CN105693650A - Zinc-ion fluorescent probe compound, and preparation method and application thereof - Google Patents
Zinc-ion fluorescent probe compound, and preparation method and application thereof Download PDFInfo
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- CN105693650A CN105693650A CN201610202164.1A CN201610202164A CN105693650A CN 105693650 A CN105693650 A CN 105693650A CN 201610202164 A CN201610202164 A CN 201610202164A CN 105693650 A CN105693650 A CN 105693650A
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- BJEIVTGIAKKITK-UHFFFAOYSA-N Cc1c(C=N)cc(C=O)cc1-c1nc2ccccc2[o]1 Chemical compound Cc1c(C=N)cc(C=O)cc1-c1nc2ccccc2[o]1 BJEIVTGIAKKITK-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
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- C—CHEMISTRY; METALLURGY
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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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- 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
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
Abstract
The invention discloses a zinc-ion fluorescent probe compound, and a preparation method and application thereof, relating to the technical field of analytical chemistry. The chemical molecular formula of the zinc-ion fluorescent probe compound is C15H13NO4, and the zinc-ion fluorescent probe compound is prepared by carrying out derivation by using 2-(2'-hydroxyphenyl)benzooxazole as a mother structure. The probe has the advantages of simple molecular structure, high yield, high zinc ion selectivity, high sensitivity, high interference resistance to other metal ions, and low sensitivity for pH value variations, is more suitable to be applied in animal and plant systems, and is an ideal zinc-ion sensing molecule.
Description
Technical field
The present invention relates to technical field of analytical chemistry, particularly relate to a kind of zinc ion fluorescent compound, preparation method and application thereof。
Background technology
Zn2+It is a kind of important trace element, the many physiological process in animal and plant body play an important role, for instance all many-sides such as the conduction of nerve signal and adjustment, gene expression, apoptosis and enzyme catalysis。Therefore, Zn2+Detection, especially active somatic cell and tissue in Zn2+Mensuration and Induced Fluorescence Microscopy become one of chemist and biologists are paid special attention in recent years field。But it is different from other transiting state metal ion, Zn2+Owing to outermost electron is distributed as 3d104s0And do not show any wave spectrum or magnetic signal, so design synthesizes high selectivity and highly sensitive Zn2+Fluorescent probe is just particularly important。
Traditional Z n2+The design of fluorescent probe is generally divided into the mechanism such as Intramolecular electron transfer (ICT), Photo-induced electron transfer (PET), FRET (fluorescence resonance energy transfer) (FRET), distortion Intramolecular electron transfer (TICT) and imines isomerization principle。But these mechanism also exist some defects, for instance ICT is relatively larger by the impact of pH value, PET is relatively larger by the impact of structure, and TICT and imines isomerization are Zn2+Combination cause the Result of Indirect Measurement of distortion in its molecule。And after excited state intramolecular proton transfer (ESIPT) mechanism refers to that some organic molecule light excites, in molecule, the proton on a certain group (being generally hydroxyl or amino) is transferred on the hetero atoms such as molecule interior contiguous N, O, S, forms the process of tautomer。As itself and Zn2+When combining, ESIPT process is suppressed, and shows Stokes shift (Stokesshift), it is achieved to Zn2+Detection。
Desirable Zn2+Fluorescent probe also should be provided simultaneously with high, the good fat-soluble double water solublity of chemical light good stability, selectivity and susceptiveness, deleterious cellular effects is little and to the character such as Cellular pH value environment is insensitive, thus realizing its extensive use in biological field。
Summary of the invention
It is an object of the present invention to propose the zinc ion fluorescent compound that a kind of molecular structure is simple, productivity is high, zinc ion has good selectivity and susceptiveness。
Further object is that a kind of technique of proposition is simple, raw material is easy to get, the preparation method of zinc ion fluorescent compound easy to implement。
Another object of the present invention is in that to propose the application of a kind of zinc ion fluorescent compound。
