CN112362628A - Fluorescent probe for detecting L-tryptophan - Google Patents
Fluorescent probe for detecting L-tryptophan Download PDFInfo
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- CN112362628A CN112362628A CN202011265609.3A CN202011265609A CN112362628A CN 112362628 A CN112362628 A CN 112362628A CN 202011265609 A CN202011265609 A CN 202011265609A CN 112362628 A CN112362628 A CN 112362628A
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- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 title claims abstract description 97
- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 52
- 229960004799 tryptophan Drugs 0.000 title claims abstract description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 38
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 26
- 238000001514 detection method Methods 0.000 claims abstract description 24
- 239000007788 liquid Substances 0.000 claims abstract description 20
- 238000002189 fluorescence spectrum Methods 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 14
- 230000008859 change Effects 0.000 claims abstract description 13
- IFGCUJZIWBUILZ-UHFFFAOYSA-N sodium 2-[[2-[[hydroxy-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid Chemical compound [Na+].C=1NC2=CC=CC=C2C=1CC(C(O)=O)NC(=O)C(CC(C)C)NP(O)(=O)OC1OC(C)C(O)C(O)C1O IFGCUJZIWBUILZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000005284 excitation Effects 0.000 claims abstract description 6
- 238000004993 emission spectroscopy Methods 0.000 claims abstract description 4
- 239000011259 mixed solution Substances 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- 239000000523 sample Substances 0.000 abstract description 16
- 230000035945 sensitivity Effects 0.000 abstract description 5
- 150000001413 amino acids Chemical class 0.000 description 11
- 238000004448 titration Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 230000009286 beneficial effect Effects 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 238000011897 real-time detection Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- OTTFEJLDNFEPGG-UHFFFAOYSA-N 2-amino-2-(1h-indol-2-yl)propanoic acid Chemical compound C1=CC=C2NC(C(N)(C(O)=O)C)=CC2=C1 OTTFEJLDNFEPGG-UHFFFAOYSA-N 0.000 description 1
- 241001120493 Arene Species 0.000 description 1
- 150000008575 L-amino acids Chemical class 0.000 description 1
- -1 Methyl Chemical group 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000003832 immune regulation Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
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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
- G01N21/6402—Atomic fluorescence; Laser induced fluorescence
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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"
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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
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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Abstract
The invention discloses a fluorescent probe for detecting L-tryptophan and application and a detection method thereof, and the fluorescent probe is prepared from methyl column [5] arene, a dichloromethane solution and ethanol. The method for detecting L-tryptophan by using the fluorescent probe comprises the following steps: 1) taking a fluorescent probe; 2) adding the liquid to be detected into the fluorescent probe, standing for 10-20min, then performing fluorescence emission spectrometry at a fixed excitation wavelength of 270nm, and drawing a change curve of the fluorescence intensity at the laser wavelength; 3) and (3) calculating the fluorescence emission spectrum intensity change value before and after the liquid to be detected is added into the fluorescent probe solution according to the curve of the step 2), and detecting the L-tryptophan. The probe provided by the invention has the characteristics of capability of detecting L-tryptophan, and is high in detection sensitivity, low in detection cost, simple in sample treatment, convenient to operate, rapid in determination and capable of detecting in real time.
Description
Technical Field
The invention relates to a fluorescent probe and application and a detection method thereof, in particular to a fluorescent probe for detecting L-tryptophan and an application and a detection method thereof.
Background
Amino acid is the basic composition substance of protein, and the intake of amino acid is the only way for human body to obtain nitrogen source, therefore, amino acid plays an extremely important role in the growth and development process of organism, and the role is mainly reflected in that: 1. is a constituent of human tissue; 2. various substances constituting the human body; 3. supplying heat; 4. immune regulation; 5. as an important carrier in vivo, plays a role in transportation; 6. and (4) an oxidation function. After the amino acid is absorbed by human body, a part of the amino acid is directly used for synthesizing protein, a part of the amino acid is oxidized and decomposed, wherein the nitrogen-containing part is used for synthesizing other necessary amino acid, and a part of the amino acid is decomposed as energy and is discharged out of the body in the form of urea.
