CN105859706A - Organic compound capable of fluorescently recognizing zinc ions and preparing and using method thereof - Google Patents

Organic compound capable of fluorescently recognizing zinc ions and preparing and using method thereof Download PDF

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CN105859706A
CN105859706A CN201610280714.1A CN201610280714A CN105859706A CN 105859706 A CN105859706 A CN 105859706A CN 201610280714 A CN201610280714 A CN 201610280714A CN 105859706 A CN105859706 A CN 105859706A
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organic compound
zinc ion
fluorescence
zinc ions
solution
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CN105859706B (en
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高妍
王伟
刘清雷
董岩
钟佳琪
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University of Science and Technology Liaoning USTL
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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"
    • G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
    • 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
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
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Abstract

The invention relates to an organic compound capable of fluorescently recognizing zinc ions and a preparing and using method thereof. Coumarin aldehyde and thiosemicarbazide are subjected to amine-aldehyde condensation and then subjected to a cyclization reaction with 2-bromoacetophenone to prepare the organic compound. Blue fluorescence can be generated when zinc ions are added into a dilute solution of the organic compound HM capable of fluorescently recognizing the zinc ions, while no fluorescence change exists when other positive ions are added. The organic compound has the advantages that ion selectivity is high, and the zinc ions and other positive ions can be effectively distinguished; the lower detection limit is low and can reach 1.4nM, and the organic compound can be used for monitoring the content of trace level zinc ions in a chemical system and a water system; operation is easy, and a complex buffering system is not needed; recognition is convenient, the light emitting range is about 500 nm, macroscopic blue light is emitted, and therefore the organic compound has practical application prospects; the organic compound can be used for detecting zinc ions in living cells.

