CN106147761A - The activation of a kind of carbon quantum dot, separation and bovine serum albumin molecule is carried out fluorescently-labeled method - Google Patents
The activation of a kind of carbon quantum dot, separation and bovine serum albumin molecule is carried out fluorescently-labeled method Download PDFInfo
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- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6439—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" with indicators, stains, dyes, tags, labels, marks
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Abstract
The invention discloses the activation of a kind of carbon quantum dot, separation and the fluorescence labeling method to bovine serum albumin molecule, belong to biological technical field.The method uses citric acid to be raw material, obtains carbon quantum dot by the method for directly pyrolysis；Again this carbon quantum dot is chemically modified, at N hydroxysuccinimide (NHS) ester that its Surface Creation is active；This NHS ester can react with the bovine serum albumin containing primary amine groups, thus realizes the fluorescent labeling to bovine serum albumin molecule.Raw material of the present invention is easy to get, inexpensively, and operation is easy, it is easy to control.Due to the avirulence of carbon quantum dot itself and anti-light Bleachability so that this have wider application prospect to the fluorescence labeling method containing primary amine groups biomolecule.
Description
Technical field
The invention belongs to biological technical field, be specifically related to the preparation method of a kind of carbon quantum dot through chemical modification, can
For to the fluorescent labeling of bovine serum albumin it can also be used to for the fluorescent labeling of other biomolecule containing primary amine groups.
Background technology
Fluorescence labeling method refers to the group or molecule with fluorescent characteristic be coupled with biomolecule by chemical reaction
Get up so that biomolecule has fluorescent characteristic, consequently facilitating people follow the tracks of the behavior of biomolecule.The most widely used is glimmering
Light group is Cy3, Cy5 etc., and they are all organic fluorescence elements, can be used for labelling biomolecule (Hagner-McWhirter.,
Laurin Y.,Larsson A.,Bjerneld E.J.,O.Cy5total protein normalization in
Western blot analysis (the total protein standardization of Cy5 labelling in western blot analysis) .Analytical
Biochemistry 2015；486:54-61.).But there is certain shortcoming, such as their anti-light bleachability very in them
Difference, it is impossible to stand the ultra-vioket radiation of long period, this (Wang L., Fan J., Qiao the most unfavorable to some research work
X.,Peng X.,Dai B.,Wang B.et al.Novel asymmetric Cy5dyes:Synthesis,
(albumen is glimmering for photostabilities and high sensitivity in protein fluorescence labeling
The synthesis of antisymmetry Cy5 dyestuff, light stability and high sensitivity novel in signal) .Journal Of
Photochemistry And Photobiology A-Chemistry2010；210:168-172.), use in this article has
In machine fluorescein 1h, light degradation is about 10%.And heavy metal quantum dot (CdS, CdSe etc.) technology that development in recent years is got up,
Also (Jiang's tea, Xu Shukun, Yang Dongzhi, etc. the preparation of, CdS quantum dot and thin to make fluorescent labeling field increase again a newcomer
After birth primary fluorescence labelling .2007.26 (5): 1-4.), but to be toxicity higher for its disadvantage, the destruction to biological tissue
Property is bigger.
Carbon quantum dot, as a kind of novel carbon nanomaterial, has significant skin effect, quantum size effect, presents
Go out a lot of novel physicochemical property, such as, can send the fluorescence of certain wavelength under the irradiation of uviol lamp.Simultaneously because it is this
Quantum dot is nontoxic, cheap, preparation is simple, environmental friendliness, becomes the focus of Recent study.At present in the research of carbon quantum dot
Majority is limited to its preparation method (Bhunia S.K., Saha A., Maity A.R., Ray S.C., Jana N.R.Carbon
(biological based on carbon nano dot becomes Nanoparticle-based Fluorescent Bioimaging Probes
As probe) .Scientific Reports2013；3:1473；Dong Y.,Shao J.,Chen C.,Li H.,Wang R.,
Chi Y.et al.Blue luminescent graphene quantum dots and graphene oxide
Prepared by tuning the carbonization degree of citric acid is (by regulating the carbon of citric acid
Change degree prepares blue-fluorescence graphene quantum dot and graphene oxide) .Carbon 2012；50:4738-4743.), and for
The report of its actual application is little, is particularly applied to the fluorescently-labeled report to biomolecule less.
