CN110487761A - Detect fluorescence probe of mercury ion and preparation method thereof and application method - Google Patents
Detect fluorescence probe of mercury ion and preparation method thereof and application method Download PDFInfo
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Abstract
The invention discloses fluorescence probe of detection mercury ion and preparation method thereof and application methods.The present invention constructs the novel fluorescence system with two photon emission using xanthene and benzyne, and is introduced directly into mercury ion at meso- loop coils and sets part, can carry out specificly-response to mercury ion.Probe conjugated system itself due to meso- thiosemicarbazides presence and be destroyed, unstressed configuration transmitting.But when there are under conditions of mercury ion, due to the intramolecular desulfurization cyclization that mercury ion promotes, so that meso- loop coils are opened, probe molecule launches strong red fluorescence.Xanthene provided by the invention and benzyne, which construct " on-off " the type mercury ion probe with two-phpton property, has good response to mercury ion solution, it can be realized the sensitive quantitative detection to mercury ion micro in sample, with easy to operate, it is low in cost, respond it is sensitive, it is easy to spread and application the advantages that.
Description
Technical field
The invention belongs to small organic molecule fluorescence probe fields, and in particular to a kind of to make as mercury ion fluorescence probe
Oxa anthracenes derivative and preparation method thereof and application method.
Background technique
Mercury is a kind of air that is distributed widely in serious physiological-toxicity, the heavy metal of water and soil.Elemental Mercury and mercury
Ion can be converted to methyl mercury by microbial action, further by all means enter food chain and in vivo by
Grade accumulation eventually enters into the human body, generates great destruction to systems such as brain, the nervous centralis of human body, can cause language
It makes peace the serious diseases such as memory capability obstacle, even results in the death of organism.In recent years, in the industrial production with mercury
Frequent application, caused by environmental pollution and the biohazard that thus causes get worse.Therefore, development is highly sensitive and high
The mercury ion detecting method of selectivity realizes real-time, original position, dynamic, the content for specifically detecting Mercury in Water Body ion, for
Ensure that people's life waits safely with important theory significance and practical value.
Fluorescence detection is able to achieve real-time, In to biological sample due to its outstanding detection sensitivity and selectivity
Line detects and the extensive concern by researcher.2- (2 '-hydroxy phenyl) benzothiazoles fluorescent molecule is because it is with good
Photostability, high molar extinction coefficient and quantum yield and there is unique excited state intramolecular proton transfer (ESIPT) etc.
Unique optical properties and become one of most important fluorescent parent of this method, obtained in the fluorescence detection of a variety of testing molecules
It is widely applied.
The small-molecule fluorescent probe for detecting mercury ion developed at present is based primarily upon between mercury ion and sulphur atom
Specific binding affinity and design.When there are under conditions of mercury ion, mercaptal or thioamides in probe molecule etc.
Functional group is selectively hydrolyzed by mercury ion and is removed sulphur atom in the form of two sulphur ligands of HgS or mercury etc., and probe point is caused
The photoluminescent property of son changes, to realize the specific recognition to mercury ion.
However, currently based on probe that mercaptal or thioamides are probes report group (referring to summary Mahato,
P.；Saha,S.；Das,P.；Agarwalla H.；Das, Amitava.RSC Adv., 2014,4,36140-36174.) often with
Cumarin, fluorescein, BODIPY, rhodamine etc. are fluorescence mother group, and wavelength is concentrated mainly on the regions such as blue-green-Huang-near-infrared,
It is often difficult to penetrate the deep tissues of biology in Bioexperiment, is unfavorable for it and is accurately examined in complicated biosystem
It surveys.In addition, the detection limit of current mercury ion fluorescence probe is relatively high, it is difficult to micro or even denier sample containing mercury ion
Product carry out quantitative detection.
Summary of the invention
The present invention in order to overcome the above-mentioned defects in the prior art, proposes a kind of oxa anthracenes of quantitative detection mercury ion
Two-photon fluorescence probe (TPL1).It can be to the mercury ion progress quantitative detection of denier in sample using the present invention.
Core of the invention is to construct the novel fluorescence system with two photon emission using xanthene and benzyne, and
Mercury ion is introduced directly at meso- loop coils and sets part, can carry out specificly-response to mercury ion.Probe itself is conjugated
System due to meso- thiosemicarbazides presence and be destroyed, unstressed configuration transmitting.But when there are under conditions of mercury ion, by
In the intramolecular desulfurization cyclization that mercury ion promotes, so that meso- loop coils are opened, it is glimmering that probe molecule launches strong red
Light.Through the above scheme, the fluorescence response for obtaining " on-off " type realizes highly sensitive, specific detection to mercury ion.