For reaching this purpose, on the one hand, the present invention by the following technical solutions:
A kind of zinc ion fluorescent compound, its chemical molecular formula is C15H13NO4, molecular structural formula is:
Preferably, described zinc ion fluorescent compound is, to obtain through derivatization with 2-(2 '-hydroxy phenyl) benzoxazole compound for precursor structure。
On the other hand, the present invention is by the following technical solutions:
The preparation method of a kind of zinc ion fluorescent compound, follows these steps to carry out:
Step A, 2-(2 '-hydroxy phenyl) benzothiazole is dissolved in trifluoroacetic acid solution, is dividedly in some parts hexamethylenetetramine and raw material is carried out formylated, after purification, obtain intermediate I；
Step B, sodium borohydride is gradually added in the methanol solution of intermediate I reacts；
It is purified after step C, decompression evaporative removal solvent；
Step D, by the recrystallization in dichloromethane of the organic facies after purification in step C, it is thus achieved that finalization compound。
Preferably, the chemical molecular formula of the described intermediate I in step A is C15H9NO4, molecular structural formula is:
Preferably, described its chemical molecular formula of finalization compound is C15H13NO4, molecular structural formula is:
Preferably, in step A, carrying out step A2, step A2 after raw material carries out formylated is be heated to reflux to reacting completely；
Preferably, carrying out step A3, step A3 after step A2 is, adds hcl acidifying, and adopt ethyl acetate solution to extract after the solution cooling after reacting completely；
Preferably, carrying out step A4, step A4 after step A3 is, dries with anhydrous sodium sulfate after the step A3 organic facies saturated aqueous common salt obtained is rinsed；
Preferably, step A5, step A5 are carried out after step A4 for adopting column chromatography mode that organic facies dried in step A4 is easily separated the described intermediate I of acquisition；
Preferably, 2-(2 '-hydroxy phenyl) benzothiazole is 1:2 with the mol ratio of hexamethylenetetramine；
Preferably, in step A5, the eluant that described column chromatography mode adopts includes ethyl acetate, normal hexane；
Preferably, in step A5, the ratio of ethyl acetate and normal hexane is 7:1。
Preferably, in step B, the mol ratio of intermediate I and sodium borohydride is 1:4；
Preferably, in step B, under condition of ice bath, sodium borohydride is dividedly in some parts in the methanol solution of intermediate I。
Preferably, in step C, column chromatography mode is adopted to be purified；
Preferably, in step C, the eluant that described column chromatography mode adopts includes ethyl acetate, normal hexane；
Preferably, in step C, the ratio of ethyl acetate and normal hexane is 1:1。
Another further aspect, the present invention by the following technical solutions:
The application of a kind of zinc ion fluorescent compound, zinc ion fluorescent is for the detection of zinc ion in zooblast。
Further aspect, the present invention by the following technical solutions:
The application of a kind of zinc ion fluorescent compound, zinc ion fluorescent is for the conduction in plant and the detection of zinc ion in plant。
The invention have the benefit that
Zinc ion fluorescent molecular structure of compounds provided by the invention is simple, productivity is high, other metal ion disturbance ability zinc ion selectivity is good, highly sensitive, anti-is strong, pH value change is insensitive, and it is more suitably applied in animals and plants system, is a kind of desirably zinc ion sensor molecules。
The preparation method technique of zinc ion fluorescent compound provided by the invention is simple, raw material is easy to get, easy to implement and probe productivity high。
Accompanying drawing explanation
Fig. 1 is the synthetic route chart of zinc ion fluorescent compound provided by the invention；
Fig. 2 is zinc ion fluorescent compound provided by the invention selective light spectrogram to different metal ion in HEPES buffer solution；
Fig. 3 is that zinc ion fluorescent compound provided by the invention adds fluorescence intensity change block diagram after different metal ion in HEPES buffer solution；
Fig. 4 is that zinc ion fluorescent compound provided by the invention is gradually added into Zn in HEPES buffer solution2+Rear ultra-violet absorption spectrum variation diagram；
Fig. 5 is that zinc ion fluorescent compound provided by the invention is gradually added into Zn in HEPES buffer solution2+Rear fluorescence emission spectrum variation diagram；
