CN113433102B - Fluorescent carbon dot and fluorescence kit for detecting ciprofloxacin prepared by same - Google Patents
Fluorescent carbon dot and fluorescence kit for detecting ciprofloxacin prepared by same Download PDFInfo
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- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 title claims abstract description 62
- 229960003405 ciprofloxacin Drugs 0.000 title claims abstract description 31
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 229910052799 carbon Inorganic materials 0.000 title claims abstract description 14
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical class NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000002790 naphthalenes Chemical class 0.000 claims abstract description 11
- 238000002189 fluorescence spectrum Methods 0.000 claims abstract description 8
- 238000012360 testing method Methods 0.000 claims abstract description 8
- 239000000243 solution Substances 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 8
- XOOMNEFVDUTJPP-UHFFFAOYSA-N naphthalene-1,3-diol Chemical compound C1=CC=CC2=CC(O)=CC(O)=C21 XOOMNEFVDUTJPP-UHFFFAOYSA-N 0.000 claims description 8
- 229960003638 dopamine Drugs 0.000 claims description 7
- CTENFNNZBMHDDG-UHFFFAOYSA-N Dopamine hydrochloride Chemical group Cl.NCCC1=CC=C(O)C(O)=C1 CTENFNNZBMHDDG-UHFFFAOYSA-N 0.000 claims description 6
- AHMIDUVKSGCHAU-UHFFFAOYSA-N Dopaquinone Natural products OC(=O)C(N)CC1=CC(=O)C(=O)C=C1 AHMIDUVKSGCHAU-UHFFFAOYSA-N 0.000 claims description 6
- AHMIDUVKSGCHAU-LURJTMIESA-N L-dopaquinone Chemical compound [O-]C(=O)[C@@H]([NH3+])CC1=CC(=O)C(=O)C=C1 AHMIDUVKSGCHAU-LURJTMIESA-N 0.000 claims description 6
- -1 aminonaphthalene compound Chemical class 0.000 claims description 6
- 229960001149 dopamine hydrochloride Drugs 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 2
- 229910052802 copper Inorganic materials 0.000 claims 2
- 239000010949 copper Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 238000001514 detection method Methods 0.000 abstract description 10
- 229910000365 copper sulfate Inorganic materials 0.000 abstract description 4
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical group [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 description 16
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 6
- 229910001431 copper ion Inorganic materials 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000000108 ultra-filtration Methods 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910021642 ultra pure water Inorganic materials 0.000 description 2
- 239000012498 ultrapure water Substances 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003640 drug residue Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000005375 photometry Methods 0.000 description 1
- 238000012372 quality testing Methods 0.000 description 1
- 150000007660 quinolones Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000002525 ultrasonication Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
技术领域technical field
本发明涉及药物检测领域，具体涉及一种荧光碳点及其制备的检测环丙沙星的荧光试剂盒。The invention relates to the field of drug detection, in particular to a fluorescent carbon dot and a fluorescent kit for detecting ciprofloxacin prepared therefrom.
背景技术Background technique
药物在食品、环境等中的残留检测是药物分析的一项重要内容。长期食用抗生素残留超标的食品，以及长期生活在抗生素残留超标的环境中，都会给人类健康带来很大危害，因此，环丙沙星残留的检测日益引起人们的重视。Drug residue detection in food, environment, etc. is an important content of drug analysis. Long-term consumption of food with excessive antibiotic residues and long-term living in an environment with excessive antibiotic residues will bring great harm to human health. Therefore, the detection of ciprofloxacin residues has increasingly attracted people's attention.
环丙沙星具有抗菌谱广、抗菌活性强、毒副作用低、临床疗效高等特点，使之成为目前国内外临床应用最广泛的一种喹诺酮类药物，我国药典中规定的标准检测方法为高效液相色谱法，此外，报道的方法还有：分光光度法、荧光光度法等。相较于高效液相色谱法，光谱法成本较底，更易于实施，无需富集分离操作，被广泛用于水质检测和医疗运用中，更易于实施。Ciprofloxacin has the characteristics of broad antibacterial spectrum, strong antibacterial activity, low toxicity and side effects, and high clinical efficacy, making it the most widely used quinolones in clinical practice at home and abroad. The standard detection method stipulated in the Chinese Pharmacopoeia is high-efficacy solution In addition, the reported methods include: spectrophotometry, fluorescence photometry and so on. Compared with high-performance liquid chromatography, spectrometry is cheaper, easier to implement, and does not require enrichment and separation operations. It is widely used in water quality testing and medical applications, and is easier to implement.
