CN102830104A - Method of preparing microcapsule pH (Potential Of Hydrogen) sensor - Google Patents
Method of preparing microcapsule pH (Potential Of Hydrogen) sensor Download PDFInfo
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- CN102830104A CN102830104A CN2012103113290A CN201210311329A CN102830104A CN 102830104 A CN102830104 A CN 102830104A CN 2012103113290 A CN2012103113290 A CN 2012103113290A CN 201210311329 A CN201210311329 A CN 201210311329A CN 102830104 A CN102830104 A CN 102830104A
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- polyelectrolyte
- caco
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Abstract
The invention discloses a method of preparing a microcapsule pH (Potential of Hydrogen) sensor. The method comprises the following steps of: reacting calcium-containing inorganic salt and carbonate-containing inorganic salt to prepare porous calcium carbonate colloid microparticles in the presence of a polyelectrolyte with an amino group in a side chain; dispersing the porous calcium carbonate colloid microparticles in buffer solution of an isothiocyanate group-containing pH sensitive fluorescent dye and a pH inertial fluorescent dye serving as a reference; after oscillating or magnetically stirring for a period of time, marking dye molecules on the polyelectrolyte; after centrifugally cleaning, alternately adsorbing the polyelectrolyte with reverse charge to the colloid particles; and then removing calcium carbonate microparticles through complexation through ethylene diamine tetraacetic acid to obtain hollow microcapsules. The preparation method has the advantages of easiness, convenience, quickness, wide material source and high production efficiency; and since the obtained microcapsules are simultaneously marked with the pH sensitive fluorescent dye and the pH inertial fluorescent dye serving as the reference, the method has the characteristic of producing response to pH of a local environment and has good application prospect.
Description
Technical field
The present invention relates to a kind of method for preparing microcapsules pH sensor.Especially utilize the luminescent dye molecule covalent labeling to realize the method for pH sensing to the internal layer cyst wall.
Background technology
H
+The vital movement of ion pair biosome plays important regulation, and the generation of some biological phenomenas often is accompanied by H in the cell
+The variation of ion concentration is like the cell death of cell differentiation and sequencing.Therefore the measurement of pH has very important significance to the explanation of life mechanism and the prediction of disease pathology on the unicellular level.
Microcapsules are through film forming matter the space in the capsule and the capsule external space to be kept apart to form the material of particular geometric configuration.The preparation method of microcapsules is a lot, wherein, is template with colloidal particles, utilizes layer-by-layer on the template particulate, to assemble polymer ultra-thin film, removes that the microcapsules that prepare after the template have structure and performance is controlled, is prone to give characteristics such as various unique functions.The shape of microcapsules is main with spherical structure, also can be oval, square or rectangular, polygon and various irregularly shaped.Microcapsules all have crucial application in food, medicine, cosmetics, bioengineering and organizational project.
Microcapsules have many good qualities as the pH sensor: because the cyst wall of microcapsules has semi-permeable diaphragm character, and micromolecular analyte can freely see through, macromolecular substances (like protein) then can not see through on the one hand; Therefore can protect dye molecule, avoiding intracellular albumen to adhere to influences its fluorescence property, also can reduce the murder by poisoning of dye molecule pair cell simultaneously.On the other hand; The fluorescent dye of pH fluorescent dye sensitive and pH inertia can be embedded into microcapsules inside or covalent labeling simultaneously to cyst wall; Thereby realize the ratio fluorescent measurement, avoid some uncertain factors (unevenness of fluorescent dye embedding and mark, the uncertainty of fluorescent dye concentration in the experiment; The fluctuation of excitation source) influence makes measurement more accurate.
The preparation method of common microcapsules pH sensor at first is embedded into the glucosan of luminescent dye molecule mark in the template particulate, and behind its surface-assembled multilayer film, removes template, is embedded in microcapsules inside thereby will singly plant the responsive dye molecule of pH.But there is expensive raw materials in this preparation method, the shortcoming that utilization ratio is low and pH dynamic test scope is narrower, these drawbacks limit its promotion and application.
