CN105859706B - A kind of organic compound and its preparation and application of fluorescence identifying zinc ion - Google Patents
A kind of organic compound and its preparation and application of fluorescence identifying zinc ion Download PDFInfo
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- CN105859706B CN105859706B CN201610280714.1A CN201610280714A CN105859706B CN 105859706 B CN105859706 B CN 105859706B CN 201610280714 A CN201610280714 A CN 201610280714A CN 105859706 B CN105859706 B CN 105859706B
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- organic compound
- zinc ion
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- 0 C*C(*=C1)=C(*)CC2=C1C(C)=CC(C)(O)O2 Chemical compound C*C(*=C1)=C(*)CC2=C1C(C)=CC(C)(O)O2 0.000 description 3
- CJCBAGAEDPCARE-BCUDILNBSA-M Cc(cc1)c(/C=N\[N-](C([NH-])=S)=C)c([U]2)c1C(C1=C[I]1NC)=CC2=[U] Chemical compound Cc(cc1)c(/C=N\[N-](C([NH-])=S)=C)c([U]2)c1C(C1=C[I]1NC)=CC2=[U] CJCBAGAEDPCARE-BCUDILNBSA-M 0.000 description 1
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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
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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"
- 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
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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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- 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
Abstract
The present invention relates to a kind of organic compound and its preparation and application of fluorescence identifying zinc ion, cumarin aldehyde carries out amine aldehyde condensation with thiosemicarbazides, and then carrying out cyclization with 2 bromoacetophenones again is made；Zinc ion is added in the weak solution of the organic compound HM of fluorescence identifying zinc ion and produces blue-fluorescence, adds other cation unstressed configuration changes.It is an advantage of the invention that：Ion selectivity is good, can effectively distinguish zinc ion and other cations；Monitoring lower-cut is low, can reach 1.4nM, the monitoring available for chemical system and aqueous systems trace level zinc ion concentration；It is easy to operate, it is not necessary to complicated buffer system；Identification is convenient, and light emitting region is macroscopic blue light, possesses actual application prospect in 500nm or so；It can be used for the zinc ion detection in active somatic cell.
Description
Technical field
The present invention relates to chemical analysis ion detection field, the organic compound of fluorescence identifying zinc ion and its preparation and make
Use method.
Background technology
Zinc ion is trace element important in human body, its content in human body is only second to ferro element, in human body very
More physiological activities, for example, Apoptosis, gene expression, enzyme regulation and control etc. all be unable to do without Zn-ef ficiency.If zinc-deficiency may result in very much
Disease.ZINC IN SOIL ion concentration is too low or too high can all cause the growth to plant unfavorable.It can be seen from the above that either in human body
It is interior or zinc ion is all a kind of extremely important material in nature.The common method of detection for zinc ion has energy
Spectrum, atomic absorption spectrum and conventional chemical analysis etc., these methods need instrument or more complicated operation costly.
How to carry out simple and effective detection to it is a problem that can not be ignored.
In recent years, in ion detection field, colorimetric method or fluorescence method since easy to operate, instrument such as is easy to get at the reason and becomes
The hot spot of research.In view of this, a kind of high selectivity is studied, the identification receptor compound of easily prepared and application zinc ion is
Highly significant with commercial promise.
The content of the invention
For overcome the deficiencies in the prior art, the object of the present invention is to provide a kind of organic compound of fluorescence identifying zinc ion
And its preparation and application, it is easy to operate, zinc ion and other cations can be effectively distinguished, while available in active somatic cell
Zinc ion detection.