Summary of the invention
For overcoming the organic fluorescence element price containing active group in prior art much more expensive and anti-light Bleachability
Can be poor, it is impossible to standing ultraviolet and irradiate for a long time, ultraviolet irradiation for a long time can make organic fluorescence element generation photodissociation,
Technical staff carry out long-time fluorescence imaging observe when, the stability of fluoroscopic image such as can not be guaranteed at the problem, this
Bright providing the activation of a kind of carbon quantum dot, separation and the fluorescence labeling method to bovine serum albumin molecule, the method is with inexpensively
Citric acid be raw material, first prepare the carbon quantum dot with fluorescent characteristic, then carry out chemical activation, separation, and finally apply
In the fluorescent labeling to bovine serum albumin.
The present invention relates to the activation of a kind of carbon quantum dot, separation and the fluorescence labeling method to bovine serum albumin molecule, tool
Body step is as follows:
(1) weigh the citric acid of 1.0～3.0g, carry out pyrolytic reaction at 180 DEG C in an oven, it is thus achieved that carbon quantum dot, produce
Thing oxolane dissolves；In the tetrahydrofuran solution of carbon quantum dot add 0.8～1.6g N-hydroxysuccinimide, 1.2
～2.0g dicyclohexylcarbodiimide and 8～25mL tetrahydrofuran solvents, controlling temperature is 55～65 DEG C, reacts under magnetic agitation
3～6h, generate the carbon quantum dot of N-hydroxysuccinimide activation；
(2) refrigerating chamber that the product of step (1) is put into refrigerator continues more than 1h, refilters removing solid, takes out
Supernatant；Supernatant is placed into freezer compartment of refrigerator, repeats the operation of last time, until solution separates out without solid；
(3) supernatant that step (2) obtains is taken out, the oxolane being distilled off in solution, add cold water, fully shake
Swing, add ethyl acetate immediately, continue fully vibration, separate ester layer；
(4) take the ester layer that 2～5mL steps (3) obtain, therein ethyl acetate solvent is evaporated off, add 12mL phosphate and delay
Dissolved liquid dissolves；Take this solution of 4mL, add the phosphate buffered solution of 6mL bovine serum albumin, react 8h at 25 DEG C, it is thus achieved that carbon
Quantum dot-labeled bovine serum albumen solution, it is achieved the fluorescent labeling of bovine serum albumin molecule.
Further, present invention can apply in other fluorescent labeling containing primary amine groups biomolecule.
Compared with prior art, the present invention has following technical effect that
1, the price of the carbon quantum dot that the present invention activates through NHS is more cheap than the existing organic fluorescence containing active group element
Much.
2, the present invention activates through NHS carbon quantum dot is anti-light Bleachability is better than organic fluorescence element.
3, the invention provides a kind of activation to carbon quantum dot, separation method, and be achieved in bovine serum albumin is divided
The fluorescent labeling of son.This method can extend to the fluorescent labeling to all biomolecule containing primary amine groups, thus has wide
General application prospect.
Accompanying drawing explanation
Fig. 1 is the carbon quantum dot transmission electron microscope picture in the present invention；As seen from the figure, the size of carbon quantum dot is about 3nm.