L-tryptophan, also known as alpha-aminoindolylpropanoic acid, of the formula C11H12N2O2White to yellowish white crystals or crystalline powders. No odor or slight odor, and coloring after long-term illumination. Is stable when heated in dark with acid. It is easily decomposed in the presence of other amino acids, saccharides, and aldehydes. Can be used as food enhancer and antioxidant. Also can be used in medicine.
Based on the importance of amino acids to the growth and development of human bodies, the detection of the content and the variety of amino acids in food is particularly important, and the fluorescent probe is a novel detection reagent which is popular with people due to the advantages of high sensitivity, low detection cost, simple sample treatment, convenient operation, rapid determination and real-time detection, so that the research on the fluorescent probe for detecting L-tryptophan and the fluorescent probe detection method is necessary.
Disclosure of Invention
The invention aims to provide a fluorescent probe for detecting L-tryptophan and application and a detection method thereof. The probe provided by the invention has the characteristics of capability of detecting L-tryptophan, and is high in detection sensitivity, low in detection cost, simple in sample treatment, convenient to operate, rapid in determination and capable of detecting in real time.
The technical scheme of the invention is as follows: a fluorescent probe for detecting L-tryptophan is prepared from methyl column [5] arene, dichloromethane solution and ethanol.
The fluorescent probe for detecting L-tryptophan is prepared by the following method: and (3) taking the methyl column [5] arene, and dissolving the arene by using a mixed solution of dichloromethane and ethanol to obtain the fluorescent probe.
The fluorescent probe for detecting L-tryptophan is a methyl column [5]]The concentration of aromatic hydrocarbon is 4.0 × 10-4mol/L-6.0×10-4mol/L; in the mixed solution of the dichloromethane and the ethanol, the volume ratio of the dichloromethane to the ethanol is 90-99: 1-10.
The fluorescent probe for detecting L-tryptophan is a methyl column [5]]The concentration of aromatic hydrocarbon is 5.0 × 10-4mol/L; in the mixed solution of the dichloromethane and the ethanol, the volume ratio of the dichloromethane to the ethanol is 98: 2.
the application of the fluorescent probe in detecting L-tryptophan is provided.
A method for detecting L-tryptophan by using the fluorescent probe comprises the following steps:
1) taking a fluorescent probe;
2) adding the liquid to be detected into the fluorescent probe, standing for 10-20min, then performing fluorescence emission spectrometry at a fixed excitation wavelength of 270nm, and drawing a change curve of the fluorescence intensity at the laser wavelength;
3) and (3) calculating the fluorescence emission spectrum intensity change value before and after the liquid to be detected is added into the fluorescent probe solution according to the curve of the step 2), and detecting the L-tryptophan.
In the method for detecting L-tryptophan by using the fluorescent probe, in the step 3), when the fluorescence emission spectrum intensity changes and red shift occurs before and after the liquid to be detected is added, it is indicated that the liquid to be detected contains L-tryptophan; and when the fluorescence emission spectrum intensity does not change and does not generate red shift before and after the liquid to be detected is added, indicating that the liquid to be detected does not contain L-tryptophan.
The invention has the advantages of
Compared with the prior art, the invention has the following beneficial effects:
1. the fluorescent probe can detect L-tryptophan as long as the fluorescent probe contains the L-tryptophan, and has the advantages of high detection sensitivity and specificity. Namely, the probe is used for specifically detecting the L-tryptophan, has low detection cost and high detection efficiency, and is beneficial to the analysis of a complex microscopic system.
2. The methyl column [5] arene in the probe can form a subject-object inclusion with the L-tryptophan, so that the fluorescence intensity of the fluorescent probe is reduced and red shift occurs, and the L-tryptophan can be simply, quickly and sensitively detected.
3. Compared with the traditional detection method, the detection cost is greatly reduced, the operation is convenient, and the real-time detection can be realized.
In conclusion, the probe can carry out specificity detection on the L-tryptophan, has low detection cost and high detection efficiency, and is beneficial to the analysis of a complex microscopic system. In addition, when the probe is used for detection, the probe also has the advantages of higher sensitivity, simple sample treatment, convenient operation, quick determination and real-time detection.
