CN114989188A - Fluorescent probe for detecting active amine and application thereof - Google Patents
Fluorescent probe for detecting active amine and application thereof Download PDFInfo
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- CN114989188A CN114989188A CN202210605309.8A CN202210605309A CN114989188A CN 114989188 A CN114989188 A CN 114989188A CN 202210605309 A CN202210605309 A CN 202210605309A CN 114989188 A CN114989188 A CN 114989188A
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Abstract
Description
技术领域technical field
本发明属于分析化学技术领域,具体涉及一种检测活性胺的荧光探针及其应用。The invention belongs to the technical field of analytical chemistry, and particularly relates to a fluorescent probe for detecting active amine and its application.
背景技术Background technique
生物活性胺是由腐烂动物组织中赖氨酸的细菌脱羧反应产生的一类最重要的生物源胺。它们通常存在于腐臭的高蛋白食物中,如肉和鱼。一旦形成,生物活性胺就会释放到周围环境中,并在大气中产生难闻的气味。生物活性伯二胺很容易通过摄入、吸入或皮肤接触进入人体,造成严重的健康危害,包括食物中毒、呼吸损伤和胃肠道损伤。因此,为了维持食品安全,有必要开发适当的技术来测定肉类和鱼类中的生物活性胺以便检测食物是否腐败。Bioactive amines are the most important class of biogenic amines produced by bacterial decarboxylation of lysine in decaying animal tissues. They are usually found in rancid, high-protein foods such as meat and fish. Once formed, bioactive amines are released into the surrounding environment and cause unpleasant odors in the atmosphere. Bioactive primary diamines can easily enter the human body through ingestion, inhalation or skin contact and cause serious health hazards including food poisoning, respiratory injury and gastrointestinal damage. Therefore, in order to maintain food safety, it is necessary to develop appropriate techniques for the determination of biologically active amines in meat and fish in order to detect food spoilage.
目前已经发展了多种检测生物活性胺的分析方法,包括气相色谱-质谱(GC-MS)、电化学、分光光度法和高效液相色谱法(HPLC)。然而,这些方法受限于样品制备繁琐、程序耗时以及仪器昂贵等问题。而基于发色团的荧光探针具有操作简便、灵敏度高、特异性强的特点,有利于生物胺的检测。科研工作者们对发色团与胺的相互作用机理提出了几种不同的解释,包括形成席夫碱、去质子化过程、氨基解反应、亲核加成、胺交换与环化等。这些手段丰富了监测生物二胺的方法,然而,这些探针仍然存在着一些局限性:少数在荧光“关闭”模式下工作,灵敏度相对较低,甚至为假阳性反应;探针的设计基于生物胺的碱性和亲核性,使探针容易受到其他胺的干扰;这些结构复杂的探针需要繁琐的制备过程。因此,迫切需要开发结构简单的小分子有机荧光探针,对食品中的生物二胺进行快速、高选择性的检测。Various analytical methods have been developed for the detection of biologically active amines, including gas chromatography-mass spectrometry (GC-MS), electrochemistry, spectrophotometry, and high performance liquid chromatography (HPLC). However, these methods are limited by cumbersome sample preparation, time-consuming procedures, and expensive instrumentation. The chromophore-based fluorescent probe has the characteristics of simple operation, high sensitivity and strong specificity, which is beneficial to the detection of biogenic amines. Researchers have proposed several different explanations for the interaction mechanism between chromophore and amine, including formation of Schiff base, deprotonation process, aminolysis reaction, nucleophilic addition, amine exchange and cyclization. These methods enrich the methods for monitoring biological diamines, however, these probes still have some limitations: a few work in the fluorescence "off" mode, the sensitivity is relatively low, and even false positive reactions; the design of the probes is based on biological The basicity and nucleophilicity of amines make the probes susceptible to interference from other amines; these structurally complex probes require a tedious preparation process. Therefore, there is an urgent need to develop small-molecule organic fluorescent probes with simple structures for rapid and highly selective detection of biological diamines in food.
