CN112557355B - Method for detecting bismuth ions in biological fluid by rare earth fluorescent probe - Google Patents
Method for detecting bismuth ions in biological fluid by rare earth fluorescent probe Download PDFInfo
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- CN112557355B CN112557355B CN202011264947.5A CN202011264947A CN112557355B CN 112557355 B CN112557355 B CN 112557355B CN 202011264947 A CN202011264947 A CN 202011264947A CN 112557355 B CN112557355 B CN 112557355B
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- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
Abstract
The invention discloses a method for detecting bismuth ions in biological fluid by a rare earth fluorescent probe, wherein the used rare earth fluorescent probe is a molecular probe formed by 7-amino-4-methyl-2-quinolinone modified diethyltriaminepentaacetic acid and terbium ions, the rare earth fluorescent probe detects the bismuth ions by utilizing the principle that ammonia carboxylic molecules and the bismuth ions form an ultra-stable chelate so as to quench the fluorescence of the rare earth fluorescent probe, and has ultrahigh sensitivity.
Description
Technical Field
The invention belongs to the technical field of luminescence detection, and particularly relates to a method for detecting bismuth ions in biological fluid by using a rare earth fluorescent probe.
Background
Bismuth has been widely used in the pharmaceutical industry as a main pharmaceutical ingredient for treating gastrointestinal diseases. Bismuth is also an important ingredient in many cosmetics. However, the long-term excessive use of drugs and cosmetics containing bismuth compounds causes damage to the nervous system and kidneys. Currently detecting bismuth (Bi) 3+ ) The method mainly comprises a spectrophotometry method, an inductively coupled plasma mass spectrometry method, a plasma atomic absorption spectrometry method, an electrochemical method and an ethylenediaminetetraacetic acid titration method. Titration is a constant analysis method, which cannot determine trace amounts of Bi 3+ Various spectroscopy methods based on plasma require complicated instruments and sample preparation, and electrochemical methods, although simpler, require modification of recognition reagents on electrodes. Chinese patent publication No. CN 107417694A, 2017, zhang Ensheng, ju Ping, zhang Yuqi, wang Jijiang, zhang Yantu, a colorimetric and fluorescent double-response type bismuth ion detection probe and a preparation method thereof, and discloses a method for detecting bismuth ions by a rhodamine dye fluorescent probe; chinese patent publication No. CN 108285462A, 2018, chen Denglong, liu Zhipeng, bai Xin, liu Jinling, chen Jialian, chen Min, a method for detecting Bi 3+ The symmetrical double rhodamine-based fluorescent probe discloses a method for detecting bismuth ions by using a rhodamine dye fluorescent probe. The reported organic dye type fluorescent probes generally require relatively complicated organic synthesis and are hardly soluble in water, and have to be measured using an organic solvent-water mixed phase. Therefore, there is a need for the development of simple, sensitive, rapid, and aqueous solution for the detection of trace amounts of Bi 3+ The method of (1).
Disclosure of Invention
The invention aims to: aiming at the interference of some protein molecules, inorganic acid and sulfydryl molecules in biological body fluid (blood and urine) on the detection of most molecular probes in different degrees, the invention provides a method for detecting bismuth ions in the biological body fluid by using a rare earth fluorescent probe for eliminating the interference.
The technical scheme is as follows: in order to achieve the purpose, the method for detecting bismuth ions in biological fluid by using the rare earth fluorescent probe is characterized by comprising the following steps:
adding a silver sheet into the sample solution, standing, taking out the silver sheet, adding the sample solution into a polyether sulfone film rotary separation column for centrifugal separation, adding a bismuth ion rare earth fluorescent probe solution into the centrifugally separated supernatant, mixing, measuring the terbium ion characteristic fluorescence intensity of the mixed solution by using a fluorescence spectrophotometer, and measuring the bismuth ion content of the sample solution according to a working curve of the terbium ion fluorescence intensity and the bismuth ion concentration; the bismuth ion rare earth fluorescent probe is a molecular probe formed by 7-amino-4-methyl-2-quinolinone modified diethyl triaminepentaacetic acid and terbium ions. The bismuth ion rare earth fluorescent probe provided by the invention detects bismuth ions by utilizing a new principle that ammonia carboxyl molecules and bismuth ions can form ultrastable chelate to quench fluorescence of the rare earth fluorescent probe.