发明内容Contents of the invention
本发明提出了一种荧光碳点及其制备的检测环丙沙星的荧光试剂盒，本方法通过配制简单的试剂盒，试剂盒分A和B两种溶液，其中A液为制备的无光碳点，B液为硫酸铜溶液，将A液与B液混合后，加入环丙沙星，测试荧光光谱，可以根据建立的工作曲线计算出样本中的环丙沙星含量，实现对对其快速检测，适用性较强，检测效率高，灵敏度高。The present invention proposes a fluorescent carbon dot and a fluorescent kit for detecting ciprofloxacin prepared by the same. The method prepares a simple kit, and the kit is divided into two kinds of solutions A and B, wherein A liquid is a prepared non-light Carbon dots, liquid B is copper sulfate solution, after mixing liquid A and liquid B, add ciprofloxacin, test the fluorescence spectrum, the content of ciprofloxacin in the sample can be calculated according to the established working curve, and it can be compared Rapid detection, strong applicability, high detection efficiency and high sensitivity.
实现本发明的技术方案是：Realize the technical scheme of the present invention is:
一种检测环丙沙星的荧光试剂盒，试剂盒分A和B两种溶液，其中A液为制备的无光碳点，A液无荧光，加入B液后反应15分钟，测试荧光光谱。然后在试剂盒的两种混合液中加入环丙沙星，由于环丙沙星与B液中的二价铜离子有较强的络合作用，反应后，混合液荧光减弱，测试方法为荧光关-开-关型。A fluorescent kit for detecting ciprofloxacin. The kit is divided into two solutions, A and B, wherein the A solution is a prepared matte carbon dot, and the A solution has no fluorescence. After adding the B solution, react for 15 minutes, and test the fluorescence spectrum. Then add ciprofloxacin to the two mixtures of the kit. Since ciprofloxacin has a strong complexation with the divalent copper ions in liquid B, after the reaction, the fluorescence of the mixture is weakened. The test method is fluorescence Off-on-off type.
所述溶液A的制备步骤为：将萘类衍生物和多巴胺类似物分别溶于无水乙醇中，两种溶液分别超声，使其完全溶解，将混合液转移至微波合成管中，于微波合成仪中60-190℃反应1-100min。反应结束后移出，10000转/分钟离心10分钟，去掉沉淀，超滤后保存为A液，或旋干保存粉末，使用时按照使用浓度溶解制备。The preparation steps of the solution A are as follows: respectively dissolving the naphthalene derivatives and the dopamine analogues in absolute ethanol, ultrasonicating the two solutions respectively to dissolve them completely, transferring the mixed solution to a microwave synthesis tube, and performing the microwave synthesis React in the instrument at 60-190°C for 1-100min. Remove after the reaction, centrifuge at 10,000 rpm for 10 minutes, remove the precipitate, store it as liquid A after ultrafiltration, or spin dry to store the powder, and prepare it by dissolving according to the concentration used.
优选地，所述萘类衍生物包括胺基萘化合物和羟基萘化合物，所述多巴胺类似物包括多巴胺或多巴醌。Preferably, the naphthalene derivatives include aminonaphthalene compounds and hydroxynaphthalene compounds, and the dopamine analogs include dopamine or dopaquinone.
所述胺基萘化合物为1,3-二羟基萘及其同分异构体，羟基萘化合物为1，3-二羟基萘及其同分异构体；多巴胺为盐酸多巴胺，多巴醌为盐酸多巴醌。The aminonaphthalene compound is 1,3-dihydroxynaphthalene and its isomers, and the hydroxynaphthalene compound is 1,3-dihydroxynaphthalene and its isomers; dopamine is dopamine hydrochloride, and dopaquinone is Dopaquinone Hydrochloride.
所述萘类衍生物和多巴胺类似物的摩尔比为（100:1）-（1:100）微波反应温度为60-190℃，反应时间为1-100min。The molar ratio of the naphthalene derivatives to the dopamine analogs is (100:1)-(1:100). The microwave reaction temperature is 60-190° C., and the reaction time is 1-100 min.