发明内容SUMMARY OF THE INVENTION
针对现有技术中的问题,本发明提供一种检测生物活性胺的荧光探针,具有响应速度快、抗干扰能力强的特点。In view of the problems in the prior art, the present invention provides a fluorescent probe for detecting biologically active amines, which has the characteristics of fast response speed and strong anti-interference ability.
本发明的另一目的是提供一种上述荧光探针在食品腐败过程中的快速检测。Another object of the present invention is to provide a rapid detection of the above-mentioned fluorescent probe in the process of food spoilage.
为实现上述目的,本发明采用如下技术方案。In order to achieve the above objects, the present invention adopts the following technical solutions.
一种检测胺的荧光探针,2',7'-二氯-3-氧代-3H-螺环[异苯并呋喃-1,9'-黄嘌呤]-3',6'-二乙酸二酯,简称CHW-Cl,其化学结构式如式(I)所示:A fluorescent probe for the detection of amines, 2',7'-dichloro-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthine]-3',6'-diacetic acid Diester, referred to as CHW-Cl, its chemical structure is shown in formula (I):
式(I)。Formula (I).
所述胺为除氨基酸外的胺类化合物。优选地,所述胺选自腐胺、尸胺、精胺、亚精胺、酪胺、苯乙胺、组胺或色胺;最优选为尸胺。The amines are amine compounds other than amino acids. Preferably, the amine is selected from putrescine, cadaverine, spermine, spermidine, tyramine, phenethylamine, histamine or tryptamine; most preferably cadaverine.
上述荧光探针的制备方法,包括以下步骤:The preparation method of the above-mentioned fluorescent probe comprises the following steps:
(1)4-氯间苯二酚和邻苯二甲酸酐在过氧乙酸加热反应,反应结束后将反应混合物加入冰水中,过滤获得沉淀,洗涤后干燥,得到2′,7′-二氯荧光素:(1) 4-chlororesorcinol and phthalic anhydride are heated and reacted in peracetic acid. After the reaction is completed, the reaction mixture is added to ice water, filtered to obtain a precipitate, washed and dried to obtain 2′,7′-dichloromethane Fluorescein:
; ;
(2)4-二甲氨基吡啶和吡啶加入2′,7′-二氯荧光素的二氯甲烷的悬浮液中,滴加酰氯进行反应,反应结束后分离提纯,得到荧光探针:(2) 4-dimethylaminopyridine and pyridine are added to a suspension of 2′,7′-dichlorofluorescein in dichloromethane, acid chloride is added dropwise to carry out the reaction, and after the reaction is completed, separation and purification are performed to obtain a fluorescent probe:
。 .
步骤(1)中,所述加热反应的温度为90°C;加热时间为24h。In step (1), the temperature of described heating reaction is 90 ℃; Heating time is 24h.
步骤(2)中,所述分离提纯的步骤为:反应混合物加水稀释后以二氯甲烷萃取,有机相依次以饱和氯化铵溶液和饱和氯化钠溶液洗涤,有机相用无水硫酸镁干燥,抽滤,减压移除溶剂;用少量二氯甲烷溶解残余物,加入残余物等体积的中性硅胶粉,吸附后移除溶剂,将得到的粉末填柱;以体积比为10:4的环己烷:乙酸乙酯为层析液过硅胶柱,真空移除层析液,得到荧光探针。In step (2), the separation and purification steps are as follows: the reaction mixture is diluted with water and then extracted with dichloromethane, the organic phase is washed with saturated ammonium chloride solution and saturated sodium chloride solution in turn, and the organic phase is dried with anhydrous magnesium sulfate , suction filtration, and remove the solvent under reduced pressure; dissolve the residue with a small amount of dichloromethane, add an equal volume of neutral silica gel powder to the residue, remove the solvent after adsorption, and fill the column with the obtained powder; the volume ratio is 10:4 The cyclohexane:ethyl acetate is the chromatographic liquid and passes through the silica gel column, and the chromatographic liquid is removed in vacuo to obtain the fluorescent probe.