Fig. 2 be the photo that compares of carbon quantum dot dissolubility in ethyl acetate that carbon quantum dot and NHS modify and ester layer and
The fluorescence spectrum of water layer；Wherein: (a) is the photo of carbon quantum dot；B () is the photo of NHS modified carbon quantum dot, it is clear that the present invention
In carbon quantum dot insoluble in ethyl acetate (upper strata is ester layer), ester layer is Clear & Transparent；C () is the fluorescence spectrum of ester layer, it is clear that
The fluorescence of ester layer is the most weak, illustrates that the carbon quantum dot prepared by the present invention is insoluble in ethyl acetate；And the carbon quantum dot modified through NHS
There is in ethyl acetate good dissolubility (upper strata is ester layer), containing a large amount of carbon quantum dot in ester layer；D () is ester layer and water
The fluorescence spectrum of layer, it is clear that carbon quantum dot dissolubility in ethyl acetate that NHS modifies is good.
Fig. 3 is the infrared spectrogram of the carbon quantum dot that carbon quantum dot and NHS modify in the present invention.
Fig. 4 is that the carbon quantum dot aqueous solution that in the present invention, NHS modifies irradiates through hand-held ultraviolet lamp (8W) in cuvette
Fluorescence spectrum figure after regular hour；Wherein: the illustration peak value display fluorescence intensity in the upper right corner and the relation of irradiation time；
As seen from the figure, after uviol lamp Continuous irradiation 60min, the fluorescence intensity of the NHS modified carbon quantum dot in the present invention only declines
It is about 5%.
Fig. 5 be carbon quantum dot labelling in embodiment 1 bovine serum albumen solution gel electrophoresis images (on) and the most glimmering
Radiograph (under)；Wherein: (a) is the band of Marker, illustrate that used molecular weight of albumen is at about 66kD；(b1～b3) is
Unlabelled bovine serum albumin band, fluorescence photo shows that it does not has fluorescence；(c1～c3) is respectively addition 20,5 and 10 μ L carbon
The band of quantum dot-labeled bovine serum albumen solution；Fluorescence photo shows that they all have fluorescence, and fluorophor and albumen
It is well combined, segregation phenomenon does not occur, illustrate that they are that covalent bond couples.
Detailed description of the invention
Below in conjunction with accompanying drawing and the principles of science, the present invention is further explained.
With single citric acid as raw material, at 180 DEG C, through melting, be pyrolyzed, reacting, ultimately generate carbon quantum dot.Pyrolysis,
In course of reaction, dehydration occurring between citric acid molecule, process is as shown below:
Possible dewatering type has: de-between the dehydration between dehydration, hydroxyl and methylene hydrogen between carboxyl, hydroxyl
Water etc., intermolecular dehydration is the process of a completely random, between molecule after dehydration, it is possible to create cychc hydrocarbon, its surface
Containing the group such as hydroxyl, carboxyl, aqueous solution presents acidity, utilizes the chemism of these surface carboxyl groups, it is possible to achieve to carbon amounts
The chemical modification of son point.As shown in Figure 1, its size of transmission electron microscope image exists the X rays topographs of the carbon quantum dot generated
About 3nm, interplanar distance is 0.22nm.
