CN110487761B - Fluorescent probe for detecting mercury ions and preparation method and use method thereof - Google Patents
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Abstract
The invention discloses a fluorescent probe for detecting mercury ions and a preparation method and a use method thereof. The invention utilizes xanthene and benzyne to construct a novel fluorescent system with two-photon emission, and directly introduces mercury ion identification part at the meso-position spiro ring, so that the system can perform specific response to mercury ions. The conjugated system of the probe is destroyed due to the existence of meso-position thiosemicarbazide, and no fluorescence is emitted. However, in the presence of mercury ions, the meso-position spiro ring is opened due to the intramolecular desulfurization cyclization reaction promoted by the mercury ions, and the probe molecules emit strong red fluorescence. The on-off type mercury ion probe with two-photon property constructed by xanthene and benzyne has good response to the mercury ion solution, can realize sensitive quantitative detection of trace mercury ions in a sample, and has the advantages of simple and convenient operation, low cost, sensitive response, easy popularization and application and the like.
Description
Technical Field
The invention belongs to the field of organic small-molecule fluorescent probes, and particularly relates to a xanthene derivative used as a mercury ion fluorescent probe, and a preparation method and a use method thereof.
Background
Mercury is a heavy metal with severe physiological toxicity that is widely distributed in air, water and soil. Simple substance mercury and mercury ions can be converted into methyl mercury through the action of microorganisms, further enter a food chain through various ways, are gradually accumulated in organisms and finally enter the human body, generate great destructive effect on systems of the brain, the central nervous system and the like of the human body, and can cause serious diseases such as language and memory disorder and even death of the organisms. In recent years, with the frequent use of mercury in industrial production, the environmental pollution and the resulting biohazard caused by mercury have become increasingly serious. Therefore, a mercury ion detection method with high sensitivity and high selectivity is developed, the content of mercury ions in a water body is detected in real time, in situ, dynamically and specifically, and the method has important theoretical significance and practical value for guaranteeing the life safety of people and the like.
Fluorescence detection methods have received much attention from researchers because of their excellent detection sensitivity and selectivity, and the ability to perform real-time, on-line detection of biological samples. The 2- (2' -hydroxyphenyl) benzothiazole fluorescent molecule is one of the most important fluorescent parent substances of the method due to good light stability, high molar extinction coefficient and quantum yield and unique optical properties such as unique Excited State Intramolecular Proton Transfer (ESIPT), and is widely applied to the fluorescent detection of various molecules to be detected.
Small molecule fluorescent probes for detecting mercury ions that have been developed so far are designed mainly based on the specific binding force between mercury ions and sulfur atoms. Under the condition of mercury ions, functional groups such as thioacetal or thioamide in the probe molecules are selectively hydrolyzed by the mercury ions and sulfur atoms are removed in the forms of HgS or mercury disulfide ligands and the like, so that the fluorescence property of the probe molecules is changed, and the specific recognition of the mercury ions is realized.
However, the current probes based on thioacetal or thioamide as the probe reporter group (see for review Mahato, p.; Saha, s.; Das, p.; agarwasla h.; Das, amitava. rsc adv.,2014,4, 36140-36174.) often use coumarin, fluorescein, BODIPY, rhodamine, etc. as the fluorescent parent group, the wavelength is mainly concentrated in the blue-green-yellow-near infrared region, etc., and the deep tissues of the organism are difficult to penetrate in the biological experiment, which is not favorable for accurate detection in a complex biological system. In addition, the detection limit of the existing mercury ion fluorescent probe is relatively high, and the quantitative detection of trace or even ultra-trace mercury ion samples is difficult.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention provides a xanthene two-photon fluorescent probe (TPL1) for quantitatively detecting mercury ions. The invention can be used for quantitatively detecting the trace mercury ions in the sample.
The core of the invention is that a novel fluorescent system with two-photon emission is constructed by xanthene and benzyne, and a mercury ion identification part is directly introduced at the meso-position spiro ring, so that the system can perform specific response to mercury ions. The conjugated system of the probe is destroyed due to the existence of meso-position thiosemicarbazide, and no fluorescence is emitted. However, in the presence of mercury ions, the meso-position spiro ring is opened due to the intramolecular desulfurization cyclization reaction promoted by the mercury ions, and the probe molecules emit strong red fluorescence. By the scheme, on-off fluorescent response is obtained, and high-sensitivity and specific detection on mercury ions is realized.
