CN115404070A - Method for rapidly detecting mercury ion adsorption capacity of lipopolysaccharide by using fluorescent labeling method - Google Patents
Method for rapidly detecting mercury ion adsorption capacity of lipopolysaccharide by using fluorescent labeling method Download PDFInfo
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- CN115404070A CN115404070A CN202110574610.2A CN202110574610A CN115404070A CN 115404070 A CN115404070 A CN 115404070A CN 202110574610 A CN202110574610 A CN 202110574610A CN 115404070 A CN115404070 A CN 115404070A
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- tetraphenylethylene
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- 239000002158 endotoxin Substances 0.000 title claims abstract description 37
- 229920006008 lipopolysaccharide Polymers 0.000 title claims abstract description 35
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title abstract description 14
- 238000003234 fluorescent labeling method Methods 0.000 title description 2
- 238000001179 sorption measurement Methods 0.000 title description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 19
- -1 mercury ions Chemical class 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 230000035945 sensitivity Effects 0.000 claims abstract description 9
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- ZWPWLKXZYNXATK-UHFFFAOYSA-N bis(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(C)C=C1 ZWPWLKXZYNXATK-UHFFFAOYSA-N 0.000 claims abstract description 6
- PAJHPMLKBHFAPU-UHFFFAOYSA-N 1-methyl-2-(1,2,2-triphenylethenyl)benzene Chemical group CC1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 PAJHPMLKBHFAPU-UHFFFAOYSA-N 0.000 claims abstract description 4
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- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 abstract description 16
- 239000007850 fluorescent dye Substances 0.000 abstract description 7
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Abstract
The invention designs and synthesizes a preparation method and application of a specific detection mercury ion concentration and lipopolysaccharide diagnostic reagent with high selectivity and high sensitivity, and the molecular formula of the prepared tetra-styrene fluorescent compound is C 46 H 64 N 4 O 8 The molecular weight is 801.0380, and the molecular structure is:
Description
Technical Field
The invention relates to the field of metal ion detection, in particular to a preparation method and application of a tetra-styrene fluorescent compound for specifically identifying pump ions and lipopolysaccharide.
Background
The pump, commonly known as mercury, is a highly toxic and unnecessary element, and the pump is in the form of an element in water and soil pondsMigration and transformation in the atmosphere and biosphere, occurring widely in nature. Due to the biological aggregation and the difficult biodegradability, pumps generated in various ways finally enter fresh water and marine ecosystems, and are circularly transferred and enriched through food chains (especially fishes), thereby causing great harm to the earth ecosystems and human health. Pump ion (Hg) 2+ ) Is the most stable inorganic form in biological environment, and has carcinogenicity, high solubility and cytotoxicity. The World Health Organization (WHO) specifies Hg in drinking water 2+ The concentration must be lower than 6 mug/L (30 nmol/L), and even a very low concentration of pump ions, long-term intake can cause damage to the nervous system and the immune system. Thus quickly and efficiently detecting Hg in biological systems and environments 2+ It is very necessary.
The traditional main methods for detecting metal ions include atomic absorption spectrometry, inductively coupled plasma-mass spectrometry, spectrophotometry, electrochemical technology, high performance liquid chromatography, surface enhanced raman spectrometry, and the like. These methods have the advantages of high sensitivity and accuracy, but are complicated, time-consuming, expensive, and not suitable for wide use. As an excellent modern analysis means, the fluorescence analysis method has the technical characteristics of high sensitivity, strong selectivity, high space-time resolution and the like compared with the traditional method. Fluorescent probe molecules can also penetrate through cell membranes to enter cells, detect metal ions in the cells, and are widely applied to the aspects of biosensing, fluorescence imaging and the like.