Description

The organic compound of a kind of fluorescence identifying zinc ion and preparation and application thereof
Technical field
The present invention relates to chemical analysis ion detection field, the organic compound of fluorescence identifying zinc ion and preparation thereof and user Method.
Background technology
Zinc ion is trace element important in human body, and its content in human body is only second to ferrum element, a lot of raw in human body Reason activity, such as, apoptosis, gene expression, enzyme regulation and control etc. all be unable to do without zinc element.If zinc deficiency may result in a lot Disease.ZINC IN SOIL ion concentration is the lowest or the highest all can cause the growth to plant unfavorable.As can be seen here, no matter it is people Internal or zinc ion is all a kind of extremely important material in nature.Conventional method is detected for zinc ion and has energy Spectrum, atomic absorption spectrum and conventional chemical analysis etc., these methods need instrument costly or more complicated operation. How it being carried out simple and effective detection is a problem that can not be ignored.
In recent years, become in ion detection field, colorimetry or fluorescence method grind due to the reason such as easy and simple to handle, instrument is easy to get The focus studied carefully.In view of this, study a kind of high selectivity, easily prepared and application the identification receptor compound of zinc ion is Highly significant with commercial promise.
Summary of the invention
For overcoming the deficiencies in the prior art, it is an object of the invention to provide a kind of fluorescence identifying zinc ion organic compound and Preparation and application, simple to operate, can effectively distinguish zinc ion and other cation, be simultaneously available in active somatic cell Zinc ion detects.
For achieving the above object, the present invention is achieved through the following technical solutions:
A kind of organic compound of fluorescence identifying zinc ion, the structural formula of this organic compound HM is:
The preparation method of the organic compound of a kind of fluorescence identifying zinc ion, coumarin aldehyde and thiosemicarbazides carry out amine al conjunction, Carrying out cyclization the most again to prepare with 2-bromoacetophenone, concrete operations comprise the following steps:
1) the coumarin aldehyde of 1 part and the thiosemicarbazides of 1～2 part are added simultaneously to glacial acetic acid and the alcohol mixed solvent of 9-12 part In, the glacial acetic acid of described mixed solvent and the volume ratio of ethanol be: 1:(5～10), and heated and stirred refluxes, heating-up temperature be 70～ 85 DEG C, the heated and stirred time is 6～8 hours, and the structural formula obtaining M, M is:
2) return stirring during the M of 1 part and the 2-bromoacetophenone of 1～2 part join the alcohol solvent of 12～16 parts, stirred Heating 75～80 DEG C in journey, the heated and stirred time is 8～9 hours, prepares HM.
Step 1) described in ethanol be dehydrated alcohol, step 2) described in alcohol solvent be dehydrated alcohol.
The using method of the organic compound of a kind of fluorescence identifying zinc ion, at the organic compound HM of fluorescence identifying zinc ion Weak solution in add zinc ion produce blue-fluorescence, add other cation unstressed configuration change.
The using method of the organic compound of a kind of fluorescence identifying zinc ion, places organic in 13 transparent volumetric flasks of 10ml The weak solution of compound HM, the most respectively dropping cation Ca2+,Mg2+,Ni2+,Co2+,Cu2+,Hg2+,Zn2+,Ba2+, Ag+,Pb2+,Fe3+,Cr3+,Cd2+Solution, organic compound HM weak solution has in the sample bottle of zinc ion by without glimmering dripping Light is to producing stronger blue-fluorescence change, and drips the solution of other cation, and unstressed configuration changes.
The weak solution mass percent of described organic compound HM is 0.376mg/100ml, and organic compound HM's is dilute Solution is the DMSO/H of organic compound HM2O solution；Wherein DMSO/H2Dimethyl sulfoxide DMSO in O solution With water H2The volume ratio of O is 3:7.
The using method of the organic compound of a kind of fluorescence identifying zinc ion, examines zinc ion in the Hep G2 cell lived Survey, 5%CO at 37 DEG C2Incubator processes the cell of 30 minutes, intracellular observation with organic compound HM dyeing Less than there being change in fluorescence, when with Zn2+After processing 30 minutes, it was observed that intracellular have blue-fluorescence；Described organic compound Thing HM is 10 μMs；Zn2+It it is 20 μMs.
Compared with prior art, the invention has the beneficial effects as follows:
1) ion selectivity is good, can effectively distinguish zinc ion and other cation；
2) Monitoring lower-cut is low, can reach 1.4nM, can be used for chemical system and the monitoring of aqueous systems trace level zinc ion concentration；
3) simple to operate, it is not necessary to complicated buffer system；
4) identify that conveniently light emitting region, at about 500nm, for macroscopic blue light, has actual application prospect；
5) may be used for the zinc ion detection in active somatic cell.
Accompanying drawing explanation
Fig. 1 is that the probe with organic compound HM is at DMSO/H2O solution adds the ultraviolet before and after metal ion become Change figure.
Fig. 2 is that the probe with organic compound HM is at DMSO/H2O solution adds the fluorescence before and after metal ion become Change figure.
Fig. 3 is that the probe with organic compound HM at Hep G2 intracellular bio-imaging figure (just adds before zinc ion Ordinary light).