Summary of the invention
The purpose of this invention is to provide a kind of method of utilizing the direct mark of luminescent dye molecule to prepare microcapsules pH sensor to the internal layer cyst wall simply and rapidly.
The method for preparing microcapsules pH sensor of the present invention may further comprise the steps:
1) in concentration is the Ca (NO of 0.33M
3)
2Add side chain in the WS and have amino polyelectrolyte, the concentration of polyelectrolyte is 2mg/mL, stirs it is mixed; Stir the Na that adds 0.33M down again
2CO
3The WS, Na
2CO
3The WS and Ca (NO
3)
2The volume ratio of the WS is 1:1, continues to stir 45～60s, and standing and reacting is collected the gained particulate then, washs, and obtains being doped with the CaCO of amino polyelectrolyte
3Colloidal particles, freeze-drying;
2) get the CaCO of 50mg step 1) gained
3Colloidal particles are dispersed in the NaHCO of pH 9.4
3/ Na
2CO
3In the damping fluid, add the pH fluorescent dye sensitive and as the fluorescent dye of the pH inertia of reference; Stir, centrifugal washing obtains being doped with the CaCO of fluorescence labeling polyelectrolyte
3Colloidal particles;
3) in the NaCl of 0.5M solution, be electronegative polyelectrolyte and the step 2 of 0.2～10mg/mL with concentration) CaCO that obtains
3After colloidal particles mixed 10～15min, the water cyclic washing was removed the not electronegative polyelectrolyte of absorption, obtains the CaCO that skin is coated with electronegative polyelectrolyte
3Colloidal particles;
4) in the NaCl of 0.5M solution, with concentration polyelectrolyte and the CaCO of step 3) of the positively charged of 0.2～10mg/mL
3After colloidal particles mixed 10～15min, the water cyclic washing was removed the not polyelectrolyte of the positively charged of absorption, obtains the CaCO that skin is coated with the polyelectrolyte of positively charged
3Colloidal particles;
5) repeating step 3 alternately) and 4), obtain being assembled with the CaCO of polyelectrolyte multilayer film
3Colloidal particles;
6) with the CaCO of step 5) gained
3Colloidal particles are distributed in the sodium ethylene diamine tetracetate solution of pH=7,0.2M, remove CaCO
3Colloidal particles obtain microcapsules pH sensor.
Among the present invention, it is PAH hydrochloride (PAH), polylysine (PLL) or polyethyleneimine (PEI) that described side chain has amino polyelectrolyte; Described pH fluorescent dye sensitive is a kind of among fluorescein isothiocynate (FITC) and isothiocyanic acid Oregon green (OGITC) or two kinds; The fluorescent dye of pH inertia is an isothiocyanic acid tetramethyl rhodamine (RITC); Described electronegative polyelectrolyte is kayexalate (PSS) or dextran sulfate acid sodium (DS); The polyelectrolyte of described positively charged is PAH hydrochloride (PAH) or chitosan hydrochloride (CS).
Principle of the present invention is: the fluorescent dye that in the damping fluid of the lime carbonate colloidal particles of the amino polyelectrolyte that mixes, adds the band isothiocyanate group; Reaction through amino and isothiocyanate group with the fluorescent dye of pH fluorescent dye sensitive and pH inertia with tense marker to the amino polyelectrolyte that is entrained in the calcium carbonate microparticle; Assemble polyelectrolyte multilayer film through electrostatic interaction at microparticle surfaces then; Use ethylenediamine tetraacetic acid (EDTA) complexing to remove calcium carbonate microparticle again; In this process, the inner fluorescently-labeled polyelectrolyte of lime carbonate discharges and combines with the electronegative polyelectrolyte of microparticle surfaces absorption immediately or be embedded in microcapsules inside.PH fluorescent dye sensitive and give microcapsules pH sensing capabilities as the fluorescent dye of the pH inertia of reference can accurately reflect the pH of surrounding environment.
