CN108752272B - 8-aminoquinoline amide derivative, preparation method, application and fluorescence analysis method thereof - Google Patents
8-aminoquinoline amide derivative, preparation method, application and fluorescence analysis method thereof Download PDFInfo
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Abstract
Hair brushThe invention discloses an 8-aminoquinoline amide derivative, a preparation method, application and a fluorescence analysis method thereof, wherein the preparation method of the 8-aminoquinoline amide derivative comprises the following steps: 1a) weighing N-bromoacetyl-8-aminoquinoline, propynylamine and acetonitrile, dissolving the N-bromoacetyl-8-aminoquinoline and the propynylamine in the acetonitrile, and then adding potassium carbonate to obtain a reaction mixture; 2a) stirring the reaction mixture obtained in the step 1a) at room temperature for reaction, filtering and removing the solvent, and then eluting by column chromatography to obtain the 8-aminoquinoline amide derivative, wherein the 8-aminoquinoline amide derivative can be applied to the field of fluorescent probes, and the derivative, the preparation method and the application thereof, and the method for performing fluorescence analysis based on the derivative can simultaneously perform fluorescence analysis on Zn2+And Cd2+And (6) detecting.
Description
Technical Field
The invention relates to a derivative, a preparation method and application thereof, and a method for fluorescence analysis based on the derivative, in particular to an 8-aminoquinoline amide derivative, a preparation method and application thereof, and a method for fluorescence analysis of the derivative.
Background
Metals are generally present in ionic form in living organisms, and they play a very important role in various physiological and pathological processes of living organisms. Zinc ion (Zn)2+) The natural flower has higher content, is the second most necessary element of human body, and is known as the 'life flower' of human body. Proper amount of Zn in human body2+Can help wound healing, promote infant growth, and maintain normal functions of taste and smell. Lack of Zn2+Can cause a plurality of diseases such as slow development, dysnoesia, decline of immunity and reproductive function, and the like; zn2+Excessive intake can also cause diseases such as alzheimer's disease, prostatic hyperplasia, immune system disorders, and acute renal failure. Cadmium ion (Cd)2+) The method is widely applied to industrial production of smelting, electroplating and the like of minerals, and is one of a plurality of heavy metal pollutants. By ingestion of contaminated food and water, Cd2+Can enter into organism through digestive system and is difficult to excrete, and then is enriched in liver and kidney, and interferes with renal function and reproductive function, causing serious diseases such as renal insufficiency, calcium metabolism disorder and cancer. Therefore, development for convenient and efficient analysis and detection of Zn2+And Cd2+The reagent and the method have important research significance and application value.
In a plurality of assaysDetection of Zn2+And Cd2+Of the methods (2), the fluorescent probe technology has attracted extensive attention and rapidly developed due to its excellent properties of non-invasiveness to samples, particularly biological samples, highly sensitive response to analytes under specific conditions, convenience of detection, and capability of performing trace analysis (Zn)2+A fluorescent probe: sens.actors B-chem.2018, 254: 533 and 541; j.mater.chem.c 2017, 5: 9651-; sens.activators B-chem.2017, 245: 129-136; sens.actors B-chem.2017, 244: 1045-1053; j.photochem.photoobiol.a 2017, 334: 86-100 parts of; synth.met.2017, 232: 17-24; methods 2017, 9: 1119-1124; sens.activators B-chem.2016, 227: 242-247; RSC adv.2016, 6: 11388, 11399; photochem. photobiol.a 2016, 321: 99 to 109; lumines.2016, 177: 40-47; sens.actuators B-chem.2015, 207: 563 and 570; RSC adv.2015, 5: 44463 and 44469; RSC adv.2015, 5: 41905-41913; sens.actors B-chem.2013, 176: 775-781; cd [ Cd ]2+A fluorescent probe: sens.actors B-chem.2017, 251: 877-884; dye pigment.2017, 139: 208-217; org.biomol.chem.2017, 15: 2211-2216; new j. chem.2017, 41: 14746-14753; j.fluorosc.2017, 27: 1109-1115; hem.eur.j.2016, 22: 8579-8585; dye pigment.2016, 133: 339 and 344; tetrahedron 2016, 72: 3213-3220; dalton trans.2015, 44: 5763-; dalton trans.2015, 44: 104-; tetrahedron lett.2015, 56: 1322-1327; sens.activators B-chem.2014, 204: 655 and 658; j.phys.chem.a 2011, 115: 8234-8241). However, Zn has been reported so far2+And Cd2+Most of the fluorescent probes are monoselective probes and can only detect Zn2+And Cd2+One of which is a metal ion. At the same time, due to Zn2+And Cd2+Are all group IIB elements, have highly similar physical and chemical properties, and contain much Zn2+And Cd2+The monoselective fluorescent probe showed to be specific for Zn2+And Cd2+Similar fluorescent response signals, causing interference with the detection of both ions. And, these Zn2+And Cd2+Most fluorescent probes are based on single emission peak intensity analysis and are easily subjected to instrumentsThe interference of various external factors such as errors, change of detection environment, human errors and the like on the fluorescence detection signal.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides an 8-aminoquinoline amide derivative, a preparation method, an application and a fluorescence analysis method thereof, and the derivative, the preparation method, the application and the fluorescence analysis method thereof can simultaneously carry out Zn2+And Cd2+And (6) detecting.
In order to achieve the purpose, the chemical structure of the 8-aminoquinoline amide derivative is
The preparation method of the 8-aminoquinoline amide derivative comprises the following steps:
1a) weighing N-bromoacetyl-8-aminoquinoline, propynylamine and acetonitrile, dissolving the N-bromoacetyl-8-aminoquinoline and the propynylamine in the acetonitrile, and then adding potassium carbonate to obtain a reaction mixture, wherein the proportion of the N-bromoacetyl-8-aminoquinoline, the propynylamine, the potassium carbonate and the acetonitrile is 100 mg: (20-70) mg: (50-100) mg: (5-10) mL;
2a) stirring the reaction mixture obtained in the step 1a) at room temperature for reaction, filtering and removing the solvent, and then eluting by column chromatography to obtain the 8-aminoquinoline amide derivative.
The room-temperature stirring reaction in the step 2a) lasts for 12-36 h;
in the specific process of column chromatography elution in the step 2a), a mixture of petroleum ether and ethyl acetate with the boiling point of 60-90 ℃ is used as an eluent for elution, wherein the volume ratio of the petroleum ether to the ethyl acetate is (5-20): 1.
Said 8-aminoquinoline amide derivative as Zn2+Application of fluorescent probe.