To achieve 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 organic compound HM are：
A kind of preparation method of the organic compound of fluorescence identifying zinc ion, cumarin aldehyde carry out amine aldehyde contracting with thiosemicarbazides
Close, then carrying out cyclization with 2- bromoacetophenones again is made, and concrete operations comprise the following steps：
1) 1 part of cumarin aldehyde and 1~2 part of thiosemicarbazides be added at the same time 9-12 parts glacial acetic acid and ethanol mixing it is molten
In agent, the glacial acetic acid of the mixed solvent and the volume ratio of ethanol are：1:(5~10), heating stirring reflux, heating-up temperature 70
~85 DEG C, when the heating stirring time is 6~8 small, M is obtained, the structural formula of M is：
2) 1 part of M is added in 12~16 parts of alcohol solvent with 1~2 part of 2- bromoacetophenones and is refluxed, stirred
75~80 DEG C are heated in journey, when the heating stirring time is 8~9 small, HM is made.
Ethanol described in step 1) is absolute ethyl alcohol, and the alcohol solvent described in step 2) is absolute ethyl alcohol.
A kind of application method of the organic compound of fluorescence identifying zinc ion, in the organic compound of fluorescence identifying zinc ion
Zinc ion is added in the weak solution of HM and produces blue-fluorescence, adds other cation unstressed configuration changes.
A kind of application method of the organic compound of fluorescence identifying zinc ion, is placed with 13 transparent volumetric flasks of 10ml
The weak solution of machine compound HM, is added dropwise cation Ca respectively wherein2+,Mg2+,Ni2+,Co2+,Cu2+,Hg2+,Zn2+,Ba2+,Ag+,
Pb2+,Fe3+,Cr3+,Cd2+Solution, organic compound HM weak solutions are in drop has the sample bottle of zinc ion by unstressed configuration to generation
Stronger blue-fluorescence change, and the solution of other cations is added dropwise, unstressed configuration change.
The weak solution mass percent of the 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) DMSO and water H in O solution2The body of O
Product is than being 3:7.
A kind of application method of the organic compound of fluorescence identifying zinc ion, carries out zinc ion in Hep G2 cells living
Detection, the 5%CO at 37 DEG C2With the cell of organic compound HM dyeing processing 30 minutes in incubator, do not observe into the cell
There is change in fluorescence, when with Zn2+After processing 30 minutes, it was observed that there is blue-fluorescence into the cell；The organic compound HM is 10 μ
M；Zn2+For 20 μM.
Compared with prior art, the beneficial effects of the invention are as follows：
1) ion selectivity is good, can effectively distinguish zinc ion and other cations；
2) Monitoring lower-cut is low, can reach 1.4nM, available for chemical system and the prison of aqueous systems trace level zinc ion concentration
Survey；
3) it is easy to operate, it is not necessary to complicated buffer system；
4) identification is convenient, and light emitting region is macroscopic blue light, possesses actual application prospect in 500nm or so；
5) it can be used for the zinc ion detection in active somatic cell.
Brief description of the drawings
Fig. 1 is the probe with organic compound HM in DMSO/H2The ultraviolet change before and after metal ion is added in O solution
Figure.
Fig. 2 is the probe with organic compound HM in DMSO/H2The change in fluorescence before and after metal ion is added in O solution
Figure.
Fig. 3 be with organic compound HM probe add zinc ion before in bio-imaging figure intracellular Hep G2 (just
Ordinary light).
Fig. 4 be with organic compound HM probe add zinc ion after in bio-imaging figure intracellular Hep G2 (just
Ordinary light).
It is (dark in intracellular Hep G2 bio-imaging figure before zinc ion that Fig. 5 is that the probe with organic compound HM adds
Room).
It is (dark in intracellular Hep G2 bio-imaging figure after zinc ion that Fig. 6 is that the probe with organic compound HM adds
Room).
Embodiment
The present invention is described in detail with reference to Figure of description, it should be noted that the implementation of the present invention is unlimited
In following embodiment.
Embodiment one：
The synthesis of compound M：By the cumarin aldehyde of 5mmol and the thiosemicarbazides of 5mmol, 10ml absolute ethyl alcohols and ice are dissolved in
The volume ratio of the in the mixed solvent of acetic acid, in the mixed solvent absolute ethyl alcohol and glacial acetic acid is 8:1.When heating stirring 7 is small, it is back to
Reaction terminates (TLC tracking), and heating-up temperature is 80 DEG C, and cooling has solid precipitation, is filtered, and crude product uses column chromatography (petroleum ether：
Diethyl=7:3) faint yellow solid M, yield 74%, are obtained.