Mercury ion fluorescence probe of the present invention is named as 1- (3 '-(diethylamino) -6 '-((4- methoxyphenyl) second
Alkynyl) -3- oxo spiral shell [isoindoline -1,9'- xanthene] -2- base) -3- phenylthiourea, shown in structural formula such as formula (I):
Above-mentioned mercury ion fluorescence probe the preparation method is as follows: by the iodo- 3H- of a certain amount of 3'- (diethylamino) -6'-
Spiral shell [isobenzofuran -1,9'- xanthene] -3- ketone (1), cuprous iodide, bis- (triphenylphosphine) palladium chlorides, 4- acetylenylbenzene methyl ether
(2) it is dissolved in tetrahydrofuran with triethylamine, stirring at normal temperature 4 hours, reaction solution is filtered with diatomite, solvent is spin-dried for, uses ethyl alcohol
Washing, dry compound 3 '-(diethylamino) -6 '-((4- methoxyphenyl) acetenyl) -3H- spiral shell [isobenzofuran -
1,9'- xanthene] -3- ketone (3).By a certain amount of 3 '-(diethylamino) -6 '-((4- methoxyphenyl) acetenyl) -3H- spiral shells
[isobenzofuran -1,9'- xanthene] -3- ketone (3) is dissolved in methanol, and hydrazine hydrate is added, is heated to reflux 24 hours, into reaction solution
Water is added, has solid precipitation, is filtered under diminished pressure, ethyl alcohol recrystallization obtains -6 '-((4- methoxyl group of 2- amino -3 '-(diethylamino)
Phenyl) acetenyl) spiral shell [isoindoline -1,9'- xanthene] -3- ketone (4).By a certain amount of 2- amino -3 '-(diethylamino) -
6 '-((4- methoxyphenyl) acetenyl) spiral shell [isoindoline -1,9'- xanthene] -3- ketone (4) and phenyl isothiocyanate are dissolved in nothing
In water DMF, after being stirred at room temperature 48 hours, water is added into reaction solution, ethyl acetate extraction merges organic layer, anhydrous sodium sulfate
Be dried to obtain 1- (3 '-(diethylamino) -6 '-((4- methoxyphenyl) acetenyl) -3- oxo spiral shells [isoindoline -1,
9'- xanthene] -2- base) -3- phenylthiourea (5), it may be assumed that TPL1.
Above-mentioned probe to prepare reaction equation as follows:
The application method of above-mentioned mercury ion fluorescence probe is as follows:
Step 1: compound shown in the formula (I) of same concentrations, configuration being added into the buffer solution of various concentration mercury ion
The standard solution containing compound shown in formula (I) of at least five kinds of difference mercury ion contents；
Shown buffer solution can be phosphate buffer solution, Tris-HCl buffer solution, HEPES buffer solution or boron
Acid-sodium borate buffer solution；
The pH value of shown standard solution is 5~11；
The concentration of compound shown in formula (I) is 1nM~1 μM in shown standard solution；
The content of mercury ion is 0.1nM~1mM in shown standard solution；
Step 2: measuring the fluorescence emission spectrum of the standard solution, excitation wavelength 520nm, with ion concentration of mercury respectively
For abscissa, with I581For ordinate, standard curve is established；
I581Indicate the standard solution in the fluorescence emission peak intensity value that wavelength is at 581nm；
Step 3: compound shown in formula (I) being added into sample to be tested, controls formula (I) in its concentration and the standard solution
The concentration of shown compound is equal；Its fluorescence emission spectrum in the case where excitation wavelength is the exciting light of 520nm is measured, i.e., according to standard
The mercury ion content of sample to be tested is calculated in curve.
The present invention has a characteristic that
1) fluorescence probe provided by the invention is pale red solid powder, molecular structure optical stability.
2) fluorescence probe provided by the invention, solution is to the concentration sensitive of mercury ion, with the increase of ion concentration of mercury,
Observe that the fluorescence of its aqueous solution becomes red from colourless under ultraviolet lamp.
3) fluorescence probe provided by the invention, launch wavelength 581nm are responded for fluorescence " on-off " type, can be disappeared significantly
Influence of the testing conditions difference to result, improves the sensitivity of detection when except detection.
4) fluorescence probe provided by the invention is in a linear relationship to ion concentration of mercury, can be used for mercury ion precise measurement.