Fig. 4 is that the probe with organic compound HM at Hep G2 intracellular bio-imaging figure (just adds after zinc ion Ordinary light).
Fig. 5 is (dark at Hep G2 intracellular bio-imaging figure before the probe with organic compound HM adds zinc ion Room).
Fig. 6 is (dark at Hep G2 intracellular bio-imaging figure after the probe with organic compound HM adds zinc ion Room).
Detailed description of the invention
Below in conjunction with Figure of description, the present invention is described in detail, it should be noted that the enforcement of the present invention be not limited to Under embodiment.
Embodiment one:
The synthesis of compound M: by coumarin aldehyde and the thiosemicarbazides of 5mmol of 5mmol, be dissolved in 10ml dehydrated alcohol With in the mixed solvent of glacial acetic acid, in mixed solvent, the volume ratio of dehydrated alcohol and glacial acetic acid is 8:1.Heated and stirred 7 hours, Being back to reaction and terminate (TLC tracking), heating-up temperature is 80 DEG C, and cooling has solid to separate out, sucking filtration, crude product column chromatography Separate (petroleum ether: diethyl=7:3), obtain faint yellow solid M, yield 74%.
The synthesis of compound (HM): 5mmol compound M and 5mmol bromoacetophenone are dissolved in 25ml dehydrated alcohol In, course of reaction separates out a large amount of crocus solid, is back to reaction and terminates (TLC tracking), sucking filtration, crude product post layer Analysis separates (petroleum ether: diethyl=6:4), obtains crocus solid organic compounds HM, yield 59%.
Embodiment two:
The organic compound HM of fluorescence identifying zinc ion, utilizes coumarin aldehyde and thiosemicarbazides to carry out amine al conjunction, then exists Carrying out cyclization with 2-bromoacetophenone to prepare, its structural formula is:
The preparation method of the organic compound HM of fluorescence identifying zinc ion:
A) 1 part of coumarin aldehyde and 1.2 parts of thiosemicarbazides are added simultaneously to the volume ratio of 10 parts and are: 1:6 glacial acetic acid: ethanol In mixed solvent, heated and stirred backflow (heating-up temperature 82 DEG C, mixing time is 8 hours), obtain M.
B) during the M of 1 part and the 2-bromoacetophenone of 1.2 parts join the dehydrated alcohol of 15 parts, return stirring prepares organic compound Thing HM.
The structural formula of organic compound HM is:
Embodiment three:
The synthesis of compound M: by coumarin aldehyde and the thiosemicarbazides of 10 parts of 5 parts, be dissolved in 50 parts of dehydrated alcohol and ice vinegar In the mixed solvent of acid, in mixed solvent, the volume ratio of dehydrated alcohol and glacial acetic acid is 5:1.Heated and stirred 8 hours, backflow Terminating (TLC tracking) to reaction, heating-up temperature is 78 DEG C, and cooling has solid to separate out, and sucking filtration, crude product uses column chromatography (petroleum ether: diethyl=7:3), obtains faint yellow solid M, yield 67%.
The synthesis of compound (HM): 5 parts of compound M and 10 parts of bromoacetophenones are dissolved in 60 parts of dehydrated alcohol, Separating out a large amount of crocus solid in course of reaction, be back to reaction and terminate (TLC tracking), sucking filtration, crude product column chromatography divides From (petroleum ether: diethyl=6:4), obtain crocus solid organic compounds HM, yield 55%.
Nuclear-magnetism sign data:1H NMR(600MHz,DMSO)δ:12.559(s,1H,NH),11.371(s,1H,OH), 8.698 (s, 1H, CH=N), 7.870 (d, J=6.5Hz, 2H, Ar), 7.689 (d, J=8.5Hz, 1H, Ar), 7.438 (t, J=7.0Hz, 3H, Ar), 7.340 (d, J=7.0Hz, 1H, Ar), 6.989 (d, J=8.5Hz, 1H, Ar), 6.253 (s, 1H, Ar), 2.502 (s, 3H, CH3).13C NMR(150MHz,DMSO)δ:160.25,159.69,154.21,152.37,129.11,128.28,127.65, 126.10,113.59,112.65,111.32,106.57.
The organic compound HM utilizing fluorescence identifying zinc ion carries out zinc ion detection:
The DMSO/H of 0.0377mg this organic compound HM is placed respectively in 13 10ml water white transparency volumetric flasks2O (v/v=3:7) solution, the most respectively dropping cation Ca2+,Mg2+,Ni2+,Co2+,Cu2+,Hg2+,Zn2+,Ba2+,Ag+, Pb2+,Fe3+,Cr3+,Cd2+Aqueous solution, after mix homogeneously, it is seen that in the sample bottle containing zinc ion, liquid has blue glimmering Light, in other sample bottle, liquid is unchanged, is placed under 254nm uviol lamp and becomes apparent from, sees Fig. 1, Fig. 2.Wherein DMSO/H2O PH value of solution=7.2.
The organic compound HM utilizing fluorescence identifying zinc ion carries out zinc ion in cell and detects:
5%CO at 37 DEG C2Incubator processes 30 minutes with the organic compound HM dyeing of 10 μMs (molal weights) Cell, intracellular do not observe have change in fluorescence, when with Zn2+After (20 μMs) process 30 minutes, utilize Olympus Ix73 fluorescence microscope can be observed intracellular have a blue-fluorescence, and Fig. 3-Fig. 6, for changing before and after cell dyeing.
This organic compound is HM, and its preparation method carries out amine al conjunction for first coumarin aldehyde and thiosemicarbazides, then exists Carry out cyclization with 2-bromoacetophenone to prepare；The weak solution of this compound itself does not have fluorescent effect, after adding zinc ion Send stronger blue-fluorescence and the addition of other cation can not produce similar change in fluorescence phenomenon, and lowest detection is limited to 1.4μM.Therefore, the single selective fluorescence of this organic compound energy high sensitivity is than colour discrimination zinc ion, and other is positive This identification process of ion pair does not interferes with, and can be conveniently and quickly used for the detection of zinc ion.