The 8-aminoquinoline amide derivative of the invention is Zn2+The method of performing fluorescence analysis comprises the steps of:
1b) weighing 8-aminoquinoline amide derivatives and acetonitrile, and dissolving the 8-aminoquinoline amide derivatives in the acetonitrile to obtain acetonitrile solution of the 8-aminoquinoline amide derivatives, wherein the concentration of the 8-aminoquinoline amide derivatives in the acetonitrile solution of the 8-aminoquinoline amide derivatives is (1-10) mM;
2b) putting the acetonitrile solution of the 8-aminoquinoline amide derivative obtained in the step 1b) into a centrifuge tube, and then respectively adding M groups of Zn with different volumes into the centrifuge tube2+Performing constant volume on the standard solution by using HEPES buffer solution to obtain M groups of mixed solutions, wherein the concentration of the 8-aminoquinoline amide derivative in the M groups of mixed solutions is (10-50) mu M, and the 8-aminoquinoline amide derivative and Zn in the M groups of mixed solutions2+The ratio of the amounts of substances of (a) to (b) is 1: (0-5), then placing the obtained M groups of mixed solutions into a constant-temperature water bath for heat preservation, respectively placing the M groups of mixed solutions into a quartz cuvette after the effects are balanced, then measuring the fluorescence emission spectra of the M groups of mixed solutions, and finally carrying out Zn comparison according to the fluorescence emission spectra of the M groups of mixed solutions2+Fluorescence analysis was performed.
Placing the obtained M groups of mixed solution in the step 2b) into a thermostatic water bath at 25 ℃ for heat preservation (5-10) min;
in the process of measuring the fluorescence emission spectrum of the M groups of mixed solutions in the step 2b), the excitation and emission slit width is (2.5-5) nm, the voltage of the photomultiplier is 700V, and the excitation is carried out through the wavelength of (320-350) nm.
The 8-aminoquinoline amide derivative is used as Cd2+Application of fluorescent probe.
The 8-aminoquinoline amide derivative of the invention is Cd2+The method of performing fluorescence analysis comprises the steps of:
1c) weighing 8-aminoquinoline amide derivatives and acetonitrile, and dissolving the 8-aminoquinoline amide derivatives in the acetonitrile to obtain acetonitrile solution of the 8-aminoquinoline amide derivatives, wherein the concentration of the 8-aminoquinoline amide derivatives in the acetonitrile solution of the 8-aminoquinoline amide derivatives is (1-10) mM;
2c) putting the acetonitrile solution of the 8-aminoquinoline amide derivative obtained in the step 1c) into a centrifugal tube, and then dividing the centrifugal tube into the centrifugal tubeAdding N groups of Cd with different volumes2+Performing constant volume on the standard solution by acetonitrile to obtain N groups of mixed solutions, wherein the concentration of the 8-aminoquinoline amide derivative in the N groups of mixed solutions is (10-50) mu M, and the 8-aminoquinoline amide derivative and Cd in the N groups of mixed solutions2+The ratio of the amounts of substances of (a) to (b) is 1: (0-4.2), then placing the obtained N groups of mixed solutions into a constant-temperature water bath for heat preservation, respectively placing the N groups of mixed solutions into a quartz cuvette after the action is balanced, measuring the fluorescence emission spectra of the N groups of mixed solutions, and finally carrying out Cd pairing on Cd according to the fluorescence emission spectra of the N groups of mixed solutions2+Fluorescence analysis was performed.
Placing the N groups of mixed solution obtained in the step 2c) into a thermostatic water bath at 25 ℃ for heat preservation (5-10) min;
in the process of measuring the fluorescence emission spectra of the N groups of mixed solutions in the step 2c), the excitation and emission slit width is (2.5-5) nm, the photomultiplier voltage is 700V, and the excitation is performed with the wavelength of 330-350 nm.
The invention has the following beneficial effects:
the 8-aminoquinoline amide derivative, the preparation method, the application and the fluorescence analysis method thereof select and introduce 8-aminoquinoline which has excellent spectral performance and is easy to combine with metal ions as a fluorophore during specific operation, improve the selectivity of metal ions by utilizing the deprotonation and isomerization characteristics of an amide structure in the 8-aminoquinoline amide derivative, and introduce a propynyl amine group in the 8-aminoquinoline amide derivative to form a proper cavity structure so as to coordinate with the metal ions. Therefore, the 8-aminoquinoline amide derivative can detect Zn in different solvents in a distinguishing way through different binding modes of metal ions and ligands2+And Cd2+. In water, three N atoms and alkynyl groups in 8-aminoquinoline amide derivatives and Zn2+Coordination is carried out and deprotonation of the hydrogen on the amide takes place; in acetonitrile, amide in the 8-aminoquinoline amide derivative is isomerized to form an enol structure with C ═ N double bonds, and three N atoms and alkynyl after isomerization are reacted with Cd2+Coordination is carried out to achieve binding by different binding mechanismsRealize the differential detection of Zn in different solvents2+And Cd2+The purpose of (1). In addition, 8-aminoquinoline amide derivatives bind to Zn separately2+And Cd2+After ionization, obvious new fluorescence emission peak is generated in the long wave direction of the original fluorescence emission peak, so that Zn can be respectively treated in different solvents2+And Cd2+The dual-wavelength fluorescence ratio detection effectively reduces the interference of factors such as external environment change and the like on fluorescence signal measurement, and has high detection specificity. Experiments prove that other common metal ions in water can be used for Zn in the detection process2+Does not generate obvious interference; in acetonitrile, other common metal ion pairs Cd2+The analysis of (2) does not generate obvious interference, the detection sensitivity is high, and Zn is used as2+Or Cd2+The obvious fluorescent response can be generated when the concentration is 4 mu M, the response time is short, and Zn is favored2+Or Cd2+The rapid detection of (2). Finally, the 8-aminoquinoline amide derivative provided by the invention is a bifunctional ratio type fluorescent probe, has the advantages of simple synthesis method, low synthesis cost, high detection efficiency, convenience in detection and simplicity in operation, and has wide application prospects in the fields of environment, biology and the like.