Beneficial effect of the present invention is:
Technological process of the present invention is simple, and preparation speed is fast, and controllability is good, and material source is extensive, is suitable for a large amount of preparations of microcapsules; Utilization has the polyelectrolyte reaction in-situ that mixes in dye molecule and the template particulate of reactive group; The ratio of conservation and different fluorescence molecules can be through rate of charge control; The microcapsules that obtain since with tense marker the fluorescent dye of pH fluorescent dye sensitive and pH inertia, have the pH sensing capabilities.Wherein two kinds of pH sensitive dyes are measured the pH value with the microcapsules pH sensor of tense marker through the ratio fluorescent method, and accuracy rate is higher, has wider linear pH responding range.
Description of drawings
The CaCO that Fig. 1 a) mixes for PAH
3The stereoscan photograph of particulate, the CaCO that b) mixes for PAH
3Stereoscan photograph after amplify the part of particulate.
Fig. 2 be doping PAH the calcium carbonate microparticle mark FITC, OGITC and RITC ternary fluorescent dye are also removed the microcapsules (PAH-FITC-OGITC-RITC-(PSS/PAH) that lime carbonate obtains after skin has been assembled 3.5 PSS/PAH bilayers
3PSS, below abbreviation expression identical meanings) dried stereoscan photograph.
Fig. 3 is PAH-FITC-OGITC-RITC-(PSS/PAH) a)
3The fluorescent microscope photo of PSS microcapsules (FITC passage) b) is PAH-FITC-OGITC-RITC-(PSS/PAH)
3The fluorescent microscope photo of PSS microcapsules (RITC passage), microcapsules are scattered in the water.
Fig. 4 is PAH-FITC-RITC-(PSS/PAH) a)
3The fluorescent microscope photo of PSS microcapsules (FITC passage) b) is PAH-FITC-RITC-(PSS/PAH)
3The fluorescent microscope photo of PSS microcapsules (RITC passage), microcapsules are scattered in the water.
Fig. 5 is PAH-OGITC-RITC-(PSS/PAH) a)
3The fluorescent microscope photo of PSS microcapsules (OGITC passage) b) is PAH-OGITC-RITC-(PSS/PAH)
3The fluorescent microscope photo of PSS microcapsules (RITC passage), microcapsules are scattered in the water.
Fig. 6 is PAH-FITC-OGITC-RITC-(PSS/PAH) a)
3The fluorescence spectrum figure of PSS microcapsules in different pH buffer b) is PAH-FITC-RITC-(PSS/PAH)
3The fluorescence spectrum figure of PSS microcapsules in different pH buffer c) is PAH-OGITC-RITC-(PSS/PAH)
3The fluorescence spectrum figure of PSS microcapsules in different pH buffer.
Fig. 7 is PAH-FITC-OGITC-RITC-(PSS/PAH)
3PSS, PAH-FITC-RITC-(PSS/
PAH)
3PSS, PAH-OGITC-RITC-(PSS/PAH)
3The pH calibration curve of PSS microcapsules in different pH buffer.
Fig. 8 is PAH-FITC-OGITC-RITC-(DS/CS) a)
3The fluorescent microscope photo of DS microcapsules (FITC passage) b) is PAH-FITC-OGITC-RITC-(DS/CS)
3The fluorescent microscope photo of DS microcapsules (RITC passage), microcapsules are scattered in the damping fluid of pH 5.0.
Fig. 9 is PAH-FITC-OGITC-RITC-(DS/CS)
3The fluorescence spectrum figure of DS microcapsules in different pH buffer.
Figure 10 is PAH-FITC-OGITC-RITC-(DS/CS)
3The pH calibration curve of DS microcapsules in different pH buffer.
