CN113527196B - Be used for detecting Al 3+ And Zn 2+ Compounds of (C), preparation method and application thereof - Google Patents
Be used for detecting Al 3+ And Zn 2+ Compounds of (C), preparation method and application thereof Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 27
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- 239000007850 fluorescent dye Substances 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 7
- 229960000583 acetic acid Drugs 0.000 claims description 5
- 239000012362 glacial acetic acid Substances 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 238000006482 condensation reaction Methods 0.000 claims description 4
- 235000019441 ethanol Nutrition 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000012295 chemical reaction liquid Substances 0.000 claims description 2
- 238000001917 fluorescence detection Methods 0.000 claims description 2
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract description 15
- 238000001514 detection method Methods 0.000 abstract description 14
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical class C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 230000002457 bidirectional effect Effects 0.000 abstract 1
- 230000000536 complexating effect Effects 0.000 abstract 1
- 239000011701 zinc Substances 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 238000002189 fluorescence spectrum Methods 0.000 description 9
- 229910021645 metal ion Inorganic materials 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000000523 sample Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000011573 trace mineral Substances 0.000 description 2
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000000840 electrochemical analysis Methods 0.000 description 1
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- 230000000926 neurological effect Effects 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/86—Hydrazides; Thio or imino analogues thereof
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- 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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Abstract
The invention discloses a method for detecting Al 3+ And Zn 2+ A preparation method and application thereof. The N' - (2-hydroxy-5- (camphor-3-methylene) benzylidene) pyridine formylhydrazine prepared by taking camphor derivative 2-hydroxy-5- (camphor-3-methylene) benzaldehyde as raw material can be selectively combined with Al 3+ And Zn 2+ Complexing to make its fluorescence quickly increase, and with green and orange fluorescence, its detection limit can be up to 12.1nM and 14.2nM, and said compound can be used as fluorescent probe for bidirectional detection of Al 3+ And Zn 2+ Has good application value.
Description
Technical Field
The invention belongs to the technical field of fine organic synthesis, and in particular relates to a method for detecting Al 3+ And Zn 2+ A preparation method and application thereof.
Background
Zinc ions are not only trace elements essential to the human body but also trace elements essential to all organisms. It plays a key role in regulating apoptosis, nucleic acid and protein metabolism, nerve signal transmission, immune system and other molecular mechanismsActing as a medicine. However, zinc ion metabolism disorders are associated with neurological diseases such as Alzheimer's disease, parkinson's disease, epilepsy, etc. Aluminum is the most abundant metal element in the crust and is also an essential element for the human body. Aluminum is widely present in our lives so we do not have to worry about under-intake, but excessive intake can lead to diseases such as alzheimer's disease, parkinson's disease, osteoporosis, neurological problems, etc. Therefore, design and development of a system capable of effectively detecting Al in biological systems and environments 3+ And Zn 2+ Has very important significance.
In recent years, various methods such as electrochemical analysis, atomic absorption spectroscopy, isotope chromatography and chromatography are used for trace Al 3+ And Zn 2+ And (5) detecting elements. However, the traditional detection methods have the defects of complex pretreatment, expensive equipment, complicated operation, time-consuming detection and the like, and are not suitable for real-time detection of on-site samples. Compared with the traditional detection method, the fluorescent probe detection technology has the advantages of simple sample preparation, high response speed, high sensitivity, good selectivity, simple and convenient operation and the like. Widely applied to the fields of chemistry, medicine, environmental science, life science and the like. In particular, in recent years, fluorescent probes have been developed in the directions of high efficiency, minute quantity, microscopic and real time.
In recent years, a large number of organic molecular fluorescent probes for metal ion detection have been developed. However, some of these fluorescent probes require more organic solvent systems, limiting their use. Although many of the reported probes have the advantage of high selectivity for a single analyte, differentially responsive probes that can detect multiple analytes would be more effective and desirable in practical applications. Compared with a one-to-one probe, the detection method of one probe for a plurality of analytes has the advantages of high efficiency, simplicity, short time, low cost and the like, and is more concerned in metal ion detection. Therefore, the development of the fluorescent probe with high water solubility and multiple targets and simultaneous detection has great significance.
Disclosure of Invention
This section is intended to outline some aspects of embodiments of the invention and to briefly introduce some preferred embodiments. Some simplifications or omissions may be made in this section as well as in the description summary and in the title of the application, to avoid obscuring the purpose of this section, the description summary and the title of the invention, which should not be used to limit the scope of the invention.
