyl chitosan namo fluorescence probe of the characteristics of luminescence.
TPE-NCS fluorescence probe TPE mark rate made from this example is 9.31%.
Embodiment 5:
1) it weighs 1g carboxyl chitosan (viscosity average molecular weigh is 1,000,000, and acetyl degree is 5%, carboxylation degree 60%) and is added to eggplant
In shape bottle, it is scattered in 10mL DMSO, 48h is swollen at 50 DEG C, TPEITC, TPEITC and chitosan are then added into eggplant-shape bottle
The molar ratio of middle amino is 20%, reacts 48h, obtains solution A and is poured into 250mL beaker；
2) 100mL tetrahydrofuran is added into solution A, is stood after mixing evenly to solution and is layered, removes supernatant, from
The heart, gained sediment is dissolved with 20mL dehydrated alcohol and ultrasonic disperse 20min, centrifugation, and precipitating 5mL tri-distilled water is dissolved, is obtained
To solution B；
3) solution B is fitted into be placed in tri-distilled water in the bag filter that molecular cut off is 3500 and is dialysed 4 days, be lyophilized, obtain
Obtain the carboxyl chitosan TPE-NCS of fluorescent marker；
4) it weighs 0.5g TPE-NCS and is dissolved in the acetum that 10mL volume fraction is 1%, obtain the fluorescence mark of 50mg/mL
Remember carboxyl chitosan solution C；
5) the polyphosphoric acids sodium solution that mass fraction is 40% is prepared, by polyphosphoric acids sodium solution with Solute mass ratio for 1:
5 ratio is added dropwise in solution C, is vigorously stirred 1h, and centrifugation removes supernatant, and 10mL tri-distilled water is added and obtains, and there is aggregation to lure
Lead the carboxyl chitosan namo fluorescence probe of the characteristics of luminescence.
TPE-NCS fluorescence probe TPE mark rate made from this example is 12.01%.
Claims (2)
1. a kind of preparation method of the carboxyl chitosan namo fluorescence probe with aggregation-induced emission characteristic, which is characterized in that
Include the following steps:
1) be 10,000-100 ten thousand, acetyl degree 5%-20% by viscosity average molecular weigh, the carboxyl chitosan of carboxylation degree 20%-60% disperses
In DMSO, it is swollen 12-48h at 50-65 DEG C, then TPEITC, TPEITC and amino in chitosan are added into the solution
Molar ratio is 1%-20%, reacts 24-48h, obtains solution A；
2) it is added tetrahydrofuran into solution A, the volume ratio of tetrahydrofuran and solution A is 10, is stood after mixing evenly to solution
Layering removes supernatant, centrifugation, and gained sediment dehydrated alcohol ultrasonic disperse 20min is centrifuged, and precipitating tri-distilled water is molten
Solution, obtains solution B；
3) solution B is fitted into be placed in tri-distilled water in the bag filter that molecular cut off is 3500 and is dialysed 4-5 days, be lyophilized, obtain
The carboxyl chitosan of fluorescent marker；
4) the fluorescent marker carboxyl chitosan of step 3) is dissolved in the acetum that volume fraction is 1%, obtains fluorescent marker
Carboxyl chitosan solution C；
5) the polyphosphoric acids sodium solution that mass fraction is 1-40% is prepared, by polyphosphoric acids sodium solution with Solute mass ratio for 1:5
Ratio be added dropwise to solution C, be vigorously stirred 0.5-1h, be centrifuged, remove supernatant, be added tri-distilled water, obtain have aggregation inducing
The carboxyl chitosan namo fluorescence probe of the characteristics of luminescence.
2. a kind of carboxyl chitosan namo fluorescence probe with aggregation-induced emission characteristic, which is characterized in that by claim 1
The method is prepared.
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| CN110894424A (en) * | 2018-09-13 | 2020-03-20 | 中国科学院大连化学物理研究所 | Fluorescent material based on quantum dot-aggregation-induced emission molecules |
| CN110426323B (en) * | 2019-08-30 | 2020-10-20 | 浙江大学 | Method for measuring permeability and coverage of chitosan slurry |
| CN114316084B (en) * | 2021-12-15 | 2022-10-11 | 武汉大学 | AIE functionalized modified chitin material capable of being fluorescently traced, preparation method and application |
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| CN101962450A (en) * | 2010-10-20 | 2011-02-02 | 武汉大学 | Aqueous phase preparation method for chitosan-quantum dot fluorescent probe |
| CN104945537A (en) * | 2015-05-26 | 2015-09-30 | 浙江大学 | Preparation method of water-soluble chitosan-base aggregation-induced light-emitting fluorescent probe |
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| CN101962450A (en) * | 2010-10-20 | 2011-02-02 | 武汉大学 | Aqueous phase preparation method for chitosan-quantum dot fluorescent probe |
| CN104945537A (en) * | 2015-05-26 | 2015-09-30 | 浙江大学 | Preparation method of water-soluble chitosan-base aggregation-induced light-emitting fluorescent probe |
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| "基于AIE现象发光机理的纳米荧光探针的设计及肿瘤细胞靶向成像的研究";李民;《中国博士学位论文全文数据库 医药卫生科技辑》;20141215(第12期);E079-9 |
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