Drawings
FIG. 1a is a graph showing fluorescence response spectra of 8-aminoquinoline amide derivatives of the present invention to various common metal ions in water;
FIG. 1b is a photograph showing the response of 8-aminoquinoline amide derivatives of the present invention to various common metal ions in water under 365nm UV light;
FIG. 2a is a graph showing fluorescence response spectra of 8-aminoquinoline amide derivatives of the present invention to various common metal ions in acetonitrile;
FIG. 2b is a photograph of 8-aminoquinoline amide derivatives of the present invention responding to various common metal ions in acetonitrile under 365nm UV lamp irradiation;
FIG. 3a shows the interaction of 8-aminoquinoline amide derivatives of the present invention with Zn in water2+Performing a fluorescence emission spectrum of the fluorescence analysis;
FIG. 3b is a diagram showing 8-aminoquinoline amide derivatives according to the present inventionDetection of Zn in water by organisms2+Fluorescence intensity of (2) to Zn2+Working curve graph of concentration;
FIG. 4a shows the control of Cd in acetonitrile by 8-aminoquinoline amide derivatives of the present invention2+Performing a fluorescence emission spectrum of the fluorescence analysis;
FIG. 4b shows the detection of Cd in acetonitrile by 8-aminoquinoline amide derivatives of the present invention2+Fluorescence intensity of (2) to Cd2+Working curve graph of concentration;
FIG. 5a shows the detection of Zn in water by 8-aminoquinoline amide derivatives of the present invention2+Working curve of fluorescence intensity versus time of action of (a);
FIG. 5b shows the detection of Cd in acetonitrile by 8-aminoquinoline amide derivatives of the present invention2+Working plot of fluorescence intensity versus time of action.
Detailed Description
The invention is described in further detail below with reference to the accompanying drawings:
the chemical structure of the 8-aminoquinoline amide derivative is
Example one
The preparation method of the 8-aminoquinoline amide derivative comprises the following steps:
1a) weighing N-bromoacetyl-8-aminoquinoline, propynylamine and acetonitrile, dissolving the N-bromoacetyl-8-aminoquinoline and the propynylamine in the acetonitrile, and then adding potassium carbonate to obtain a reaction mixture, wherein the proportion of the N-bromoacetyl-8-aminoquinoline, the propynylamine, the potassium carbonate and the acetonitrile is 100 mg: 20 mg: 100 mg: 5 mL;
2a) stirring the reaction mixture obtained in the step 1a) at room temperature for reaction, filtering and removing the solvent, and then eluting by column chromatography to obtain the 8-aminoquinoline amide derivative.
The room-temperature stirring reaction in the step 2a) lasts for 36 h;
in the specific process of column chromatography elution in the step 2a), a mixture of petroleum ether and ethyl acetate with the boiling point of 60-90 ℃ is used as an eluent for elution, wherein the volume ratio of the petroleum ether to the ethyl acetate is 20: 1.
Example two
The preparation method of the 8-aminoquinoline amide derivative comprises the following steps:
1a) weighing N-bromoacetyl-8-aminoquinoline, propynylamine and acetonitrile, dissolving the N-bromoacetyl-8-aminoquinoline and the propynylamine in the acetonitrile, and then adding potassium carbonate to obtain a reaction mixture, wherein the proportion of the N-bromoacetyl-8-aminoquinoline, the propynylamine, the potassium carbonate and the acetonitrile is 100 mg: 70 mg: 50 mg: 10 mL;
2a) stirring the reaction mixture obtained in the step 1a) at room temperature for reaction, filtering and removing the solvent, and then eluting by column chromatography to obtain the 8-aminoquinoline amide derivative.
The room-temperature stirring reaction in the step 2a) lasts for 12 hours;
in the specific process of column chromatography elution in the step 2a), a mixture of petroleum ether and ethyl acetate with the boiling point of 60-90 ℃ is used as an eluent for elution, wherein the volume ratio of the petroleum ether to the ethyl acetate is 5: 1.
EXAMPLE III
The preparation method of the 8-aminoquinoline amide derivative comprises the following steps:
1a) weighing N-bromoacetyl-8-aminoquinoline, propynylamine and acetonitrile, dissolving the N-bromoacetyl-8-aminoquinoline and the propynylamine in the acetonitrile, and then adding potassium carbonate to obtain a reaction mixture, wherein the proportion of the N-bromoacetyl-8-aminoquinoline, the propynylamine, the potassium carbonate and the acetonitrile is 100 mg: 50 mg: 80 mg: 8 mL;
2a) stirring the reaction mixture obtained in the step 1a) at room temperature for reaction, filtering and removing the solvent, and then eluting by column chromatography to obtain the 8-aminoquinoline amide derivative.
The room-temperature stirring reaction in the step 2a) lasts for 25 hours;
in the specific process of column chromatography elution in the step 2a), a mixture of petroleum ether and ethyl acetate with the boiling point of 60-90 ℃ is used as an eluent for elution, wherein the volume ratio of the petroleum ether to the ethyl acetate is 12: 1.
Example four
The preparation method of the 8-aminoquinoline amide derivative comprises the following steps:
1a) weighing N-bromoacetyl-8-aminoquinoline, propynylamine and acetonitrile, dissolving the N-bromoacetyl-8-aminoquinoline and the propynylamine in the acetonitrile, and then adding potassium carbonate to obtain a reaction mixture, wherein the proportion of the N-bromoacetyl-8-aminoquinoline, the propynylamine, the potassium carbonate and the acetonitrile is 100 mg: 30 mg: 60 mg: 6 mL;
2a) stirring the reaction mixture obtained in the step 1a) at room temperature for reaction, filtering and removing the solvent, and then eluting by column chromatography to obtain the 8-aminoquinoline amide derivative.
The room-temperature stirring reaction in the step 2a) lasts for 15 h;
in the specific process of column chromatography elution in the step 2a), a mixture of petroleum ether and ethyl acetate with the boiling point of 60-90 ℃ is used as an eluent for elution, wherein the volume ratio of the petroleum ether to the ethyl acetate is 8: 1.
EXAMPLE five
The preparation method of the 8-aminoquinoline amide derivative comprises the following steps:
1a) weighing N-bromoacetyl-8-aminoquinoline, propynylamine and acetonitrile, dissolving the N-bromoacetyl-8-aminoquinoline and the propynylamine in the acetonitrile, and then adding potassium carbonate to obtain a reaction mixture, wherein the proportion of the N-bromoacetyl-8-aminoquinoline, the propynylamine, the potassium carbonate and the acetonitrile is 100 mg: 60 mg: 90 mg: 8 mL;
2a) stirring the reaction mixture obtained in the step 1a) at room temperature for reaction, filtering and removing the solvent, and then eluting by column chromatography to obtain the 8-aminoquinoline amide derivative.
The room-temperature stirring reaction in the step 2a) lasts for 30 hours;
in the specific process of column chromatography elution in the step 2a), a mixture of petroleum ether and ethyl acetate with the boiling point of 60-90 ℃ is used as an eluent for elution, wherein the volume ratio of the petroleum ether to the ethyl acetate is 18: 1.