Tetraphenylethylene (TPE) has a propeller-shaped structure with a peripheral benzene ring capable of freely rotating, is a typical AIE fluorescent luminophore, and a derivative of the Tetraphenylethylene (TPE) generally contains a larger conjugated system in a molecule, has very strong fluorescence quantum yield, shows a plurality of unique photoelectric properties and biological activities, and has wide application prospects in the fields of photoelectric materials, biosensing, fluorescence imaging and the like. The tetra-styrene compound is simple and convenient to synthesize, easy to functionalize and easy to design a fluorescent probe which has high selectivity on substances such as specific ions, biological macromolecules and the like. The method has the advantages of high selectivity, low detection limit, low biological toxicity and the like in the chemical sensing field, so that the method is widely applied to ion detection in environment and organisms.
Lipopolysaccharide (LPS, endotoxin) is the main component of gram-negative bacteria cell outer membrane, and consists of lipid A, core polysaccharide and O-antigen repeating unit. LPS has an amphiphilic structure, namely a hydrophilic head and a hydrophobic tail, can provide a hydrophilic barrier for thalli to protect bacteria from severe environment and harmful substances, and researches show that after thalli cells are destroyed, LPS is released to generate toxin, which is a main pathogenesis causing shock and is also a main cause of death of critically ill patients. In the immune system, even small amounts of LPS can cause a violent reaction that can affect organ and cellular function and structure, alter metabolic function, raise body temperature, affect hemodynamics, cause sepsis and septic shock. Therefore, accurate measurement of LPS is very important for the diagnosis of cell function and disease. The methods for detecting lipopolysaccharide reported at present include limulus reagent assay for endotoxin, gas chromatography-mass spectrometry, and electrochemical assay. Although these methods have made some progress in the detection of LPS, these methods have faced practical problems of high cost, low sensitivity and low selectivity, so it is very urgent to develop a cheap, well-soluble and relatively sensitive fluorescent probe for detecting LPS.
By combining the analysis, the invention designs and synthesizes the specific pump ion concentration detection diagnosis compound with the tetrastyrene and the hydrophilicity, and the specific pump ion concentration detection diagnosis compound can be applied to Hg 2+ The analysis and detection of (2). The specific pump ion concentration detection diagnostic reagent can detect Hg in a pure water solution 2+ The method has the characteristics of high sensitivity, good selectivity, low detection cost and the like. Simultaneously, the compound and Hg 2+ The formed complex can detect Lipopolysaccharide (LPS) in cells, which is of great significance in researching the function of Lipopolysaccharide (LPS) in bacteria and related diseases, and can detect Hg in organisms 2+ One direction is indicated by further studies.
Disclosure of Invention
The invention aims to solve the problems, and provides a preparation method and application of a specific detection pump ion concentration and lipopolysaccharide diagnostic reagent with high selectivity and high sensitivity.
The technical scheme of the invention is as follows:
the invention designs and synthesizes a preparation method and application of a specific pump ion concentration detection diagnostic reagent with high selectivity and high sensitivity, and the molecular formula of the prepared tetra-styrene fluorescent compound is C 46 H 64 N 4 O 8 The molecular weight is 801.0380, and the molecular structure is:
the preparation steps are as follows:
1) 4,4',4 ", 4'" -tetramethyltetraphenylethylene: magneton and zinc powder (18.66g, 285mmol) are added into a 500mL three-neck round-bottom flask, 200mL of anhydrous tetrahydrofuran is added under argon atmosphere, stirring is carried out for 10min under ice bath condition, then titanium tetrachloride (10mL, 95mmol) is measured by a disposable syringe and slowly dripped into the round-bottom flask, stirring is carried out for 10min at 0 ℃, then the temperature is raised to 85 ℃, reflux is carried out for 2h, and then natural cooling is carried out to room temperature. A solution of 4,4' -dimethylbenzophenone (8 g, 38.05mmol) dissolved in 30mL of anhydrous tetrahydrofuran was added to the reaction system with a one-shot syringe under ice bath conditions, stirred at 0 ℃ for 30min and then heated to 85 ℃ for reflux for 24h. After the reaction was stopped and the reaction system was naturally cooled to room temperature, the reaction solution was transferred from a 500mL three-necked flask to a 1000mL beaker, 100mL 10wt% potassium carbonate solution and 500mL ethyl acetate were added to the reaction solution, 200mL distilled water was added to the beaker, and the extraction was repeated until the inorganic phase color changed. The organic phase after drying over anhydrous magnesium sulfate was freed of the solvent by rotary evaporator to give 6.77g of a white solid powder in 91.59% yield.