The present invention has been made in view of the above and/or problems occurring in the prior art.
In order to solve the technical problems, the invention provides the following technical scheme: be used for detecting Al 3+ And Zn 2+ The compound has the following structural formula:
another object of the present invention is to provide a method for detecting Al as described above 3+ And Zn 2+ The compound is prepared by condensation reaction of 2-hydroxy-5- (camphor-3-methylene) benzaldehyde and pyridine-2-formylhydrazine;
the synthetic route is as follows:
as the invention, the method is used for detecting Al 3+ And Zn 2+ A preferred embodiment of the process for the preparation of the compounds of (1) wherein: the condensation reaction is carried out by adding 2-hydroxy-5- (camphor-3-methylene) benzaldehyde and pyridine-2-formylhydrazine into solvent; adding glacial acetic acid and carrying out reflux reaction; and concentrating the reaction liquid, cooling and separating out solid, washing and suction filtering to obtain the target product.
As the invention, the method is used for detecting Al 3+ And Zn 2+ A preferred embodiment of the process for the preparation of the compounds of (1) wherein: the molar ratio of the 2-hydroxy-5- (camphor-3-methylene) benzaldehyde to the pyridine-2-formylhydrazine is 1:1-2.
As the invention, the method is used for detecting Al 3+ And Zn 2+ A preferred embodiment of the process for the preparation of the compounds of (1) wherein: the solvent is added into the solvent to be mixed with the solvent,adding into absolute ethyl alcohol.
As the invention, the method is used for detecting Al 3+ And Zn 2+ A preferred embodiment of the process for the preparation of the compounds of (1) wherein: the addition amount of the glacial acetic acid is 0.3-1.5% of the volume of the solvent.
As the invention, the method is used for detecting Al 3+ And Zn 2+ A preferred embodiment of the process for the preparation of the compounds of (1) wherein: and the reflux reaction is carried out for 12-24 hours.
As the invention, the method is used for detecting Al 3+ And Zn 2+ A preferred embodiment of the process for the preparation of the compounds of (1) wherein: and washing and suction filtering, namely washing and suction filtering by using ethanol.
Another object of the present invention is to provide a method for detecting Al as described above 3+ And Zn 2+ Fluorescence detection of Al in the compounds of (2) 3+ And Zn 2+ Is used in the field of applications.
Another object of the present invention is to provide a method for detecting Al as described above 3+ And Zn 2+ Preparation of compounds for detecting Al 3+ And Zn 2+ Is used in the dual-functional fluorescent probe.
Compared with the prior art, the invention has the following beneficial effects:
the invention uses the N' - (2-hydroxy-5- (camphor-3-methylene) benzylidene) pyridine formylhydrazine prepared by taking the camphor derivative 2-hydroxy-5- (camphor-3-methylene) benzaldehyde as the raw material, and can bidirectionally identify Al 3+ And Zn 2+ The fluorescence is rapidly enhanced under 365nM ultraviolet light, green and orange fluorescence is generated, the detection limit reaches 12.1nM and 14.2nM, and the compound can be used as a sensitive fluorescent probe for bi-directional detection of Al 3+ And Zn 2+ 。
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings that are needed in the description of the embodiments will be briefly described below, it being obvious that the drawings in the following description are only some embodiments of the present invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art. Wherein:
FIG. 1 is a graph showing the fluorescence spectrum selectivity of N' - (2-hydroxy-5- (camphor-3-methylene) benzylidene) pyridine formylhydrazine for interaction with various metal ions;
FIG. 2 is a graph of N' - (2-hydroxy-5- (camphor-3-methylene) benzylidene) pyridine formylhydrazine with varying concentrations of Al 3+ And (3) a fluorescence spectrum result graph of the reaction.
FIG. 3 is a graph of N' - (2-hydroxy-5- (camphor-3-methylene) benzylidene) pyridine formylhydrazine with varying concentrations of Zn 2+ And (3) a fluorescence spectrum result graph of the reaction.
Detailed Description
In order that the above-recited objects, features and advantages of the present invention will become more apparent, a more particular description of the invention will be rendered by reference to specific embodiments thereof which are illustrated in the appended drawings.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, but the present invention may be practiced in other ways other than those described herein, and persons skilled in the art will readily appreciate that the present invention is not limited to the specific embodiments disclosed below.
Further, reference herein to "one embodiment" or "an embodiment" means that a particular feature, structure, or characteristic can be included in at least one implementation of the invention. The appearances of the phrase "in one embodiment" in various places in the specification are not necessarily all referring to the same embodiment, nor are separate or alternative embodiments mutually exclusive of other embodiments.