一种上述荧光探针在检测溶液和食品中活性胺的应用。An application of the above fluorescent probe in detecting active amines in solutions and foods.
本发明的机理如下:The mechanism of the present invention is as follows:
2',7'-二氯-3-氧代-3H-螺环[异苯并呋喃-1,9'-黄嘌呤]-3',6'-二乙酸二酯的两个乙酸酯基被活性胺进攻,先加成再消去,释放出羟基,五元环打开,π电子转移,形成一个大的共轭体系,产生强烈的荧光:Two acetate groups of 2',7'-dichloro-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthine]-3',6'-diacetic acid diester Attacked by an active amine, it is added and then eliminated to release a hydroxyl group, the five-membered ring is opened, and the π electrons are transferred to form a large conjugated system, resulting in strong fluorescence:
。 .
本发明具有以下优点:The present invention has the following advantages:
本发明提供的活性胺荧光探针属于小分子类荧光探针,目前针对活性胺识别的小分子荧光探针报道的并不多,尤其是快速检测生物腐败产生的活性胺的荧光探针更是鲜有报道。本发明提供的活性胺荧光探针,当向其加入活性胺后荧光显著增强,该结果及其现象为食品腐败检快速检测试纸的应用奠定了理论基础。The active amine fluorescent probe provided by the present invention belongs to the small molecule fluorescent probe. Currently, there are not many reports on the small molecule fluorescent probe recognized by the active amine, especially the fluorescent probe for rapidly detecting the active amine produced by biological spoilage. Rarely reported. In the active amine fluorescent probe provided by the present invention, when the active amine is added to the active amine fluorescent probe, the fluorescence is significantly enhanced, and the result and its phenomenon lay a theoretical foundation for the application of the rapid detection test paper for food spoilage detection.
附图说明Description of drawings
图1为探针CHW-Cl的氢谱;Fig. 1 is the hydrogen spectrum of probe CHW-Cl;
图2为探针CHW-Cl的碳谱;Fig. 2 is the carbon spectrum of probe CHW-Cl;
图3为探针CHW-Cl与尸胺(1,5-戊二胺)作用的滴定实验;其中激发波长为480 nm;探针的浓度:10 µM;Figure 3 shows the titration experiment of the probe CHW-Cl and cadaverine (1,5-pentanediamine); the excitation wavelength is 480 nm; the concentration of the probe: 10 µM;
图4为探针CHW-Cl与尸胺作用的动力学实验;其中激发波长为430 nm;探针的浓度:10 µM。尸胺浓度为275 µM,测试时间:100 min;Figure 4 shows the kinetic experiment of the interaction between the probe CHW-Cl and cadaverine; the excitation wavelength is 430 nm; the concentration of the probe: 10 µM. Cadaverine concentration 275 µM, test time: 100 min;
图5为探针CHW-Cl在无水乙醇中的选择性;其中激发波长为480 nm;探针的浓度:10 µM,选择性离子的浓度为10 mM,活性胺(尸胺)浓度为100 μM;Figure 5 shows the selectivity of the probe CHW-Cl in absolute ethanol; the excitation wavelength is 480 nm; the concentration of the probe is 10 µM, the concentration of the selective ion is 10 mM, and the concentration of the active amine (cadaverine) is 100 μM;
图6为同一根香蕉的多段在不同时间段下,与探针CHW-Cl作用后的照片;Fig. 6 is the photograph of the multi-segment of the same banana under different time periods, after the action of the probe CHW-Cl;
图7为同一批活泥鳅死亡后在不同时间段下,与浸泡里探针CHW-Cl溶液的干燥试纸作用后的照片。Figure 7 is a photo of the same batch of live loach that interacts with the dry test paper soaked in the CHW-Cl solution of the probe at different time periods after death.
具体实施方式Detailed ways
下面结合实施例和附图对本发明做进一步说明,但本发明不受下述实施例的限制。The present invention will be further described below with reference to the embodiments and the accompanying drawings, but the present invention is not limited by the following embodiments.
