CN110156798B - Preparation method and application of supramolecular probe solution - Google Patents
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Abstract
The invention discloses a preparation method and application of a supramolecular probe solution, wherein the probe solution is prepared by reacting trans-heptatomic cucurbituril and 4- (4-dimethylamino styryl) quinoline hydrochloride serving as raw materials in an acetic acid-sodium acetate buffer solution to form a supramolecular probe, and then adjusting the pH value to be =5.5 by using acetic acid and a saturated sodium acetate solution. The application thereof is the application in the identification of L-amino acid. The invention provides a preparation method of a novel fluorescent probe, and the fluorescent probe can be used for identifying L-amino acid and has the characteristics of short synthetic route and low price.
Description
Technical Field
The invention relates to a preparation method and application of a supramolecular probe solution, belonging to the field of chemistry.
Background
Amino acids are a generic term for a class of organic compounds containing amino and carboxyl groups, are basic constituent units of biologically functional macromolecular proteins, and are basic substances constituting proteins required for animal nutrition. Various vegetables, fruits, grains and meats contain abundant amino acids. Amino acids have important effects, and for example, a compound preparation (Minnogen) prepared from arginine and deoxycholic acid is an effective medicine for treating syphilis, viral jaundice and other diseases; lysine can promote brain development, is a component of liver and gallbladder, can promote fat metabolism, regulate pineal gland, mammary gland, corpus luteum and ovary, and prevent cell degeneration; phenylalanine participates in eliminating loss of kidney and bladder functions; tryptophan can promote the production of gastric juice and pancreatic juice.
And the optical analysis method based on the fluorescence spectrum and the ultraviolet-visible spectrum is popular because of the advantages of simple operation, high sensitivity, low detection limit, short time consumption and the like. The detection principle is that probe molecules can be selectively combined with certain amino acid, and optical signals are generated through fluorescence quenching, fluorescence enhancement and ultraviolet-visible spectrum change, so that the purpose of detection is achieved.
However, no fluorescent probe for recognizing L-amino acids has been reported at present.
Disclosure of Invention
The invention aims to provide a preparation method and application of a supramolecular probe solution. The invention provides a novel preparation method of a fluorescent probe, the prepared probe can identify L-amino acid, and the preparation method has the characteristics of simple preparation process and convenience in operation.
The technical scheme of the invention is as follows: a preparation method of a supramolecular probe solution comprises the step of reacting trans-hepta-cucurbituril and 4- (4-dimethylamino styryl) quinoline hydrochloride serving as raw materials in an acetic acid-sodium acetate buffer solution with the pH =5.5 to form a supramolecular probe, so that the supramolecular probe solution can be prepared.
The acetic acid-sodium acetate buffer solution is prepared by mixing acetic acid and a saturated sodium acetate solution and adjusting the pH value.
In the preparation method of the supramolecular probe solution, the molar ratio of the trans-hepta-cucurbituril to the 4- (4-dimethylaminostyryl) quinoline hydrochloride is 1: 1.
The preparation method of the supramolecular probe solution comprises the following specific steps: dissolving trans-form seven-element cucurbituril in an acetic acid-sodium acetate buffer solution to obtain a solution A; dissolving 4- (4-dimethylamino styryl) quinoline hydrochloride in an acetic acid-sodium acetate buffer solution to obtain a solution B; and mixing the solution A and the solution B to obtain the supramolecular probe solution.
The molar concentration of the supramolecular probe in the supramolecular probe solution is 2 × 10-5mol/L。
The application of the supramolecular probe solution prepared by the preparation method of the supramolecular probe solution in L-amino acid recognition.
The application of the supramolecular probe solution in the identification of L-amino acid is disclosed, wherein the L-amino acid refers to L-arginine, L-lysine, L-phenylalanine and L-tryptophan.
The application of the supramolecular probe solution in the L-amino acid recognition specifically comprises the following steps: and mixing the supramolecular probe solution with the liquid to be detected, and observing the color change of the mixed solution under natural light or the fluorescence change under ultraviolet light to obtain whether the liquid to be detected contains the L-amino acid.
The invention has the advantages of
The fluorescent probe solution provided by the invention is used as a fluorescent reagent, and can be used for directly carrying out in-situ recognition on L-amino acid. The fluorescent probe solution provided by the invention can be prepared only by taking trans-heptatomic cucurbituril and 4- (4-dimethylamino styryl) quinoline hydrochloride as raw materials, reacting in an acetic acid-sodium acetate buffer solution and adjusting the pH value, and has the advantages of simple preparation process and convenience in operation.