Adding a silver sheet into the sample solution, standing for 10-15 minutes, taking out the silver sheet, adding an ethanolamine aqueous solution and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide solid, fully mixing, standing for 30-40 minutes, and adding the sample solution into a polyether sulfone membrane rotary separation column for centrifugal separation.
Adding an N-ethylmaleimide aqueous solution into the sample solution, mixing, standing for 30-40 minutes, adding an ethanolamine aqueous solution and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide solid, fully mixing, standing for 30-40 minutes, and adding the sample solution into a polyether sulfone membrane rotary separation column for centrifugal separation.
Wherein the molecular weight cut-off range of the polyethersulfone membrane rotary separation column is 10-50kDa.
Adding the bismuth ion rare earth fluorescent probe solution into the supernatant obtained by centrifugal separation, mixing for 10-15 minutes, and measuring the terbium ion characteristic fluorescence intensity of the mixed solution by using a fluorescence spectrophotometer.
Wherein the molar ratio of the 7-amino-4-methyl-2-quinolinone-diethyltriaminepentaacetic acid to terbium ions is 1:1.
The preparation method of the bismuth ion rare earth fluorescent probe comprises the following steps: respectively dissolving equal molar amounts of 7-amino-4-methyl-2-quinolinone and diethyltriaminepentaacetic dianhydride in anhydrous dimethylformamide, adding anhydrous triethylamine into an anhydrous dimethylformamide solution of the diethyltriaminepentaacetic dianhydride, dropwise stirring and adding the anhydrous dimethylformamide solution of the 7-amino-4-methyl-2-quinolinone, reacting under the condition of stirring in a dark place, adding a rare earth terbium aqueous solution, and mixing to obtain a rare earth fluorescent probe 7-amino-4-methyl-2-quinolinone-diethyltriaminepentaacetic acid-terbium bismuth ion, namely the rare earth fluorescent probe.
Wherein the aqueous solution of the rare earth terbium is an aqueous solution formed by nitrate or hydrochloride of terbium.
Preferably, the biological fluid is human blood or urine.
The method for detecting bismuth ions in biological fluid by using the rare earth fluorescent probe is applied to the detection of bismuth ions in biological samples, environmental water and medicines.
The bismuth ion rare earth fluorescent probe actually used in the invention is a diethyl triaminepentaacetic acid and rare earth bismuth ion (Bi) connected with 7-amino-4-methyl-2-quinolinone 3+ ) Forming the molecular probe. The principle of the bismuth ion rare earth fluorescent probe for determining bismuth ions is that bismuth ions can replace terbium ions in the rare earth fluorescent probe by utilizing the ultrahigh stability constant of aminocarboxyl complexes of the bismuth ions, so that the fluorescence of the rare earth fluorescent probe is quenched to detect the bismuth ions (Bi) 3+ ). Meanwhile, the method eliminates the interference of some common coexisting substances in the biological body fluid sample by adding the masking agent and processing the sample by using the membrane centrifugal separation column, and can directly measure the micro/trace bismuth ions in the biological body fluid by using the bismuth ion rare earth fluorescent probe.
Has the advantages that: compared with the prior art, the tyrosine rare earth luminescent probe has the following advantages:
1. compared with the reported bismuth ion probe or determination method, the invention utilizes the new determination principle of the prepared bismuth ion fluorescent probe, and utilizes the determination principle that bismuth ions can replace rare earth ions in the rare earth fluorescent probe due to the ultrahigh stability constant of the aminocarboxy complex of the bismuth ions, so that the fluorescence of the rare earth fluorescent probe is quenched to detect the bismuth.
2. The method eliminates the interference of some common coexisting objects in the biological body fluid sample, so that the bismuth ion rare earth fluorescent probe can directly measure the micro/trace bismuth ions in the biological body fluid, and the measurement error is avoided.
3. The fluorescent probe for measuring bismuth ions utilizes the luminescence of rare earth ions, the long fluorescence life of the rare earth ions allows the interference of various non-specific fluorescence (such as background fluorescence or interference fluorescence) to be eliminated by a time-resolved fluorescence technology, a high signal-to-noise ratio can be obtained, and the fluorescent probe has an advantage of measuring the bismuth ions in a sample (such as biological body fluid) with strong background fluorescence.