Example 1
2-hydroxy-5- (camphor-3-methylene) benzaldehyde (0.284 g,1 mmol), pyridine-2-formylhydrazine (0.274 g,2 mmol), 15mL of absolute ethyl alcohol and 3 drops of glacial acetic acid (0.15 mL) are added into a three-neck flask, reflux reaction is carried out for 12h, and the reaction progress is monitored by TLC until the reaction of 2-hydroxy-5- (camphor-3-methylene) benzaldehyde is completed, and then the reaction is stopped; concentrating the reaction solution to remove part of ethanol, cooling and separating out solid, suction filtering, washing and suction filtering with cold ethanol to obtain 244mg of target product N' - (2-hydroxy-5- (camphor-3-methylene) benzylidene) pyridine formylhydrazine, wherein the compound has the structural formula:
characterization of the above N' - (2-hydroxy-5- (camphor-3-methylene) benzylidene) pyridine formylhydrazine resulted in: 1 H NMR(600MHz,DMSO-d 6 )δ:12.56(s,1H),11.75(s,1H),8.89(s,1H),8.73(d,J＝4.7Hz,1H),8.14(d,J＝7.8Hz,1H),8.10–8.04(m,1H),7.68(q,J＝5.1Hz,2H),7.55(dd,J＝8.6,2.2Hz,1H),7.09(s,1H),7.03(d,J＝8.5Hz,1H),3.14(d,J＝4.1Hz,1H),2.16(tt,J＝11.7,9.2,4.5Hz,1H),1.78(ddd,J＝13.5,11.2,3.7Hz,1H),1.48(ddd,J＝12.4,9.1,3.7Hz,1H),1.37(ddd,J＝13.6,9.1,4.7Hz,1H),0.97(s,3H),0.92(s,3H),0.73(s,3H). 13 C NMR(150MHz,DMSO-d 6 )δ:207.11,160.94,158.76,150.00,149.55,149.09,140.50,138.53,132.98,132.29,127.68,126.94,126.54,123.31,119.46,117.65,56.80,48.97,46.79,40.53,30.65,26.03,20.64,18.46,9.76.
from the characterization data, the purity of the prepared reaction product N' - (2-hydroxy-5- (camphor-3-methylene) benzylidene) pyridine formylhydrazine is 98%; the product yield was calculated to be 86%.
Example 2
N' - (2-hydroxy-5- (camphor-3-methylene) benzylidene) pyridine formylhydrazine was dissolved in acetonitrile to prepare a 1mM concentration solution and diluted to 10. Mu.M with acetonitrile/PBS (v/v=3/7, pH=7.4, 10 mM) solution for use. The fluorescence spectra of the different metal ions on N' - (2-hydroxy-5- (camphor-3-methylene) benzylidene) pyridine formylhydrazine were measured using fluorescence spectroscopy using a solution of the different metal ions in deionized water and diluted to 10. Mu.M, as shown in FIG. 1. The results show that, compared with other metal ions, only Al 3+ And Zn 2+ Can cause obvious change of fluorescence spectrum of the compound, which indicates that the compound can bidirectionally detect Al 3+ And Zn 2+ 。
Example 3
N' - (2-hydroxy-5- (camphor-3-methylene) benzylidene) pyri-dineThe pyridine formylhydrazine was dissolved in acetonitrile to prepare a 1mM solution, and diluted to 10. Mu.M with acetonitrile/PBS (v/v=3/7, pH=7.4, 10 mM) solution. Also Al is as follows 3+ Solutions in acetonitrile/PBS (v/v=3/7, ph=7.4, 10 mM) were prepared at concentrations of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 μm. Al with different concentrations is measured by adopting a fluorescence spectrum analysis method 3+ Fluorescence spectra of N' - (2-hydroxy-5- (camphor-3-methylene) benzylidene) pyridine formylhydrazine are shown in FIG. 2. The result shows that the fluorescence intensity of the compound is obviously and gradually enhanced at the emission wavelength of about 500nm, which indicates that the compound can be used for detecting Al 3+ Is provided.