Fig. 6 is that zinc ion fluorescent compound provided by the invention adds different equivalent Zn in HEPES buffer solution2+Rear fluorescence intensity and Zn2+Concentration relationship curve chart；
Fig. 7 is zinc ion fluorescent compound provided by the invention and and Zn2+Combine fluorescence intensity and the pH value variation relation figure of the complex formed；
Fig. 8 a to Fig. 8 c is that zinc ion fluorescent compound provided by the invention detects Zn in HepG2 cell2+Fluorescence imaging figure；
Fig. 9 a and Fig. 9 b is the zinc ion fluorescent compound provided by the invention conduction in plant and to Zn2+The fluorogram of detection。
Detailed description of the invention
Technical scheme is further illustrated below in conjunction with accompanying drawing and by detailed description of the invention。
The present invention proposes a kind of zinc ion fluorescent compound, the benzothiazole group with excited state intramolecular proton transfer (ESIPT) characteristic is performed the derivatization and forms, it is specially with 2-(2 '-hydroxy phenyl) benzoxazole compound for precursor structure, obtaining through derivatization, its chemical molecular formula is C15H13NO4, molecular structural formula is:
Zinc ion fluorescent molecular structure of compounds provided by the invention is simple, productivity is high, other metal ion disturbance ability zinc ion selectivity is good, highly sensitive, anti-is strong, pH value change is insensitive, and it is more suitably applied in animals and plants system, is a kind of desirably zinc ion sensor molecules。
Concrete, zinc ion fluorescent compound provided by the invention is to Zn2+Identification there is high selectivity, other metal ion disturbance ability anti-is strong；Having high sensitivity, lowest detectable limit reaches 78nM；PH value change is insensitive, and in the scope of pH value 1 to 8, fluorescence intensity is not affected by pH value change, with Zn2+Combine the complex formed when pH value is about 7, and fluorescence intensity reaches maximum。
Further, the preparation method that present invention also offers above-mentioned zinc ion fluorescent compound, as it is shown in figure 1, its preparation method specifically follows these steps to carry out:
Step A1,2-(2 '-hydroxy phenyl) benzothiazole (400mg, 1.89mmol) is dissolved in 30mL trifluoroacetic acid solution, is then dividedly in some parts hexamethylenetetramine (489mg, 3.78mmol) and raw material is carried out formylated。
Step A2, it is heated to reflux to reacting completely, it is preferred that adopt TLC method detection reaction process to judge whether complete to react。
Step A3, after the solution cooling after reacting completely, add hcl acidifying, and adopt ethyl acetate solution to extract, it is preferred that add the hydrochloric acid of 30mL6M, then extract three times with ethyl acetate solution, each 20mL。
Step A4, to step A3 obtain organic facies saturated aqueous common salt rinse after dry with anhydrous sodium sulfate, it is preferred that be rinsed with 40mL saturated aqueous common salt。
Step A5, purification, it is preferred to use organic facies dried in step A4 is easily separated acquisition yellow powder intermediate I, (eluant: ethyl acetate/normal hexane=7:1), productivity 91% by column chromatography mode。
The chemical molecular formula of intermediate I is C15H9NO4, molecular structural formula is:
Preferably, 2-(2 '-hydroxy phenyl) benzothiazole is 1:2 with the mol ratio of hexamethylenetetramine。
Step B, by intermediate I (100mg, 0.374mmol) it is dissolved in 15mL methanol solution, under condition of ice bath, by sodium borohydride (57mg, 1.5mmol) it is dividedly in some parts in the methanol solution of intermediate I and reacts, until stirring bubble-free generates。
Step C, reduce pressure and boil off major part solvent and methanol after be purified, it is preferred to use column chromatography mode is purified, (eluant: ethyl acetate/normal hexane=7:1)。
Step D, by the recrystallization in dichloromethane of the organic facies after purification in step C, it is thus achieved that the probe compound of white needles, productivity 89%。
Now the data of hydrogen spectrogram, carbon spectrogram and mass spectrum are as follows:
1HNMR(300MHz,CDCl3): 11.92 (1H, s), 8.01 (1H, d, J=1.7Hz), 7.74 (1H, m), 7.62 (1H, m), 7.49 (2H, d, J=1.7Hz), 7.40 (1H, m), 4.84 (2H, d, J=5.7Hz), 4.73 (2H, d, J=5.7Hz) .FT-IR (KBr, νmax,cm-1): 3292,2910,2848,1633,1549,1460,1260,1119,1035,862,772,740,476.MS (EI) m/z:CalcdforC15H13NO4[M+H]+272.1；Found272.0；[M-OH]-254.1；Found254.0.
