CN104555980A - Aspirin-based carbon quantum dot and biological application thereof - Google Patents
Aspirin-based carbon quantum dot and biological application thereof Download PDFInfo
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Abstract
The invention discloses an aspirin-based carbon quantum dot and application thereof in aspects of cell imaging and anti-inflammatory treatment, belonging to the technical field of nano-drugs. The invention in particular relates to a carbon quantum dot with strong fluorescent properties prepared from a hydrazine hydrate solution by utilizing a microwave heating method under the condition that aspirin dissolution is promoted. The carbon quantum dot prepared by the method is very stable under hyper-salt concentration and physiological pH conditions, blue-fluorescence is maintained, the carbon quantum dot can enter the cell nucleus, and the cells are effectively traced; and meanwhile, the original anti-inflammatory effect of aspirin is remained, and inflammatory cells can be effectively inhibited in an acute inflammation model constructed by utilizing carrageenin. In addition, the prepared aspirin carbon quantum dot is low in toxicity and does not influence liver and kidney functions and organs such as the heart, liver, spleen and kidney in in-vivo application, and the aim that the nanometer material has dual effects of diagnosis and treatment can be achieved.
Description
Technical field
The invention belongs to Nano medication technical field, be specifically related to prepare a kind of carbon quantum dot based on acetylsalicylic acid, this carbon quantum dot can be obtained by microwave heating acetylsalicylic acid and hydrazine hydrate, there is hyperfluorescenceZeng Yongminggaoyingguang character, and remain the pharmaceutical activity of acetylsalicylic acid, thus can be applied to cell imaging and anti-inflammatory treatment aspect.
Background technology
In the last few years, nanotechnology was used for transhipment and the treatment of gene/drug, or was applied in medical science as diagnostic probe, and the combination of this nanotechnology and medical science is called nanosecond medical science.And the key problem of this field face how to design a kind of multifunctional nano material, the diagnosis of disease can either be used for, can be used as again the treatment of disease.There is the newcomer of carbon quantum dot as carbon nanomaterial family of photoluminescent property, cause the extensive concern of scholar in field of nanometer technology.The carbon quantum dot size of these surface passivations is less than 10nm usually, and owing to having stable photoluminescent property, the advantages such as wide excitation spectrum and adjustable transmitting peak position are applied to biomarker.Compare with semiconductor-quantum-point with traditional organic dye, carbon quantum dot has good biocompatibility and hypotoxicity, therefore, has a good application prospect in nanosecond medical science.
As NSAID (non-steroidal anti-inflammatory drug) main representative, acetylsalicylic acid (acetylsalicylic acid) has had the history of upper a century, though its effect gets the nod, remains in problem such as damage gi tract, poorly water-soluble etc.Although never stop for the modification of acetylsalicylic acid, what really can be actually applied is little.Therefore, find and a kind ofly can improve the water-soluble of acetylsalicylic acid, can alleviate again it is the key addressed this problem to GI damage.
Whether at present, carbon quantum dot is mainly used in the transhipment of bio-imaging or medicine/gene in biomedicine, and the research of medicine directly being made carbon quantum dot has no report, make carbon quantum dot artifact activity retain and more have no research for medicine.If acetylsalicylic acid is prepared into carbon quantum dot, can improve that it is water-soluble, application prospect can be had in spike, anti-inflammatory and control cardiovascular and cerebrovascular diseases again.
Summary of the invention
The object of the present invention is to provide a kind of multifunctional carbon quantum dot based on acetylsalicylic acid and biologic applications.By the modification to conventional medicament acetylsalicylic acid, to be water-solublely improved.Carbon quantum dot prepared by the present invention is highly stable under high salt concentration and physiological pH condition, maintains blue-fluorescence, and can enter nucleus, carries out effective spike to cell; Also retains the original anti-inflammatory efficacy of acetylsalicylic acid simultaneously, in the acute inflammation model built utilizing carrageenin, can effectively suppress inflammatory cell to produce; In addition, prepared acetylsalicylic acid carbon quantum dot toxicity is less, and application can not have an impact to liver function, kidney merit and the internal organs such as the heart, liver,spleen,kidney in vivo, can realize the target that nano material has diagnosis and treatment double effects.
