CN106243244A - A kind of carboxyl chitosan namo fluorescence probe with aggregation-induced emission characteristic and preparation method thereof - Google Patents

A kind of carboxyl chitosan namo fluorescence probe with aggregation-induced emission characteristic and preparation method thereof Download PDF

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CN106243244A
CN106243244A CN201610632880.3A CN201610632880A CN106243244A CN 106243244 A CN106243244 A CN 106243244A CN 201610632880 A CN201610632880 A CN 201610632880A CN 106243244 A CN106243244 A CN 106243244A
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carboxyl chitosan
aggregation
tpe
chitosan
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CN106243244B (en
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王征科
刘亚蓝
胡巧玲
唐本忠
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Zhejiang University ZJU
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
    • C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
    • C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • 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
    • G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/145—Heterocyclic containing oxygen as the only heteroatom

Abstract

A kind of carboxyl chitosan namo fluorescence probe with aggregation-induced emission characteristic disclosed by the invention, its preparation method key step includes: tetraphenylethylene fluorescence molecule (TPE) is tagged on carboxyl chitosan chain (NCS) the TPE NCS obtaining having aggregation-induced emission (AIE) characteristic；Sodium polyphosphate is utilized to prepare TPE NCS nanoparticle by ionic cross-linking.The namo fluorescence probe that the present invention prepares has good dispersibility in aqueous, and there is aggregation-induced emission characteristic, compared with conventional fluorescent probe, there is the advantages such as highly sensitive, good light stability, fluorescence spectrum are not drifted about, nano-particles size stable uniform, easy storage.Additionally, due to carboxyl chitosan inherent character, this probe has good biocompatibility, and dispersibility good in the range 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