The chemical molecular formula of finalization compound is C15H13NO4, molecular structural formula is:
Preferably, in step B, the mol ratio of intermediate I and sodium borohydride is 1:4。
The embodiment that characterize of the present invention zinc ion fluorescent compound property is given below:
Embodiment one:
Different metal solion (the Zn of 10 equivalents it is separately added in the HEPES buffer solution (20mM, pH=7.0) of 10 μMs of zinc ion fluorescent compounds provided by the invention2+、K+、Na+、Ca2+、Ba2+、Mg2+、Al3+、Fe3+、Cd2+、Cu2+), measure different metal ion exist under, the fluorescence emission spectrum of probe molecule as in figure 2 it is shown, as can be seen from Figure, except Cu2+The addition of other metal ions outer will not cause fluorescence spectrum that significantly change occurs, and only adds Zn2+After, just there is very big enhancing in fluorescence spectrum, illustrates that this probe is to Zn2+There is good selectivity。
Embodiment two:
Different metal solion (the K of 10 equivalents it is separately added in the HEPES buffer solution (20mM, pH=7.0) of 10 μMs of zinc ion fluorescent compounds provided by the invention+、Na+、Ca2+、Ba2+、Mg2+、Al3+、Fe3+、Cd2+、Cu2+), continue thereafter with the Zn of dropping 10 equivalents2+Solution, measures probe Molecular Detection Zn under different metal ion exists2+Capacity of resisting disturbance, as it is shown on figure 3, as can be seen from Figure, except Fe3+、Cd2+And Cu2+Outside making its fluorescence intensity reduce, other metal ions are little on its impact, illustrate that this probe has stronger capacity of resisting disturbance。
Embodiment three
Zn is progressively dripped in the HEPES buffer solution (20mM, pH=7.0) of 10 μMs of zinc ion fluorescent compounds provided by the invention2+Solution, measures its ultra-violet absorption spectrum, as shown in Figure 4, along with Zn2+Addition, the absworption peak at 295nm and 322nm place is gradually lowered, and occurs in that new peak at 362nm place, and this illustrates this probe molecule and Zn2+Define new complex。
Embodiment four
Zn is progressively dripped in the HEPES buffer solution (20mM, pH=7.0) of 10 μMs of zinc ion fluorescent compounds provided by the invention2+Solution, measures its fluorescence emission spectrum, as it is shown in figure 5, along with Zn2+Addition, the fluorescence emission peak of probe molecule moves to 451nm from 471nm, and along with the enhancing of fluorescence intensity, this illustrates this probe molecule and Zn2+After combining, it is suppressed that its ESIPT process, show stoke shift (Stokesshift)。Probe molecule is to Zn2+Quantitative measurement can be studied by the linear calibration curve that fluorescence titration as shown in Figure 6 is tested。As it can be seen, Zn2+Concentration within the scope of 1-10 μM time with the fluorescence intensity of probe molecule, there is good linear relationship, linear equation is: y=9.51993x+83.48985, R2=0.9848, Kd=1.19 × 103M-1, lowest detectable limit reaches 78nM, and this illustrates that this probe can the detection Zn of rapid sensitive2+。
Embodiment five
HEPES buffer solution (20mM to 10 μMs of glimmering zinc ion fluorescent compounds provided by the invention, pH=7.0) hydrochloric acid of variable concentrations or sodium hydroxide solution it are separately added in regulate solution ph, measure the fluorescence emission spectrum of the corresponding pH value solution of often group, additionally with same method measuring probe molecule and Zn2+The complex the formed response to pH, as it is shown in fig. 7, result shows: fluorescent probe molecule is insensitive to pH value change, in the scope of pH value 1 to 8, fluorescence intensity is not affected by pH value change, with Zn2+Combine the complex formed when pH value is about 7, and fluorescence intensity reaches maximum, illustrates that this probe is suitable for being applied in living things system。