Novel two-photon oxa anthracenes " on-off " type mercury ion probe provided by the invention has mercury ion solution good
Response, can be realized the sensitive quantitative detection to mercury ion in sample, have it is easy to operate, it is low in cost, respond it is sensitive, easily
In the promotion and application the advantages that.
Detailed description of the invention
Fig. 1: the nuclear magnetic resonance spectroscopy of fluorescence probe TPL1.
Fig. 2: fluorescence probe TPL1 to the color response figure of mercury ion aqueous solution.
Fig. 3: fluorescence probe TPL1 to the fluorescence response figure of mercury ion aqueous solution.
Fig. 4: fluorescence probe TPL1 in buffer mercury ion ultraviolet titration curve, wherein concentration and probe concentration be 1.0 μM.
Fig. 5: fluorescence probe TPL1 in buffer mercury ion fluorescence titration curve, wherein excitation wavelength be 520nm, visit
Needle concentration is 1.0 μM.
Fig. 6: fluorescence probe TPL1 to the fluorescence response figure of common coexisting ion, and wherein excitation wavelength is 520nm, and probe is dense
Degree is 1.0 μM, and ion concentration is 10.0 μM.
Specific embodiment
Experimental method used in following embodiments is conventional method unless otherwise specified.
The materials, reagents and the like used in the following examples obtains from commercial channels unless otherwise specified.
Compound number in embodiment corresponds to the number in above compound.
The synthesis of embodiment 1, compound TPL1
Compound 3 '-(diethylamino) -6 '-((4- methoxyphenyl) acetenyl) -3H- spiral shell [isobenzofuran -1,
9'- xanthene] -3- ketone (3) synthesis
By the iodo- 3H- spiral shell of 4g 3'- (diethylamino) -6'- [isobenzofuran -1,9'- xanthene] -3- ketone (1)
(8mmol), 80mg cuprous iodide (0.4mmol), bis- (triphenylphosphine) palladium chlorides (0.2mmol) of 0.16g and 20mL triethylamine
It is dissolved in 60mL tetrahydrofuran, after 1.3g 4- acetylenylbenzene methyl ether (9.6mmol) room temperature reaction being added 4 hours, reaction solution is used
Diatomite filtering, is spin-dried for solvent, with ethanol washing, dry compound 3 '-(diethylamino) -6 '-((4- methoxyphenyl)
Acetenyl) -3H- spiral shell [isobenzofuran -1,9'- xanthene] -3- ketone (3), the compound can be directly used in next step react.
Compound 2- amino -3 '-(diethylamino) -6 '-((4- methoxyphenyl) acetenyl) spiral shell [isoindoline -
1,9'- xanthene] -3- ketone (4) synthesis
By 25g compound 3 '-(diethylamino) -6 '-((4- methoxyphenyl) acetenyl) -3H- spiral shell [different benzo furan
Mutter -1,9'- xanthene] -3- ketone (3) (50mmol) is dissolved in 1L methanol, 40mL hydrazine hydrate is added, is heated to reflux 24 hours, to anti-
Addition 1.5L water in liquid is answered, there are a large amount of white solids to be precipitated, filtering obtains beige solid compound 2- ammonia after vacuum drying
Base -3 '-(diethylamino) -6 '-((4- methoxyphenyl) acetenyl) spiral shell [isoindoline -1,9'- xanthene] -3- ketone (4),
The compound can be directly used for reacting in next step.
Compound 1- (3 '-(diethylamino) -6 '-((4- methoxyphenyl) acetenyl) -3- oxo spiral shell [different dihydro Yin
Diindyl -1,9'- xanthene] -2- base) -3- phenylthiourea (5) synthesis
By 1.14g 2- amino -3 '-(diethylamino) -6 '-((4- methoxyphenyl) acetenyl) spiral shell [different dihydro Yin
Diindyl -1,9'- xanthene] -3- ketone (4) (2mmol) and 0.4mL phenyl isothiocyanate be dissolved in 20mL anhydrous DMF, it is small to be stirred at room temperature 48
500mL water is added into reaction solution by Shi Hou, and ethyl acetate extraction merges organic layer, and anhydrous sodium sulfate is dried to obtain 1.3g 1-
(3 '-(diethylamino) -6 '-((4- methoxyphenyl) acetenyl) -3- oxo spiral shell [isoindoline -1,9'- xanthene] -2-
Base) -3- phenylthiourea (5), it may be assumed that TPL1, yield 99%.Nuclear magnetic resonance map such as Fig. 1.
