CN110437821A - A kind of preparation method and products thereof targeting green fluorescence carbon quantum dot and application - Google Patents
A kind of preparation method and products thereof targeting green fluorescence carbon quantum dot and application Download PDFInfo
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- CN110437821A CN110437821A CN201910767212.5A CN201910767212A CN110437821A CN 110437821 A CN110437821 A CN 110437821A CN 201910767212 A CN201910767212 A CN 201910767212A CN 110437821 A CN110437821 A CN 110437821A
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Abstract
The present invention provides preparation method of a kind of targeting green fluorescence carbon quantum dot and products thereof and application, the preparation method of the green fluorescence carbon quantum dot including carbon quantum dot synthesis and target peptide modification.The carbon quantum dot can be used for bio-imaging, detection and radiography tracer etc.；This carbon quantum dot preparation condition and environmental requirement are very friendly, can synthesize in common laboratory, and preparation flow is simple, yield is high, toxicity is low, fluorescence intensity and form stable, the raw material sources of use are in extensive citric acid as carbon source, price is just declared, strong operability, is suitable for mass production.
Description
Technical field
The present invention relates to field of nano-luminescent material more particularly to carbon quantum dot, specifically a kind of green fluorescence carbon quantum
Preparation method of point and products thereof and application.
Background technique
Since 2004, the Xu of South Carolina, USA university et al. had found that the carbon quantum of bright fluorescence can be issued for the first time
Since point.Carbon quantum dot is just used as a kind of nano material of novel luminescence generated by light by the concern of numerous researchers.Carbon quantum
Point is the fluorescent nano material that carbonaceous skeleton and surface group with partial size less than 10 nanometers are constituted, and it can divide well
It dissipates in water or other solvents.Compared to some traditional organic dyestuff and quantum dot, carbon quantum dot has good biofacies
Capacitive, photostability, hypotoxicity.Furthermore its preparation process is simple, conditions environmental require be not it is very harsh, raw material is also very low
It is honest and clean.Based on above advantage, carbon quantum dot is gradually applied to many fields, such as bio-imaging, pharmaceutical carrier, biology and change
/ bio-sensing, catalyst, opto-electronic device etc..
Already present cell marking probe mainly still concentrates on 400-900nm wave band, but much fluorescence currently on the market
Probe leads to that its light quantum intensity is lower and lifetime of excited state is very short since constant is quenched with very high, and fluorescence is easily quenched,
The long-term observation being unfavorable for during cell research；Also some fluorescence probes are since its excitation wavelength is in ultraviolet region, excitation
Energy is also higher to be caused to irradiate the progress for causing biggish damage to cell, and being unfavorable for research for a long time.In addition, in tumour
Therapy field, many researchers are all dedicated to research high performance material will be normal using tumor tissue specificity as tracer
Tissue is accurately distinguished out with tumor tissues by fluorescence intensity, prognosis and the appropriate therapeutic scheme of selection is determined, to improve subsequent
The effect of oncotherapy has highly important clinical value.
Summary of the invention
It is easily quenched for existing cell fluorescence label probe, is big to cellular damage and targeted molecular can not be modified to tracer
The deficiencies of cell, the purpose of the present invention is to provide a kind of preparation methods for targeting green fluorescence carbon quantum dot.
Another object of the present invention is: providing a kind of targeting green fluorescence carbon quantum dot product of above method preparation.
Another object of the present invention is to: a kind of application of the said goods is provided.
