CN104945537B - A kind of preparation method of water soluble chitosan-based aggregation-induced emission fluorescence probe - Google Patents
A kind of preparation method of water soluble chitosan-based aggregation-induced emission fluorescence probe Download PDFInfo
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- 229920001661 Chitosan Polymers 0.000 title claims abstract description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 239000000523 sample Substances 0.000 title claims abstract description 25
- 230000002776 aggregation Effects 0.000 title claims abstract description 20
- 238000004220 aggregation Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 22
- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 61
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 26
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 239000000706 filtrate Substances 0.000 claims description 21
- 238000001215 fluorescent labelling Methods 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- 239000008367 deionised water Substances 0.000 claims description 14
- 229910021641 deionized water Inorganic materials 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 14
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 13
- 238000005119 centrifugation Methods 0.000 claims description 13
- 229940014800 succinic anhydride Drugs 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 230000006196 deacetylation Effects 0.000 claims description 7
- 238000003381 deacetylation reaction Methods 0.000 claims description 7
- 238000000502 dialysis Methods 0.000 claims description 7
- 239000006228 supernatant Substances 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- 239000012895 dilution Substances 0.000 claims description 6
- 238000010790 dilution Methods 0.000 claims description 6
- 235000019441 ethanol Nutrition 0.000 claims description 6
- 125000005909 ethyl alcohol group Chemical group 0.000 claims description 6
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 claims description 6
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims 1
- 238000011068 loading method Methods 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 230000000717 retained effect Effects 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 4
- 238000001514 detection method Methods 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 238000012544 monitoring process Methods 0.000 abstract description 3
- 230000001413 cellular effect Effects 0.000 abstract description 2
- 230000036267 drug metabolism Effects 0.000 abstract description 2
- 238000002189 fluorescence spectrum Methods 0.000 abstract description 2
- 239000012046 mixed solvent Substances 0.000 abstract description 2
- 230000004048 modification Effects 0.000 abstract description 2
- 238000012986 modification Methods 0.000 abstract description 2
- 230000035945 sensitivity Effects 0.000 abstract description 2
- 230000035322 succinylation Effects 0.000 abstract description 2
- 238000010613 succinylation reaction Methods 0.000 abstract description 2
- 238000003384 imaging method Methods 0.000 abstract 1
- 230000021523 carboxylation Effects 0.000 description 5
- 238000006473 carboxylation reaction Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000010148 water-pollination Effects 0.000 description 1
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- Polysaccharides And Polysaccharide Derivatives (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
A kind of preparation method of water soluble chitosan-based aggregation-induced emission fluorescence probe disclosed by the invention, key step includes：Tetraphenylethylene fluorescence molecule is tagged to the TPE CS with AIE characteristics are obtained on chitosan chain；Using acetic acid/methanol mixed solvent system, succinylation modification is carried out to TPE CS, so that TPE N CS are made.Fluorescence probe produced by the present invention has good water solubility, and with aggregation-induced emission characteristic, high with sensitivity compared with conventional fluorescent probe, good light stability, without being quenched during high concentration, the advantages of fluorescence spectrum does not drift about, imaging effect is good.It is expected to be applied to the fields such as Cellular tracking, drug metabolism detection, environmental monitoring.
Description
Technical field
The present invention relates to a kind of preparation method of the water soluble chitosan-based fluorescence probe with aggregation-induced emission characteristic.
Background technology
Fluorescence probe is that, using fluorescent material as indicator, and it is glimmering to produce indicator under the exciting of certain wavelength light
Light, the qualitative or quantitative analysis to tested substance is realized by the fluorescence produced by detection.Currently, fluorescence probe mainly should
For fields such as biological, medical science and environmental monitorings, so water-soluble fluorescent probe is with a wide range of applications.But it is traditional
Fluorescence probe is faced with aggregation inducing and (ACQ) effect and cytotoxicity two large problems is quenched.Aggregation-induced emission（AIE）Fluorescence point
The discovery of son undoubtedly provides a kind of thinking solved the above problems.AIE effects cause fluorescence probe easy to use, and AIE
System does not have toxicity to cell, does not interfere with stechiology and cell propagation.Chitosan（CS）As a kind of rich in amino
Natural polysaccharide, it is nontoxic and be readily biodegradable with good biocompatibility and bioactivity, it is widely used in biological doctor
Field.Therefore, preparing a kind of water soluble chitosan-based fluorescent probe molecule has important scientific meaning and good application
Prospect.