Owing to a large amount of polar group is contained on carbon quantum dot surface, therefore carbon quantum dot has stronger polarity, can be complete with water
Entirely dissolve each other, oxolane also has preferable dissolubility, but dissolubility is very poor in ethyl acetate, such as accompanying drawing 2 (a) institute
Show.The carboxyl on its surface can react with N-hydroxysuccinimide (NHS) and dicyclohexylcarbodiimide (DCC):
Generate active NHS ester.Due to the structure of carbon quantum dot Surface Creation ester, then its dissolving in ethyl acetate
Degree increases, as shown in accompanying drawing 2 (b).Accompanying drawing 2 (a) is carbon quantum dot dissolving situation in ethyl acetate, and accompanying drawing 2 (b) is NHS
The carbon quantum dot that ester is modified dissolving situation in ethyl acetate.It can be seen that before modification reaction, carbon quantum dot is the most insoluble
In ethyl acetate, and after NHS modifies, its dissolubility in ethyl acetate significantly increases, and accompanying drawing 2 (c) and (d) demonstrate
The fact that.Accompanying drawing 2 (c) shows: the fluorescence of ethyl acetate layer is the most weak, sends out almost without fluorescence near 450～500nm
Penetrate；And accompanying drawing 2 (d) display: the carbon quantum dot content in ester layer modified through NHS substantially increases, and ester layer demonstrates stronger
Fluorescent emission, has stronger fluorescent emission near 450nm, but water layer still has certain fluorescence, and this explanation is not
All of carbon quantum dot all there occurs reaction with NHS.According to this character, the method utilizing extraction can be by modified outcome from instead
Answer in system and separate, it is achieved the separation of the carbon quantum dot that NHS ester is modified and purification.Its esterification can be demonstrate,proved by infrared spectrum
Bright, as shown in Figure 3.Accompanying drawing 3 (a) is the infrared spectrogram of carbon quantum dot, and carbon quantum dot is at 3449cm-1There is the last one broad peak at place,
For the hydroxyl in carboxyl and the stretching vibration peak of alcoholic extract hydroxyl group；The carbonyl (carboxycarbonyl, ketone carbonyl) of carbon quantum dot and C=C absorb
Superposition produce a wide absworption peak.Accompanying drawing 3 (b) is the infrared spectrogram of the carbon quantum dot that NHS modifies, it is clear that at 1700cm-1
Make a big difference both near, 1863 and 1732cm-1Place is the characteristic peak of NHS.
The carbon quantum dot that the obtained NHS of the present invention modifies, has good anti-light bleachability, as shown in Figure 4.At purple
Under the prolonged exposure of outer lamp, in 1h, its fluorescence intensity drops to about 5%.
Owing to the NHS ester on carbon quantum dot surface is more active, can be anti-with the molecule containing primary amine groups under conditions of extremely gentleness
Should.Such as: the carbon quantum dot that NHS modifies can be reacted with bovine serum albumin:
The NHS ester on the primary amine groups in bovine serum albumin polypeptide chain and carbon quantum dot surface reacts, and final acquisition has fluorescence
The bovine serum albumin molecule of the carbon quantum dot labelling of character.The gel electrophoresis images of accompanying drawing 5 demonstrates itself and bovine serum albumin
Reaction, gel electrophoresis experiment proves: carbon quantum dot and bovine serum albumin molecule, by being chemically bonded, illustrate between them certain
There occurs chemical reaction.From accompanying drawing 5 it can also be seen that after bovine serum albumin reacts with carbon quantum dot, its molecular weight slightly increases
Greatly (molecular weight of bovine serum albumin is 66kD)；Further, since being chemically bonded of bovine serum albumin and protein molecular so that cattle
Serum protein molecule has fluorescent characteristic.This method can extend to react with the more biomolecule Han primary amine groups, is used for
Fluorescent labeling to biomolecule.Owing to carbon quantum dot has avirulence and anti-light Bleachability so that the carbon quantum of NHS ester activation
Point has the best application prospect in biological fluorescent labelling field.
Below by way of specific embodiment, the invention will be further described.But the present invention is not limited to following embodiment.
Embodiment 1
(1) 1.0g citric acid is joined in the container of stainless steel, and shakeout, put into and baking oven is heated to 180 DEG C, hold
After continuous reaction 60min, cool down under room temperature.Add 10mL oxolane, fully dissolve more than 5h, it is thus achieved that the tetrahydrochysene furan of carbon quantum dot
Mutter solution.
(2) step (1) product will add 0.8g N-hydroxysuccinimide, 1.2g dicyclohexylcarbodiimide and 8mL
Tetrahydrofuran solvent, controlling temperature is 65 DEG C, reacts 3h under magnetic agitation.Product puts into the refrigerating chamber of refrigerator, allows unreacted
N-hydroxysuccinimide and dicyclohexylcarbodiimide separate out, and take out supernatant.Supernatant is placed into freezer compartment of refrigerator, weight
The operation of multiple last time, until separating out without solid in solution.