The 8-aminoquinoline amide derivative is subjected to nuclear magnetic resonance hydrogen spectrum measurement and nuclear magnetic resonance carbon spectrum measurement respectively, and the measurement results are as follows:
hydrogen nuclear magnetic resonance spectroscopy:1H NMR(400MHz,CDCl3)，δ(ppm)：2.05(br，1H)，2.28(t，J＝2.4Hz，1H)，3.61(d，J＝2.4Hz，2H)，3.69(s，2H)，7.42–7.45(m，1H)，7.49–7.55(m，2H)，8.14(dd，J＝1.6，8.3Hz，1H)，8.81(dd，J＝2.0，7.0Hz，1H)，8.84(dd，J＝1.6，4.2Hz，1H)，11.12(br，1H)。
nuclear magnetic resonance carbon spectrum measurement:13C NMR(100MHz，CDCl3)，δ(ppm)：38.1，52.0，72.1，81.1，116.5，121.5，121.7，127.2，128.0，134.0，136.1，138.8，148.5，169.6。
said 8-aminoquinoline amide derivative as Zn2+Application of fluorescent probe.
EXAMPLE six
The 8-aminoquinoline amide derivative of the invention is Zn2+The method of performing fluorescence analysis comprises the steps of:
1b) weighing 8-aminoquinoline amide derivatives and acetonitrile, and dissolving the 8-aminoquinoline amide derivatives in the acetonitrile to obtain acetonitrile solution of the 8-aminoquinoline amide derivatives, wherein the concentration of the 8-aminoquinoline amide derivatives in the acetonitrile solution of the 8-aminoquinoline amide derivatives is 10 mM;
2b) putting the acetonitrile solution of the 8-aminoquinoline amide derivative obtained in the step 1b) into a centrifuge tube, and then respectively adding 26 groups of Zn with different volumes into the centrifuge tube2+Performing constant volume on the standard solution by using HEPES buffer solution to obtain 26 groups of mixed solutions, wherein the concentration of the 8-aminoquinoline amide derivative in the 26 groups of mixed solutions is 20 mu M, and the 8-aminoquinoline amide derivative and Zn in the 26 groups of mixed solutions are2+The ratio of the amounts of the substances of (a) to (b) is 1: 0. 1: 0.2, 1: 0.4, 1: 0.6, 1: 0.8, 1: 1. 1: 1.2, 1: 1.4, 1: 1.6, 1: 1.8, 1: 2. 1: 2.2, 1: 2.4, 1: 2.6, 1: 2.8, 1: 3. 1: 3.2, 1: 3.4, 1: 3.6, 1: 3.8, 1: 4. 1: 4.2, 1: 4.4, 1: 4.6, 1: 4.8 and 1: 5, then placing the 26 groups of mixed solutions into a constant-temperature water bath for heat preservation, respectively placing the 26 groups of mixed solutions into a quartz cuvette after the effects are balanced, then measuring the fluorescence emission spectra of the 26 groups of mixed solutions, and finally carrying out Zn treatment according to the fluorescence emission spectra of the 26 groups of mixed solutions2+Fluorescence analysis was performed.
Placing the 26 groups of mixed solutions obtained in the step 2b) into a thermostatic water bath at 25 ℃ for heat preservation for 10 min;
in the process of measuring the fluorescence emission spectrum of the 26 groups of mixed solutions in the step 2b), the width of the excitation and emission slit is 5nm, the voltage of the photomultiplier is 700V, and the excitation is carried out by the wavelength of 321 nm.
EXAMPLE seven
The 8-aminoquinoline amide derivative of the invention is Zn2+The method of performing fluorescence analysis comprises the steps of:
1b) weighing 8-aminoquinoline amide derivatives and acetonitrile, and dissolving the 8-aminoquinoline amide derivatives in the acetonitrile to obtain acetonitrile solution of the 8-aminoquinoline amide derivatives, wherein the concentration of the 8-aminoquinoline amide derivatives in the acetonitrile solution of the 8-aminoquinoline amide derivatives is 1 mM;
2b) putting the acetonitrile solution of the 8-aminoquinoline amide derivative obtained in the step 1b) into a centrifuge tube, and then respectively adding 14 groups of Zn with different volumes into the centrifuge tube2+Performing constant volume on the standard solution by using HEPES buffer solution to obtain 14 groups of mixed solutions, wherein the concentration of the 8-aminoquinoline amide derivative in the 14 groups of mixed solutions is 50 mu M, and the 8-aminoquinoline amide derivative and Zn in the 14 groups of mixed solutions are2+The ratio of the amounts of substances of (a) to (b) is 1: 0. 1: 0.4, 1: 0.8, 1: 1.2, 1: 1.4, 1: 1.8, 1: 2.2, 1: 2.6, 1: 3. 1: 3.4, 1: 3.8, 1: 4.2, 1: 4.6 and 1: 5, then placing the obtained 14 groups of mixed solutions into a constant-temperature water bath for heat preservation, respectively placing the 14 groups of mixed solutions into a quartz cuvette after the effects are balanced, then measuring the fluorescence emission spectra of the 14 groups of mixed solutions, and finally carrying out Zn treatment according to the fluorescence emission spectra of the 14 groups of mixed solutions2+To perform fluorescenceAnd (4) performing light analysis.
Placing the 14 groups of mixed solutions obtained in the step 2b) into a thermostatic water bath at 25 ℃ for heat preservation for 5 min;
in the process of measuring the fluorescence emission spectrum of the 14 groups of mixed solutions in the step 2b), the excitation and emission slit width is 2.5nm, the voltage of the photomultiplier is 700V, and the excitation is carried out by the wavelength of 350 nm.
Example eight
The 8-aminoquinoline amide derivative of the invention is Zn2+The method of performing fluorescence analysis comprises the steps of:
1b) weighing 8-aminoquinoline amide derivatives and acetonitrile, and dissolving the 8-aminoquinoline amide derivatives in the acetonitrile to obtain acetonitrile solution of the 8-aminoquinoline amide derivatives, wherein the concentration of the 8-aminoquinoline amide derivatives in the acetonitrile solution of the 8-aminoquinoline amide derivatives is 10 mM;
2b) putting the acetonitrile solution of the 8-aminoquinoline amide derivative obtained in the step 1b) into a centrifuge tube, and then respectively adding 26 groups of Zn with different volumes into the centrifuge tube2+Performing constant volume on the standard solution by using HEPES buffer solution to obtain 26 groups of mixed solutions, wherein the concentration of the 8-aminoquinoline amide derivative in the 26 groups of mixed solutions is 10 mu M, and the 8-aminoquinoline amide derivative and Zn in the 26 groups of mixed solutions are2+The ratio of the amounts of the substances of (a) to (b) is 1: 0. 1: 0.2, 1: 0.4, 1: 0.6, 1: 0.8, 1: 1. 1: 1.2, 1: 1.4, 1: 1.6, 1: 1.8, 1: 2. 1: 2.2, 1: 2.4, 1: 2.6, 1: 2.8, 1: 3. 1: 3.2, 1: 3.4, 1: 3.6, 1: 3.8, 1: 4. 1: 4.2, 1: 4.4, 1: 4.6, 1: 4.8, 1: 5, then placing the 26 groups of mixed solutions into a constant-temperature water bath for heat preservation, respectively placing the 26 groups of mixed solutions into a quartz cuvette after the effects are balanced, then measuring the fluorescence emission spectra of the 26 groups of mixed solutions, and finally carrying out Zn treatment according to the fluorescence emission spectra of the 26 groups of mixed solutions2+Fluorescence analysis was performed.