2) 4,4',4 ", 4'" -tetrabromomethyltetraphenylethylene: 4,4', 4' -tetramethyltetraphenylethylene (1g 2.57mmol), N-bromosuccinimide (2.012g, 11.307mmol), dibenzoyl peroxide (117.95mg, 486.93. Mu. Mol) and magneton were put into a dry 250mL three-neck round-bottom flask, 150mL carbon tetrachloride was added under argon atmosphere and heated to 85 ℃ and stirred for 4h, and the reaction solution underwent a color change from colorless to orange-red to pale yellow. Stopping heating, naturally cooling to room temperature, removing part of succinimide by suction filtration, washing a filter cake by using minimum dichloromethane, and adding 4g of silica gel powder into the filtrate to prepare a sample by rotary evaporation. The crude product was isolated and purified by silica gel column chromatography (dichloromethane/petroleum ether =1/4,v/v) to give 577mg of pale yellow solid powder with a yield of 32.08%.
3) 4,4',4 ", 4'" -tetrakis (diethanolamino) methyl tetraphenylethylene: 4,4', 4' -tetrabromomethyltetraphenylethylene (100mg, 0.142mmoL), diethanolamine (89.57mg, 0.852mmoL), potassium carbonate (117.75 mg,0.852 mmoL) and magnetite were taken in a dry 100mL three-necked round bottom flask, 15mL of acetonitrile was added under argon atmosphere, heated to 85 ℃ and stirred for 4 hours. Stopping heating, naturally cooling to room temperature, removing potassium carbonate by suction filtration, washing a filter cake by using a small amount of dichloromethane, and separating and purifying the filtrate by silica gel column chromatography to obtain 59mg of pale yellow solid powder with the yield of 51.86%.
The mass ratio of 4,4' -dimethyl benzophenone to titanium tetrachloride is 1: 2.15
The mass ratio of 4,4', 4' -methyl bromomethyl tetraphenylethylene to N-bromosuccinimide is 1: 2.012
The mass ratio of 4,4', 4' -tetrabromomethyl tetraphenylethylene to diethanolamine is 1: 0.89
The application of the diagnostic reagent for specifically detecting the concentrations of mercury ions and lipopolysaccharides prepared in the above way is used for quickly detecting the concentrations of metal mercury ions and biomolecular lipopolysaccharides.
The invention has the advantages that: the preparation method has the advantages of simple process, easily obtained raw materials and easy implementation, and the prepared diagnostic reagent for specifically detecting the concentrations of mercury ions and lipopolysaccharide has high selectivity on metal mercury ions and biomolecular lipopolysaccharide and has high application value.
Drawings
FIG. 1 is an aqueous solution (concentration: 1X 10) of a diagnostic reagent for specifically detecting the concentration of mercury ions -5 mol/L) of different metal ions at the same concentration
Graph comparing the change in fluorescence intensity after reaction.
FIG. 2 is an aqueous solution of a diagnostic reagent for specifically detecting the concentration of mercury ions (concentration: 1X 10) -5 mol/L) with the same concentration of different metal ions
Graph comparing the change of UV absorbance after reaction.
FIG. 3 is an aqueous solution (concentration 1X 10) of a diagnostic reagent for specifically detecting the concentration of mercury ions -5 mol/L) with different concentrations of HgCl 2 And (3) a solution reaction fluorescence intensity change graph.