Embodiment
Further specify the present invention below in conjunction with instance, but these instances are not used for limiting the present invention.
1) with NaCO
3And Ca (NO
3)
2Be made into the WS of 0.33M respectively; Get 20mL Ca (NO
3)
2Solution adds 40mg PAH, stirs it is mixed; Under mechanical raking rapidly to wherein adding 20mL NaCO
3Solution continue to stir 1 minute, let its standing and reacting then, precipitated fully until all particulates that generate; With the centrifugal collection of gained particulate, wash 3 times, obtain the CaCO that diameter is about the 4-6 micron
3Colloidal particles, freeze-drying.Its stereoscan photograph is seen Fig. 1;
2) get step 1) gained CaCO
3Colloidal particles 50mg places the centrifuge tube of 50mL, adds the NaHCO of 30mL pH=9.4
3/ Na
2CO
3Damping fluid adds 65 μ L FITC (1mg/mL), 71 μ L OGITC (1mg/mL), and 178 μ L RITC (1mg/mL) place centrifuge tube on the oscillator then, and concussion is spent the night; With particulate for several times, remove unreacted fluorescent dye, obtain being doped with the CaCO of PAH-FITC-OGITC-RITC with the pure water washing
3Colloidal particles;
3) with step 2) CaCO that is doped with PAH-FITC-OGITC-RITC of gained
3Colloidal particles are distributed in the 6mL water, add 3mL PSS (6mg/mL is among the 0.5M NaCl), hatch 10 minutes, wash 3 times; Particulate is distributed in the 6mL water again, adds 3mL PAH (6mg/mL is among the 0.5M NaCl), hatched 10 minutes, wash three times, repeat above process and obtain CaCO
3(PAH-FITC-OGITC-RITC)-
(PSS/PAH)
3The colloidal particles of PSS structure;
4) colloidal particles with the step 3) gained are distributed in the EDTA solution of a large amount of pH=7,0.2M, react 30 minutes, remove CaCO
3Colloidal particles are washed with massive laundering then; Dried PAH-FITC-OGITC-RITC-(PSS/PAH)
3The stereoscan photograph of PSS microcapsules pH sensor is seen Fig. 2; The fluorescent microscope photo of the microcapsules pH sensor that disperses in the water is seen Fig. 3.The fluorescence spectrum figure of this microcapsules pH sensor in the buffer solution of different pH values sees Fig. 6 a; PH value calibration curve according to the ratio calculation of 530nm place in the fluorogram and 590nm place fluorescence intensity obtains is seen Fig. 7.
Step is with instance 1, but in step 2) in add 65 μ L FITC (1mg/mL), 89 μ L RITC (1mg/mL), the fluorescent microscope photo of the microcapsules pH sensor that obtains after the stoning is seen Fig. 4.The fluorescence spectrum figure of this microcapsules pH sensor in the buffer solution of different pH values sees Fig. 6 b; PH value calibration curve according to the ratio calculation of 530nm place in the fluorogram and 590nm place fluorescence intensity obtains is seen Fig. 7.
Step is with instance 1, but in step 2) in add 71 μ L OGITC (1mg/mL), 89 μ L RITC (1mg/mL), the fluorescent microscope photo of the microcapsules pH sensor that obtains after the stoning is seen Fig. 5.The fluorescence spectrum figure of this microcapsules pH sensor in the buffer solution of different pH values sees Fig. 6 c; PH value calibration curve according to the ratio calculation of 530nm place in the fluorogram and 590nm place fluorescence intensity obtains is seen Fig. 7.