B液为硫酸铜溶液：称取CuSO4•5H2O 0.0125 g，溶于5 mL超纯水中，超声使其完全溶解，得到B液。Solution B is a copper sulfate solution: weigh 0.0125 g of CuSO 4 •5H 2 O, dissolve it in 5 mL of ultrapure water, and ultrasonically dissolve it completely to obtain Solution B.
优选地，本发明还提供一种荧光碳点，具体制备步骤如下将上述A液的制备。Preferably, the present invention also provides a fluorescent carbon dot, and the specific preparation steps are as follows: the preparation of the above liquid A.
具体的，本发明利用1,3-二羟基萘和盐酸多巴胺制备一种荧光碳点，步骤如下：Specifically, the present invention utilizes 1,3-dihydroxynaphthalene and dopamine hydrochloride to prepare a fluorescent carbon dot, and the steps are as follows:
称取1,3-二羟基萘0.0100 g（0.062 mmol）和盐酸多巴胺0.0118 g（0.062 mmol），溶于5 mL无水乙醇。两种溶液分别超声，使其完全溶解，将混合液转移至微波合成管中，于微波合成仪中160℃反应30分钟。反应结束后移出，10000转/分钟离心10分钟，去掉沉淀，超滤后保存为A液，或旋干保存粉末，使用时按照使用浓度溶解制备。Weigh 0.0100 g (0.062 mmol) of 1,3-dihydroxynaphthalene and 0.0118 g (0.062 mmol) of dopamine hydrochloride, and dissolve them in 5 mL of absolute ethanol. The two solutions were sonicated separately to dissolve them completely, and the mixture was transferred to a microwave synthesis tube, and reacted in a microwave synthesizer at 160°C for 30 minutes. Remove after the reaction, centrifuge at 10,000 rpm for 10 minutes, remove the precipitate, store it as liquid A after ultrafiltration, or spin dry to store the powder, and prepare it by dissolving according to the concentration used.
本发明的有益效果是：The beneficial effects of the present invention are:
（1）本发明按照一定比例取A溶液和B溶液于PBS缓冲溶液中，加入一定量的环丙沙星，然后进行荧光光谱测试。根据建立的工作曲线，可以计算环丙沙星的含量。(1) In the present invention, solution A and solution B are put into PBS buffer solution according to a certain ratio, a certain amount of ciprofloxacin is added, and then the fluorescence spectrum test is carried out. According to the established working curve, the content of ciprofloxacin can be calculated.
（2）本发明利用制备的碳点制备试剂盒，进行荧光滴定实验，测试加入不同浓度环丙沙星后的荧光强度变化。加入环丙沙星后，试剂盒的A液和B液混合后产生的绿色荧光减弱，溶液的荧光强度随着环丙沙星浓度的增加而降低，能够实现对环丙沙星的快速以及定量检测。(2) The present invention uses the prepared carbon dot preparation kit to carry out fluorescence titration experiments to test the changes in fluorescence intensity after adding different concentrations of ciprofloxacin. After adding ciprofloxacin, the green fluorescence produced by mixing liquid A and liquid B of the kit is weakened, and the fluorescence intensity of the solution decreases with the increase of the concentration of ciprofloxacin, which can realize the rapid and quantitative detection of ciprofloxacin detection.
附图说明Description of drawings
为了更清楚地说明本发明实施例或现有技术中的技术方案，下面将对实施例或现有技术描述中所需要使用的附图作简单地介绍，显而易见地，下面描述中的附图仅仅是本发明的一些实施例，对于本领域普通技术人员来讲，在不付出创造性劳动的前提下，还可以根据这些附图获得其他的附图。In order to more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the following will briefly introduce the drawings that need to be used in the description of the embodiments or the prior art. Obviously, the accompanying drawings in the following description are only These are some embodiments of the present invention. Those skilled in the art can also obtain other drawings based on these drawings without creative work.
图1为实施例1中A液与B液混合后随时间的荧光光谱变化。Fig. 1 is the change of fluorescence spectrum over time after liquid A and liquid B are mixed in Example 1.