The present invention utilizes microwave heating method, and acetylsalicylic acid is dissolved in deionized water by early stage under the booster action of hydrazine hydrate, and can obtain hyperfluorescenceZeng Yongminggaoyingguang after microwave heating, have the carbon quantum dot of pharmaceutical activity, its distribution of sizes is at 2 ~ 6nm.After separating-purifying, this carbon quantum dot can be applied to cell imaging and anti-inflammatory treatment aspect.
The raw material that the present invention adopts is all the commercial material that can have directly bought, do not need further process, directly mix according to a certain percentage, therefore experimental implementation is easy, dangerous little, and have good experimental repeatability, can produce in batches, the carbon quantum dot obtained has high fluorescence quantum efficiency simultaneously.
The preparation of the carbon quantum dot based on acetylsalicylic acid of the present invention, comprises the steps: that (1) is by the carbon quantum dot of microwave method preparation based on acetylsalicylic acid; (2) separating-purifying is carried out to prepared carbon quantum dot.
(1) based on the preparation of the carbon quantum dot of acetylsalicylic acid: joined by 1.0 ~ 2.5g acetylsalicylic acid in the aqueous solution containing 0.5 ~ 2mL, mass concentration 98% hydrazine hydrate, the cumulative volume of whole system controls at 10 ~ 20mL; Then this solution is put into microwave oven, heat 6 ~ 10 minutes under 80 ~ 100W, thus obtain the carbon quantum dot with blue-fluorescence;
(2) separating-purifying of carbon quantum dot: add in 50 ~ 100mL deionized water in the carbon quantum dot prepared by step (1), ultrasonic disperse product, then by the carbon quantum dot that molecular weight is 1800 ~ 10000 prepared by dialysis bag separating-purifying, dialysis is after 3 ~ 7 days, it is the water system filter filtration of 0.22 ~ 0.45 μm by product aperture in dialysis bag, products therefrom is concentrated into 10 ~ 20mL after rotary evaporation, last freeze-drying concentrated solution, obtains the carbon quantum dot powder based on acetylsalicylic acid of brown color.
Accompanying drawing explanation
Fig. 1: the transmission electron microscope photo (a) of the carbon quantum dot based on acetylsalicylic acid utilizing microwave method to prepare, grain size distribution plan (b), high-resolution-ration transmission electric-lens photo (c), and powder diffractogram (d), carbon quantum dot distribution of sizes prepared by explanation is narrower, monodispersity good, has obvious lattice;
Fig. 2: uv-absorbing spectrogram (a) of the carbon quantum dot based on acetylsalicylic acid utilizing microwave method to prepare, fluorescence excitation spectrum (in b solid line) and emission spectrum (in b dotted line), and carbon quantum dot photo of (in b right illustration) under (in b left illustration) and UV-light under the light of room, the carbon quantum dot prepared by explanation has very strong blue-fluorescence;
Fig. 3: the infrared spectrum of the carbon quantum dot based on acetylsalicylic acid utilizing microwave method to prepare, the carbon quantum dot prepared by explanation remains the Acetyl Groups in acetylsalicylic acid;
Fig. 4: the beta stability line (a) of carbon quantum dot in different concns KCl salts solution based on acetylsalicylic acid utilizing microwave method to prepare, and the beta stability line (b) in different pH solution, illustrate that carbon quantum dot has good stability, can living things system be applied to;
Fig. 5: the Laser Scanning Confocal Microscope picture after the carbon quantum dot based on acetylsalicylic acid prepared by utilization and cervical cancer cell Dual culture.Wavelength is details in a play not acted out on stage, but told through dialogues picture (a) under the optical excitation of 400nm, light field picture (b), and picture (c) after light field details in a play not acted out on stage, but told through dialogues superposition, illustrates that carbon quantum dot may be used for cell imaging;
Fig. 6: the carbon quantum dot prepared by utilization is in rat Ti Nei antiphlogistic effects Histological section result.Blank group (a, b, c) inflammatory cell layer is thicker, has a large amount of inflammatory cell, and acetylsalicylic acid group (d, e, f) and obviously alleviating based on carbon quantum dot group (g, h, the i) inflammation of acetylsalicylic acid, inflammatory cell reduces relatively;
Fig. 7: acetylsalicylic acid and the carbon quantum dot based on acetylsalicylic acid are on the impact of Biochemical Indices In Serum.Based on the carbon quantum dot of acetylsalicylic acid to hepatic functional index gpt (a), and glutamic-oxal(o)acetic transaminase (b) has no significant effect, and also has no significant effect renal function index blood urea nitrogen (c) and creatinine (d);
Fig. 8: acetylsalicylic acid and the carbon quantum dot based on acetylsalicylic acid are on the impact of internal organs.The heart (i) of abdominal injection carbon quantum dot group rat, liver (j), spleen (k), kidney (l) and blank group (a, b, c, d) and acetylsalicylic acid group (e, f, g, h) in corresponding organ without obvious histological differences.