Placing the 26 groups of mixed solutions obtained in the step 2b) into a thermostatic water bath at 25 ℃ for heat preservation for 10 min;
in the process of measuring the fluorescence emission spectrum of the 26 groups of mixed solutions in the step 2b), the width of the excitation and emission slit is 5nm, the voltage of the photomultiplier is 700V, and the excitation is carried out through the wavelength of 320 nm.
Example nine
The 8-aminoquinoline amide derivative of the invention is Zn2+The method of performing fluorescence analysis comprises the steps of:
1b) weighing 8-aminoquinoline amide derivatives and acetonitrile, and dissolving the 8-aminoquinoline amide derivatives in the acetonitrile to obtain acetonitrile solution of the 8-aminoquinoline amide derivatives, wherein the concentration of the 8-aminoquinoline amide derivatives in the acetonitrile solution of the 8-aminoquinoline amide derivatives is 2 mM;
2b) putting the acetonitrile solution of the 8-aminoquinoline amide derivative obtained in the step 1b) into a centrifuge tube, and then respectively adding 26 groups of Zn with different volumes into the centrifuge tube2+Performing constant volume on the standard solution by using HEPES buffer solution to obtain 26 groups of mixed solutions, wherein the concentration of the 8-aminoquinoline amide derivative in the 26 groups of mixed solutions is 20 mu M, and the 8-aminoquinoline amide derivative and Zn in the 26 groups of mixed solutions are2+The ratio of the amounts of the substances of (a) to (b) is 1: 0. 1: 0.2, 1: 0.4, 1: 0.6, 1: 0.8, 1: 1. 1: 1.2, 1: 1.4, 1: 1.6, 1: 1.8, 1: 2. 1: 2.2, 1: 2.4, 1: 2.6, 1: 2.8, 1: 3. 1: 3.2, 1: 3.4, 1: 3.6, 1: 3.8, 1: 4. 1: 4.2, 1: 4.4, 1: 4.6, 1: 4.8, 1: 5, then placing the 26 groups of mixed solutions into a constant-temperature water bath for heat preservation, respectively placing the 26 groups of mixed solutions into a quartz cuvette after the effects are balanced, then measuring the fluorescence emission spectra of the 26 groups of mixed solutions, and finally carrying out Zn treatment according to the fluorescence emission spectra of the 26 groups of mixed solutions2+Fluorescence analysis was performed.
Placing the 26 groups of mixed solutions obtained in the step 2b) into a thermostatic water bath at 25 ℃ for heat preservation for 8 min;
in the process of measuring the fluorescence emission spectrum of the 26 groups of mixed solutions in the step 2b), the width of the excitation and emission slit is 5nm, the voltage of the photomultiplier is 700V, and the excitation is carried out by the wavelength of 340 nm.
Example ten
The invention is as described8-aminoquinoline amide derivative of (2) p-Zn2+The method of performing fluorescence analysis comprises the steps of:
1b) weighing 8-aminoquinoline amide derivatives and acetonitrile, and dissolving the 8-aminoquinoline amide derivatives in the acetonitrile to obtain acetonitrile solution of the 8-aminoquinoline amide derivatives, wherein the concentration of the 8-aminoquinoline amide derivatives in the acetonitrile solution of the 8-aminoquinoline amide derivatives is 8 mM;
2b) putting the acetonitrile solution of the 8-aminoquinoline amide derivative obtained in the step 1b) into a centrifuge tube, and then respectively adding 13 groups of Zn with different volumes into the centrifuge tube2+Performing constant volume on the standard solution by using HEPES buffer solution to obtain 13 groups of mixed solutions, wherein the concentration of the 8-aminoquinoline amide derivative in the 13 groups of mixed solutions is 40 mu M, and the 8-aminoquinoline amide derivative and Zn in the 13 groups of mixed solutions2+The ratio of the amounts of the substances of (a) to (b) is 1: 0. 1: 0.4, 1: 1. 1: 1.2, 1: 1.8, 1: 2.4, 1: 2.6, 1: 3.2, 1: 3.4, 1: 4. 1: 4.6, 1: 4.8 and 1: and 5, then placing the 13 groups of mixed solutions into a constant-temperature water bath for heat preservation, respectively placing the 13 groups of mixed solutions into a quartz cuvette after the effects are balanced, then measuring the fluorescence emission spectra of the 13 groups of mixed solutions, and finally carrying out Zn treatment according to the fluorescence emission spectra of the 13 groups of mixed solutions2+Fluorescence analysis was performed.
Placing the 13 groups of mixed solutions obtained in the step 2b) into a thermostatic water bath at 25 ℃ for heat preservation for 9 min;
in the process of measuring the fluorescence emission spectrum of the 13 groups of mixed solutions in the step 2b), the width of the excitation and emission slit is 2.5nm, the voltage of the photomultiplier is 700V, and the excitation is carried out by the wavelength of 340 nm.
The 8-aminoquinoline amide derivative is used as Cd2+Application of fluorescent probe.
EXAMPLE eleven
The 8-aminoquinoline amide derivative of the invention is Cd2+The method of performing fluorescence analysis comprises the steps of:
1c) weighing 8-aminoquinoline amide derivatives and acetonitrile, and dissolving the 8-aminoquinoline amide derivatives in the acetonitrile to obtain acetonitrile solution of the 8-aminoquinoline amide derivatives, wherein the concentration of the 8-aminoquinoline amide derivatives in the acetonitrile solution of the 8-aminoquinoline amide derivatives is 10 mM;
2c) putting the acetonitrile solution of the 8-aminoquinoline amide derivative obtained in the step 1c) into a centrifugal tube, and respectively adding 22 groups of Cd with different volumes into the centrifugal tube2+Standard solution, then fixing the volume by acetonitrile to obtain 22 groups of mixed solution, wherein the concentration of the 8-aminoquinoline amide derivative in the 22 groups of mixed solution is 20 mu M, and the 8-aminoquinoline amide derivative and Cd in the 22 groups of mixed solution2+The ratio of the amounts of the substances of (a) to (b) is 1: 0. 1: 0.2, 1: 0.4, 1: 0.6, 1: 0.8, 1: 1. 1: 1.2, 1: 1.4, 1: 1.6, 1: 1.8, 1: 2. 1: 2.2, 1: 2.4, 1: 2.6, 1: 2.8, 1: 3. 1: 3.2, 1: 3.4, 1: 3.6, 1: 3.8, 1: 4 and 1: 4.2, then placing the obtained 22 groups of mixed solutions into a constant-temperature water bath for heat preservation, respectively placing the 22 groups of mixed solutions into a quartz cuvette after the effects are balanced, measuring the fluorescence emission spectra of the 22 groups of mixed solutions, and finally carrying out Cd pairing on Cd according to the fluorescence emission spectra of the 22 groups of mixed solutions2+Fluorescence analysis was performed.