The object of the invention is realized by following proposal: a kind of preparation method targeting green fluorescence carbon quantum dot, including such as
Lower step:
(1) carbon quantum dot synthesizes:
At room temperature, first citric acid and ethylenediamine are mixed, is re-dissolved in formamide, molar ratio is that 1:5:32 solution is put into ultrasonic wave
Ultrasound 10 minutes, are transferred to hydrothermal reaction kettle to citric acid after completely dissolution, react 4 hours at 180-200 DEG C in washer,
Peony mixed liquor is obtained, obtains dark red solution after remaining after taking-up using 0.22 micron membrane filter of syringe-type removal bulky grain,
It is added acetone precipitation 30 minutes by the volume ratio of 1:3, is centrifuged with centrifuge, 8000-10000rpm, 25 minutes, sucks supernatant
Liquid, then with being washed for several times than ethanol/acetone mixed liquor in equal volume, be finally dried in vacuo, obtain dark powder；By dark powder with 6.25
The concentration of mcg/ml is dispersed in water, and addition quality is dark 4 to 7 times of silty amount of sodium borohydride, is stirred at room temperature 4 hours, molten
Liquid is transferred to 1000Da bag filter, carries out dialysis 24 hours with deionized water, aqueous solution of nitric acid is added in the powder being freeze-dried
First flow back 12h, then is neutralized to neutrality with sodium carbonate, is dialysed 24 hours in ionized water, obtains target after finally freeze-dried
Carbon quantum dot；
(2) preparation method of the green fluorescence carbon quantum dot of target peptide modification:
Cetrorelix gonadotropin-releasing hormone (GRH) GnRH antagonist (oophoroma target peptide), PBS, EDC and NHS are mixed, and
It is stirred at normal temperature uniformly.Then quantum dot solution (0.05 grams per milliliter) is added in mixed solution, stirs at normal temperature
24 hours.It dialyses 24 hours after stirred to 1000Da bag filter, obtains target titanium finally by vacuum freeze drier
The carbon quantum dot powder of modification, whole process are protected from light as far as possible.
The reaction temperature is preferably 200 DEG C, and the reaction time is preferably 4 hours.
The revolving speed that the centrifugation uses is preferably 9500rpm.
The Cetrorelix gonadotropin-releasing hormone (GRH) GnRH antagonist (oophoroma target peptide), PBS, EDC and NHS
Molar ratio is 3:500:6 ~ 12:12.
The present invention provides a kind of targeting green fluorescence carbon quantum dot, is prepared according to any of the above-described the method.
The present invention provides a kind of application for targeting green fluorescence carbon quantum dot in cell fluorescence imaging.
The carbon quantum dot can be used for bio-imaging, detection and radiography tracer etc.；This carbon quantum dot preparation condition
It is very friendly with environmental requirement, can be synthesized in common laboratory, preparation flow is simple, yield is high, toxicity is low, fluorescence intensity with
Form stable, the raw material sources of use are in extensive citric acid as carbon source, and price is just declared, strong operability, are suitable for a large amount of
Production.
The present invention has the advantages that
(1) carbon quantum dot solution can be obtained by one step hydro thermal method, preparation condition and environmental requirement are very friendly, general
Laboratory can synthesize；
(2) preparation flow is simple, and yield is high, fluorescence intensity and form stable；
(3) material used is extensive citric acid, is used as carbon source, and price is just declared, strong operability, is suitable for mass production；
(4) EDC/NHS priming reaction is utilized, the carboxyl on the amino and quantum dot in target peptide is connected chemically, synthesizes target
To the carbon quantum dot of tumour.It can apply and cell imaging or neoplasm tracing.
Detailed description of the invention
Fig. 1 is the fluorescence emission spectrum of carbon quantum dot prepared by embodiment 1；
Fig. 2 is carbon quantum dot laser co-focusing figure prepared by embodiment 1, and cell used is human body ovarian cancer cell A2780,
Green fluorescence figure；
Fig. 3 is carbon quantum dot laser co-focusing figure prepared by embodiment 1, and cell used is human body ovarian cancer cell A2780,
It is superimposed light field figure.
Specific embodiment
Below by way of specific embodiment, the technical scheme of the present invention will be further described.Embodiment below is to this
The further explanation of invention, and do not limit the scope of the invention.
Embodiment 1
A kind of targeting green fluorescence carbon quantum dot, is prepared as follows step:
1. the preparation method of green fluorescence carbon quantum dot:
Step 1, at room temperature, by 12 grams and 21 milliliters of ethylenediamine mixing of citric acid, it is re-dissolved in 80 milliliters of formamides, mixed liquor is put
Enter ultrasound 10 minutes in ultrasonic cleaner, is transferred to hydrothermal reaction kettle after completely dissolution to citric acid；
Step 2, water heating kettle is placed in baking oven, is reacted 4 hours at 200 DEG C, obtains peony mixed liquor, used after taking-up
Dark red solution is obtained after 0.22 micron membrane filter removal bulky grain residual；
Step 3,10 milliliters of dark red solutions are taken to add 30 milliliters of acetone precipitations 30 minutes, with 9500rpm centrifuge centrifugation 25
After minute, supernatant is sucked, then washed 3 times with 20 milliliters of ethyl alcohol and 20 milliliters of acetone mixtures, be finally dried in vacuo, obtain
0.1 gram of dark powder；
Step 4, it disperses 0.1 gram of dark powder in 15 ml deionized waters, addition quality is dark 4 to 7 times of silty amount of boron
Sodium hydride is stirred at room temperature 4 hours, and solution is transferred to 1000Da bag filter, with deionized water dialysis 24 hours, has been freeze-dried
Powder is added aqueous solution of nitric acid and first flows back 12h, then is neutralized to neutrality with sodium carbonate, is dialysed 24 hours in ionized water, is most passed through afterwards
Target carbon quantum dot is obtained after freeze-drying.