实施例1 荧光探针的合成Example 1 Synthesis of Fluorescent Probes
2',7'-二氯-3-氧代-3H-螺环[异苯并呋喃-1,9'-黄嘌呤]-3',6'-二乙酸二酯的合成:Synthesis of 2',7'-dichloro-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthine]-3',6'-diacetic acid diester:
将4-氯间苯二酚(14.4 g,99.6 mmol)和邻苯二甲酸酐(7.3 g,49.3 mmol)溶解在过氧乙酸(50 mL)中,并将所得溶液在90°C下加热24小时;冷却至室温,将反应混合物缓慢加入1 L冰水中搅拌,过滤后,用冰水洗涤沉淀并干燥,得到2′,7′-二氯荧光素,不用提纯,直接投下一步;4-Chlororesorcinol (14.4 g, 99.6 mmol) and phthalic anhydride (7.3 g, 49.3 mmol) were dissolved in peracetic acid (50 mL) and the resulting solution was heated at 90 °C for 24 After cooling to room temperature, the reaction mixture was slowly added to 1 L of ice water and stirred. After filtration, the precipitate was washed with ice water and dried to obtain 2′,7′-dichlorofluorescein, which was directly put into the next step without purification;
将4-二甲氨基吡啶(15μmol,0.1 eq)和吡啶(0.33 mmol,2.2 eq)添加到2′,7′-二氯荧光素(0.15 mmol,1 eq)和二氯甲烷(2.0 mL)的悬浮液中;逐滴添加酰氯(0.33 mmol,2.2 eq),并搅拌所得溶液1小时;用水稀释,用二氯甲烷萃取,用饱和氯化铵水溶液和饱和食盐水清洗有机相,将有机相用无水硫酸镁干燥,抽滤,减压移除溶剂;用少量二氯甲烷充分溶解残余物,加入与残余物体积近似相等的中性硅胶粉,充分搅拌后,真空移除溶剂,得到粗产物-硅胶粉的粉末,随后将其干法上柱;通过硅胶柱层析(环己烷:乙酸乙酯=10:4,体积比)纯化得到产品,即荧光探针;4-Dimethylaminopyridine (15 μmol, 0.1 eq) and pyridine (0.33 mmol, 2.2 eq) were added to a mixture of 2′,7′-dichlorofluorescein (0.15 mmol, 1 eq) and dichloromethane (2.0 mL) Suspension; acid chloride (0.33 mmol, 2.2 eq) was added dropwise, and the resulting solution was stirred for 1 hour; diluted with water, extracted with dichloromethane, the organic phase was washed with saturated aqueous ammonium chloride and saturated brine, and the organic phase was washed with dried over anhydrous magnesium sulfate, suction filtered, and the solvent was removed under reduced pressure; the residue was fully dissolved with a small amount of dichloromethane, neutral silica gel powder approximately equal in volume to the residue was added, and after thorough stirring, the solvent was removed in vacuo to obtain a crude product -The powder of silica gel powder, which is then dry-column; purified by silica gel column chromatography (cyclohexane:ethyl acetate=10:4, volume ratio) to obtain the product, that is, the fluorescent probe;
其中,1H NMR (500 MHz,DMSO-d6) δ 8.07 (d, J = 10.0 Hz, 1H), δ 7.83 (dt,J = 25.0 Hz, J =10.0 Hz, 2H), δ 7.59 (s, J = 0 Hz, 2H), δ 7.50 (d, J = 10.0Hz, 2H), δ 7.07 (s, J = 0 Hz, 2H), δ 2.36 (s, J =0, 6H);Wherein, 1 H NMR (500 MHz, DMSO-d 6 ) δ 8.07 (d, J = 10.0 Hz, 1H), δ 7.83 (dt, J = 25.0 Hz, J =10.0 Hz, 2H), δ 7.59 (s, J = 0 Hz, 2H), δ 7.50 (d, J = 10.0Hz, 2H), δ 7.07 (s, J = 0 Hz, 2H), δ 2.36 (s, J =0, 6H);
13C NMR (126 MHz, DMSO-d6) δ 168.46, 151.69, 149.80, 148.70, 136.59,131.34, 129.05, 126.00, 125.86, 124.54, 122.33, 118.26, 113.74, 40.50, 40.33,40.17, 40.00, 39.83, 39.66, 39.50, 20.85.; 13 C NMR (126 MHz, DMSO-D 6 ) Δ 168.46, 151.69, 149.80, 148.70, 136.59,131.34, 129.05, 126.00, 125.86, 124.54, 122.26, 113.74, 40.33,40.00.00.6.6.6.6.6.6.6.6.6.6.6.8. , 39.50, 20.85.;
1H NMR如图1;13C NMR如图2。 1 H NMR is shown in Figure 1; 13 C NMR is shown in Figure 2.