Embodiment
Below in conjunction with embodiment, the present invention is further elaborated, instead of will limit the invention with this.
Embodiment 1
(1) based on the preparation of the carbon quantum dot of acetylsalicylic acid: being joined by 2g acetylsalicylic acid containing 1.08mL mass concentration is in the hydrazine hydrate aqueous solution of 98%, the cumulative volume of whole system is 10mL.Microwave power is 100W, and the time is 8 minutes.Obtain the carbon quantum dot based on acetylsalicylic acid with blue-fluorescence.
(2) separating-purifying of carbon quantum dot: add 80mL deionized water in the carbon quantum dot prepared by step (1), ultrasonic disperse product, the carbon quantum dot prepared by dialysis bag separating-purifying being 3500 with molecular weight, dialysis is after 7 days, products therefrom is filtered with the water system filter that particle diameter is 0.22 μm, be concentrated into 10mL after rotary evaporation after, freeze-drying obtains the carbon quantum dot powder (brown color) based on acetylsalicylic acid, and output is about 50mg.
Visible the obtained carbon quantum dot distribution of sizes based on acetylsalicylic acid is observed at 2 ~ 6nm, as shown in Figure 1 under transmission electron microscope.
Embodiment 2
(1) based on the preparation of the carbon quantum dot of acetylsalicylic acid: joined by 1g acetylsalicylic acid in the aqueous solution of 98% hydrazine hydrate containing 1.08mL, the cumulative volume of whole system is 10mL.Microwave power is 100W, and the time is 7 minutes.Obtain the carbon quantum dot based on acetylsalicylic acid with blue-fluorescence.
(2) separating-purifying of carbon quantum dot: add 50mL deionized water in the carbon quantum dot prepared by step (1), ultrasonic disperse product, the carbon quantum dot prepared by dialysis bag separating-purifying being 3500 with molecular weight, dialysis is after 7 days, products therefrom is filtered with the water system filter that particle diameter is 0.22 μm, after rotary evaporation, be concentrated into 5mL, freeze-drying obtains the carbon quantum dot powder (brown color) based on acetylsalicylic acid, and output is about 30mg.Gained carbon quantum dot has hyperfluorescenceZeng Yongminggaoyingguang character, as shown in Figure 2 b.
Embodiment 3
(1) based on the preparation of the carbon quantum dot of acetylsalicylic acid: joined by 2g acetylsalicylic acid in the aqueous solution of 98% hydrazine hydrate containing 0.54mL, the cumulative volume of whole system is 10mL.Microwave power is 100W, and the time is 8 minutes.Obtain the carbon quantum dot based on acetylsalicylic acid with blue-fluorescence.
(2) separating-purifying of carbon quantum dot: add 60mL deionized water in the carbon quantum dot prepared by step (1), ultrasonic disperse product, the carbon quantum dot prepared by dialysis bag separating-purifying being 3500 with molecular weight, dialysis is after 7 days, products therefrom is filtered with the water system filter that particle diameter is 0.45 μm, be concentrated into 5mL after rotary evaporation after, freeze-drying obtains the carbon quantum dot powder (brown color) based on acetylsalicylic acid, and output is about 40mg.Through infrared test, known carbon quantum dot remains the ethanoyl in acetylsalicylic acid, as shown in Figure 3
Embodiment 4
(1) based on the preparation of the carbon quantum dot of acetylsalicylic acid: joined by 2g acetylsalicylic acid in the aqueous solution of 98% hydrazine hydrate containing 2.16mL, the cumulative volume of whole system is 10mL.Microwave power is 100W, and the time is 8 minutes.Obtain the carbon quantum dot based on acetylsalicylic acid with blue-fluorescence.