In order to verify the beneficial effects of the invention, the inventor carries out a great deal of experimental research, and part of the experimental processes and results are as follows:
determination of methyl column [5] by molar ratio method]The fluorescence spectrum data between the aromatic hydrocarbon and the L-tryptophan comprises the following specific steps: a methyl column [5]]Aromatic hydrocarbon and L-tryptophan are respectively prepared into 1.0 multiplied by 10-2mol/L and 2.0X 10-1The solution of mol/L is reserved and the methyl column is fixed [5]]Aromatic concentration of 5.0 × 10-4mol/L, changing the concentration of L-tryptophan and preparing CL-tryptophan/CMethyl column [5]]Aromatic hydrocarbonsA solution of 0, 0.2, 0.4, 0.6, 0.8, 1.0, 1.2, 1.4, 1.6, 1.8, 2.0, 2.2, 2.4, 2.6, 2.8, at an excitation wavelength of 270nm, an excitation slit of 5nm, an emission slit of 5nm,the fluorescence emission spectrum of the solution was measured at 490V (FIG. 4, 5).
Quantitative analysis
The concentration obtained by the invention is 5.0X 10-4The detection results are shown in FIG. 6, and it can be seen that the concentrations of L-tryptophan in the standard solutions are different after different volume fractions are added, and the different concentrations of L-tryptophan can cause the fluorescence sensitization of the fluorescent probe solution to different degrees. Then, a nuclear magnetic titration experiment was performed in which the probe standard solution was added to solutions containing L-tryptophan at different concentrations (the detection results are shown in FIG. 7), and from this, it was deduced that the action pattern of L-tryptophan and the probe is shown in the inset of FIG. 8.
Description of the drawings:
FIG. 1 shows 5.0X 10-4mol/L methyl column [5]EtOH/CH of aromatic hydrocarbons at different ethanol volume fractions2Cl2Fluorescence emission spectra in mixed solution;
FIG. 2 shows EtOH/CH2Cl2(fEtOH98%) methyl column [5] in mixed solution]Fluorescence emission spectra of different concentrations of aromatic hydrocarbons;
FIG. 3 shows an L-amino acid p-methyl column [5]]Aromatic hydrocarbons (5.0X 10)-4Influence of mol. L-1) fluorescence intensity;
FIG. 4 is a fluorescence spectrum of methyl pillar [5] arene of an L-tryptophan titration probe;
FIG. 5 shows fluorescence emission with CL-tryptophan/CMeP5A graph of the relationship of the changes;
FIG. 6 is a graph of a linear fit of different concentrations of L-tryptophan to the change in fluorescence intensity of probe titration;
in FIG. 7 (a) is L-tryptophan1HNMR titration spectrogram; (b) (c), (d), (e), (f), (g), (h), (i) and (j) are each a methyl column [5]]The aromatic hydrocarbon concentration is 0.23, 0.57, 1.11, 1.31, 1.67, 2.11, 2.47, 2.75 and 3.05X 10-4Of L-tryptophan at mol. L-11HNMR titration spectrogram; (k) is a methyl column [5]]Process for preparing aromatic hydrocarbons1HNMR titration spectrogram;
FIG. 8 is a modeling of guest-host interactions between methyl column [5] arenes and L-tryptophan;
FIG. 9 is a mass spectrum of methyl column [5] arene @ L-tryptophan.
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 1: a fluorescent probe for detecting L-tryptophan is prepared by the following method: mixing dichloromethane and ethanol according to a volume ratio of 98: 2 mixing to obtain a mixture, and taking a methyl column [5]]Aromatic hydrocarbon is dissolved in the mixed solution to prepare a methyl column [5]]The concentration of aromatic hydrocarbon is 5.0 × 10-4mol/L fluorescent probe.
Example 2: a fluorescent probe for detecting L-tryptophan is prepared by the following method: mixing dichloromethane and ethanol according to a volume ratio of 90: 10 mixing to obtain a mixture, and collecting the mixture to a methyl column [5]]Aromatic hydrocarbon is dissolved in the mixed solution to prepare a methyl column [5]]The concentration of aromatic hydrocarbon is 4.0 × 10-4mol/L fluorescent probe.