The content of the invention
In view of the above-mentioned deficiencies in the prior art, it is an object of the present invention to provide a kind of water soluble chitosan-based aggregation-induced emission
The preparation method of fluorescence probe.
The method that the present invention prepares water soluble chitosan-based aggregation-induced emission fluorescence probe, comprises the following steps：
1）Using chitosan that viscosity average molecular weigh is 10,000-100 ten thousand, deacetylation 60%-95% as solute, using DMSO as solvent,
The solution that chitosan concentration is 0.1g/mL is configured, 24-48h is swelled at 50-65 DEG C, then TPEITC is added (containing different into the solution
The tetraphenylethylene derivative of thiocyanates functional group), the mol ratio of TPEITC and amino in chitosan is 1%-20%, reaction
24-48h, obtains solution A；
2）Add absolute ethyl alcohol into solution A, the volume ratio of absolute ethyl alcohol and solution A is 20, stood after stirring to
Solution is layered, and removes supernatant, after centrifugation, and precipitation volume fraction is dissolved for 2% acetum, filtrate is filtrated to get；
3）By tetrahydrofuran and deionized water with volume ratio 1:1 mixed configuration dialyzate, by step 2）Filtrate load cut
Stay and be placed in dialysing 5-7 days in dialyzate in the bag filter that molecular weight is 3500, with mass fraction in 5% NaOH after taking-up
And filtrate, centrifuge and wash lyophilized, obtain fluorescence labeling chitosan；
4）By step 3）Fluorescence labeling chitosan be dissolved in volume fraction be 2% acetum in, obtain fluorescence labeling shell
Glycan concentration is 10mg/mL solution, then adds the methanol that volume is above-mentioned 2 times of acetum volume thereto, obtains solution
B；The acetone soln of succinic anhydride is configured, and is instilled in solution B, makes succinic anhydride and amino in fluorescence labeling chitosan
Mol ratio is 1:1-3:1, stirring reaction 1-3h, obtain solution C；Solution C is fitted into the bag filter that molecular cut off is 3500
It is placed in dialysing in deionized water to solution C in neutrality, takes out the solution C after dialysis and freeze, obtains water soluble chitosan-based poly-
Collect induced luminescence fluorescence probe.
The present invention is by by tetraphenylethylene（TPE）Fluorescence molecule is tagged on chitosan chain and obtained with AIE characteristics
TPE-CS, then succinylation modification is carried out using acetic acid/methanol mixed solvent system, so that being made has aggregation-induced emission special
The water-soluble fluorescent probe molecule of property（TPE-N-CS）.The present invention product TPE-N-CS molecular formula as shown in figure 1, its1H cores
Magnetic resonance spectrogram is as shown in Figure 2.
Because the N- acylation reactions of chitosan destroy intramolecular and intermolecular hydrogen bonding, cause crystallinity to reduce, introduce carboxylic
Base improves hydrophily, therefore the product of the present invention has good water solubility, and with aggregation-induced emission characteristic, with tradition
Fluorescence probe is compared, high with sensitivity, good light stability, and without being quenched during high concentration, the advantages of fluorescence spectrum does not drift about is imaged
Effect is good.It is expected to be applied to the fields such as Cellular tracking, drug metabolism detection, environmental monitoring.
Brief description of the drawings
Fig. 1 is water soluble chitosan-based aggregation-induced emission fluorescent probe molecule structural representation.