实施例2 荧光探针对不同浓度尸胺的响应Example 2 Response of fluorescent probes to different concentrations of cadaverine
配制5 mL浓度为1 mM尸胺的无水乙醇溶液及浓度为1 mM的实施例1制备的荧光探针母液作为备用。配制探针浓度为10 µM,分别与不同浓度的尸胺(0-275 μM)相互作用,并进行荧光检测(λex = 480 nm),计算各体系中荧光强度,建立荧光强度与尸胺浓度标准曲线。如图3所示,在测试浓度范围内,随着尸胺浓度的增加,反应体系荧光强度逐渐呈线性增加,经计算,检测限LOD为52.26nM。Prepare 5 mL of anhydrous ethanol solution of cadaverine with a concentration of 1 mM and the fluorescent probe stock solution prepared in Example 1 with a concentration of 1 mM as spares. Probes were prepared at a concentration of 10 µM, interacted with different concentrations of cadaverine (0-275 µM), and were subjected to fluorescence detection (λ ex = 480 nm), the fluorescence intensity in each system was calculated, and the fluorescence intensity and cadaverine concentration were established. standard curve line. As shown in Figure 3, within the tested concentration range, with the increase of the cadaverine concentration, the fluorescence intensity of the reaction system gradually increased linearly, and after calculation, the detection limit LOD was 52.26nM.
实施例3 荧光探针对饱和浓度尸胺的响应动力学Example 3 Response kinetics of fluorescent probes to saturated cadaverine
配制5 mL浓度为1 mM尸胺的无水乙醇溶液及浓度为1 mM的本发明所述检测活性胺的荧光探针母液作为备用。配制探针和尸胺的溶液,其浓度分别为:探针10 µM;尸胺浓度:275 μM。进行荧光检测(λex = 480 nm,),每隔5 min测试一次,测试100 min,计算各体系中随时间变化的荧光强度,建立荧光强度与作用时间标准曲线。如图4所示,大约反应90min,反应体系荧光强度达到饱和状态。Prepare 5 mL of anhydrous ethanol solution with a concentration of 1 mM cadaverine and a fluorescent probe stock solution for the detection of active amines according to the present invention with a concentration of 1 mM as backup. Prepare solutions of probe and cadaverine at the following concentrations: probe 10 µM; cadaverine concentration: 275 µM. Fluorescence detection (λ ex = 480 nm, ) was carried out, and the test was performed every 5 min for 100 min. The fluorescence intensity of each system was calculated over time, and a standard curve of fluorescence intensity and action time was established. As shown in Fig. 4, after about 90 minutes of reaction, the fluorescence intensity of the reaction system reached a saturated state.