(2) separating-purifying of carbon quantum dot: add 80mL deionized water in the carbon quantum dot prepared by step (1), ultrasonic disperse product, the carbon quantum dot prepared by dialysis bag separating-purifying being 3500 with molecular weight, dialysis is after 7 days, products therefrom is filtered with the water system filter that particle diameter is 0.22 μm, be concentrated into 10mL after rotary evaporation after, freeze-drying obtains the carbon quantum dot powder (brown color) based on acetylsalicylic acid, and output is about 50mg.Then compound concentration is the KCl salts solution of 0,0.25,0.5,0.75,1.0,1.25,1.5,1.75 and 2.0mol/L, and the pH utilizing hydrochloric acid and sodium hydroxide to regulate deionized water to obtain is the aqueous solution of 1.8,2.3,3.2,4.2,4.9,6.1,7.2,8.1,8.9,9.8,10.8 and 12.5, the carbon quantum dot of 0.1g is added subsequently in above-mentioned often kind of solution (3mL), finally detect solution fluorescence intensity, as shown in Figure 4.
Embodiment 5
(1) based on the carbon quantum dot of acetylsalicylic acid preparation and purify as described in Example 1.
(2) because the prepared carbon quantum dot based on acetylsalicylic acid has photoluminescent property, consider that it can be used for cell marking.Human cervical carcinoma cell is inoculated in the special plate of Laser Scanning Confocal Microscope with 200,000/hole, cultivates in containing 37 DEG C of cell culture incubators of 5% carbonic acid gas.After overnight cell is adherent, replaced medium, adds carbon quantum dot, and final concentration is 20 μ g/mL.Dual culture, after 6 hours, abandons substratum, and phosphate buffered saline(PBS) rinses 2 times, and 4% paraformaldehyde fixes 10 minutes, and phosphate buffered saline(PBS) rinses 2 times.When excitation wavelength is 400nm, observe visible under laser confocal microscope, whole cell, in blue (Fig. 5), illustrates that carbon quantum dot enters cytoplasm, and can pass nuclear membrane, enter nucleus, carry out significant notation to cell.
Embodiment 6
(1) based on the carbon quantum dot of acetylsalicylic acid preparation and purify as described in Example 1.
(2) because the mechanism of acetylsalicylic acid performance anti-inflammatory action is that its ester bond is by the serine residue generation acetylization reaction with cyclooxygenase; thus suppress prostaglandin E2 to be formed; play anti-inflammatory action; and we do not destroy the ester bond of acetylsalicylic acid in the reaction, therefore illustrate that its biological action should retain in theory.For investigating the biologic activity of the prepared carbon quantum dot based on acetylsalicylic acid, we choose male Wistar rat (160 ~ 180g), abdominal injection isopyknic phosphate buffered saline(PBS), acetylsalicylic acid and carbon quantum dot (20mg/kg) solution based on acetylsalicylic acid respectively.After half an hour, the trevira sponge being of a size of 2.0 × 1.0 × 0.5cm is infiltrated after mass concentration is the Carrageenan solution of 1%, takes out, implant rat back subcutaneous, finally use 3/0 operation stitching suturing with thread management.Postoperative 5 hours, mass concentration was the fixing execution of paraformaldehyde cardiac perfusion of 4%, gets subcutis, fixing, dewaters step by step, carries out histological stain.
Basis of microscopic observation is visible, and blank group (injection phosphate buffered saline(PBS)) inflammatory cell layer is thicker, has a large amount of inflammatory cell, as neutrophil leucocyte, lymphocytic infiltration (Fig. 6); And inject acetylsalicylic acid and the carbon quantum dot group (Fig. 6) based on acetylsalicylic acid, inflammation obviously alleviates, and inflammatory cell reduces relatively.Illustrate that the carbon quantum dot based on acetylsalicylic acid still remains original anti-inflammatory activity, and effect is better than simple medicine acetylsalicylic acid.Analyze reason, on the one hand because nano material specific surface area is relatively large, because its surface binding site is relatively many in unit volume; On the other hand, carbon quantum dot is more water-soluble than simple medicine acetylsalicylic acid to increase, and slightly positive electricity, can promote that it circulates in vivo and enters in cell.
Embodiment 7
(1) based on the carbon quantum dot of acetylsalicylic acid preparation and purify as described in Example 1.
(2) bio-toxicity of the carbon quantum dot based on acetylsalicylic acid prepared by investigation.We are by interior animal experiment, observe its impact on the index such as liver function, kidney merit in serum biochemistry.Male Wistar rat (160 ~ 180g) is abdominal injection isopyknic phosphate buffered saline(PBS), acetylsalicylic acid and carbon quantum dot (20mg/kg) solution based on acetylsalicylic acid respectively.Got eyeball blood respectively at 1,3 and 7 day, be collected in not containing in the heparin tube of heparin, leave standstill 1 ~ 2 hour, centrifugal 5 minutes of 3000rpm, gets supernatant and detects for biochemical indicator.