Fig. 2 is water soluble chitosan-based aggregation-induced emission fluorescent probe molecule1H nmr spectrums.
Embodiment
The present invention is further illustrated below in conjunction with accompanying drawing and instantiation.
Embodiment 1：
1）Weigh 1g chitosans (viscosity average molecular weigh is 10,000, deacetylation 60%) to be added in eggplant-shape bottle, add 10mL
DMSO, is swelled 24h at 50 DEG C, then adds TPEITC into eggplant-shape bottle, and the mol ratio of TPEITC and amino in chitosan is 1%,
24h is reacted, solution A is obtained and is poured into 250mL beakers；
2）200mL absolute ethyl alcohols are added into solution A, are stood after stirring to solution layering, supernatant, centrifugation is removed
Afterwards, it will precipitate and dissolved with 40mL volume fractions for 2% acetum, be filtrated to get filtrate；
3）By tetrahydrofuran and deionized water with volume ratio 1:1 mixed configuration dialyzate, loads molecular cut off by filtrate
To be placed in dialysing 5 days in dialyzate in 3500 bag filter, used after taking-up in the NaOH that mass fraction is 5% and filtrate, centrifugation
And wash lyophilized, obtain fluorescence labeling chitosan TPE-CS；
4）Weigh 0.5g TPE-CS to be dissolved in the acetums of 50mL 2%, add 100mL methanol dilutions, obtain solution B；
Weigh 0.1637g succinic anhydrides to be dissolved in 5mL acetone, configure the acetone soln of succinic anhydride, and instilled in solution B, made
The mol ratio of succinic anhydride and amino in fluorescence labeling chitosan is 1:1, stirring reaction 1h, obtain solution C；Solution C is loaded
Molecular cut off takes out the solution C after dialysis, freezed to be placed in dialysing in deionized water to neutrality in 3500 bag filter,
Obtain water soluble chitosan-based aggregation-induced emission fluorescence probe.
TPE-N-CS fluorescence probes TPE mark rates made from this example are 0.83%, and carboxylation degree is 45%.
Embodiment 2：
1）Weigh 1g chitosans (viscosity average molecular weigh is 10,000, deacetylation 60%) to be added in eggplant-shape bottle, add 10mL
DMSO, is swelled 24h at 55 DEG C, then adds TPEITC into eggplant-shape bottle, and the mol ratio of TPEITC and amino in chitosan is 5%,
24h is reacted, solution A is obtained and is poured into 250mL beakers；
2）200mL absolute ethyl alcohols are added into solution A, are stood after stirring to solution layering, supernatant, centrifugation is removed
Afterwards, it will precipitate and dissolved with 40mL volume fractions for 2% acetum, be filtrated to get filtrate；
3）By tetrahydrofuran and deionized water with volume ratio 1:1 mixed configuration dialyzate, loads molecular cut off by filtrate
To be placed in dialysing 5 days in dialyzate in 3500 bag filter, used after taking-up in the NaOH that mass fraction is 5% and filtrate, centrifugation
And wash lyophilized, obtain fluorescence labeling chitosan TPE-CS；
4）Weigh 0.5g TPE-CS to be dissolved in the acetums of 50mL 2%, add 100mL methanol dilutions, obtain solution B；
Weigh 0.1583g succinic anhydrides to be dissolved in 5mL acetone, configure the acetone soln of succinic anhydride, and instilled in solution B, made
The mol ratio of succinic anhydride and amino in fluorescence labeling chitosan is 1:1, stirring reaction 1h, obtain solution C；Solution C is loaded
Molecular cut off takes out the solution C after dialysis, freezed to be placed in dialysing in deionized water to neutrality in 3500 bag filter,
Obtain water soluble chitosan-based aggregation-induced emission fluorescence probe.
TPE-N-CS fluorescence probes TPE mark rates made from this example are 1.71%, and carboxylation degree is 46.6%.