Embodiment 4
Step is with instance 1, but in step 2) in add 48 μ L FITC (0.68mg/mL), 36 μ L OGITC (1mg/mL); 126 μ L RITC (0.68mg/mL) in the step 3), are dispersed in colloidal particles in the 5mL water; Add 5mL DS (1mg/mL; 0.5M among the NaCl), hatched 10 minutes, wash 3 times; Particulate is distributed in the 5mL water again, adds 5mL CS (1mg/mL is among the 0.5M NaCl), hatched 10 minutes, wash three times, repeat above process and obtain CaCO
3(PAH-FITC-OGITC-RITC)-(DS/CS)
3The particulate of DS structure; The fluorescent microscope photo of the microcapsules pH sensor that obtains after the stoning is seen Fig. 8.The fluorescence spectrum figure of this microcapsules pH sensor in different pH buffer sees Fig. 9; PH value calibration curve according to the ratio calculation of 526nm place in the fluorogram and 587nm place fluorescence intensity obtains is seen Figure 10.
Step is with instance 4, but in step 2) in add 48 μ L FITC (0.68mg/mL), 126 μ L RITC (0.68mg/mL) finally obtain PAH-FITC-RITC-(DS/CS)
3DS microcapsules pH sensor.
Embodiment 6
Step is with instance 4, but in step 2) in add 36 μ L OGITC (1mg/mL), 126 μ L RITC (0.68mg/mL) finally obtain PAH-OGITC-RITC-(DS/CS)
3DS microcapsules pH sensor.
Claims (5)
1. method for preparing microcapsules pH sensor may further comprise the steps:
1) in concentration is the Ca (NO of 0.33M
3)
2Add side chain in the WS and have amino polyelectrolyte, the concentration of polyelectrolyte is 2mg/mL, stirs it is mixed; Stir the Na that adds 0.33M down again
2CO
3The WS, Na
2CO
3The WS and Ca (NO
3)
2The volume ratio of the WS is 1:1, continues to stir 45～60s, and standing and reacting is collected the gained particulate then, washs, and obtains being doped with the CaCO of amino polyelectrolyte
3Colloidal particles, freeze-drying;
2) get the CaCO of 50mg step 1) gained
3Colloidal particles are dispersed in the NaHCO of pH 9.4
3/ Na
2CO
3In the damping fluid, add the pH fluorescent dye sensitive and as the fluorescent dye of the pH inertia of reference; Stir, centrifugal washing obtains being doped with the CaCO of fluorescence labeling polyelectrolyte
3Colloidal particles;
3) in the NaCl of 0.5M solution, be electronegative polyelectrolyte and the step 2 of 0.2～10mg/mL with concentration) CaCO that obtains
3After colloidal particles mixed 10～15min, the water cyclic washing was removed the not electronegative polyelectrolyte of absorption, obtains the CaCO that skin is coated with electronegative polyelectrolyte
3Colloidal particles;
4) in the NaCl of 0.5M solution, with concentration polyelectrolyte and the CaCO of step 3) of the positively charged of 0.2～10mg/mL
3After colloidal particles mixed 10～15min, the water cyclic washing was removed the not polyelectrolyte of the positively charged of absorption, obtains the CaCO that skin is coated with the polyelectrolyte of positively charged
3Colloidal particles;
5) repeating step 3 alternately) and 4), obtain being assembled with the CaCO of polyelectrolyte multilayer film
3Colloidal particles;
6) with the CaCO of step 5) gained
3Colloidal particles are distributed in the sodium ethylene diamine tetracetate solution of pH=7,0.2M, remove CaCO
3Colloidal particles obtain microcapsules pH sensor.
2. the method for preparing microcapsules pH sensor according to claim 1 is characterized in that it is PAH hydrochloride, polylysine or polyethyleneimine that described side chain has amino polyelectrolyte.
3. the method for preparing microcapsules pH sensor according to claim 1 is characterized in that described pH fluorescent dye sensitive is a kind of in green of fluorescein isothiocynate and isothiocyanic acid Oregon or two kinds; The fluorescent dye of said pH inertia is an isothiocyanic acid tetramethyl rhodamine.