Placing the 22 groups of mixed solutions obtained in the step 2c) into a thermostatic water bath at 25 ℃ for heat preservation for 10 min;
in the process of measuring the fluorescence emission spectra of the 22 groups of mixed solutions in step 2c), the excitation and emission slit width was 5nm, the photomultiplier voltage was 700V, and excitation was performed with a wavelength of 335 nm.
Example twelve
The 8-aminoquinoline amide derivative of the invention is Cd2+The method of performing fluorescence analysis comprises the steps of:
1c) weighing 8-aminoquinoline amide derivatives and acetonitrile, and dissolving the 8-aminoquinoline amide derivatives in the acetonitrile to obtain acetonitrile solution of the 8-aminoquinoline amide derivatives, wherein the concentration of the 8-aminoquinoline amide derivatives in the acetonitrile solution of the 8-aminoquinoline amide derivatives is 1 mM;
2c) placing the acetonitrile solution of the 8-aminoquinoline amide derivative obtained in the step 1c)Adding 13 groups of Cd with different volumes into the centrifuge tube respectively2+Standard solution, then fixing the volume by acetonitrile to obtain 13 groups of mixed solution, wherein the concentration of the 8-aminoquinoline amide derivative in the 13 groups of mixed solution is 50 mu M, and the 8-aminoquinoline amide derivative and Cd in the 13 groups of mixed solution2+The ratio of the amounts of the substances of (a) to (b) is 1: 0. 1: 0.4, 1: 0.8, 1: 1. 1: 1.6, 1: 1.8, 1: 2. 1: 2.2, 1: 2.8, 1: 3. 1: 3.2, 1: 3.8 and 1: 4.2, then placing the 13 groups of mixed solutions into a constant-temperature water bath for heat preservation, respectively placing the 13 groups of mixed solutions into a quartz cuvette after the effects are balanced, measuring the fluorescence emission spectra of the 13 groups of mixed solutions, and finally carrying out Cd pairing on Cd according to the fluorescence emission spectra of the 13 groups of mixed solutions2+Fluorescence analysis was performed.
Placing the 13 groups of mixed solutions obtained in the step 2c) into a thermostatic water bath at 25 ℃ for heat preservation for 5 min;
in the process of measuring the fluorescence emission spectra of the 13 sets of mixed solutions in step 2c), the excitation and emission slit width was 2.5nm, the photomultiplier voltage was 700V, and excitation was performed with a wavelength of 350 nm.
EXAMPLE thirteen
The 8-aminoquinoline amide derivative of the invention is Cd2+The method of performing fluorescence analysis comprises the steps of:
1c) weighing 8-aminoquinoline amide derivatives and acetonitrile, and dissolving the 8-aminoquinoline amide derivatives in the acetonitrile to obtain acetonitrile solution of the 8-aminoquinoline amide derivatives, wherein the concentration of the 8-aminoquinoline amide derivatives in the acetonitrile solution of the 8-aminoquinoline amide derivatives is 10 mM;
2c) putting the acetonitrile solution of the 8-aminoquinoline amide derivative obtained in the step 1c) into a centrifugal tube, and respectively adding 12 groups of Cd with different volumes into the centrifugal tube2+Standard solution, then fixing the volume by acetonitrile to obtain 12 groups of mixed solution, wherein the concentration of 8-aminoquinoline amide derivatives in 12 groups of mixed solution is 10 mu M, and the concentration of 8-aminoquinoline amide derivatives and Cd in 12 groups of mixed solution2+The ratio of the amounts of the substances of (a) to (b) is 1: 0. 1: 0.4, 1: 0.6, 1: 1.2 of,1: 1.4, 1: 1.6, 1: 1.8, 1: 2.8, 1: 3. 1: 3.2, 1: 3.8 and 1: 4.2, then placing the obtained 12 groups of mixed solutions into a constant-temperature water bath for heat preservation, respectively placing the 12 groups of mixed solutions into a quartz cuvette after the effects are balanced, measuring the fluorescence emission spectra of the 12 groups of mixed solutions, and finally carrying out Cd pairing on Cd according to the fluorescence emission spectra of the 12 groups of mixed solutions2+Fluorescence analysis was performed.
Placing the 12 groups of mixed solutions obtained in the step 2c) into a thermostatic water bath at 25 ℃ for heat preservation for 10 min;
in the process of measuring the fluorescence emission spectra of 12 sets of mixed solutions in step 2c), the excitation and emission slit width was 5nm, the photomultiplier voltage was 700V, and excitation was performed with a wavelength of 330 nm.
Example fourteen
The 8-aminoquinoline amide derivative of the invention is Cd2+The method of performing fluorescence analysis comprises the steps of:
1c) weighing 8-aminoquinoline amide derivatives and acetonitrile, and dissolving the 8-aminoquinoline amide derivatives in the acetonitrile to obtain acetonitrile solution of the 8-aminoquinoline amide derivatives, wherein the concentration of the 8-aminoquinoline amide derivatives in the acetonitrile solution of the 8-aminoquinoline amide derivatives is 8 mM;
2c) putting the acetonitrile solution of the 8-aminoquinoline amide derivative obtained in the step 1c) into a centrifugal tube, and respectively adding 22 groups of Cd with different volumes into the centrifugal tube2+And (3) carrying out constant volume on the standard solution by using acetonitrile to obtain 22 groups of mixed solutions, wherein the concentration of the 8-aminoquinoline amide derivative in the 22 groups of mixed solutions is 30 mu M, and the 8-aminoquinoline amide derivative and Cd in the 22 groups of mixed solutions2+The ratio of the amounts of the substances of (a) to (b) is 1: 0. 1: 0.2, 1: 0.4, 1: 0.6, 1: 0.8, 1: 1. 1: 1.2, 1: 1.4, 1: 1.6, 1: 1.8, 1: 2. 1: 2.2, 1: 2.4, 1: 2.6, 1: 2.8, 1: 3. 1: 3.2, 1: 3.4, 1: 3.6, 1: 3.8, 1: 4 and 1: 4.2, then placing the obtained 22 groups of mixed solutions into a constant-temperature water bath for heat preservation, respectively placing the 22 groups of mixed solutions into a quartz cuvette after the functions of the mixed solutions are balanced, and measuring the fluorescence emission light of the 22 groups of mixed solutionsSpectrum, and finally, the fluorescence emission spectrum of 22 groups of mixed solutions is used for Cd2+Fluorescence analysis was performed.