Embodiment 3：
1）Weigh 1g chitosans (viscosity average molecular weigh is 100,000, deacetylation 80%) to be added in eggplant-shape bottle, add 10mL
DMSO, is swelled 36h at 55 DEG C, TPEITC is then added into eggplant-shape bottle, TPEITC and amino in chitosan mol ratio are
10%, 24h is reacted, solution A is obtained and is poured into 250mL beakers；
2）200mL absolute ethyl alcohols are added into solution A, are stood after stirring to solution layering, supernatant, centrifugation is removed
Afterwards, it will precipitate and dissolved with 40mL volume fractions for 2% acetum, be filtrated to get filtrate；
3）By tetrahydrofuran and deionized water with volume ratio 1:1 mixed configuration dialyzate, loads molecular cut off by filtrate
To be placed in dialysing 6 days in dialyzate in 3500 bag filter, used after taking-up in the NaOH that mass fraction is 5% and filtrate, centrifugation
And wash lyophilized, obtain fluorescence labeling chitosan TPE-CS；
4）Weigh 0.5g TPE-CS to be dissolved in the acetums of 50mL 2%, add 100mL methanol dilutions, obtain solution B；
Weigh 0.3224g succinic anhydrides to be dissolved in 5mL acetone, configure the acetone soln of succinic anhydride, and instilled in solution B, made
The mol ratio of succinic anhydride and amino in fluorescence labeling chitosan is 1.5:1, stirring reaction 2h, obtain solution C；Solution C is filled
Enter and be placed in dialysing in deionized water to neutrality in the bag filter that molecular cut off is 3500, take out the solution C after dialysis, freeze
It is dry, obtain water soluble chitosan-based aggregation-induced emission fluorescence probe.
TPE-N-CS fluorescence probes TPE mark rates made from this example are 2.77%, and carboxylation degree is 62.3%.
Embodiment 4：
1）Weigh 1g chitosans (viscosity average molecular weigh is 100,000, deacetylation 85%) to be added in eggplant-shape bottle, add 10mL
DMSO, is swelled 36h at 60 DEG C, TPEITC is then added into eggplant-shape bottle, TPEITC and amino in chitosan mol ratio are
15%, 36h is reacted, solution A is obtained and is poured into 250mL beakers；
2）200mL absolute ethyl alcohols are added into solution A, are stood after stirring to solution layering, supernatant, centrifugation is removed
Afterwards, it will precipitate and dissolved with 40mL volume fractions for 2% acetum, be filtrated to get filtrate；
3）By tetrahydrofuran and deionized water with volume ratio 1:1 mixed configuration dialyzate, loads molecular cut off by filtrate
To be placed in dialysing 6 days in dialyzate in 3500 bag filter, used after taking-up in the NaOH that mass fraction is 5% and filtrate, centrifugation
And wash lyophilized, obtain fluorescence labeling chitosan TPE-CS；
4）Weigh 0.5g TPE-CS to be dissolved in the acetums of 50mL 2%, add 100mL methanol dilutions, obtain solution B；
Weigh 0.4548g succinic anhydrides to be dissolved in 5mL acetone, configure the acetone soln of succinic anhydride, and instilled in solution B, made
The mol ratio of succinic anhydride and amino in fluorescence labeling chitosan is 2:1, stirring reaction 3h, obtain solution C；Solution C is loaded
Molecular cut off takes out the solution C after dialysis, freezed to be placed in dialysing in deionized water to neutrality in 3500 bag filter,
Obtain water soluble chitosan-based aggregation-induced emission fluorescence probe.
TPE-N-CS fluorescence probes TPE mark rates made from this example are 4.92%, and carboxylation degree is 73.7%.