The green fluorescence carbon quantum dot prepared is subjected to fluoremetry, sees attached drawing 1, it is known that carbon quantum prepared by the present invention
Point transmitting green fluorescence.
2. the preparation method of the green fluorescence carbon quantum dot of target peptide modification:
Step 1, Cetrorelix gonadotropin-releasing hormone (GRH) GnRH antagonist 27mg, 60 μm of ol of final concentration incorporate 5 milliliters
PBS (0.01M, pH 7.4), adds EDC23mg, 120 μm of ol and NHS 28mg of final concentration, 240 μm of ol of final concentration, and
It is stirred evenly under room temperature；
Step 2, in 2 ml deionized waters, 0.1 gram of carbon quantum dot is added and is added in the mixed solution of step 1, mixes again
The solution of conjunction stirs 24 hours at normal temperature；
Step 3, solution step 2 obtained is dialysed 24 hours, and the carbon quantum dot of target titanium modification after purification is obtained；
Step 4, target quantum dot powder is obtained by vacuum freeze drier, whole process is protected from light as far as possible.
3. the method that targeting carbon quantum dot is used to mark human ovarian cancer's cell A2780:
Step 1, cell concentration is diluted to 10000/milliliter with cell counter when passage cell and instills the every hole 150 of four points of wares
Microlitre put incubator be incubated for it is spare；
Step 2, after waiting cells adherent, suck culture medium, PBS cleaning is primary, every hole instill 150 microlitres of concentration be 15 micrograms/
The targeting quantum dot solution of milliliter, puts back to incubator and is incubated for altogether 6 hours；
Step 3, quantum dot solution is sucked after 6 hours, PBS is cleaned 3 times, paraformaldehyde is added, 150 microlitres of every hole fixes 30 points
Clock；
Step 4, paraformaldehyde is sucked, PBS is cleaned 3 times, and every hole adds the anti-fluorescent quenching liquid of the drop of 500 microlitres of PBS and one, is put sharp
It is observed under light Laser Scanning Confocal Microscope.
If Fig. 2 is carbon quantum dot laser co-focusing figure prepared by embodiment 1, cell used is human body ovarian cancer cell
A2780, green fluorescence figure；It is carbon quantum dot laser co-focusing figure prepared by embodiment 1 with Fig. 3, cell used is human body
Ovarian cancer cell A2780 is superimposed light field figure such as attached drawing 2, and shown in attached drawing 3, cellular morphology is good, can be used for viable cell labelling.
Embodiment 2
A kind of targeting green fluorescence carbon quantum dot, is prepared as follows step:
1. the preparation method of green fluorescence carbon quantum dot:
Step 1, at room temperature, by 12 grams and 21 milliliters of ethylenediamine mixing of citric acid, it is re-dissolved in 80 milliliters of formamides, mixed liquor is put
Enter ultrasound 10 minutes in ultrasonic cleaner, is transferred to hydrothermal reaction kettle after completely dissolution to citric acid；
Step 2, water heating kettle is placed in baking oven, is reacted 6 hours at 180 DEG C, obtains peony mixed liquor, filter is used after taking-up
Dark red solution is obtained after (0.22 micron) removal bulky grain residual of film；
Step 3,20 milliliters of dark red solutions is taken to add 20 milliliters of acetone precipitations 30 minutes, with centrifuge (8000rpm, 30 points
Clock) centrifugation after, suck supernatant, then washed 3 times with 20 milliliters of ethyl alcohol and 20 milliliters of acetone mixtures, be finally dried in vacuo, obtain
To 0.08 gram of dark powder；
Step 4, it disperses 0.08 gram of dark powder in 15 ml deionized waters, excess sodium borohydrate (the 4 to 7 of dark powder is added
Times), it is stirred at room temperature 4 hours, solution is transferred to bag filter (1000Da), with deionized water dialysis 24 hours, has been freeze-dried
Powder is added 15 milliliters of 3M aqueous solution of nitric acid and first flows back 12 hours, then is neutralized with sodium carbonate, is dialysed 24 hours in ionized water, most
Afterwards, target carbon quantum dot is obtained after freeze-dried.