4. The response time of the bismuth ion rare earth fluorescent probe is less than 5 minutes, and the speed of measuring bismuth ions is high; the detection limit is as low as 0.1pM, which is 100 times lower than that of the existing bismuth ion determination methods; can be directly used in aqueous solution; provides a simple, convenient and rapid method for detecting bismuth ions in biological samples, environmental water and medicines.
Drawings
FIG. 1 is a graph of the fluorescent response of a bismuth ion rare earth fluorescent probe to bismuth ion concentration;
FIG. 2 is a working curve of bismuth ion in aqueous solution measured by bismuth ion rare earth fluorescent probe;
FIG. 3 is the selectivity of bismuth ion rare earth fluorescent probe for measuring bismuth ion;
FIG. 4 is the response time of bismuth ion measurement by bismuth ion rare earth fluorescent probe;
FIG. 5 is a working curve of bismuth ion rare earth fluorescent probe for measuring bismuth ion in blood plasma;
FIG. 6 is a working curve of bismuth ion rare earth fluorescent probe for measuring bismuth ion in urine.
Detailed Description
The technical solution of the present invention will be described in detail below with reference to the accompanying drawings and examples.
The experimental methods described in the examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
Example 1
Preparation of bismuth ion rare earth fluorescent probe
12mg of 7-amino-4-methyl-2-quinolinone and 25mg of diethyltriaminepentaacetic dianhydride were dissolved in 200. Mu.L and 1400. Mu.L of anhydrous dimethylformamide, 100. Mu.L of anhydrous triethylamine was added to the anhydrous dimethylformamide solution of diethyltriaminepentaacetic dianhydride, and the anhydrous dimethylformamide solution of 7-amino-4-methyl-2-quinolinone was dropwise added with stirring, and reacted for 2 hours under stirring away from light to obtain 7-amino-4-methyl-2-quinolinone-modified diethyltriaminepentaacetic acid (7-amino-4-methyl-2-quinolinone-diethyltriaminepentaacetic acid). Adding 1 mu L of 7-amino-4-methyl-2-quinolinone-diethyl triaminepentaacetic acid into 4mL of aqueous solution, adding 1 mu L of aqueous solution of 40mM terbium nitrate, and fully mixing to obtain the rare earth fluorescent probe 7-amino-4-methyl-2-quinolinone-diethyl triaminepentaacetic acid-terbium.
Example 2
Fluorescent response of bismuth ion rare earth fluorescent probe to bismuth ion in aqueous solution
mu.L of the bismuth ion rare earth fluorescent probe prepared in example 1 was added to 930. Mu.L of a phosphate buffer solution (0.1mM, pH 4.8) to obtain a mixed solution, 20. Mu.L of a bismuth ion solution having a predetermined concentration was added to the mixed solution to prepare mixed solutions containing bismuth ions 0,0.1,1, 10, and 100pM, respectively, and the fluorescence intensity of terbium ions at a wavelength of 545nm was measured for these mixed solutions. FIG. 1 is a fluorescence spectrum of these mixed solutions, the fluorescence intensity of the bismuth ion rare earth fluorescent probe decreases with the increase of the concentration of bismuth ions in the solution, and in the range of 0-30pM concentration, the fluorescence intensity of the bismuth ion rare earth fluorescent probe has a linear relationship with the concentration of bismuth ions (FIG. 2), and can be used as a working curve for measuring bismuth ions, and the detection limit for detecting bismuth ions is as low as 0.1pM.
The bismuth ion rare earth prepared by the inventionThe fluorescent probe has good determination selectivity, as shown in figure 3, under the existence of 35pM of interference ions, the fluorescence of the bismuth ion rare earth fluorescent probe (0.5 mu M) is removed by Fe 3+ In addition to causing a small decrease (by addition of H) 2 O 2 Oxidation elimination) and is hardly interfered by other ions. Even Ag + 、Ni 2+ 、Co 2+ 、Mn 2+ The concentration of Cd is improved by 1000 times 2+ 、Fe 2+ 、Pb 2+ Increased by 500 times, cu 2+ Is increased by 100 times, cr 3+ 、Hg 2+ The concentration of the bismuth ion rare earth fluorescence probe is increased by 50 times, and the fluorescence of the bismuth ion rare earth fluorescence probe is reduced<5 percent, so the bismuth ion is measured by the bismuth ion rare earth fluorescent probe with high selectivity, and other metal ions are not interfered.