4. the method for preparing microcapsules pH sensor according to claim 1 is characterized in that said electronegative polyelectrolyte is kayexalate or dextran sulfate acid sodium.
5. the method for preparing microcapsules pH sensor according to claim 1, the polyelectrolyte that it is characterized in that said positively charged are PAH hydrochloride or chitosan hydrochloride.
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Cited By (8)
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|---|---|---|---|---|
| CN103487420A (en) * | 2013-09-29 | 2014-01-01 | 浙江大学 | Method for preparing microcapsule pH sensor |
| CN103543150A (en) * | 2013-09-03 | 2014-01-29 | 郑州大学 | Gel-based pH sensor preparation method thereof |
| CN104001484A (en) * | 2014-05-26 | 2014-08-27 | 齐鲁工业大学 | Preparation method of pH responsiveness polyphenol amine microcapsules |
| CN104001484B (en) * | 2014-05-26 | 2016-11-30 | 齐鲁工业大学 | A kind of preparation method of pH response poly-phenol amine microcapsule |
| CN108866036A (en) * | 2018-07-24 | 2018-11-23 | 浙江大学 | A kind of cascade enzyme reaction microballoon and preparation method thereof with antibacterial functions |
| WO2019033594A1 (en) * | 2017-08-16 | 2019-02-21 | 西安电子科技大学 | Ph-responsive ultrasensitive fluorescent nanoprobe and preparation method therefor |
| CN114062334A (en) * | 2021-10-25 | 2022-02-18 | 中国科学技术大学 | Fluorescent probe for measuring oxygen and hydrogen ions, preparation method and application |
| CN115322982A (en) * | 2022-08-15 | 2022-11-11 | 北京工商大学 | Preparation method and application of cell-loaded microcapsule |
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| CN103543150A (en) * | 2013-09-03 | 2014-01-29 | 郑州大学 | Gel-based pH sensor preparation method thereof |
| CN103543150B (en) * | 2013-09-03 | 2015-11-04 | 郑州大学 | A kind of gel base pH sensor and preparation method thereof |
| CN103487420A (en) * | 2013-09-29 | 2014-01-01 | 浙江大学 | Method for preparing microcapsule pH sensor |
| CN103487420B (en) * | 2013-09-29 | 2015-08-12 | 浙江大学 | A kind of method preparing microcapsule pH sensor |
| CN104001484A (en) * | 2014-05-26 | 2014-08-27 | 齐鲁工业大学 | Preparation method of pH responsiveness polyphenol amine microcapsules |
| CN104001484B (en) * | 2014-05-26 | 2016-11-30 | 齐鲁工业大学 | A kind of preparation method of pH response poly-phenol amine microcapsule |
| US11291736B2 (en) | 2017-08-16 | 2022-04-05 | Xidian University | pH-responsive ultrasensitive fluorescent nanoprobe, preparation and using method thereof |
| WO2019033594A1 (en) * | 2017-08-16 | 2019-02-21 | 西安电子科技大学 | Ph-responsive ultrasensitive fluorescent nanoprobe and preparation method therefor |
| CN108866036A (en) * | 2018-07-24 | 2018-11-23 | 浙江大学 | A kind of cascade enzyme reaction microballoon and preparation method thereof with antibacterial functions |
| CN114062334A (en) * | 2021-10-25 | 2022-02-18 | 中国科学技术大学 | Fluorescent probe for measuring oxygen and hydrogen ions, preparation method and application |
| CN114062334B (en) * | 2021-10-25 | 2023-10-27 | 中国科学技术大学 | Fluorescent probe for measuring oxygen and hydrogen ions, preparation method and application |
| CN115322982A (en) * | 2022-08-15 | 2022-11-11 | 北京工商大学 | Preparation method and application of cell-loaded microcapsule |
| CN115322982B (en) * | 2022-08-15 | 2023-08-15 | 北京工商大学 | Preparation method and application of cell-loaded microcapsule |
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Application publication date: 20121219 |