The mercury ion fluorescent probe is named as 1- (3 ' - (diethylamino) -6' - ((4-methoxyphenyl) ethynyl) -3-oxospiro [ isoindoline-1, 9' -xanthene ] -2-yl) -3-phenylthiourea, and the structural formula is shown as the formula (I):
the preparation method of the mercury ion fluorescent probe comprises the following steps: dissolving a certain amount of 3'- (diethylamino) -6' -iodo-3H-spiro [ isobenzofuran-1, 9 '-xanthene ] -3-one (1), cuprous iodide, bis (triphenylphosphine) palladium dichloride, 4-ethynylanisole (2) and triethylamine in tetrahydrofuran, stirring at normal temperature for 4 hours, filtering the reaction solution with diatomite, drying the solvent by spinning, washing with ethanol, and drying to obtain a compound, namely 3' - (diethylamino) -6'- ((4-methoxyphenyl) ethynyl) -3H-spiro [ isobenzofuran-1, 9' -xanthene ] -3-one (3). Dissolving a certain amount of 3'- (diethylamino) -6' - ((4-methoxyphenyl) ethynyl) -3H-spiro [ isobenzofuran-1, 9 '-xanthen ] -3-one (3) in methanol, adding hydrazine hydrate, heating and refluxing for 24 hours, adding water to the reaction solution, separating out a solid, filtering under reduced pressure, and recrystallizing ethanol to obtain 2-amino-3' - (diethylamino) -6'- ((4-methoxyphenyl) ethynyl) spiro [ isoindoline-1, 9' -xanthen ] -3-one (4). Dissolving certain amounts of 2-amino-3 '- (diethylamino) -6' - ((4-methoxyphenyl) ethynyl) spiro [ isoindoline-1, 9 '-xanthen ] -3-one (4) and phenyl isothiocyanate in anhydrous DMF, stirring at room temperature for 48 hours, adding water to the reaction solution, extracting with ethyl acetate, combining organic layers, and drying over anhydrous sodium sulfate to obtain 1- (3' - (diethylamino) -6'- ((4-methoxyphenyl) ethynyl) -3-oxospiro [ isoindoline-1, 9' -xanthen ] -2-yl) -3-phenylthiourea (5), that is: TPL 1.
The reaction formula for preparing the probe is as follows:
the application method of the mercury ion fluorescent probe comprises the following steps:
step 1: adding the compound shown in the formula (I) with the same concentration into buffer solutions with different concentrations of mercury ions, and preparing at least 5 standard solutions containing the compound shown in the formula (I) with different mercury ion contents;
the buffer solution can be phosphate buffer solution, Tris-HCl buffer solution, HEPES buffer solution or boric acid-sodium borate buffer solution;
the pH value of the standard solution is 5-11;
the concentration of the compound shown in the formula (I) in the standard solution is 1 nM-1 μ M;
the content of mercury ions in the standard solution is 0.1 nM-1 mM;
step 2: respectively measuring the fluorescence emission spectra of the standard solution with excitation wavelength of 520nm, mercury ion concentration as abscissa and I581Establishing a standard curve for the ordinate;
I581representing the fluorescence emission peak intensity value of the standard solution at the wavelength of 581 nm;
and step 3: adding a compound shown in a formula (I) into a sample to be detected, and controlling the concentration of the compound to be detected to be equal to the concentration of the compound shown in the formula (I) in the standard solution; and (3) measuring the fluorescence emission spectrum of the sample under the excitation light with the excitation wavelength of 520nm, namely calculating the mercury ion content of the sample to be measured according to the standard curve.
The invention has the following characteristics:
1) the fluorescent probe provided by the invention is light red solid powder, and the molecular structure is stable in optics.
2) The solution of the fluorescent probe provided by the invention is sensitive to the concentration of mercury ions, and the fluorescence of the aqueous solution is observed to change from colorless to red under an ultraviolet lamp along with the increase of the concentration of the mercury ions.
3) The fluorescent probe provided by the invention has an emission wavelength of 581nm, is a fluorescent 'on-off' type response, can greatly eliminate the influence of detection condition difference on a result during detection, and improves the detection sensitivity.
4) The fluorescent probe provided by the invention has a linear relation to the concentration of mercury ions, and can be used for accurately measuring the mercury ions.
The novel two-photon xanthene on-off mercury ion probe provided by the invention has good response to a mercury ion solution, can realize sensitive quantitative detection on mercury ions in a sample, and has the advantages of simplicity and convenience in operation, low cost, sensitive response, easiness in popularization and application and the like.
Drawings
FIG. 1: nuclear magnetic resonance hydrogen spectrum of fluorescent probe TPL 1.
FIG. 2: color response graph of fluorescent probe TPL1 to mercury ion aqueous solution.
FIG. 3: fluorescence response graph of fluorescent probe TPL1 to mercury ion water solution.
FIG. 4: UV titration curves of fluorescent probe TPL1 for mercury ions in buffer, with probe concentration of 1.0. mu.M.
FIG. 5: fluorescence titration curve of fluorescent probe TPL1 for mercury ions in buffer with excitation wavelength of 520nm and probe concentration of 1.0. mu.M.
FIG. 6: fluorescence response graph of fluorescent probe TPL1 to common coexisting ions, wherein the excitation wavelength is 520nm, the probe concentration is 1.0. mu.M, and the ion concentration is 10.0. mu.M.
Detailed Description
The experimental procedures used in the following examples are all conventional procedures unless otherwise specified.
Materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
The compound numbers in the examples correspond to those in the above-mentioned compounds.