FIG. 4 is an aqueous solution (concentration 1X 10) of a diagnostic reagent for specifically detecting the concentration of mercury ions -5 mol/L) HgCl was added 2 Solution (Hg) 2 The concentration is 1.961 × 10 -4 mol/L) to form a coordination compound. Adding Glycine (Glycine), L-glutamic acid (L-Glu.acid), D-Fructose (D-Fructose), egg yolk lecithin (E.Y.Lec), dried tetracid (Myri.acid), na with the same concentration 3 PO 4 ，KH 2 PO 4 D-Cysteine (D-Cysteine), 5' -adenosine triphosphate disodium salt (ATP), lipopolysaccharide (LPS) response fluorescence intensity change chart.
Detailed Description
The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to the following examples.
Example (b):
the invention designs and synthesizes a preparation method and application of a diagnosis reagent with high selectivity and high sensitivity for specifically detecting mercury ion concentration and lipopolysaccharide, and the molecular formula of the prepared tetra-styrene fluorescent compound is C 46 H 64 N 4 O 8 Molecular weight ofIs 801.0380, the molecular structure is:
the preparation steps are as follows:
1) 4,4',4 ", 4'" -tetramethyltetraphenylethylene: adding magnetons and zinc powder into a 500mL three-neck round-bottom flask, adding anhydrous tetrahydrofuran under the argon atmosphere, stirring for 10min under an ice bath condition, measuring titanium tetrachloride by using a disposable syringe, slowly dropping the titanium tetrachloride into the round-bottom flask, stirring for 10min at 0 ℃, heating to 85 ℃, refluxing for 2h, and naturally cooling to room temperature. Under the ice bath condition, a 4,4' -dimethylbenzophenone solution dissolved in 30mL of anhydrous tetrahydrofuran is added into the reaction system by a disposable syringe, stirred at 0 ℃ for 30min and then heated to 85 ℃ for reflux for 24h. After the reaction is stopped, the reaction system is naturally cooled to room temperature, the reaction liquid is transferred to a 1000mL beaker from a 500mL three-neck flask, 10wt% of potassium carbonate solution and 500mL ethyl acetate are added into the reaction liquid, distilled water is added into the beaker, and the extraction is repeatedly carried out until the inorganic phase color changes. The organic phase dried over anhydrous magnesium sulfate was subjected to solvent removal using a rotary evaporator to obtain a white solid powder.
The reaction formula is as follows:
2) 4,4',4 ", 4'" -tetrabromomethyltetraphenylethylene: 4,4', 4' -tetramethyltetraphenylethylene, N-bromosuccinimide, dibenzoyl peroxide and magnetons are taken in a dry 250mL three-neck round-bottom flask, 150mL carbon tetrachloride is added under argon atmosphere, then the mixture is heated to 85 ℃, and stirred for 4 hours, so that the color of the reaction solution can change from colorless to orange-red to light yellow. Stopping heating, naturally cooling to room temperature, removing part of succinimide through suction filtration, washing a filter cake with a small amount of dichloromethane, and adding silica gel powder into the filtrate to prepare a sample through rotary evaporation. The crude product was isolated and purified by silica gel column chromatography (dichloromethane/petroleum ether =1/4,v/v) to give a pale yellow solid powder.
The reaction formula is as follows:
3) 4,4',4 ", 4'" -tetrakis (diethanolamino) methyl tetraphenylethylene: adding acetonitrile into a dry 100mL three-mouth round-bottom flask containing 4,4', 4' -tetrabromomethyl tetraphenylethylene, diethanol amine, potassium carbonate and magnetons in an argon atmosphere, heating to 85 ℃, stirring for 4h, stopping heating, naturally cooling to room temperature, performing suction filtration to remove the potassium carbonate, washing a filter cake with a small amount of dichloromethane, and separating, separating and purifying the filtrate by silica gel column chromatography to obtain light yellow solid powder. 1 H NMR(400MHz，CDCl 3 )δ(ppm)：7.10(d，J＝8HZ，8H)，6.99(d，J＝8HZ，8H)， 3.57(t，J＝8HZ，16H)，3.49(s，8H)，2.68(t，J＝4HZ，16H)； 13 C NMR(100MHz， CDCl 3 )δ(ppm)：142.60，140.50，138.00，131.62，128.95，59.94，59.66，57.89.MS(ESI + ) (m/z)：[M+H] + calcd for C 46 H 65 N 4 O 8 ：801.4797，found，801.4782.