The synthesis of compound (HM)：5mmol compound M and 5mmol bromoacetophenones are dissolved in 25ml absolute ethyl alcohols, instead
A large amount of crocus solids are separated out during answering, reaction is back to and terminates (TLC tracking), are filtered, crude product uses column chromatography (oil
Ether：Diethyl=6:4) crocus solid organic compounds HM, yield 59%, are obtained.
Embodiment two：
The organic compound HM of fluorescence identifying zinc ion, carries out amine aldehyde condensation, then using cumarin aldehyde and thiosemicarbazides
It is made carrying out cyclization with 2- bromoacetophenones, its structural formula is：
The preparation method of the organic compound HM of fluorescence identifying zinc ion：
A) volume ratio that 1 part of cumarin aldehyde and 1.2 parts of thiosemicarbazides are added to 10 parts at the same time is：1:6 glacial acetic acid：Ethanol
In the mixed solvent, heating stirring reflux (82 DEG C of heating-up temperature, when mixing time is 8 small), obtains M.
B) 1 part of M and 1.2 part of 2- bromoacetophenones, which are added in 15 parts of absolute ethyl alcohol, is refluxed obtained organic compound
Thing HM.
The structural formula of organic compound HM is：
Embodiment three：
The synthesis of compound M：By 5 parts of cumarin aldehyde and 10 parts of thiosemicarbazides, 50 parts of absolute ethyl alcohols and ice vinegar are dissolved in
The volume ratio of the in the mixed solvent of acid, in the mixed solvent absolute ethyl alcohol and glacial acetic acid is 5:1.When heating stirring 8 is small, it is back to anti-
It should terminate (TLC tracking), heating-up temperature is 78 DEG C, and cooling has solid precipitation, is filtered, and crude product uses column chromatography (petroleum ether：Two
Second=7:3) faint yellow solid M, yield 67%, are obtained.
The synthesis of compound (HM)：5 parts of compound M and 10 parts of bromoacetophenones are dissolved in 60 parts of absolute ethyl alcohols, are reacted
During separate out a large amount of crocus solids, be back to reaction and terminate (TLC tracking), filter, crude product uses column chromatography (oil
Ether：Diethyl=6:4) crocus solid organic compounds HM, yield 55%, are obtained.
Nuclear-magnetism characterize 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.
Zinc ion detection is carried out using the organic compound HM of fluorescence identifying zinc ion：
Place the DMSO/H of 0.0377mg organic compounds HM respectively in 13 10ml water white transparency volumetric flasks2O(v/
V=3:7) solution, is added dropwise cation Ca respectively wherein2+,Mg2+,Ni2+,Co2+,Cu2+,Hg2+,Zn2+,Ba2+,Ag+,Pb2+,Fe3 +,Cr3+,Cd2+Aqueous solution, after mixing, it is seen that liquid has blue-fluorescence, other samples in the sample bottle containing zinc ion
Liquid is unchanged in product bottle, is placed under 254nm ultraviolet lamps and becomes apparent from, sees Fig. 1, Fig. 2.Wherein DMSO/H2O pH value of solution=7.2.
Zinc ion in cell is carried out using the organic compound HM of fluorescence identifying zinc ion to detect：
The 5%CO at 37 DEG C2Handled 30 minutes with the organic compound HM dyeing of 10 μM (molal weight) in incubator
Cell, do not observe has change in fluorescence into the cell, when with Zn2+After (20 μM) are handled 30 minutes, Olympus ix73 fluorescence is utilized
Microscope can be observed have blue-fluorescence into the cell, Fig. 3-Fig. 6, be the front and rear change of cell dyeing.