1H NMR (400MHz, Chloroform-d) δ 8.11 (d, J=7.5Hz, 1H), 7.80-7.65 (m, 2H), 7.58-
7.51 (m, 3H), 7.47 (d, J=1.6Hz, 1H), 7.34 (d, J=8.0Hz, 1H), 7.27 (t, J=7.7Hz, 2H), 7.19-
7.13 (m, 2H), 7.12-7.08 (m, 2H), 6.99-6.89 (m, 3H), 6.68 (d, J=8.1Hz, 1H), 6.58 (d, J=
8.9Hz, 1H), 6.54 (d, J=2.5Hz, 1H), 6.39 (dd, J=8.9,2.6Hz, 1H), 3.90 (s, 3H), 3.48-3.30
(m, 4H), 1.23 (t, J=7.0Hz, 6H).
Embodiment 2, compound TPL1 are to the color response of mercury ion
Compound concentration is the dimethyl sulfoxide (DMSO) of the fluorescence probe TPL1 of the detection mercury ion of the present invention of 1mM
It is stand-by to test mother liquor solution.This mother liquor for measuring 10 μ L is added drop-wise in the phosphate buffer of a certain concentration mercury ion, and uses phase
The phosphate buffer constant volume answered is to 10mL, so that the concentration of probe is 1.0 μM in test fluid, ion concentration of mercury is 10.0 μM
Carry out color response test.As shown in Figures 2 and 3, after mercury ion aqueous solution being added, the color of solution is observed visually by no discoloration
For red, while the fluorescence of solution also becomes shiny red fluorescence from almost unstressed configuration, and it is straight to show that probe TPL1 has mercury ion
The developing response of sight.
Embodiment 3, various concentration mercury ion detect the ultraviolet titration of compound TPL1
Compound concentration is the dimethyl sulfoxide (DMSO) of the fluorescence probe TPL1 of the detection mercury ion of the present invention of 1mM
It is stand-by to test mother liquor solution.This mother liquor for measuring 10 μ L is added drop-wise to respectively in the phosphate buffer of various concentration mercury ion, and
With corresponding phosphate buffer constant volume to 10mL, so that the concentration of probe is 1.0 μM, ion concentration of mercury 0- in test fluid
3.0 μM of progress absorption spectrum tests.Ultraviolet absorption curve in each system is obtained, absorbance and ion concentration of mercury standard curve are established.
As shown in figure 4, absorbance gradually increases at 526nm with the increase of ion concentration of mercury, and with ion concentration of mercury (0-3.0 μM)
In good linear relationship.
Embodiment 4, various concentration mercury ion detect the fluorescence titration of compound TPL1
Compound concentration is the dimethyl sulfoxide (DMSO) of the fluorescence probe TPL1 of the detection mercury ion of the present invention of 1mM
It is stand-by to test mother liquor solution.This mother liquor for measuring 10 μ L is added drop-wise to respectively in the phosphate buffer of various concentration mercury ion, and
With corresponding phosphate buffer constant volume to 10mL, so that the concentration of probe is 1.0 μM, ion concentration of mercury 0- in test fluid
1.5 μM of progress fluorescence detections (λ ex=520nm, λ em=581nm).Fluorescence intensity in each system is obtained, fluorescence intensity and mercury are established
Ion concentration standard curve.As shown in figure 5, fluorescence intensity gradually increases at 581nm with the increase of ion concentration of mercury, work as mercury
When ion concentration reaches 1.0 μM, reaction system fluorescence intensity reaches saturation state.In addition, at low concentrations, fluorescence intensity and mercury
Good linear relationship (R is presented between the concentration (0-0.3 μM) of ion2=0.99), probe TPL1 limits the detection of mercury ion
Up to 5.7nM.
Embodiment 5, compound TPL1 are to the selectivity of common coexisting ion
Compound concentration is the dimethyl sulfoxide (DMSO) of the fluorescence probe TPL1 of the detection mercury ion of the present invention of 1mM
It is stand-by to test mother liquor solution.Compound concentration is the various different ions of 10mM, and the solution of small molecule is as spare.Measure 10 μ L's
This mother liquor is added drop-wise to different in measured ion or the phosphate buffer of small molecule respectively, and is determined with corresponding phosphate buffer
Hold 10mL, so that the concentration of probe is 1.0 μM in test fluid, it is 2.0 μM of progress fluorescence to the concentration of measured ion or small molecule
It detects (λ ex=520nm, λ em=581nm).Fluorescence intensity in each system is obtained, the histogram of fluorescence intensity Yu each ion is established.