The green fluorescence carbon quantum dot of 1 preparation is subjected to fluoremetry, sees attached drawing 1, it is known that, carbon quantum prepared by the present invention
Point transmitting green fluorescence.
2. the preparation method of the green fluorescence carbon quantum dot of target peptide modification, with embodiment 1.
3. the method that targeting carbon quantum dot is used to mark human ovarian cancer's cell A2780, with embodiment 1.
Embodiment 3
A kind of targeting green fluorescence carbon quantum dot, is prepared as follows step:
1. the preparation method of green fluorescence carbon quantum dot:
Step 1, at room temperature, by 12 grams and 21 milliliters of ethylenediamine mixing of citric acid, it is re-dissolved in 80 milliliters of formamides, mixed liquor is put
Enter ultrasound 10 minutes in ultrasonic cleaner, is transferred to hydrothermal reaction kettle after completely dissolution to citric acid；
Step 2, water heating kettle is placed in baking oven, is reacted 5 hours at 190 DEG C, obtains peony mixed liquor, filter is used after taking-up
Dark red solution is obtained after (0.22 micron) removal bulky grain residual of film；
Step 3,10 milliliters of dark red solutions is taken to add 30 milliliters of acetone precipitations 30 minutes, with centrifuge (9500rpm, 25 points
Clock) centrifugation after, suck supernatant, then washed 3 times with 20 milliliters of ethyl alcohol and 20 milliliters of acetone mixtures, be finally dried in vacuo, obtain
To 0.1 gram of dark powder；
Step 4, it disperses 0.1 gram of dark powder in 15 ml deionized waters, excess sodium borohydrate (the 4 to 7 of dark powder is added
Times), it is stirred at room temperature 4 hours, solution is transferred to bag filter (1000Da), with deionized water dialysis 24 hours, has been freeze-dried
Powder is added 15 milliliters of 3M aqueous solution of nitric acid and first flows back 6 hours, then is neutralized with sodium carbonate, is dialysed 24 hours in ionized water, most
Afterwards, target carbon quantum dot is obtained after freeze-dried.
2. the green fluorescence carbon quantum dot of target peptide modification, is prepared according to the following steps:
Step 1, Cetrorelix gonadotropin-releasing hormone (GRH) GnRH antagonist 27mg, 60 μm of ol of final concentration incorporate 5 milliliters
PBS (0.01M, pH 7.4), adds EDC46mg, 240 μm of ol and NHS 28mg of final concentration, 240 μm of ol of final concentration, and
It is stirred evenly under room temperature；
Step 2, in 2 ml deionized waters, the carbon quantum dot of 0.1 gram of embodiment 1 is added and the mixed solution of step 1 is added
In, the solution mixed again stirs 24 hours at normal temperature；
Step 3, solution step 2 obtained is dialysed 24 hours, and the carbon quantum dot of target titanium modification after purification is obtained；
Step 4, target quantum dot powder is obtained by vacuum freeze drier, whole process is protected from light as far as possible.
3. the method that targeting carbon quantum dot is used to mark human ovarian cancer's cell A2780, with embodiment 1.