The bismuth ion rare earth fluorescent probe prepared by the invention has quick response time when being used for determining bismuth ions, the fluorescence intensity does not change within 5 minutes (figure 4), and the existence of the bismuth ions can be rapidly determined.
Example 3
Determination of bismuth ion in human blood by bismuth ion rare earth fluorescent probe
Taking 0.3mL of human plasma sample, diluting with water by 10 times, adding a newly polished silver sheet, standing for 10 minutes, taking out the silver sheet, adding 100 mu L of 0.1M ethanolamine and 10mg of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, fully mixing, standing for 30 minutes, adding the sample solution into a 10-50kDa polyether sulfone membrane rotary separation column, performing centrifugal separation (10000 rpm multiplied by 5 minutes), and then retaining a supernatant. mu.L of the bismuth ion rare earth fluorescent probe prepared in example 1 and 20. Mu.L of the supernatant were added to 930. Mu.L of a phosphate buffer solution (0.1mM, pH 4.8), respectively, mixed well for 10 minutes, and the Tb of the sample solution at a wavelength of 545nm was measured 3+ The concentration of bismuth ions is obtained according to the working curve of the fluorescence intensity of the bismuth ion rare earth fluorescence probe and the concentration of bismuth ions in the embodiment 2 and the measured fluorescence intensity of the sample solution. FIG. 5 shows a graph showing the operation curve without eliminating the influence of the interfering substances without the above-mentioned sample treatment (the supernatant obtained by directly centrifuging a human plasma sample after diluting the sample with water), a graph showing the operation curve without eliminating the influence of the interfering substances after the above-mentioned sample treatment, and a graph showing the operation curve in the case of b and the operation in the aqueous solutionThe curves are substantially identical, demonstrating that the effect of interfering species on the assay is eliminated. Table 1 shows the results of measuring bismuth ion in human serum samples, and the recovery rate was 97-102%.
TABLE 1
The result shows that the prepared bismuth ion rare earth fluorescent probe can be used for measuring the concentration of bismuth ions in a human serum sample with complex components.
Example 4
Bismuth ion rare earth fluorescent probe for determining bismuth ion in human urine
Taking 0.3mL of human urine sample, diluting with water by 10 times, adding a newly polished silver sheet, standing for 10 minutes, taking out the silver sheet, adding 100 mu L of 0.1M ethanolamine and 10mg of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, fully mixing, standing for 30 minutes, adding the sample solution into a 10-50kDa polyether sulfone membrane rotary separation column, performing centrifugal separation (10000 rpm is multiplied by 5 minutes), and then preserving a supernatant. mu.L of the bismuth ion rare earth fluorescent probe prepared in example 1 and 20. Mu.L of the supernatant were added to 930. Mu.L of a phosphate buffer solution (0.1mM, pH 4.8), respectively, mixed well for 10 minutes, and the Tb of the sample solution at a wavelength of 545nm was measured 3+ The concentration of bismuth ions is obtained according to the working curve of the fluorescence intensity of the bismuth ion rare earth fluorescent probe and the concentration of bismuth ions in the embodiment 2 and the measured fluorescence intensity of the sample solution. In FIG. 6, a is a working curve in which the influence of the interfering substance is not eliminated without the above-mentioned sample treatment (the supernatant obtained by directly centrifuging a human plasma specimen after diluting it with water), b is a working curve in which the influence of the interfering substance is eliminated by the above-mentioned sample treatment, and b is a working curve in which the working curve is substantially identical to that in the aqueous solution, indicating that the influence of the interfering substance on the measurement is eliminated. Table 2 shows the results of measuring bismuth ion in human urine samples, and the recovery rate is 102-105%.
TABLE 2
The result shows that the prepared bismuth ion rare earth fluorescent probe can be used for measuring the concentration of bismuth ions in a human urine sample with complex components.
Example 5
Example 5 was the same as example 3 except that 0.3mL of a human plasma sample was taken, diluted 10-fold with water, 100. Mu.L of 0.1M N-ethylmaleimide aqueous solution was added, mixed and left for 30 minutes, 100. Mu.L of 0.1M ethanolamine and 10mg of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide were added, mixed well and left for 30 minutes, and then the measurement was carried out, and the result was identical to that of example 3.