Placing the 22 groups of mixed solutions obtained in the step 2c) into a thermostatic water bath at 25 ℃ for heat preservation for 8 min;
in the process of measuring the fluorescence emission spectrum of the 22 groups of mixed solutions in the step 2c), the excitation and emission slit width is 5nm, the voltage of the photomultiplier is 700V, and the excitation is carried out with the wavelength of 340 nm.
Example fifteen
The 8-aminoquinoline amide derivative of the invention is Cd2+The method of performing fluorescence analysis comprises the steps of:
1c) weighing 8-aminoquinoline amide derivatives and acetonitrile, and dissolving the 8-aminoquinoline amide derivatives in the acetonitrile to obtain acetonitrile solution of the 8-aminoquinoline amide derivatives, wherein the concentration of the 8-aminoquinoline amide derivatives in the acetonitrile solution of the 8-aminoquinoline amide derivatives is 2 mM;
2c) putting the acetonitrile solution of the 8-aminoquinoline amide derivative obtained in the step 1c) into a centrifugal tube, and respectively adding 22 groups of Cd with different volumes into the centrifugal tube2+Standard solution, then fixing the volume by acetonitrile to obtain 22 groups of mixed solution, wherein the concentration of the 8-aminoquinoline amide derivative in the 22 groups of mixed solution is 20 mu M, and the 8-aminoquinoline amide derivative and Cd in the 22 groups of mixed solution2+The ratio of the amounts of the substances of (a) to (b) is 1: 0. 1: 0.2, 1: 0.4, 1: 0.6, 1: 0.8, 1: 1. 1: 1.2, 1: 1.4, 1: 1.6, 1: 1.8, 1: 2. 1: 2.2, 1: 2.4, 1: 2.6, 1: 2.8, 1: 3. 1: 3.2, 1: 3.4, 1: 3.6, 1: 3.8, 1: 4 and 1: 4.2, then placing the obtained 22 groups of mixed solutions into a constant-temperature water bath for heat preservation, respectively placing the 22 groups of mixed solutions into a quartz cuvette after the effects are balanced, measuring the fluorescence emission spectra of the 22 groups of mixed solutions, and finally carrying out Cd pairing on Cd according to the fluorescence emission spectra of the 22 groups of mixed solutions2+Fluorescence analysis was performed.
Placing the 22 groups of mixed solutions obtained in the step 2c) into a thermostatic water bath at 25 ℃ for heat preservation for 6 min;
in the process of measuring the fluorescence emission spectra of the 22 groups of mixed solutions in step 2c), the excitation and emission slit width was 5nm, the photomultiplier voltage was 700V, and excitation was performed with a wavelength of 335 nm.
The 8-aminoquinoline amide derivative is used as a fluorescent probe for selective research on various common metal ions in water:
adding 2 mu L of 8-aminoquinoline amide derivative acetonitrile solution with the concentration of 10mM into a centrifuge tube, and respectively adding proper amount of Zn2+Standard solution or other standard solutions of various metal ions to make Zn in the system2+Or the concentration of other various metal ions is 20 mu M, the volume is determined to be 1mL by using HEPES buffer solution, then the solutions containing the metal ions are placed in a thermostatic water bath with the temperature of 25 ℃ for heat preservation for 10min, finally, the samples are respectively placed in quartz cuvettes with the optical path of 1cm and the volume of 1mL, the width of an excitation and emission slit is set to be 5nm, the voltage of a photomultiplier is 700V, and the samples are excited by the wavelength of 321nm to measure the fluorescence emission spectrum.
FIG. 1a is a spectrum of fluorescence response of 20. mu.M 8-aminoquinoline amide derivatives in water to various common metal ions at a concentration of 20. mu.M, respectively;
FIG. 1b is a photograph of 20 μ M8-aminoquinoline amide derivatives in water under 365nm UV light in response to various common metal ions at a concentration of 20 μ M, respectively;
8-aminoquinoline amide derivative as fluorescent probe for Cd in acetonitrile2+And selectivity studies for various common metal ions:
adding 2 μ L of 10mM 8-aminoquinoline amide derivative acetonitrile solution into a centrifuge tube, and respectively adding appropriate amount of Cd2+Standard solution or other standard solutions of various metal ions to ensure that Cd in the system2+Or the concentration of other various metal ions is 20 mu M, then acetonitrile is used for fixing the volume to 1mL, solutions containing the metal ions are placed in a thermostatic water bath at 25 ℃ for heat preservation for 10min, then the samples are respectively placed in quartz cuvettes with the optical diameter of 1cm and the volume of 1mL, the width of an excitation and emission slit is set to be 5nm, the voltage of a photomultiplier is 700V, the samples are excited by the wavelength of 335nm, and the fluorescence emission spectrum of the samples is measured.
FIG. 2a is a spectrum of fluorescence response of 20. mu.M 8-aminoquinoline amide derivatives in acetonitrile to various common metal ions at a concentration of 20. mu.M, respectively;
FIG. 2b is a photograph of 20 μ M8-aminoquinoline amide derivatives in acetonitrile respectively responding to various common metal ions at a concentration of 20 μ M under 365nm UV lamp irradiation;
the results shown in FIG. 1a and FIG. 1b show that, in water, the 8-aminoquinoline amide derivative is p-Zn2+The detection of (2) is not interfered by other various common metal ions; the results shown in FIGS. 2a and 2b show that 8-aminoquinoline amide derivatives in acetonitrile are directed to Cd2+The detection of (A) is not interfered by other various common metal ions. The results shown in FIG. 1a, FIG. 1b, FIG. 2a and FIG. 2b show that the probe can selectively detect and distinguish Zn in different solvents respectively2+With Cd2+Has high detection specificity and is a dual-function fluorescent probe.
Through detection, FIG. 3a shows the Zn concentration of the 8-aminoquinoline amide derivative in water2+Fluorescence emission spectra in example six were analyzed for fluorescence; FIG. 3b is Zn 2+20 μ M8-aminoquinoline amide derivatives in water with Zn at a concentration in the range of 0-100 μ M2+After the action, the ratio of the fluorescence intensity of the system at 498-416 nm fluorescence emission wavelength to Zn2+Working curve of concentration. FIG. 4a is a diagram of the para-Cd alignment of 8-aminoquinoline amide derivatives in acetonitrile2+Fluorescence emission spectra in example eleven for fluorescence analysis were performed; FIG. 4b shows Cd 2+20 μ M8-aminoquinoline amide derivatives in acetonitrile at a concentration in the range of 0-84 μ M with Cd2 +After the action, the ratio of the fluorescence intensity of the system at the fluorescence emission wavelengths of 500 and 405nm to Cd2+Working curve of concentration.