The organic compound is HM, and its preparation method carries out amine aldehyde condensation for cumarin aldehyde first and thiosemicarbazides, then
It is made carrying out cyclization with 2- bromoacetophenones；The weak solution of the compound does not have fluorescent effect in itself, when addition zinc ion
Stronger blue-fluorescence is sent afterwards and the addition of other cations cannot produce similar change in fluorescence phenomenon, and minimum detection limit
For 1.4nM.Therefore, the single selective fluorescence colorimetric identification zinc ion of the organic compound energy high sensitivity, and other sun
The ion pair identification process does not interfere with, and can be conveniently and quickly used for the detection of zinc ion.
Claims (7)
1. a kind of organic compound of fluorescence identifying zinc ion, it is characterised in that the structural formula of organic compound HM is：
A kind of 2. preparation method of the organic compound of fluorescence identifying zinc ion according to claim 1, it is characterised in that
Cumarin aldehyde carries out amine aldehyde condensation with thiosemicarbazides, and then carrying out cyclization with 2- bromoacetophenones again is made, concrete operations bag
Include following steps：
1) 1 part of cumarin aldehyde and 1~2 part of thiosemicarbazides are added to 9-12 parts of glacial acetic acid and alcohol mixed solvent at the same time
In, the glacial acetic acid of the mixed solvent and the volume ratio of ethanol are：1:(5~10), heating stirring reflux, heating-up temperature for 70~
85 DEG C, when the heating stirring time is 6~8 small, M is obtained, the structural formula of M is：
2) 1 part of M is added in 12~16 parts of alcohol solvent with 1~2 part of 2- bromoacetophenones and is refluxed, in whipping process
75~80 DEG C of heating, when the heating stirring time is 8~9 small, is made HM.
A kind of 3. preparation method of the organic compound of fluorescence identifying zinc ion according to claim 2, it is characterised in that
Ethanol described in step 1) is absolute ethyl alcohol, and the alcohol solvent described in step 2) is absolute ethyl alcohol.
A kind of 4. application method of the organic compound of fluorescence identifying zinc ion according to claim 1, it is characterised in that
Zinc ion is added in the weak solution of the organic compound HM of fluorescence identifying zinc ion and produces blue-fluorescence, adds other cations
Unstressed configuration changes.
A kind of 5. application method of the organic compound of fluorescence identifying zinc ion according to claim 4, it is characterised in that
The weak solution of organic compound HM is placed in 13 transparent volumetric flasks of 10ml, cation Ca is added dropwise respectively wherein2+,Mg2+,
Ni2+,Co2+,Cu2+,Hg2+,Zn2+,Ba2+,Ag+,Pb2+,Fe3+,Cr3+,Cd2+Solution, organic compound HM weak solutions have in drop
Changed in the sample bottle of zinc ion by unstressed configuration to stronger blue-fluorescence is produced, and the solution of other cations is added dropwise, without glimmering
Light changes.
6. a kind of application method of the organic compound of fluorescence identifying zinc ion according to claim 4 or 5, its feature exist
In the weak solution mass percent of the organic compound HM is 0.376mg/100ml, and the weak solution of organic compound HM is
The DMSO/H of organic compound HM2O solution；Wherein DMSO/H2Dimethyl sulfoxide (DMSO) DMSO and water H in O solution2The volume ratio of O is
3:7。
A kind of 7. application method of the organic compound of fluorescence identifying zinc ion according to claim 1, it is characterised in that
Zinc ion in Hep G2 cells living is detected, the 5%CO at 37 DEG C2Handled in incubator with organic compound HM dyeing
The cell of 30 minutes, do not observe has change in fluorescence into the cell, when with Zn2+After processing 30 minutes, it was observed that there is blueness into the cell
Fluorescence；The organic compound HM is 10 μM；Zn2+For 20 μM.
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| US11604141B2 (en) | 2017-06-12 | 2023-03-14 | Georgia Tech Research Corporation | Zinc-selective fluorescent probes for emission-ratiometric imaging |
| 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 |
| 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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