Claims (6)
1. a kind of preparation method for targeting green fluorescence carbon quantum dot, which comprises the steps of:
(1) carbon quantum dot synthesizes:
At room temperature, first citric acid and ethylenediamine are mixed, is re-dissolved in formamide, molar ratio is that 1:5:32 solution is put into ultrasonic wave
Ultrasound 10 minutes, are transferred to hydrothermal reaction kettle to citric acid after completely dissolution, react 4 hours at 180-200 DEG C in washer,
Peony mixed liquor is obtained, obtains dark red solution after remaining after taking-up using 0.22 micron membrane filter of syringe-type removal bulky grain,
It is added acetone precipitation 30 minutes by the volume ratio of 1:3, is centrifuged with centrifuge, 8000-10000rpm, 25 minutes, sucks supernatant
Liquid, then with being washed for several times than ethanol/acetone mixed liquor in equal volume, be finally dried in vacuo, obtain dark powder；By dark powder with 6.25
The concentration of mcg/ml is dispersed in water, and addition quality is dark 4 to 7 times of silty amount of sodium borohydride, is stirred at room temperature 4 hours, molten
Liquid is transferred to 1000Da bag filter, carries out dialysis 24 hours with deionized water, aqueous solution of nitric acid is added in the powder being freeze-dried
First flow back 12h, then is neutralized to neutrality with sodium carbonate, is dialysed 24 hours in ionized water, obtains target after finally freeze-dried
Carbon quantum dot；
(2) preparation method of the green fluorescence carbon quantum dot of target peptide modification:
Cetrorelix gonadotropin-releasing hormone (GRH) GnRH antagonist (oophoroma target peptide), PBS, EDC and NHS are mixed, and
It is stirred at normal temperature uniformly；Then, 0.05 grams per milliliter quantum dot solution is added in mixed solution, stirs at normal temperature
24 hours；After stirred, dialysed 24 hours with 1000Da bag filter, obtain target titanium finally by vacuum freeze drier and repair
The carbon quantum dot powder of decorations, whole process are protected from light as far as possible.
2. the preparation method of targeting green fluorescence carbon quantum dot according to claim 1, which is characterized in that hydro-thermal reaction
Temperature is 200 DEG C, and the reaction time is 4 hours.
3. the preparation method of targeting green fluorescence carbon quantum dot according to claim 1, which is characterized in that the centrifugation is adopted
Revolving speed is 9500rpm.
4. the preparation method of targeting green fluorescence carbon quantum dot according to claim 1, it is characterised in that: described
Cetrorelix gonadotropin-releasing hormone (GRH) GnRH antagonist (oophoroma target peptide), the molar ratio of PBS, EDC and NHS are 3:
500:6 ~ 12:12.
5. a kind of targeting green fluorescence carbon quantum dot, it is characterised in that -4 any the methods are prepared according to claim 1.
6. a kind of application of targeting green fluorescence carbon quantum dot according to claim 5 in cell fluorescence imaging.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112345508A (en) * | 2020-11-12 | 2021-02-09 | 青岛大学 | Application of green fluorescent carbon quantum dots in tryptophan detection and tryptophan detection method |
| CN115137836A (en) * | 2021-06-29 | 2022-10-04 | 华北理工大学 | Double-targeting ischemic myocardial mitochondria system based on carbon quantum dots and preparation method thereof |
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| CN104491883A (en) * | 2014-12-30 | 2015-04-08 | 中山大学 | Nano composite for targeted medicine delivery and treatment response monitoring as well as preparation method and application of nano composite |
| US20170023580A1 (en) * | 2015-07-21 | 2017-01-26 | University Of Connecticut | Protein fluorescent nanoparticles and methods of synthesis thereof |
| CN107674675A (en) * | 2017-10-27 | 2018-02-09 | 上海纳米技术及应用国家工程研究中心有限公司 | Detection targets preparation method of carbon quantum dot turn on probes and products thereof and application with folacin receptor |
| CN109316465A (en) * | 2018-11-02 | 2019-02-12 | 孙世国 | A kind of biodegradable multiple target point targeting intelligent drug delivery system of inorganic nano, preparation method and application |
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| CN104491883A (en) * | 2014-12-30 | 2015-04-08 | 中山大学 | Nano composite for targeted medicine delivery and treatment response monitoring as well as preparation method and application of nano composite |
| US20170023580A1 (en) * | 2015-07-21 | 2017-01-26 | University Of Connecticut | Protein fluorescent nanoparticles and methods of synthesis thereof |
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| CN112345508A (en) * | 2020-11-12 | 2021-02-09 | 青岛大学 | Application of green fluorescent carbon quantum dots in tryptophan detection and tryptophan detection method |
| CN115137836A (en) * | 2021-06-29 | 2022-10-04 | 华北理工大学 | Double-targeting ischemic myocardial mitochondria system based on carbon quantum dots and preparation method thereof |
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