A kind of carboxyl chitosan namo fluorescence probe with aggregation-induced emission characteristic and Preparation method
Technical field
The present invention relates to a kind of carboxyl chitosan namo fluorescence probe with aggregation-induced emission characteristic and preparation side thereof Method.
Background technology
Fluorescent probe is using fluorescent material as indicator, and it is glimmering to make indicator produce under the exciting of certain wavelength light Light, is realized the qualitative of tested substance or quantitative analysis by the produced fluorescence of detection.Currently, fluorescent probe mainly should For fields such as biological, medical science and environmental monitorings, for different demands, corresponding probe has been probed into by substantial amounts of, totally comes Say, can be divided three classes: traditional fluorescent probe, inorganic-quantum-dot probe, novel fluorescent probe.Wherein, traditional fluorescence Probe has the defects such as 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 receives much concern because of the fluorescence property of its brilliance.Carboxyl chitosan (NCS) is that chitosan part sugar ring is by carboxylic Product after change, in the range of having the biocompatibility of excellence, biological activity, avirulence, the long anelasticity of body-internal-circulation, wide pH value Can be water-soluble etc. performance, enjoy favor at biomedical sector.Accordingly, it is considered to cell long period in biomedical research till now Spike (as research cancer development, diagnose, treat；Immunoreation and transfer after stem cell gene integrity, rise in value, point Change etc.) and wide pH value in the range of use (such as cancer patient's external pHeBetween 5.7 to 7.8) fluorescent probe compel Being essential and ask, preparing in the range of a kind of wide pH value can be water-soluble and have the fluorescent probe of long period Cellular tracking performance and have important Scientific meaning and good application prospect.
Summary of the invention
Present invention aims to the deficiencies in the prior art, it is provided that can be water-soluble and there is length in the range of a kind of wide pH value Carboxyl chitosan namo fluorescence probe with aggregation-induced emission characteristic of cycling cells spike performance and preparation method thereof.
The preparation method of the carboxyl chitosan namo fluorescence probe with aggregation-induced emission characteristic of the present invention, including such as Lower step:
1) by viscosity-average molecular weight be 10,000-100 ten thousand, acetyl degree 5%-20%, the carboxyl chitosan of carboxylation degree 20%-60% It is scattered in DMSO, swelling 12-48h at 50-65 DEG C, then the addition TPE containing isothiocyanate functionality divides in this solution Son (TPEITC), TPEITC is 1%-20% with the mol ratio of amino in chitosan, reacts 24-48h, it is thus achieved that solution A；
2) adding oxolane in solution A, the volume ratio of oxolane and solution A is 10, stand after stirring to Solution is layered, and removes supernatant, centrifugal, and gained precipitate is with appropriate dehydrated alcohol ultrasonic disperse 20min, centrifugal, precipitation is used Tri-distilled water dissolves, and obtains solution B；
3) solution B is loaded in the bag filter that molecular cut off is 3500 and be placed in tri-distilled water dialysis 4-5 days, lyophilizing, Obtain fluorescently-labeled carboxyl chitosan (TPE-NCS)；
4) by step 3) fluorescent labeling carboxyl chitosan be dissolved in the acetum that volume fraction is 1%, obtain fluorescence Labelling carboxyl chitosan solution C；
5) preparation mass fraction is the polyphosphoric acids sodium solution of 1-40%, by polyphosphoric acids sodium solution with Solute mass ratio is The ratio of 1:5 is added dropwise to solution C, it may be assumed that making sodium polyphosphate and TPE-NCS mass ratio is 1:5, is stirred vigorously 0.5-1h, from The heart, removes supernatant, adds appropriate tri-distilled water, it is thus achieved that the carboxyl chitosan nano fluorescent with aggregation-induced emission characteristic is visited Pin.
The present invention is special by being tagged to tetraphenylethylene (TPE) fluorescence molecule on carboxyl chitosan chain to obtain to have AIE Property TPE-NCS, TPE-NCS is carried out ionomer by recycling sodium polyphosphate, thus prepares that to have 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 such as figure Shown in 1, polyphosphate radical structural formula is as in figure 2 it is shown, product TPE-NCS NPsTEM as shown in Figure 3.
TPE group on product is labeled gives its aggregation-induced emission characteristic, with conventional fluorescent probe and inorganic quantum The advantages such as point probe is compared, and has highly sensitive, good light stability, and fluorescence spectrum is not drifted about, good biocompatibility.And carboxylation shell Polysaccharide is amphipathic molecule, can in dilute acid soln, neutral aqueous solution and dilute alkaline soln when carboxylation degree is between 20%-60% Molten, and because rich in amino, carboxylic group, there is good biological activity, long circulating, the long merit being detained in organism can be realized Effect.Additionally, the TPE-NCS NP after ionomersNano-particles size is homogeneous, it is easy to cell endocytosis, and is easy to storage.In a word, TPE-NCS NP prepared by this methodsNamo fluorescence probe have wide pH value solvable, can long circulating spike and aggregation-induced emission Deng good characteristic, it is expected to be applied to the fields such as cell long period spike, drug metabolism detection, pathological monitoring.
Accompanying drawing explanation
Fig. 1 is carboxyl chitosan base aggregation-induced emission fluorescent molecular structure formula.
Fig. 2 is cross-linking agent polyphosphate radical molecular structural formula.
Fig. 3 is carboxyl chitosan base aggregation-induced emission namo fluorescence probe TEM figure.
Detailed description of the invention
The present invention is further illustrated below in conjunction with accompanying drawing and instantiation.
Embodiment 1:
1) weigh 1g carboxyl chitosan (viscosity-average molecular weight is 10,000, and acetyl degree is 20%, carboxylation degree 20%) and join eggplant shape In Ping, it is scattered in 10mL DMSO, swelling 12h at 50 DEG C, then add in TPEITC, TPEITC and chitosan in eggplant-shape bottle The mol ratio of amino is 1%, reacts 24h, it is thus achieved that solution A is also poured in 250mL beaker；
2) in solution A, add 100mL oxolane, stand after stirring and be layered to solution, remove supernatant, from The heart, gained precipitate 20mL anhydrous alcohol solution ultrasonic disperse 20min, centrifugal, precipitation 5mL tri-distilled water is dissolved, To solution B；