Gpt and glutamic-oxal(o)acetic transaminase are the important Testing index of liver function, compared with blank group (injection phosphate buffered saline(PBS)), though acetylsalicylic acid group and the carbon quantum dot group slightly difference (Fig. 7) based on acetylsalicylic acid, but this difference does not have statistical significance, and each group index is all in normal range, illustrates and has no significant effect liver function.Blood urea nitrogen and creatinine are the important evaluation indexes of renal function, compared with blank group, acetylsalicylic acid group and based on acetylsalicylic acid carbon quantum dot group all in normal range (Fig. 7), no significant difference.Above biochemical index, the carbon quantum dot biological safety based on acetylsalicylic acid prepared by preliminary explanation is better, has no significant effect liver and renal function.
Embodiment 8
(1) based on the carbon quantum dot of acetylsalicylic acid preparation and purify as described in Example 1.
(2) investigate about to the bio-toxicity of the carbon quantum dot based on acetylsalicylic acid, carry out except blood serum bio-chemical analysis except getting eyeball blood, 4% paraformaldehyde is to rat (in embodiment 7) perfusion fixation simultaneously, core, liver, the organ such as spleen and kidney be fixed, dehydration and histological stain step by step, whether can cause the damage of internal organs, inflammation or other pathology with the clear and definite carbon quantum dot based on acetylsalicylic acid.
Basis of microscopic observation is visible, and compared with blank group, acetylsalicylic acid group and the carbon quantum dot group based on acetylsalicylic acid do not have obvious histological change (Fig. 8), illustrates that biological safety is better, can not cause visceral organ injury, inflammation or other pathology.
Claims (2)
1. based on a carbon quantum dot for acetylsalicylic acid, it is characterized in that: it is prepared by following steps,
(1) based on the preparation of the carbon quantum dot of acetylsalicylic acid: joined by 1.0 ~ 2.5g acetylsalicylic acid in the aqueous solution containing 0.5 ~ 2mL, mass concentration 98% hydrazine hydrate, the cumulative volume of whole system controls at 10 ~ 20mL; Then this solution is heated 6 ~ 10 minutes under 80 ~ 100W, thus obtain the carbon quantum dot with blue-fluorescence;
(2) separating-purifying of carbon quantum dot: add 50 ~ 100mL deionized water to the carbon quantum dot prepared by step (1), ultrasonic disperse product, then by the carbon quantum dot that molecular weight is 1800 ~ 10000 prepared by dialysis bag separating-purifying, dialysis is after 3 ~ 7 days, products therefrom is filtered again with the water system filter that aperture is 0.22 ~ 0.45 μm, after rotary evaporation, be concentrated into 10 ~ 20mL, last freeze-drying concentrated solution, obtain the carbon quantum dot powder based on acetylsalicylic acid of brown color.
2. a kind of application of carbon quantum dot in cell imaging or anti-inflammatory treatment based on acetylsalicylic acid according to claim 1.
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| CN108101019A (en) * | 2017-12-19 | 2018-06-01 | 重庆文理学院 | A kind of method that carbon quantum dot is prepared using expired Chinese patent drug |
| CN111077126A (en) * | 2019-12-31 | 2020-04-28 | 江苏大学 | Preparation method and application of molecular imprinting fluorescence sensor based on N-CQDs |
| CN114804071A (en) * | 2022-04-21 | 2022-07-29 | 复旦大学附属眼耳鼻喉科医院 | Carbon quantum dot material with oxidation resistance and application thereof |
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Cited By (3)
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| CN108101019A (en) * | 2017-12-19 | 2018-06-01 | 重庆文理学院 | A kind of method that carbon quantum dot is prepared using expired Chinese patent drug |
| CN111077126A (en) * | 2019-12-31 | 2020-04-28 | 江苏大学 | Preparation method and application of molecular imprinting fluorescence sensor based on N-CQDs |
| CN114804071A (en) * | 2022-04-21 | 2022-07-29 | 复旦大学附属眼耳鼻喉科医院 | Carbon quantum dot material with oxidation resistance and application thereof |
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