As shown in fig. 6, the fluorescence of other ion pair probes TPL1 has little effect.
Claims (3)
1. detecting the fluorescence probe of mercury ion, it is characterised in that: its molecular formula is C40H34N4O3S, abbreviation TPL1, structural formula are formula
(I)；
2. a kind of preparation method of the fluorescence probe of detection mercury ion described in claim 1, which is characterized in that synthesis step is such as
Under:
1) by the iodo- 3H- spiral shell of 4g 3'- (diethylamino) -6'- [isobenzofuran -1,9'- xanthene] -3- ketone, 80mg iodate is sub-
Copper, bis- (triphenylphosphine) palladium chlorides of 0.16g and 20mL triethylamine are dissolved in 60mL tetrahydrofuran, and 1.3g 4- acetenyl is added
Reaction solution is filtered with diatomite after room temperature reaction 4 hours, is spin-dried for solvent by methyl phenyl ethers anisole, with ethanol washing, dry compound
3 '-(diethylamino) -6 '-((4- methoxyphenyl) acetenyl) -3H- spiral shell [isobenzofuran -1,9'- xanthene] -3- ketone；
2) by 25g compound 3 '-(diethylamino) -6 '-((4- methoxyphenyl) acetenyl) -3H- spiral shell [isobenzofuran -
1,9'- xanthene] -3- ketone is dissolved in 1L methanol, and 40mL hydrazine hydrate is added, is heated to reflux 24 hours, 1.5L is added into reaction solution
Water has a large amount of white solids to be precipitated, and filtering obtains beige solid compound 2- amino -3 '-(diethyl amino after vacuum drying
Base) -6 '-((4- methoxyphenyl) acetenyl) spiral shell [isoindoline -1,9'- xanthene] -3- ketone；
3) by 1.14g 2- amino -3 '-(diethylamino) -6 '-((4- methoxyphenyl) acetenyl) spiral shell [isoindoline -
1,9'- xanthene] -3- ketone and 0.4mL phenyl isothiocyanate be dissolved in 20mL anhydrous DMF, after being stirred at room temperature 48 hours, to reaction solution
Middle addition 500mL water, ethyl acetate extraction, merges organic layer, and anhydrous sodium sulfate is dried to obtain 1.3g 1- (3 '-(diethyl aminos
Base) -6 '-((4- methoxyphenyl) acetenyl) -3- oxo spiral shell [isoindoline -1,9'- xanthene] -2- bases) -3- phenyl sulphur
Urea, it may be assumed that TPL1.
3. the application method of the fluorescence probe of detection mercury ion according to claim 1；It is characterized by:
1) compound shown in the formula (I) of same concentrations is added into the buffer solution of various concentration mercury ion, configuration is at least five kinds of not
With the standard solution containing compound shown in formula (I) of mercury ion content；
Shown buffer solution is phosphate buffer solution, Tris-HCl buffer solution, HEPES buffer solution or boric acid-sodium borate
Buffer solution；
The pH value of shown standard solution is 5~11；
The concentration of compound shown in formula (I) is 1nM~1 μM in shown standard solution；
The content of mercury ion is 0.1nM~1mM in shown standard solution；
2) fluorescence emission spectrum of the standard solution, excitation wavelength 520nm, with ion concentration of mercury for horizontal seat are measured respectively
Mark, with I581For ordinate, standard curve is established；
I581Indicate the standard solution in the fluorescence emission peak intensity value that wavelength is at 581nm；
3) compound shown in formula (I) is added into sample to be tested, controls chemical combination shown in formula (I) in its concentration and the standard solution
The concentration of object is equal；Its fluorescence emission spectrum in the case where excitation wavelength is the exciting light of 520nm is measured, i.e., is calculated according to standard curve
Obtain the mercury ion content of sample to be tested.
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| CN113588606A (en) * | 2021-06-28 | 2021-11-02 | 西北农林科技大学 | Non-conjugated polymer probe, dual signal ratio sensor, method and application |
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| CN103674920A (en) * | 2013-12-18 | 2014-03-26 | 南京理工大学 | Application of rhodamine B based fluorescence sensor |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113588606A (en) * | 2021-06-28 | 2021-11-02 | 西北农林科技大学 | Non-conjugated polymer probe, dual signal ratio sensor, method and application |
| CN113588606B (en) * | 2021-06-28 | 2024-03-01 | 西北农林科技大学 | Non-conjugated polymer probe, dual signal ratio sensor, method and application |
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