3) solution B is loaded in the bag filter that molecular cut off is 3500 and be placed in tri-distilled water dialysis 4 days, lyophilizing, obtain Obtain fluorescently-labeled carboxyl chitosan TPE-NCS；4) weighing 0.5g TPE-NCS, to be dissolved in the acetic acid that 10mL volume fraction is 1% molten Liquid, obtains the fluorescent labeling carboxyl chitosan solution C of 50mg/mL；
5) preparation mass fraction is the polyphosphoric acids sodium solution of 1%, by polyphosphoric acids sodium solution with Solute mass ratio as 1:5 Ratio be added dropwise in solution C, be stirred vigorously 0.5h, centrifugal, remove supernatant, add 10mL tri-distilled water and obtain and there is gathering lure Lead the carboxyl chitosan namo fluorescence probe of the characteristics of luminescence.
The TPE-NCS fluorescent probe TPE mark rate that this example prepares is 0.71%.
Embodiment 2:
1) weigh 1g carboxyl chitosan (viscosity-average molecular weight is 50,000, and acetyl degree is 15%, carboxylation degree 30%) and join eggplant shape In Ping, it is scattered in 10mL DMSO, swelling 12h at 50 DEG C, then add in TPEITC, TPEITC and chitosan in eggplant-shape bottle The mol ratio of amino is 5%, reacts 24h, it is thus achieved that solution A is also poured in 250mL beaker；
2) in solution A, add 100mL oxolane, stand after stirring and be layered to solution, remove supernatant, from The heart, gained precipitate 20mL anhydrous alcohol solution ultrasonic disperse 20min, centrifugal, precipitation 5mL tri-distilled water is dissolved, To solution B；
3) solution B is loaded in the bag filter that molecular cut off is 3500 and be placed in tri-distilled water dialysis 4 days, lyophilizing, obtain Obtain fluorescently-labeled carboxyl chitosan TPE-NCS；
4) weigh 0.5g TPE-NCS and be dissolved in the acetum that 10mL volume fraction is 1%, obtain the fluorescence mark of 50mg/mL Note carboxyl chitosan solution C；
5) preparation mass fraction is the polyphosphoric acids sodium solution of 5%, by polyphosphoric acids sodium solution with Solute mass ratio as 1:5 Ratio be added dropwise in solution C, be stirred vigorously 0.5h, centrifugal, remove supernatant, add 10mL tri-distilled water and obtain and there is gathering lure Lead the carboxyl chitosan namo fluorescence probe of the characteristics of luminescence.
The TPE-NCS fluorescent probe TPE mark rate that this example prepares is 1.35%.
Embodiment 3:
1) weigh 1g carboxyl chitosan (viscosity-average molecular weight is 200,000, and acetyl degree is 10%, carboxylation degree 35%) and join eggplant In shape bottle, it is scattered in 10mL DMSO, swelling 24h at 50 DEG C, in eggplant-shape bottle, then add TPEITC, TPEITC and chitosan The mol ratio of middle amino is 10%, reacts 36h, it is thus achieved that solution A is also poured in 250mL beaker；
2) in solution A, add 100mL oxolane, stand after stirring and be layered to solution, remove supernatant, from The heart, gained precipitate 20mL anhydrous alcohol solution ultrasonic disperse 20min, centrifugal, precipitation 5mL tri-distilled water is dissolved, To solution B；
3) solution B is loaded in the bag filter that molecular cut off is 3500 and be placed in tri-distilled water dialysis 4 days, lyophilizing, obtain Obtain fluorescently-labeled carboxyl chitosan TPE-NCS；
4) weigh 0.5g TPE-NCS and be dissolved in the acetum that 10mL volume fraction is 1%, obtain the fluorescence mark of 50mg/mL Note carboxyl chitosan solution C；
5) preparation mass fraction is the polyphosphoric acids sodium solution of 10%, by polyphosphoric acids sodium solution with Solute mass ratio for 1: The ratio of 5 is added dropwise in solution C, is stirred vigorously 1h, centrifugal, removes supernatant, and addition 10mL tri-distilled water acquisition has gathering and lures Lead the carboxyl chitosan namo fluorescence probe of the characteristics of luminescence.
The TPE-NCS fluorescent probe TPE mark rate that this example prepares is 3.58%.
Embodiment 4:
1) weigh 1g carboxyl chitosan (viscosity-average molecular weight is 500,000, and acetyl degree is 10%, carboxylation degree 40%) and join eggplant In shape bottle, it is scattered in 10mL DMSO, swelling 36h at 50 DEG C, in eggplant-shape bottle, then add TPEITC, TPEITC and chitosan The mol ratio of middle amino is 15%, reacts 36h, it is thus achieved that solution A is also poured in 250mL beaker；
2) in solution A, add 100mL oxolane, stand after stirring and be layered to solution, remove supernatant, from The heart, gained precipitate 20mL anhydrous alcohol solution ultrasonic disperse 20min, centrifugal, precipitation 5mL tri-distilled water is dissolved, To solution B；
3) solution B is loaded in the bag filter that molecular cut off is 3500 and be placed in tri-distilled water dialysis 5 days, lyophilizing, obtain Obtain fluorescently-labeled carboxyl chitosan TPE-NCS；
4) weigh 0.5g TPE-NCS and be dissolved in the acetum that 10mL volume fraction is 1%, obtain the fluorescence mark of 50mg/mL Note carboxyl chitosan solution C；
5) preparation mass fraction is the polyphosphoric acids sodium solution of 20%, by polyphosphoric acids sodium solution with Solute mass ratio for 1: The ratio of 5 is added dropwise in solution C, is stirred vigorously 1h, centrifugal, removes supernatant, and addition 10mL tri-distilled water acquisition has gathering and lures Lead the carboxyl chitosan namo fluorescence probe of the characteristics of luminescence.
The TPE-NCS fluorescent probe TPE mark rate that this example prepares is 9.31%.
Embodiment 5:
1) weigh 1g carboxyl chitosan (viscosity-average molecular weight is 1,000,000, and acetyl degree is 5%, carboxylation degree 60%) and join eggplant In shape bottle, it is scattered in 10mL DMSO, swelling 48h at 50 DEG C, in eggplant-shape bottle, then add TPEITC, TPEITC and chitosan The mol ratio of middle amino is 20%, reacts 48h, it is thus achieved that solution A is also poured in 250mL beaker；
2) in solution A, add 100mL oxolane, stand after stirring and be layered to solution, remove supernatant, from The heart, gained precipitate 20mL anhydrous alcohol solution ultrasonic disperse 20min, centrifugal, precipitation 5mL tri-distilled water is dissolved, To solution B；
3) solution B is loaded in the bag filter that molecular cut off is 3500 and be placed in tri-distilled water dialysis 4 days, lyophilizing, obtain Obtain fluorescently-labeled carboxyl chitosan TPE-NCS；
4) weigh 0.5g TPE-NCS and be dissolved in the acetum that 10mL volume fraction is 1%, obtain the fluorescence mark of 50mg/mL Note carboxyl chitosan solution C；
5) preparation mass fraction is the polyphosphoric acids sodium solution of 40%, by polyphosphoric acids sodium solution with Solute mass ratio for 1: The ratio of 5 is added dropwise in solution C, is stirred vigorously 1h, centrifugal, removes supernatant, and addition 10mL tri-distilled water acquisition has gathering and lures Lead the carboxyl chitosan namo fluorescence probe of the characteristics of luminescence.
The TPE-NCS fluorescent probe TPE mark rate that this example prepares is 12.01%.