The reaction formula is as follows:
FIG. 1 shows different metal ions of the same concentration
The fluorescence intensity after reaction with the diagnostic reagent for specifically detecting the concentration of mercury ions is compared with that of the mercury ions, and the graph can be seen that except for Hg 2+ The fluorescence intensity of the compound is not obviously influenced by other added metal ions besides the enhancement of the fluorescence, which can show that the compound has no obvious influence on Hg 2+ Has selectivity.
FIG. 2 shows different metal ions of the same concentration
And (3) comparing the ultraviolet absorbance change after the reaction with the diagnostic reagent for specifically detecting the concentration of the tribute ions. The figure shows that: except for Hg 2+ The ultraviolet absorbance is enhanced, and other added metal ions have no obvious influence on the ultraviolet absorbance of the compound, so that the compound can be proved to have effect on Hg 2+ Has selectivity.
FIG. 3 shows that HgCl with different concentrations is gradually added into the aqueous solution of the diagnostic reagent for specifically detecting the concentration of mercury ions 2 And (4) measuring a fluorescence spectrum of the solution. The figure shows that: the emission wavelength of the diagnostic reagent for specifically detecting the concentration of mercury ions and lipopolysaccharides gradually rises at 374nm and 465nm, and the concentration is increased
When the fluorescence intensity did not increase any more.
FIG. 4 shows the addition of HgCl to an aqueous solution of the diagnostic reagent for specifically detecting the concentration of mercury ions 2 Forming a complex, adding Glycine (Glycine), L-glutamic acid (L-Glu. Acid), D-Fructose (D-Fructose), egg yolk lecithin (E.Y.Lec), myristic acid (Myri. Acid), and Na at the same concentration 3 PO 4 ，KH 2 PO 4 Comparative graphs showing the change in fluorescence intensity of D-Cysteine (D-Cysteine), 5' -adenosine triphosphate disodium salt (ATP) and Lipopolysaccharide (LPS). The figure shows that: besides the enhancement of the fluorescence intensity by Lipopolysaccharide (LPS), the fluorescence intensity of the complex is not obviously influenced by adding other biological molecular compounds, which can indicate that the complex has selectivity on Lipopolysaccharide (LPS).
Claims (4)
1. The invention designs and synthesizes a preparation method and application of a diagnostic reagent with high selectivity and high sensitivity for specifically detecting mercury ion concentration and lipopolysaccharide, and tetraphenylethylene prepared in the inventionThe molecular formula of the fluorescent-like compound is C 46 H 64 N 4 O 8 The molecular weight is 801.0380, and the molecular structure is:
the preparation steps are as follows:
1) 4,4',4 ", 4'" -tetramethyltetraphenylethylene: adding magnetons and zinc powder into a 500mL three-neck round-bottom flask, adding anhydrous tetrahydrofuran under the argon atmosphere, stirring for 10min under an ice bath condition, measuring titanium tetrachloride by using a disposable syringe, slowly dropping the titanium tetrachloride into the round-bottom flask, stirring for 10min at 0 ℃, heating to 85 ℃, refluxing for 2h, and naturally cooling to room temperature. Under the ice bath condition, a 4,4' -dimethylbenzophenone solution dissolved in 30mL of anhydrous tetrahydrofuran is added into the reaction system by a disposable syringe, stirred at 0 ℃ for 30min and then heated to 85 ℃ for reflux for 24h. After the reaction is stopped, the reaction system is naturally cooled to room temperature, the reaction solution is transferred from a 500mL three-neck flask to a 1000mL beaker, 10wt% potassium carbonate solution and 500mL ethyl acetate are added into the reaction solution, 200mL distilled water is added into the beaker, and the extraction is repeated until the inorganic phase color changes. The organic phase dried over anhydrous magnesium sulfate was subjected to solvent removal using a rotary evaporator to obtain a white solid powder.