(3) oxolane being distilled off in solution, adds 15mL cold water, fully vibrates；Add ethyl acetate immediately
15mL, the product generated with extraction, remove unreacted carbon quantum dot simultaneously.Then N-hydroxysuccinimide modified carbon is obtained
The ethyl acetate solution of quantum dot.
(4) take the product of 5mL step (3), therein ethyl acetate solvent is evaporated off, add 12mL PBS (pH=7.4) molten
Solve.Take this solution of 4mL, add PBS solution (the 4mg mL of 6mL bovine serum albumin-1), react 8h at 25 DEG C, it is thus achieved that carbon quantum dot
The bovine serum albumen solution of labelling.
Embodiment 2
(1) 2.0g citric acid is joined in the container of stainless steel, and shakeout, put into and baking oven is heated to 180 DEG C, hold
After continuous reaction 60min, cool down under room temperature.Add 15mL oxolane, fully dissolve more than 5h, it is thus achieved that the tetrahydrochysene furan of carbon quantum dot
Mutter solution.
(2) by step (1) product add 1.2g N-hydroxysuccinimide, 1.8g dicyclohexylcarbodiimide and
15mL tetrahydrofuran solvent, controlling temperature is 60 DEG C, reacts 4h under magnetic agitation.Product puts into the refrigerating chamber of refrigerator, allows the most anti-
The N-hydroxysuccinimide answered and dicyclohexylcarbodiimide separate out, and take out supernatant.Supernatant is placed into refrigerator freezing
Room, repeats the operation of last time, until separating out without solid in solution.
(3) oxolane being distilled off in solution, adds 15mL cold water, fully vibrates；Add ethyl acetate immediately
15mL, the product generated with extraction, remove unreacted carbon quantum dot simultaneously.Then N-hydroxysuccinimide modified carbon is obtained
The ethyl acetate solution of quantum dot.
(4) take the product of 3mL step (3), therein ethyl acetate solvent is evaporated off, add 12mL PBS (pH=7.4) molten
Solve.Take this solution of 4mL, add PBS solution (the 4mg mL of 6mL bovine serum albumin-1), react 8h at 25 DEG C, it is thus achieved that carbon quantum dot
The bovine serum albumen solution of labelling.
Embodiment 3
(1) 3.0g citric acid is joined in the container of stainless steel, and shakeout, put into and baking oven is heated to 180 DEG C, hold
After continuous reaction 60min, cool down under room temperature.Add 20mL oxolane, fully dissolve more than 5h, it is thus achieved that the tetrahydrochysene furan of carbon quantum dot
Mutter solution.
(2) by step (1) product add 1.6g N-hydroxysuccinimide, 2.0g dicyclohexylcarbodiimide and
25mL tetrahydrofuran solvent, controlling temperature is 55 DEG C, reacts 6h under magnetic agitation.Product puts into the refrigerating chamber of refrigerator, allows the most anti-
The N-hydroxysuccinimide answered and dicyclohexylcarbodiimide separate out, and take out supernatant.Supernatant is placed into refrigerator freezing
Room, repeats the operation of last time, until separating out without solid in solution.
(3) oxolane being distilled off in solution, adds 15mL cold water, fully vibrates；Add ethyl acetate immediately
15mL, the product generated with extraction, remove unreacted carbon quantum dot simultaneously.Then N-hydroxysuccinimide modified carbon is obtained
The ethyl acetate solution of quantum dot.
(4) take the product of 2mL step (3), therein ethyl acetate solvent is evaporated off, add 12mL PBS (pH=7.4) molten
Solve.Take this solution of 4mL, add PBS solution (the 4mg mL of 6mL bovine serum albumin-1), react 8h at 25 DEG C, it is thus achieved that carbon quantum dot
The bovine serum albumen solution of labelling.