Example 4
N' - (2-hydroxy-5- (camphor-3-methylene) benzylidene) pyridine formylhydrazine was dissolved in acetonitrile to prepare a 1mM concentration solution, and diluted to 10. Mu.M with acetonitrile/PBS (v/v=3/7, pH=7.4, 10 mM) solution. Also Zn is as follows 2+ Solutions in acetonitrile/PBS (v/v=3/7, ph=7.4, 10 mM) were prepared at concentrations of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 μm. Zn with different concentrations is measured by adopting a fluorescence spectrum analysis method 2+ Fluorescence spectra of N' - (2-hydroxy-5- (camphor-3-methylene) benzylidene) pyridine formylhydrazine are shown in FIG. 3. The result shows that the fluorescence intensity of the compound is obviously and gradually enhanced at the emission wavelength of about 555nm, which indicates that the compound can be used for detecting Zn 2+ Is provided.
The invention uses the N' - (2-hydroxy-5- (camphor-3-methylene) benzylidene) pyridine formylhydrazine prepared by taking the camphor derivative 2-hydroxy-5- (camphor-3-methylene) benzaldehyde as the raw material, and can bidirectionally identify Al 3+ And Zn 2+ The fluorescence is rapidly enhanced under 365nM ultraviolet light, green and orange fluorescence is generated, the detection limit reaches 12.1nM and 14.2nM, and the compound can be used as a sensitive fluorescent probe for bi-directional detection of Al 3+ And Zn 2+ 。
It should be noted that the above embodiments are only for illustrating the technical solution of the present invention and not for limiting the same, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that the technical solution of the present invention may be modified or substituted without departing from the spirit and scope of the technical solution of the present invention, which is intended to be covered in the scope of the claims of the present invention.
Claims (10)
1. Be used for detecting Al 3+ And Zn 2+ Is characterized in that: the compound has the following structural formula:
2. the method for detecting Al according to claim 1 3+ And Zn 2+ The preparation method of the compound is characterized in that: is obtained by condensation reaction of 2-hydroxy-5- (camphor-3-methylene) benzaldehyde and pyridine-2-formylhydrazine.
3. The method for detecting Al according to claim 2 3+ And Zn 2+ The preparation method of the compound is characterized in that: the condensation reaction is carried out by adding 2-hydroxy-5- (camphor-3-methylene) benzaldehyde and pyridine-2-formylhydrazine into solvent; adding glacial acetic acid and carrying out reflux reaction; and concentrating the reaction liquid, cooling and separating out solid, washing and suction filtering to obtain the target product.
4. The method for detecting Al according to claim 3 3+ And Zn 2+ The preparation method of the compound is characterized in that: the molar ratio of the 2-hydroxy-5- (camphor-3-methylene) benzaldehyde to the pyridine-2-formylhydrazine is 1:1-2.
5. The method for detecting Al according to claim 3 or 4 3+ And Zn 2+ The preparation method of the compound is characterized in that: the solvent is added into absolute ethyl alcohol.
6. The method for detecting Al according to claim 5 3+ And Zn 2+ The preparation method of the compound is characterized in that: the addition amount of the glacial acetic acid is 0.3-1.5% of the volume of the solvent.
7. The method for detecting Al according to claim 3, 4 or 6 3+ And Zn 2+ The preparation method of the compound is characterized in that: and the reflux reaction is carried out for 12-24 hours.
8. The method for detecting Al according to claim 7 3+ And Zn 2+ The preparation method of the compound is characterized in that: and washing and suction filtering, namely washing and suction filtering by using ethanol.
9. The method for detecting Al according to claim 1 3+ And Zn 2+ Fluorescence detection of Al in the compounds of (2) 3+ And Zn 2+ Is used in the field of applications.
10. The method for detecting Al according to claim 1 3+ And Zn 2+ Preparation of compounds for detecting Al 3+ And Zn 2+ Is used in the dual-functional fluorescent probe.
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Citations (4)
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| CN110204485A (en) * | 2019-07-23 | 2019-09-06 | 哈尔滨理工大学 | A kind of double salicylaldehyde contracting 2- pyridinecarboxylic hydrazine schiff bases synthetic method and application |
| CN110484243A (en) * | 2019-09-23 | 2019-11-22 | 南京林业大学 | A kind of response type camphoryl mercury ion fluorescence probe and its preparation method and application |
| CN111233709A (en) * | 2020-01-19 | 2020-06-05 | 南京林业大学 | Ratiometric camphor-based gallium ion fluorescent probe and preparation method and application thereof |
| CN111825655A (en) * | 2020-07-08 | 2020-10-27 | 南京林业大学 | Hg detection method2+High-sensitivity fluorescent probe and preparation method and application thereof |
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| CN111233709A (en) * | 2020-01-19 | 2020-06-05 | 南京林业大学 | Ratiometric camphor-based gallium ion fluorescent probe and preparation method and application thereof |
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