2) 4,4,4 ", 4'" -tetrabromomethyltetraphenylethylene: 4,4', 4' -tetramethyltetraphenylethylene, N-bromosuccinimide, dibenzoyl peroxide and magnetons are taken in a dry 250mL three-neck round-bottom flask, 150mL carbon tetrachloride is added under argon atmosphere, then the mixture is heated to 85 ℃, and stirred for 4 hours, so that the color of the reaction solution can change from colorless to orange-red to light yellow. Stopping heating, naturally cooling to room temperature, removing part of succinimide through suction filtration, washing a filter cake with a small amount of dichloromethane, and adding silica gel powder into the filtrate to prepare a sample through rotary evaporation. The crude product was isolated and purified by silica gel column chromatography (dichloromethane/petroleum ether =1/4,v/v) to give a pale yellow solid powder.
3) 4,4',4 ", 4'" -tetrakis (diethanolamino) methyl tetraphenylethylene: 4,4', 4' -tetrabromomethyl tetraphenylethylene, diethanolamine, potassium carbonate and magnetite were taken in a dry 100mL three-necked round bottom flask, acetonitrile was added under argon atmosphere and heated to 85 ℃ with stirring for 4h. Stopping heating, naturally cooling to room temperature, removing potassium carbonate by suction filtration, washing a filter cake by using a small amount of dichloromethane, and separating and purifying the filtrate by using a silica gel column chromatography to obtain light yellow solid powder.
2. The composition of claim 1, wherein the mass ratio of 4,4' -dimethylbenzophenone to titanium tetrachloride is 1: 2.15.
3. The composition of claim 1, wherein the mass ratio of 4,4',4 ", 4'" -tetrabromomethyl tetraphenylethylene to N-bromosuccinimide is 1: 2.012.
4. The composition of claim 1, wherein the mass ratio of 4,4',4 ", 4'" -tetrabromomethyl tetraphenylethylene to diethanolamine is 1: 0.89.
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| US20080255346A1 (en) * | 2007-04-11 | 2008-10-16 | Chung-Ang University Industry-Academy Cooperation Foundation | Ratiometric fluorescent chemosensor for selective detection of Hg (II) ions |
| CN108998006A (en) * | 2018-07-20 | 2018-12-14 | 合肥工业大学 | A kind of environmental-friendly strain-responsive type fluorescence supramolecular materials and preparation method thereof |
| CN110698409A (en) * | 2019-10-23 | 2020-01-17 | 湖北理工学院 | Reactive benzimidazole fluorescent probe for specifically recognizing mercury ions as well as preparation method and application of reactive benzimidazole fluorescent probe |
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2021
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| US20080255346A1 (en) * | 2007-04-11 | 2008-10-16 | Chung-Ang University Industry-Academy Cooperation Foundation | Ratiometric fluorescent chemosensor for selective detection of Hg (II) ions |
| CN108998006A (en) * | 2018-07-20 | 2018-12-14 | 合肥工业大学 | A kind of environmental-friendly strain-responsive type fluorescence supramolecular materials and preparation method thereof |
| CN110698409A (en) * | 2019-10-23 | 2020-01-17 | 湖北理工学院 | Reactive benzimidazole fluorescent probe for specifically recognizing mercury ions as well as preparation method and application of reactive benzimidazole fluorescent probe |
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| SELVARAJ MUTHUSAMY ET AL: ""Tetraphenylethene-based fluorescent probe with aggregation-induced emission behavior for Hg2+ detection and its application"", 《ANALYTICA CHIMICA ACTA》, vol. 1148, 6 January 2021 (2021-01-06), pages 238178, XP086471959, DOI: 10.1016/j.aca.2020.12.053 * |
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