The Application Example of provided by the invention zinc ion fluorescent compound is given below, can be used for the detection of zinc ion in zooblast, the conduction in plant and the detection of zinc ion in plant。
Embodiment six
Respectively with three groups of HepG2 cells of DMEM culture medium culturing, in the HepG2 cell of first group of DMEM culture medium culturing, add 10 μMs of zinc ion fluorescent compound solutions provided by the invention, cultivate 1 hour under 37 DEG C of conditions；In the HepG2 cell of second group of DMEM culture medium culturing, it is initially charged 10 μMs of Zn2+Solution, cultivates 1 hour under 37 DEG C of conditions, adds 10 μMs of fluorescent probe molecule solution, cultivates 1 hour under 37 DEG C of conditions；In the HepG2 cell of the 3rd group of DMEM culture medium culturing, it is initially charged 10 μMs of Zn2+Solution, cultivates 1 hour under 37 DEG C of conditions, adds 10 μMs of fluorescent probe molecule solution, cultivates 1 hour, be eventually adding 10 μMs of ethylenediaminetetraacetic acid (EDTA) solution under 37 DEG C of conditions, cultivates 1 hour under 37 DEG C of conditions。After cultivation completes, rinse with PBS buffer solution respectively, be placed on inverted fluorescence microscope imaging, the imaging of first group as shown in Figure 8 a, the imaging of second group as shown in Figure 8 b, the imaging of the 3rd group as shown in Figure 8 c, it can be seen that use Zn2+After hydroponics, its fluorescence intensity strengthens, and after adding EDTA solution, its fluorescence intensity reduces, and illustrates that this probe can realize Zn in zooblast2+Detection。
Embodiment seven
Take the flower of 3 strain Dianthus chinensis prunus mume (sieb.) sieb.et zucc.s, cut the pistil containing fluorescent material, as illustrated in fig. 9, respectively the first strain, the second strain and the 3rd strain from left to right so that it is unstressed configuration under ultra violet lamp。First strain is placed on the Zn of 10 μMs2+Solution is cultivated 1 hour；Second strain is placed in the fluorescent probe molecule solution of 10 μMs and cultivates 1 hour；3rd strain is firstly placed on the Zn of 10 μMs2+Solution is cultivated 1 hour, then is placed in the fluorescent probe molecule solution of 10 μMs and cultivates 1 hour。After cultivation completes, respectively with deionized water rinsing, under ultra violet lamp, observe its phenomenon, as shown in figure 9b, use Zn2+Flower after hydroponics is positioned at left side, its filigree place unstressed configuration, uses Zn2+It is positioned at middle part with the aquicultural flower of fluorescent probe molecule again after hydroponics, the fluorescence intensity at its filigree place is stronger, being positioned at right side with the flower after fluorescent probe molecule hydroponics, there is faint fluorescence at its filigree place, conduction that this probe can be implemented in plant is described and to Zn2+Detection。
The know-why of the present invention is described above in association with specific embodiment。These descriptions are intended merely to explanation principles of the invention, and can not be construed to limiting the scope of the invention by any way。Based on explanation herein, those skilled in the art need not pay performing creative labour can associate other detailed description of the invention of the present invention, and these modes fall within protection scope of the present invention。
Claims (10)
1. a zinc ion fluorescent compound, it is characterised in that its chemical molecular formula is C15H13NO4, molecular structural formula is:
2. zinc ion fluorescent compound according to claim 1, it is characterised in that: described zinc ion fluorescent compound is, to obtain through derivatization with 2-(2 '-hydroxy phenyl) benzoxazole compound for precursor structure。
3. the preparation method of a zinc ion fluorescent compound, it is characterised in that follow these steps to carry out:
Step A, 2-(2 '-hydroxy phenyl) benzothiazole is dissolved in trifluoroacetic acid solution, is dividedly in some parts hexamethylenetetramine and raw material is carried out formylated, after purification, obtain intermediate I；
Step B, sodium borohydride is gradually added in the methanol solution of intermediate I reacts；
It is purified after step C, decompression evaporative removal solvent；
Step D, by the recrystallization in dichloromethane of the organic facies after purification in step C, it is thus achieved that finalization compound。
4. preparation method according to claim 3, it is characterised in that the chemical molecular formula of the described intermediate I in step A is C15H9NO4, molecular structural formula is:
5. preparation method according to claim 3, it is characterised in that described its chemical molecular formula of finalization compound is C15H13NO4, molecular structural formula is:
6. preparation method according to claim 3, it is characterised in that
In step A, carrying out step A2, step A2 after raw material carries out formylated is be heated to reflux to reacting completely；
Preferably, carrying out step A3, step A3 after step A2 is, adds hcl acidifying, and adopt ethyl acetate solution to extract after the solution cooling after reacting completely；
Preferably, carrying out step A4, step A4 after step A3 is, dries with anhydrous sodium sulfate after the step A3 organic facies saturated aqueous common salt obtained is rinsed；
Preferably, step A5, step A5 are carried out after step A4 for adopting column chromatography mode that organic facies dried in step A4 is easily separated the described intermediate I of acquisition；
Preferably, 2-(2 '-hydroxy phenyl) benzothiazole is 1:2 with the mol ratio of hexamethylenetetramine；
Preferably, in step A5, the eluant that described column chromatography mode adopts includes ethyl acetate, normal hexane；
Preferably, in step A5, the ratio of ethyl acetate and normal hexane is 7:1。
7. the mol ratio of preparation method according to claim 3, it is characterised in that in step B, intermediate I and sodium borohydride is 1:4；
Preferably, in step B, under condition of ice bath, sodium borohydride is dividedly in some parts in the methanol solution of intermediate I。
8. preparation method according to claim 3, it is characterised in that: in step C, adopt column chromatography mode to be purified；
Preferably, in step C, the eluant that described column chromatography mode adopts includes ethyl acetate, normal hexane；
Preferably, in step C, the ratio of ethyl acetate and normal hexane is 1:1。
9. the application of a zinc ion fluorescent compound, it is characterised in that zinc ion fluorescent is for the detection of zinc ion in zooblast。
10. the application of a zinc ion fluorescent compound, it is characterised in that zinc ion fluorescent is for the conduction in plant and the detection of zinc ion in plant。
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| CN109307661B (en) * | 2017-07-26 | 2023-09-12 | 贵州大学 | Cr in living cells 3+ 、Al 3+ Or Zn 2+ Fluorescent imaging method of (2) |
| CN110804046A (en) * | 2018-08-04 | 2020-02-18 | 南京大学 | Zinc ion proportional photoacoustic probe with mitochondrial targeting function and application thereof |
| CN110804046B (en) * | 2018-08-04 | 2022-03-25 | 南京大学 | Zinc ion proportional photoacoustic probe with mitochondrial targeting function and application thereof |
| CN110746414A (en) * | 2019-12-05 | 2020-02-04 | 台州学院 | Fluorescent probe for detecting zinc ions and preparation and application thereof |
| CN111825629A (en) * | 2020-08-12 | 2020-10-27 | 江西理工大学 | Benzoxazole fluorescent probe, preparation method and application |
| CN111825629B (en) * | 2020-08-12 | 2022-10-21 | 江西理工大学 | Benzoxazole fluorescent probe, preparation method and application |
| CN112812036A (en) * | 2021-01-19 | 2021-05-18 | 安徽医科大学第二附属医院 | Zn2+Ion-activated fluorescent probe |
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