Claims (2)

1. the preparation method of a carboxyl chitosan namo fluorescence probe with aggregation-induced emission characteristic, it is characterised in that Comprise the steps:
1) by viscosity-average molecular weight be 10,000-100 ten thousand, the carboxyl chitosan of acetyl degree 5%-20%, carboxylation degree 20%-60% dispersion In DMSO, swelling 12-48h at 50-65 DEG C, then in this solution, add TPEITC, TPEITC and amino in chitosan Mol ratio is 1%-20%, reacts 24-48h, it is thus achieved that solution A；
2) adding oxolane in solution A, oxolane is 10 with the volume ratio of solution A, stands to solution after stirring Layering, removes supernatant, centrifugal, and gained precipitate dehydrated alcohol ultrasonic disperse 20min is centrifugal, by molten for precipitation tri-distilled water Solve, obtain solution B；
3) solution B is loaded in the bag filter that molecular cut off is 3500 and is placed in tri-distilled water dialysis 4-5 days, lyophilizing, it is thus achieved that Fluorescently-labeled carboxyl chitosan；
4) by step 3) fluorescent labeling carboxyl chitosan be dissolved in the acetum that volume fraction is 1%, obtain fluorescent labeling Carboxyl chitosan solution C；
5) preparation mass fraction is the polyphosphoric acids sodium solution of 1-40%, by polyphosphoric acids sodium solution with Solute mass ratio as 1:5 Ratio be added dropwise to solution C, be stirred vigorously 0.5-1h, centrifugal, remove supernatant, add tri-distilled water, it is thus achieved that there is aggregation inducing The carboxyl chitosan namo fluorescence probe of the characteristics of luminescence.
2. a carboxyl chitosan namo fluorescence probe with aggregation-induced emission characteristic, it is characterised in that by claim 1 Described method is prepared from.
CN201610632880.3A 2016-08-04 2016-08-04 A kind of carboxyl chitosan namo fluorescence probe and preparation method thereof with aggregation-induced emission characteristic Expired - Fee Related CN106243244B (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108559008A (en) * 2018-06-25 2018-09-21 浙江大学 A kind of n-trimethyl chitosan chloride with aggregation-induced emission characteristic/heparin composite Nano fluorescence probe and preparation method thereof
CN110426323A (en) * 2019-08-30 2019-11-08 浙江大学 A kind of chitosan slurry slurries impregnability, coating property measuring method
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
CN114316084A (en) * 2021-12-15 2022-04-12 武汉大学 AIE functionalized modified chitin material capable of being fluorescently traced, preparation method and application

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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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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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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108559008A (en) * 2018-06-25 2018-09-21 浙江大学 A kind of n-trimethyl chitosan chloride with aggregation-induced emission characteristic/heparin composite Nano fluorescence probe and preparation method thereof
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
CN110426323A (en) * 2019-08-30 2019-11-08 浙江大学 A kind of chitosan slurry slurries impregnability, coating property measuring method
CN110426323B (en) * 2019-08-30 2020-10-20 浙江大学 Method for measuring permeability and coverage of chitosan slurry
CN114316084A (en) * 2021-12-15 2022-04-12 武汉大学 AIE functionalized modified chitin material capable of being fluorescently traced, preparation method and application
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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