Drawings
FIG. 1 is a graph of the UV spectrum of different mole ratios of iQ 7 to DSQ;
FIG. 2 is a graph of fluorescence spectra for different molar ratios of iQ 7 to DSQ;
FIG. 3 is a diagram showing the results of the Job method for iQ [7] and DSQ;
FIG. 4 is a graph showing the comparison of the solution changes of iQ 7 @ DSQ supramolecular probe and amino acids added thereto (a is under natural light, and b is under 365nm ultraviolet irradiation);
FIG. 5 is the diagram showing the variation of the UV-visible absorption spectrum (a) of iQ 7 @ DSQ supramolecular probe and the solution after adding different amino acids and the maximum absorption intensity (b) after adding different amino acids;
FIG. 6 is a graph showing the changes between the fluorescence emission spectra (a) of iQ 7 @ DSQ supramolecular probe and solution with different amino acids and the maximum fluorescence emission intensity (b) with different amino acids;
FIG. 7 is the ultraviolet-visible absorption spectrum (a) and the ultraviolet standard curve (b) of L-Arg with different concentrations of L-Arg added to iQ 7 @ DSQ supramolecular probe;
FIG. 8 is a fluorescence emission spectrogram (a) and a fluorescence standard curve (b) of L-Arg obtained by adding different concentrations of L-Arg to iQ 7 @ DSQ supramolecular probe;
FIG. 9 is a graph (a) of the UV-VIS absorption spectrum of an iQ 7 @ DSQ supramolecular probe with different concentrations of L-Lys solution and a graph (b) of the UV standard of L-Lys;
FIG. 10 is a fluorescence emission spectrum graph (a) and a fluorescence standard curve graph (b) of L-Lys in which different concentrations of L-Lys solution are added to iQ [7] @ DSQ supramolecular probe;
FIG. 11 is a graph of the UV-VIS absorption spectrum (a) of different concentrations of L-Phe added to iQ [7] @ DSQ supramolecular probe and the UV standard curve (b) of L-Phe;
FIG. 12 is a graph showing fluorescence emission spectra (a) and standard fluorescence spectra (b) of L-Phe in different concentrations of an iQ 7 @ DSQ supramolecular probe;
FIG. 13 is a graph (a) of the UV-VIS absorption spectrum of an iQ 7 @ DSQ supramolecular probe with different concentrations of L-Trp solution and a graph (b) of the UV standard of L-Trp;
FIG. 14 is a fluorescence emission spectrum (a) and a fluorescence standard curve (b) of L-Trp obtained by adding different concentrations of L-Trp to iQ 7 @ DSQ supramolecular probe.
Detailed Description
The present invention is further illustrated by the following examples, which are not to be construed as limiting the invention.
Examples of the invention
Example (b):
(1) preparation of acetic acid-sodium acetate buffer solution with pH = 5.5:
adding a proper amount of glacial acetic acid and a saturated sodium acetate solution into a 1000mL beaker with a proper amount of secondary distilled water, and adjusting the pH =5.5 by using a pH meter to obtain an acetic acid-sodium acetate buffer solution with the pH = 5.5.
(2) Preparing a supramolecular probe standard solution:
take iQ [7]]134.2mg, pHDissolving acetic acid-sodium acetate buffer solution of =5.5, ultrasonically treating, transferring into a 100mL volumetric flask, and fixing the volume with acetic acid-sodium acetate buffer solution of pH =5.5 to obtain solution A with concentration of 1 × 10-3moL/L for standby;
dissolving DSQ 31.1mg in pH =5.5 acetic acid-sodium acetate buffer solution, transferring into 100mL volumetric flask, and diluting with pH =5.5 acetic acid-sodium acetate buffer solution to constant volume to obtain solution B with concentration of 1 × 10-3moL/L for standby;
taking the volume ratio of 1:1 (i.e. the molar ratio is 1: 1) of the solution A and the solution B are mixed to obtain the solution with the concentration of 1 x 10-3moL/L probe solution was diluted to 2X 10 with acetic acid-sodium acetate buffer solution of pH =5.5 as necessary-5moL/L, adjusting pH =5.5 with acetic acid and saturated sodium acetate water solution to obtain iQ [7]]@ DSQ supramolecular probe solution.