实施例4 荧光探针对不同离子的选择性Example 4 Selectivity of fluorescent probes for different ions
配制5 mL浓度为10 mM的各种选择性试样的无水乙醇溶液及浓度为1 mM实施例1制备的荧光探针母液作为备用。加入20 μL探针母液和20 μL的各选择性试样溶液,摇匀后进行荧光检测(λex = 480 nm),建立荧光强度与各选择性试样的矩阵图,结果见图5,其中,1-18加入的离子分别为:过氧化氢、苯胺、乙二胺、腐胺、尸胺、正丙胺、甲醛、异亮氨酸、亚硫酸氢钠、组氨酸、丝氨酸、苯丙氨酸、半胱氨酸、亮氨酸、甘氨酸、精氨酸、赖氨酸和脯氨酸。60min后检测溶液的荧光发射光谱变化,由图5可以发现,绝大部分氨基酸和氧化性物质对化合物荧光素-Cl的荧光几乎没有影响,而乙二胺、腐胺、尸胺、正丙胺的加入使化合物荧光素-Cl的荧光显著增强。Prepare 5 mL of absolute ethanol solutions of various selective samples with a concentration of 10 mM and the fluorescent probe stock solution prepared in Example 1 with a concentration of 1 mM as spares. Add 20 μL of probe stock solution and 20 μL of each selective sample solution, shake well and perform fluorescence detection (λ ex = 480 nm), and establish a matrix diagram of fluorescence intensity and each selective sample. The results are shown in Figure 5, where , the ions added by 1-18 are respectively: hydrogen peroxide, aniline, ethylenediamine, putrescine, cadaverine, n-propylamine, formaldehyde, isoleucine, sodium bisulfite, histidine, serine, phenylalanine acid, cysteine, leucine, glycine, arginine, lysine and proline. After 60 minutes, the fluorescence emission spectrum changes of the solution were detected. From Figure 5, it can be found that most of the amino acids and oxidizing substances had almost no effect on the fluorescence of the compound fluorescein-Cl, while the fluorescence of ethylenediamine, putrescine, cadaverine, and n-propylamine had little effect. Addition significantly enhanced the fluorescence of the compound fluorescein-Cl.
应用例1 荧光探针与不同腐烂程度的香蕉作用Application Example 1 Interaction of fluorescent probes with bananas with different degrees of decay
配制浓度为50 μM的本发明所述检测活性胺的荧光探针母液作为备用。取一根完整新鲜的香蕉,剥掉外皮,取出四小块,分别放入四个样品瓶中,于0 h、5 h以及24 h后依次加入1 mL探针母液,盖好盖子放置十五分钟,放于暗箱式紫外分析仪中观察荧光亮度,并拍照记录,如图6所示。The fluorescent probe stock solution for detecting active amines according to the present invention with a concentration of 50 μM was prepared as a spare. Take a whole fresh banana, peel off the outer skin, take out four small pieces, put them into four sample bottles respectively, add 1 mL of probe mother solution after 0 h, 5 h and 24 h in turn, cover the lid and leave it for fifteen minutes, placed in a dark box UV analyzer to observe the fluorescence brightness, and photographed and recorded, as shown in Figure 6.
应用例2 荧光探针与不同腐烂程度的泥鳅作用Application Example 2 Interaction between fluorescent probes and loach with different degrees of decay
配制浓度为50 μM的本发明所述检测活性胺的荧光探针母液,用定性滤纸(快速)裁成四个等大的滤纸条,将其浸泡于探针母液中,吹干待用。取四条生长良好的活泥鳅,将其杀死后,分别放入四个干净的具塞锥形瓶,于0 h、5 h以及24 h后依次悬挂好处理好的滤纸条,盖好塞子放置15 min后,置于暗箱式紫外分析仪中观察荧光亮度,并拍照记录,如图7所示。The fluorescent probe mother solution for detecting active amines of the present invention with a concentration of 50 μM is prepared, and four equal-sized filter paper strips are cut with qualitative filter paper (quickly), soaked in the probe mother solution, and dried for use. Take four well-grown live loaches, kill them, and put them into four clean conical flasks with stoppers. After 0 h, 5 h and 24 h, hang the treated filter paper strips in turn, and close the stopper. After standing for 15 min, the fluorescence brightness was observed in a dark box UV analyzer, and photographed and recorded, as shown in Figure 7.
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