图2 加入铜离子（5 μM）15 分钟后加入不同浓度环丙沙星（0-100 μM），5分钟后体系的荧光光谱图。Fig. 2 Fluorescence spectrum of the system after adding copper ions (5 μM) for 15 minutes and adding different concentrations of ciprofloxacin (0-100 μM) for 5 minutes.
图3 加入不同浓度铜离子后体系在紫外灯照射（365 nm）下的照片。Fig. 3 Photos of the system under UV light (365 nm) after adding different concentrations of copper ions.
图4 加入铜离子（5 μM）15 分钟后加入不同浓度环丙沙星（0-100 μM），5分钟后体系在紫外灯照射（365 nm）下的照片。Fig. 4 Adding copper ions (5 μM) for 15 minutes and adding different concentrations of ciprofloxacin (0-100 μM) for 15 minutes, and the photos of the system under ultraviolet light (365 nm) after 5 minutes.
图5 加入铜离子（5 μM）15 分钟后加入不同浓度环丙沙星（0-100 μM）5分钟后体系的紫外可见光谱图。Figure 5. The UV-Vis spectra of the system after adding copper ions (5 μM) for 15 minutes and adding different concentrations of ciprofloxacin (0-100 μM) for 5 minutes.
具体实施方式detailed description
下面将结合本发明实施例，对本发明的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有付出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。The technical solutions of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention. Obviously, the described embodiments are only some of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by persons of ordinary skill in the art without making creative efforts belong to the protection scope of the present invention.
实施例1Example 1
一种荧光碳点的制备，步骤如下：A preparation of fluorescent carbon dots, the steps are as follows:
称取1,3-二羟基萘0.0100 g（0.062 mmol）和盐酸多巴胺0.0118 g（0.062 mmol），溶于5 mL无水乙醇。两种溶液分别超声，使其完全溶解，将混合液转移至微波合成管中，于微波合成仪中160℃反应30分钟。反应结束后移出，10000转/分钟离心10分钟，去掉沉淀，超滤后保存为A液，或旋干保存粉末，使用时按照使用浓度溶解制备。Weigh 0.0100 g (0.062 mmol) of 1,3-dihydroxynaphthalene and 0.0118 g (0.062 mmol) of dopamine hydrochloride, and dissolve them in 5 mL of absolute ethanol. The two solutions were sonicated separately to dissolve them completely, and the mixture was transferred to a microwave synthesis tube, and reacted in a microwave synthesizer at 160°C for 30 minutes. Remove after the reaction, centrifuge at 10,000 rpm for 10 minutes, remove the precipitate, store it as liquid A after ultrafiltration, or spin dry to store the powder, and prepare it by dissolving according to the concentration used.
实施例2Example 2
一种检测环丙沙星的试剂盒，包括：A test kit for detecting ciprofloxacin, comprising:
（1）实施例1制备的A液，浓度为40μg/ml；(1) Liquid A prepared in Example 1, the concentration is 40 μg/ml;
（2）B液为硫酸铜溶液：称取CuSO4•5H2O 0.0125 g，溶于5 mL超纯水中，超声使其完全溶解。(2) Liquid B is a copper sulfate solution: weigh 0.0125 g of CuSO 4 •5H 2 O, dissolve it in 5 mL of ultrapure water, and dissolve it completely by ultrasonication.
（3）A液无荧光，加入B液后反应15分钟，测试荧光光谱。(3) Solution A has no fluorescence. After adding solution B, react for 15 minutes and test the fluorescence spectrum.
（4）在试剂盒的两种混合液中加入环丙沙星，由于环丙沙星与B液中的二价铜离子有较强的络合作用，反应后，混合液荧光减弱，检测方法为荧光关-开-关型。(4) Add ciprofloxacin to the two mixtures of the kit. Since ciprofloxacin has a strong complexation with divalent copper ions in liquid B, after the reaction, the fluorescence of the mixture weakens. The detection method Fluorescent off-on-off type.
（5）根据建立的工作曲线计算样本中的环丙沙星含量。(5) Calculate the content of ciprofloxacin in the sample according to the established working curve.
以上所述仅为本发明的较佳实施例而已，并不用以限制本发明，凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。The above descriptions are only preferred embodiments of the present invention, and are not intended to limit the present invention. Any modifications, equivalent replacements, improvements, etc. made within the spirit and principles of the present invention shall be included in the scope of the present invention. within the scope of protection.
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