To illustrate the recognition function of the present invention, the inventors made the following experiments:
experimental example 1: preparation of supramolecular Probe solutions
In order to determine the molar ratio of the trans-form seven-membered cucurbituril (iQ 7) to the probe formed by 4- (4-dimethylaminostyryl) quinoline hydrochloride (DSQ), the inventors determined the ultraviolet absorption, fluorescence emission, etc. by the molar ratio method, and studied the interaction between iQ 7 and DSQ; and the action mole ratio of iQ 7 and DSQ is further determined by Job's method.
DSQ was dissolved in acetic acid-sodium acetate buffer solution, and diluted to 2 × 10 with acetic acid-sodium acetate buffer solution of pH =5.5-5moL/L, measuring its ultraviolet-visible absorption spectrum by using mole ratio method, then adding iQ 7]When iQ [7]]When the amount of (A) is gradually increased, the maximum absorption value is red-shifted from 492nm to 533nm by 41nm, and the absorption value at about 530nm is gradually increased and basically does not change after a certain concentration (as shown in figure 1 a); when iQ [7]]Concentration ratio to DSQ is about 1:1, at this time, iQ is increased again [7]]The maximum absorption does not substantially change (see FIG. 1 b), indicating iQ [7]]The optimal molar ratio to DSQ is 1: 1. the fixed excitation wavelength is 530nm, the voltage is 650V, the excitation and emission slit is 10, the fluorescence emission spectrum is measured by the molar ratio method, when iQ 7]When the amount of (b) is gradually increased, the maximum fluorescence emission intensity at about 653nm is gradually increased, and iQ [7]]After reaching a certain concentration, the maximum fluorescence emission intensity is basically stable (as shown in FIG. 2 a); when iQ [7]]Concentration ratio to DSQ is about 1:1, at this time, iQ is increased again [7]]By an amount such that the maximum emission intensity does not substantially change (see fig. 2 b).
Taking the fluorescent probe solution of the invention, measuring the fluorescence emission by Job's method (the fluorescence conditions are the same as above), finding that when the ratio of the concentration of DSQ to the total concentration is about 0.5, there is a maximum value, indicating that the molar ratio of iQ 7 to DSQ is 1:1 (see fig. 3).
Experimental example 2: study of the application of supramolecular Probe solutions
Qualitative analysis of iQ 7 @ DSQ supermolecule probe for L-amino acid
Taking a plurality of groups of the supramolecular probe solution, respectively adding different prepared amino acid standard solutions (the molar ratio of the supramolecular probe to each amino acid is 1: 10), standing for 10min, comparing the change of the solution color under natural light, finding that the supramolecular probe solution changes from purple to yellow (as shown in figure 4 a) after adding L-arginine or L-lysine, and finding that the fluorescence of the solution changes from blue-purple to bright yellow (as shown in figure 4 b) when the solution is irradiated by 365nm ultraviolet rays. Comparing the color change of the solution under natural light, it was found that the color of the supramolecular probe solution became lighter when L-phenylalanine or L-tryptophan was added (see FIG. 4 a), and the blue-violet fluorescence of the solution was found to be weaker when the solution was irradiated with 365nm ultraviolet light (see FIG. 4 b). When the solutions left standing for 10min were subjected to ultraviolet-visible absorption spectroscopy, respectively, it was found that the maximum absorption intensity at about 530nm decreased when L-arginine or L-lysine was added, while the maximum absorption intensity at about 530nm significantly decreased and the maximum absorption wavelength blue-shifted after the addition of L-phenylalanine and L-tryptophan (FIG. 5); when the solution left to stand for 10min was subjected to fluorescence emission spectrometry, it was found that the fluorescence was quenched at about 653nm after the addition of L-arginine or L-lysine, while the maximum emission intensity at about 653nm was significantly decreased after the addition of L-phenylalanine or L-tryptophan (FIG. 6). It shows that the iQ [7] @ DSQ supramolecular probe can rapidly and effectively identify L-arginine or L-lysine and L-phenylalanine or L-tryptophan in acetic acid-sodium acetate buffer solution with pH = 5.5.