Example 6
Example 6 was the same as example 4 except that 0.3mL of a human urine sample was taken, diluted 10-fold with water, 100. Mu.L of a 0.1M N-ethylmaleimide aqueous solution was added, the mixture was mixed well and allowed to stand for 30 minutes, 100. Mu.L of 0.1M ethanolamine and 1 mg of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide were added, the mixture was mixed well and allowed to stand for 30 minutes, and then the measurement was carried out, whereby the results were identical to those of example 3.
Claims (9)
1. A method for detecting bismuth ions in biological fluid by a rare earth fluorescent probe is characterized by comprising the following steps:
adding a silver sheet into the sample solution for reaction, taking out the silver sheet, adding ethanolamine and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide for reaction, or adding N-ethylmaleimide into the sample solution for reaction, and then adding ethanolamine and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide for reaction; adding the reacted sample solution into a polyether sulfone membrane rotating separation column for centrifugal separation, adding a bismuth ion rare earth fluorescent probe solution into the supernatant liquid of the centrifugal separation, mixing, measuring the terbium ion characteristic fluorescence intensity of the mixed solution by using a fluorescence spectrophotometer, and measuring the bismuth ion content of the sample solution according to a working curve of the terbium ion fluorescence intensity and the bismuth ion concentration; the bismuth ion rare earth fluorescent probe is a molecular probe formed by 7-amino-4-methyl-2-quinolinone modified diethyl triaminepentaacetic acid and terbium ions.
2. The method for detecting bismuth ions in biological fluid by using the rare earth fluorescent probe as claimed in claim 1, wherein the silver sheet is added into the sample solution and left to stand for 10-15 minutes, then the silver sheet is taken out, ethanolamine aqueous solution and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide solid are added into the sample solution and fully mixed, then the mixture is placed for 30-40 minutes, and the sample solution is added into a polyether sulfone membrane rotational separation column for centrifugal separation.
3. The method for detecting bismuth ions in biological fluid by using the rare earth fluorescent probe as claimed in claim 1, wherein the sample solution is added with an N-ethylmaleimide aqueous solution, mixed and then placed for 30-40 minutes, an ethanolamine aqueous solution and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide solid are added, fully mixed and then placed for 30-40 minutes, and the sample solution is added into a polyethersulfone membrane rotary separation column for centrifugal separation.
4. The method for detecting bismuth ions in biological fluid by using the rare earth fluorescent probe as claimed in any one of claims 1 to 3, wherein the molecular weight cut-off range of the polyethersulfone membrane rotary separation column is 10-50kDa.
5. The method for detecting bismuth ions in biological fluid by using the rare earth fluorescent probe as claimed in claim 1, wherein the bismuth ion rare earth fluorescent probe solution is added into the supernatant liquid obtained by centrifugal separation, and the terbium ion characteristic fluorescence intensity of the mixed liquid is measured by using a fluorescence spectrophotometer after the mixture is mixed for 10-15 minutes.
6. The method for detecting bismuth ions in biological fluid by using the rare earth fluorescent probe as claimed in claim 1, wherein the molar ratio of the 7-amino-4-methyl-2-quinolinone-diethyltriaminepentaacetic acid to terbium ions is 1:1.
7. The method for detecting bismuth ions in biological fluid by using the rare earth fluorescent probe as claimed in claim 1, wherein the preparation method of the bismuth ion rare earth fluorescent probe comprises the following steps: respectively dissolving equal molar amounts of 7-amino-4-methyl-2-quinolinone and diethyltriaminepentaacetic dianhydride in anhydrous dimethylformamide, adding anhydrous triethylamine into an anhydrous dimethylformamide solution of the diethyltriaminepentaacetic dianhydride, dropwise stirring and adding the anhydrous dimethylformamide solution of the 7-amino-4-methyl-2-quinolinone, reacting under the condition of stirring in a dark place, adding a water solution of rare earth terbium ions, and mixing to obtain the bismuth ion rare earth fluorescent probe.
8. The method for detecting bismuth ions in biological fluid by using the rare earth fluorescent probe as claimed in claim 7, wherein the aqueous solution of rare earth terbium ions is an aqueous solution formed by nitrate or hydrochloride of terbium.
9. The use of the rare earth fluorescent probe of claim 1 in the detection of bismuth ions in biological fluids, in biological samples, in environmental waters, and in drugs.
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