The results shown in FIGS. 3a and 3b show that Zn is accompanied in water2+The concentration is increased, the 8-aminoquinoline amide derivative generates an obvious red shift phenomenon of fluorescence emission wavelength, the fluorescence intensity at 416nm is gradually reduced to completely disappear, a new fluorescence emission peak is gradually generated at 498nm, and the intensity is gradually enhanced. The system has fluorescent intensity at 498 and 416nm emission wavelengthsRatio of degree depending on Zn2+The concentration increases gradually and is in a linear relation in the concentration range of 0-40 mu M when Zn is added2+The maximum is reached at a concentration of about 90. mu.M. High detection sensitivity when Zn2+Also, a significant fluorescence response was produced at a concentration of 4. mu.M. The results shown in FIGS. 4a and 4b indicate that Cd is accompanied by Cd in acetonitrile2+The concentration is increased, the fluorescence emission intensity of the 8-aminoquinoline amide derivative at 405nm is gradually reduced but not disappeared, a new fluorescence emission peak is gradually generated at 500nm, and the intensity is gradually increased. The ratio of the fluorescence intensity of the system at the emission wavelengths of 500 and 405nm is dependent on Cd2+The concentration is gradually increased and is in a linear relation in the concentration range of 0-20 mu M when the concentration of Cd is increased2+The maximum is reached at a concentration of about 60. mu.M. High detection sensitivity when Cd2+Also, a significant fluorescence response was produced at a concentration of 4. mu.M. Thus, the 8-aminoquinoline amide derivative is p-Zn2+And Cd2+Has high detection sensitivity.
FIG. 5a shows 20. mu.M Zn in water2+In the case of (2), the change in fluorescence intensity at 498nm with the incubation time of a 20. mu.M 8-aminoquinoline amide derivative was measured by excitation at 321 nm. FIG. 5b shows 20. mu.M Cd in acetonitrile2+In the case of (2), the change in fluorescence intensity at 500nm of 20. mu.M of an 8-aminoquinoline amide derivative with the incubation time was measured by excitation at a wavelength of 335 nm.
The results shown in FIGS. 5a and 5b show that 8-aminoquinoline amide derivatives have improved Zn-solubility in water2+And for Cd in acetonitrile2 +The fluorescence response time is short, and the detection is rapid.
Claims (3)
1. Based on 8-aminoquinoline amide derivative and Zn2+And Cd2+A method for performing fluorescence analysis, characterized in that the chemical structure of the 8-aminoquinoline amide derivative is
The 8-aminoquinoline amide derivative is p-Zn2+A method of performing a fluorescence assay comprisingThe following steps:
1b) weighing 8-aminoquinoline amide derivatives and acetonitrile, and dissolving the 8-aminoquinoline amide derivatives in the acetonitrile to obtain acetonitrile solution of the 8-aminoquinoline amide derivatives, wherein the concentration of the 8-aminoquinoline amide derivatives in the acetonitrile solution of the 8-aminoquinoline amide derivatives is (1-10) mM;
2b) putting the acetonitrile solution of the 8-aminoquinoline amide derivative obtained in the step 1b) into a centrifuge tube, and then respectively adding M groups of Zn with different volumes into the centrifuge tube2+Performing constant volume on the standard solution by using HEPES buffer solution to obtain M groups of mixed solutions, wherein the concentration of the 8-aminoquinoline amide derivative in the M groups of mixed solutions is (10-50) mu M, and the 8-aminoquinoline amide derivative and Zn in the M groups of mixed solutions2+The ratio of the amounts of substances of (a) to (b) is 1: (0-5), then placing the obtained M groups of mixed solutions into a constant-temperature water bath for heat preservation, respectively placing the M groups of mixed solutions into a quartz cuvette after the effects are balanced, then measuring the fluorescence emission spectra of the M groups of mixed solutions, and finally carrying out Zn comparison according to the fluorescence emission spectra of the M groups of mixed solutions2+Performing fluorescence analysis;
the 8-aminoquinoline amide derivative is p-Cd2+A method of performing fluorescence analysis comprising the steps of:
1c) weighing 8-aminoquinoline amide derivatives and acetonitrile, and dissolving the 8-aminoquinoline amide derivatives in the acetonitrile to obtain acetonitrile solution of the 8-aminoquinoline amide derivatives, wherein the concentration of the 8-aminoquinoline amide derivatives in the acetonitrile solution of the 8-aminoquinoline amide derivatives is (1-10) mM;
2c) putting the acetonitrile solution of the 8-aminoquinoline amide derivative obtained in the step 1c) into a centrifugal tube, and respectively adding N groups of Cd with different volumes into the centrifugal tube2+Performing constant volume on the standard solution by acetonitrile to obtain N groups of mixed solutions, wherein the concentration of the 8-aminoquinoline amide derivative in the N groups of mixed solutions is (10-50) mu M, and the 8-aminoquinoline amide derivative and Cd in the N groups of mixed solutions2+The ratio of the amounts of substances of (a) to (b) is 1: (0-4.2), then placing the obtained N groups of mixed solution into a constant-temperature water bath for heat preservation, and then, after the effects are balanced, placing the mixed solution into a water bath for heat preservationRespectively placing the N groups of mixed solutions into quartz cuvettes, measuring the fluorescence emission spectra of the N groups of mixed solutions, and finally carrying out Cd pairing according to the fluorescence emission spectra of the N groups of mixed solutions2+Fluorescence analysis was performed.
2. 8-aminoquinoline amide derivative based on simultaneous para-Zn according to claim 12+And Cd2+A method for performing fluorescence analysis, characterized in that,
placing the obtained M groups of mixed solution in the step 2b) into a thermostatic water bath at 25 ℃ for heat preservation (5-10) min;
in the process of measuring the fluorescence emission spectrum of the M groups of mixed solutions, the width of the excitation and emission slit is (2.5-5) nm, the voltage of the photomultiplier is 700V, and the excitation is carried out by the wavelength of (320-350) nm.
3. 8-aminoquinoline amide derivative based on simultaneous para-Zn according to claim 12+And Cd2+A method for performing fluorescence analysis, characterized in that,
placing the N groups of mixed solution obtained in the step 2c) into a thermostatic water bath at 25 ℃ for heat preservation (5-10) min;
in the process of measuring the fluorescence emission spectra of the N groups of mixed solutions in the step 2c), the excitation and emission slit width is (2.5-5) nm, the photomultiplier voltage is 700V, and the excitation is performed with the wavelength of 330-350 nm.
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