Claims (2)
1. the activation of a carbon quantum dot, separation and the fluorescence labeling method to bovine serum albumin molecule, it is characterised in that include
Following steps:
(1) weigh the citric acid of 1.0～3.0g, carry out pyrolytic reaction at 180 DEG C in an oven, it is thus achieved that carbon quantum dot, product is used
Oxolane dissolves；In the tetrahydrofuran solution of carbon quantum dot add 0.8～1.6g N-hydroxysuccinimide, 1.2～
2.0g dicyclohexylcarbodiimide and 8～25mL tetrahydrofuran solvents, controlling temperature is 55～65 DEG C, reacts 3 under magnetic agitation
～6h, generate the carbon quantum dot of N-hydroxysuccinimide activation；
(2) refrigerating chamber that the product of step (1) is put into refrigerator continues more than 1h, refilters removing solid, takes out supernatant
Liquid；Supernatant is placed into freezer compartment of refrigerator, repeats the operation of last time, until solution separates out without solid；
(3) supernatant that step (2) obtains is taken out, the oxolane being distilled off in solution, add cold water, fully vibrate, vertical
I.e. add ethyl acetate, continue fully vibration, separate ester layer；
(4) take the ester layer that 2～5mL steps (3) obtain, therein ethyl acetate solvent is evaporated off, add 12mL phosphate-buffered molten
Liquid dissolves；Take this solution of 4mL, add the phosphate buffered solution of 6mL bovine serum albumin, react 8h at 25 DEG C, it is thus achieved that carbon quantum
The bovine serum albumen solution of some labelling, it is achieved the fluorescent labeling of bovine serum albumin molecule.
Activation, separation and the fluorescent labeling side to bovine serum albumin molecule of a kind of carbon quantum dot the most as claimed in claim 1
Method application in other is containing primary amine groups biomolecule fluorescent labeling.
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Cited By (5)
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| CN107626258A (en) * | 2017-10-23 | 2018-01-26 | 安徽工业大学 | A kind of synthetic method of carbon quantum dot quaternary cationics |
| CN108120704A (en) * | 2017-12-11 | 2018-06-05 | 东莞理工学院 | A kind of fluorescence detection method of Acetamiprid |
| CN109046333A (en) * | 2018-06-25 | 2018-12-21 | 浙江工业大学 | A kind of non-loading type nano-scale composite carbon-noble metal catalyst and the preparation method and application thereof |
| CN109337678A (en) * | 2018-09-26 | 2019-02-15 | 东华大学 | A kind of preparation method of photochromic adjustable hydrophobic fluorescence carbon dots |
| CN111184875A (en) * | 2019-12-16 | 2020-05-22 | 中国科学院理化技术研究所 | Protein/carbon dot nano hybrid material and preparation method and application thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107626258A (en) * | 2017-10-23 | 2018-01-26 | 安徽工业大学 | A kind of synthetic method of carbon quantum dot quaternary cationics |
| CN108120704A (en) * | 2017-12-11 | 2018-06-05 | 东莞理工学院 | A kind of fluorescence detection method of Acetamiprid |
| CN109046333A (en) * | 2018-06-25 | 2018-12-21 | 浙江工业大学 | A kind of non-loading type nano-scale composite carbon-noble metal catalyst and the preparation method and application thereof |
| CN109046333B (en) * | 2018-06-25 | 2023-07-14 | 浙江工业大学 | Non-supported nano-sized composite carbon-noble metal catalyst and preparation method and application thereof |
| CN109337678A (en) * | 2018-09-26 | 2019-02-15 | 东华大学 | A kind of preparation method of photochromic adjustable hydrophobic fluorescence carbon dots |
| CN109337678B (en) * | 2018-09-26 | 2021-11-09 | 东华大学 | Preparation method of photochromic adjustable hydrophobic fluorescent carbon dots |
| CN111184875A (en) * | 2019-12-16 | 2020-05-22 | 中国科学院理化技术研究所 | Protein/carbon dot nano hybrid material and preparation method and application thereof |
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