Example 3: a fluorescent probe for detecting L-tryptophan is prepared by the following method: mixing dichloromethane and ethanol according to a volume ratio of 99: 1 mixing to obtain a mixture, and taking a methyl column [5]]Aromatic hydrocarbon is dissolved in the mixed solution to prepare a methyl column [5]]The concentration of aromatic hydrocarbon is 6.0 × 10-4mol/L fluorescent probe.
Example 4: a method for detecting L-tryptophan by using a fluorescent probe comprises the following steps:
1) taking any one of the fluorescent probes prepared in examples 1-3;
2) adding the liquid to be detected into the fluorescent probe, standing for 10-20min, then performing fluorescence emission spectrometry at a fixed excitation wavelength of 270nm, and drawing a change curve of the fluorescence intensity at the laser wavelength;
3) calculating the change value of fluorescence emission spectrum intensity before and after adding the liquid to be detected into the fluorescence probe solution according to the curve of the step 2), and when the fluorescence emission spectrum intensity before and after adding the liquid to be detected changes and is subjected to red shift, indicating that the liquid to be detected contains L-tryptophan; and when the fluorescence emission spectrum intensity does not change and does not generate red shift before and after the liquid to be detected is added, indicating that the liquid to be detected does not contain L-tryptophan.
The above description is only for the purpose of illustrating the present invention and the appended claims, and the scope of the present invention is not limited thereto, and any person skilled in the art can substitute or change the technical solution and the inventive concept of the present invention within the technical scope of the present invention.
Claims (7)
1. A fluorescent probe for detecting L-tryptophan, characterized in that: is prepared from methyl column (5) arene, dichloromethane solution and alcohol.
2. The fluorescent probe for detecting L-tryptophan according to claim 1, which is prepared by the following method: and (3) taking the methyl column [5] arene, and dissolving the arene by using a mixed solution of dichloromethane and ethanol to obtain the fluorescent probe.
3. The fluorescent probe for detecting L-tryptophan according to claim 2, wherein: the methyl column [5] in the fluorescent probe]The concentration of aromatic hydrocarbon is 4.0 × 10-4mol/L-6.0×10-4mol/L; in the mixed solution of the dichloromethane and the ethanol, the volume ratio of the dichloromethane to the ethanol is 90-99: 1-10.
4. The fluorescent probe for detecting L-tryptophan according to claim 3, wherein: the methyl column [5] in the fluorescent probe]The concentration of aromatic hydrocarbon is 5.0 × 10-4mol/L; in the mixed solution of the dichloromethane and the ethanol, the volume ratio of the dichloromethane to the ethanol is 98: 2.
5. use of a fluorescent probe according to any one of claims 1 to 4 for the detection of L-tryptophan.
6. A method for detecting L-tryptophan by using the fluorescent probe as claimed in any one of claims 1 to 4, comprising the steps of:
1) taking a fluorescent probe;
2) adding the liquid to be detected into the fluorescent probe, standing for 10-20min, then performing fluorescence emission spectrometry at a fixed excitation wavelength of 270nm, and drawing a change curve of the fluorescence intensity at the laser wavelength;
3) and (3) calculating the fluorescence emission spectrum intensity change value before and after the liquid to be detected is added into the fluorescent probe solution according to the curve of the step 2), and detecting the L-tryptophan.
7. The method for detecting L-tryptophan by using the fluorescent probe as claimed in claim 6, wherein the fluorescent probe comprises: in the step 3), when the fluorescence emission spectrum intensity changes and red shift occurs before and after the liquid to be detected is added, it is indicated that the liquid to be detected contains L-tryptophan; and when the fluorescence emission spectrum intensity does not change and does not generate red shift before and after the liquid to be detected is added, indicating that the liquid to be detected does not contain L-tryptophan.
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| CN115728281A (en) * | 2022-12-09 | 2023-03-03 | 山西大学 | Fluorescent probe for detecting L-tryptophan and preparation thereof |
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Application publication date: 20210212 |