Embodiment 5：
1）Weigh 1g chitosans (viscosity average molecular weigh is 1,000,000, deacetylation 95%) to be added in eggplant-shape bottle, add 10mL
DMSO, is swelled 48h at 65 DEG C, TPEITC is then added into eggplant-shape bottle, TPEITC and amino in chitosan mol ratio are
20%, 48h is reacted, solution A is obtained and is poured into 250mL beakers；
2）200mL absolute ethyl alcohols are added into solution A, are stood after stirring to solution layering, supernatant, centrifugation is removed
Afterwards, it will precipitate and dissolved with 40mL volume fractions for 2% acetum, be filtrated to get filtrate；
3）By tetrahydrofuran and deionized water with volume ratio 1:1 mixed configuration dialyzate, loads molecular cut off by filtrate
To be placed in dialysing 7 days in dialyzate in 3500 bag filter, used after taking-up in the NaOH that mass fraction is 5% and filtrate, centrifugation
And wash lyophilized, obtain fluorescence labeling chitosan TPE-CS；
4）Weigh 0.5g TPE-CS to be dissolved in the acetums of 50mL 2%, add 100mL methanol dilutions, obtain solution B；
Weigh 0.6795g succinic anhydrides to be dissolved in 10mL acetone, configure the acetone soln of succinic anhydride, and instilled in solution B,
The mol ratio for making succinic anhydride and amino in fluorescence labeling chitosan is 3:1, stirring reaction 3h, obtain solution C；Solution C is filled
Enter and be placed in dialysing in deionized water to neutrality in the bag filter that molecular cut off is 3500, take out the solution C after dialysis, freeze
It is dry, obtain water soluble chitosan-based aggregation-induced emission fluorescence probe.
TPE-N-CS fluorescence probes TPE mark rates made from this example are 7.86%, and carboxylation degree is 81%.
Claims (1)
1. a kind of preparation method of water soluble chitosan-based aggregation-induced emission fluorescence probe, it is characterised in that including following step
Suddenly：
1）It is 1,000,000 to weigh 1g viscosity average molecular weighs, and the chitosan of deacetylation 95% is added in eggplant-shape bottle, adds 10mL
DMSO, is swelled 48h at 65 DEG C, the tetraphenylethylene derivative containing isothiocyanate functionality is then added into eggplant-shape bottle
The ratio of the mol ratio of amino is 20% in TPEITC, TPEITC and chitosan, reacts 48h, obtains solution A and is simultaneously poured into
In 250mL beakers；
2）200mL absolute ethyl alcohols are added into solution A, is stood after stirring to solution layering, removes supernatant, after centrifugation,
Dissolved precipitating with 40mL volume fractions for 2% acetum, be filtrated to get filtrate；
3）By tetrahydrofuran and deionized water with volume ratio 1:1 mixed configuration dialyzate, be by filtrate loading molecular cut off
It is placed in dialysing 7 days in dialyzate in 3500 bag filter, is used after taking-up in the NaOH that mass fraction is 5% and filtrate, centrifugation is simultaneously
Washing is lyophilized, obtains fluorescence labeling chitosan TPE-CS；
4）Weigh 0.5g TPE-CS to be dissolved in the acetums of 50mL 2%, add 100mL methanol dilutions, obtain solution B；Weigh
0.6795g succinic anhydrides are dissolved in 10mL acetone, configure the acetone soln of succinic anhydride, and are instilled in solution B, make fourth two
The mol ratio of acid anhydrides and amino in fluorescence labeling chitosan is 3:1, stirring reaction 3h, obtain solution C；Solution C is loaded and retained
Molecular weight takes out the solution C after dialysis, freezed, obtain to be placed in dialysing in deionized water to neutrality in 3500 bag filter
Water soluble chitosan-based aggregation-induced emission fluorescence probe.
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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 |
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| CN103483469A (en) * | 2013-09-26 | 2014-01-01 | 上海大学 | Preparation method for water-soluble chitosan |
| CN103788230B (en) * | 2014-01-20 | 2015-12-09 | 浙江大学 | With the method for cyclic acid anhydride beautify chitosan and the application in ammonia absorbs thereof |
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| CN110426323B (en) * | 2019-08-30 | 2020-10-20 | 浙江大学 | Method for measuring permeability and coverage of chitosan slurry |
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