Quantitative analysis of L-amino acid by iQ 7 @ DSQ supermolecule probe
After L-arginine with different concentrations is added into the supramolecular probe solution, ultraviolet visible absorption spectra of the L-arginine are respectively measured, experiments show that when the L-arginine is in the concentration range of 10-220 mu mol/L, the change value of the maximum absorption value at 530nm and the concentration of the L-arginine are in linear correlation relationship, and the detection limit is 9.20 multiplied by 10-6mol/L (as shown in FIG. 7); when the concentration of the L-arginine is in the range of 4-100 mu mol/L, the change value of the maximum fluorescence emission intensity at 653nm is in linear correlation with the concentration of the L-arginine, and the detection limit is 6.65 multiplied by 10-6mol/L (as shown in FIG. 8).
The same method for detecting L-lysine shows that when L-lysine is in the concentration range of 10-220 mu mol/L, the change value of the maximum absorption value at 530nm is in linear correlation with the concentration of L-lysine, and the detection limit is 3.69 multiplied by 10-6mol/L (as shown in FIG. 9); when the concentration of L-lysine is in the range of 0-120 mu mol/L, the change value of the maximum fluorescence emission intensity at 653nm is in linear correlation with the concentration of L-lysine, and the detection limit is 7.60 multiplied by 10-6mol/L (as in FIG. 10).
The same method is used for detecting the L-phenylalanine, and the result shows that when the L-phenylalanine is in the concentration range of 0-120 mu mol/L, the change value of the maximum absorption value at 530nm and the concentration of the L-phenylalanine are in a linear correlation relationship, and the detection limit is 1.37 multiplied by 10- 5mol/L (as in FIG. 11); when the concentration of L-phenylalanine is in the range of 0-160 mu mol/L, the change value of the maximum fluorescence emission intensity at 653nm is in linear correlation with the concentration of L-phenylalanine, and the detection limit is 1.33 multiplied by 10-5mol/L (as in FIG. 12).
The same method is used for detecting L-tryptophan, and the result shows that when the L-tryptophan is in the concentration range of 0-240 mu mol/L, the change value of the maximum absorption value at 530nm is in linear correlation with the concentration of the L-tryptophan, and the detection limit is 2.69 multiplied by 10-5mol/L (as in FIG. 13); when the concentration of L-tryptophan is in the range of 0-160 mu mol/L, the change value of the maximum fluorescence emission intensity at 653nm is in linear correlation with the concentration of L-tryptophan, and the detection limit is 3.18 multiplied by 10-6mol/L (as in FIG. 14).
According to the measurement result, the supramolecular probe can realize quantitative measurement of L-arginine, L-lysine, L-phenylalanine and L-tryptophan in a certain concentration range in an acetic acid-sodium acetate buffer solution, and the method is simple and convenient and consumes less time.
Claims (3)
1. A preparation method of a supramolecular probe solution is characterized by comprising the following steps: in a pH value-5.5 acetic acid-sodium acetate buffer solution, trans-heptatomic cucurbituril and 4- (4-dimethylamino styryl) quinoline hydrochloride are used as raw materials to react to form a supramolecular probe, and then a supramolecular probe solution can be prepared; the molar ratio of the trans seven-membered cucurbituril to the 4- (4-dimethylamino styryl) quinoline hydrochloride is 1: 1; the preparation method of the supramolecular probe comprises the following steps: dissolving trans-form seven-element cucurbituril in an acetic acid-sodium acetate buffer solution to obtain a solution A; dissolving 4- (4-dimethylamino styryl) quinoline hydrochloride in an acetic acid-sodium acetate buffer solution to obtain a solution B; mixing the solution A and the solution B to obtain a supramolecular probe solution; the molar concentration of the supramolecular probe in the supramolecular probe solution is 2 multiplied by 10-5mol/L。
2. The method for preparing a supramolecular probe solution as claimed in claim 1, wherein: the acetic acid-sodium acetate buffer solution is prepared by mixing acetic acid and a saturated sodium acetate solution and adjusting the pH value.
3. Use of a supramolecular probe solution prepared by the method for the preparation of a supramolecular probe solution according to any one of claims 1-2, characterized in that: the supramolecular probe solution is applied to the recognition of L-amino acid, wherein the L-amino acid refers to L-arginine, L-lysine, L-phenylalanine and L-tryptophan; the specific method for identification is as follows: mixing the supermolecule probe solution with the liquid to be detected, and observing the color change of the mixed solution under natural light or the fluorescence change under ultraviolet light to obtain whether the liquid to be detected contains the L-amino acid; the supramolecular probe solution is applied to quantitative determination of L-arginine, L-lysine, L-phenylalanine and L-tryptophan in an acetic acid-sodium acetate buffer solution.
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