Claims (7)

1. the organic compound of a fluorescence identifying zinc ion, it is characterised in that the structural formula of this organic compound HM is:
The preparation method of the organic compound of a kind of fluorescence identifying zinc ion the most according to claim 1, its feature exists In, coumarin aldehyde and thiosemicarbazides carry out amine al conjunction, carry out cyclization the most again with 2-bromoacetophenone and prepare, specifically grasp Comprise the following steps:
1) the coumarin aldehyde of 1 part and the thiosemicarbazides of 1～2 part are added simultaneously to glacial acetic acid and the alcohol mixed solvent of 9-12 part In, the glacial acetic acid of described mixed solvent and the volume ratio of ethanol be: 1:(5～10), and heated and stirred refluxes, heating-up temperature be 70～ 85 DEG C, the heated and stirred time is 6～8 hours, and the structural formula obtaining M, M is:
2) return stirring during the M of 1 part and the 2-bromoacetophenone of 1～2 part join the alcohol solvent of 12～16 parts, stirred Heating 75～80 DEG C in journey, the heated and stirred time is 8～9 hours, prepares HM.
The preparation method of the organic compound of a kind of fluorescence identifying zinc ion the most according to claim 2, its feature exists In, step 1) described in ethanol be dehydrated alcohol, step 2) described in alcohol solvent be dehydrated alcohol.
The using method of the organic compound of a kind of fluorescence identifying zinc ion the most according to claim 1, its feature exists In, the weak solution of the organic compound HM of fluorescence identifying zinc ion adds zinc ion and produces blue-fluorescence, add other Cation unstressed configuration changes.
The using method of the organic compound of a kind of fluorescence identifying zinc ion the most according to claim 4, its feature exists In, 13 transparent volumetric flasks of 10ml are placed the weak solution of organic compound HM, drips cation the most respectively Ca2+,Mg2+,Ni2+,Co2+,Cu2+,Hg2+,Zn2+,Ba2+,Ag+,Pb2+,Fe3+,Cr3+,Cd2+Solution, organic compound HM weak solution is changed to producing stronger blue-fluorescence by unstressed configuration in dripping the sample bottle having zinc ion, and drips other sun The solution of ion, unstressed configuration changes.
6., according to the using method of the organic compound of a kind of fluorescence identifying zinc ion described in claim 4 or 5, it is special Levying and be, the weak solution mass percent of described organic compound HM is 0.376mg/100ml, organic compound HM The DMSO/H that weak solution is organic compound HM2O solution；Wherein DMSO/H2Dimethyl sulfoxide in O solution DMSO and water H2The volume ratio of O is 3:7.
The using method of the organic compound of a kind of fluorescence identifying zinc ion the most according to claim 1, its feature exists In, zinc ion in the Hep G2 cell lived is detected, 5%CO at 37 DEG C2Incubator is used organic compound HM dyeing processes the cell of 30 minutes, intracellular do not observe have change in fluorescence, when with Zn2+After processing 30 minutes, see Observing intracellular has blue-fluorescence；Described organic compound HM is 10 μMs；Zn2+It it is 20 μMs.
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CN107382901A (en) * 2017-06-22 2017-11-24 江苏大学 A kind of fluorescent sensing material based on phenyl thiazole and to cyanobiphenyl phenol and its production and use
CN108409726A (en) * 2018-01-17 2018-08-17 南通大学 A kind of cumarin 2- hydrazinobenzothiazole schiff bases Cd2+The preparation and application of fluorescence probe
WO2018231843A1 (en) * 2017-06-12 2018-12-20 Georgia Tech Research Corporation Zinc-selective fluorescent probes for emission-ratiometric imaging

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Publication number Priority date Publication date Assignee Title
WO2018231843A1 (en) * 2017-06-12 2018-12-20 Georgia Tech Research Corporation Zinc-selective fluorescent probes for emission-ratiometric imaging
US11604141B2 (en) 2017-06-12 2023-03-14 Georgia Tech Research Corporation Zinc-selective fluorescent probes for emission-ratiometric imaging
CN107382901A (en) * 2017-06-22 2017-11-24 江苏大学 A kind of fluorescent sensing material based on phenyl thiazole and to cyanobiphenyl phenol and its production and use
CN107382901B (en) * 2017-06-22 2020-06-09 江苏大学 Fluorescence sensing material based on phenylthiazole and p-cyanobiphenol, and preparation method and application thereof
CN108409726A (en) * 2018-01-17 2018-08-17 南通大学 A kind of cumarin 2- hydrazinobenzothiazole schiff bases Cd2+The preparation and application of fluorescence probe
CN108409726B (en) * 2018-01-17 2021-06-15 南通大学 Coumarin 2-hydrazinobenzothiazole Schiff base Cd2+Preparation and application of fluorescent probe

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