Example 1 Synthesis of Compound TPL1
Synthesis of the compound 3' - (diethylamino) -6' - ((4-methoxyphenyl) ethynyl) -3H-spiro [ isobenzofuran-1, 9' -xanthen ] -3-one (3)
4g (8mmol) of 3' - (diethylamino) -6' -iodo-3H-spiro [ isobenzofuran-1, 9' -xanthen ] -3-one (1), 80mg of cuprous iodide (0.4mmol),0.16g of bis (triphenylphosphine) palladium dichloride (0.2mmol) and 20mL of triethylamine were dissolved in 60mL of tetrahydrofuran, adding 1.3g of 4-ethynylanisole (9.6mmol) to react for 4 hours at room temperature, filtering the reaction liquid by using kieselguhr, drying the solvent by spinning, washing by using ethanol, and drying to obtain a compound 3' - (diethylamino) -6' - ((4-methoxyphenyl) ethynyl) -3H-spiro [ isobenzofuran-1, 9' -xanthene ] -3-ketone (3), wherein the compound can be directly used for the next reaction.
Synthesis of compound 2-amino-3 ' - (diethylamino) -6' - ((4-methoxyphenyl) ethynyl) spiro [ isoindoline-1, 9' -xanthen ] -3-one (4)
25g of the compound 3'- (diethylamino) -6' - ((4-methoxyphenyl) ethynyl) -3H-spiro [ isobenzofuran-1, 9 '-xanthen ] -3-one (3) (50mmol) was dissolved in 1L of methanol, 40mL of hydrazine hydrate was added, heating and refluxing were carried out for 24 hours, 1.5L of water was added to the reaction solution, and a large amount of white solid was precipitated, followed by filtration and vacuum drying to obtain an off-white solid compound, 2-amino-3' - (diethylamino) -6'- ((4-methoxyphenyl) ethynyl) spiro [ isoindoline-1, 9' -xanthen ] -3-one (4), which was used directly in the next reaction.
Synthesis of the compound 1- (3 ' - (diethylamino) -6' - ((4-methoxyphenyl) ethynyl) -3-oxospiro [ isoindoline-1, 9' -xanthene ] -2-yl) -3-phenylthiourea (5)
After 1.14g of 2-amino-3 '- (diethylamino) -6' - ((4-methoxyphenyl) ethynyl) spiro [ isoindoline-1, 9 '-xanthen ] -3-one (4) (2mmol) and 0.4mL of phenyl isothiocyanate were dissolved in 20mL of anhydrous DMF and stirred at room temperature for 48 hours, 500mL of water was added to the reaction solution, extracted with ethyl acetate, and the organic layers were combined and dried over anhydrous sodium sulfate to give 1.3g of 1- (3' - (diethylamino) -6'- ((4-methoxyphenyl) ethynyl) -3-oxospiro [ isoindoline-1, 9' -xanthen ] -2-yl) -3-phenylthiourea (5), that is: TPL1, yield 99%. The NMR spectrum is shown in figure 1.
1H NMR(400MHz,Chloroform-d)δ8.11(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)。
Example 2 color response of Compound TPL1 to Mercury ions
A test mother liquor solution of dimethyl sulfoxide (DMSO) of the fluorescent probe TPL1 for detecting mercury ions, which is provided by the invention, is prepared at a concentration of 1mM for later use. Measuring 10 mu L of the mother liquor, dropwise adding the mother liquor into a phosphate buffer solution with a certain concentration of mercury ions, and fixing the volume to 10mL by using the corresponding phosphate buffer solution, so that the concentration of the probe in the test solution is 1.0 mu M, and the concentration of the mercury ions is 10.0 mu M, and carrying out color response test. As shown in FIGS. 2 and 3, after the mercury ion aqueous solution is added, the color of the solution is changed from colorless to red by visual observation, and the fluorescence of the solution is also changed from almost non-fluorescence to bright red fluorescence, which indicates that the probe TPL1 has visual chromogenic response to the mercury ions.
Example 3 UV titration detection of different concentrations of Mercury ion on Compound TPL1
A test mother liquor solution of dimethyl sulfoxide (DMSO) of the fluorescent probe TPL1 for detecting mercury ions, which is provided by the invention, is prepared at a concentration of 1mM for later use. Measuring 10 mu L of the mother solution, respectively dripping the mother solution into phosphate buffer solutions with different concentrations of mercury ions, and fixing the volume to 10mL by using the corresponding phosphate buffer solutions, so that the concentration of the probe in the test solution is 1.0 mu M, and the concentration of the mercury ions is 0-3.0 mu M, and carrying out absorption spectrum test. And obtaining an ultraviolet absorption curve in each system, and establishing a standard curve of absorbance and mercury ion concentration. As shown in FIG. 4, the absorbance at 526nm gradually increased with the increase of the concentration of mercury ions, and showed a good linear relationship with the concentration of mercury ions (0-3.0. mu.M).
Example 4 fluorescent titration detection of different concentrations of Mercury ion on Compound TPL1
A test mother liquor solution of dimethyl sulfoxide (DMSO) of the fluorescent probe TPL1 for detecting mercury ions, which is provided by the invention, is prepared at a concentration of 1mM for later use. 10. mu.L of the mother solution was measured and added dropwise to phosphate buffer solutions of different concentrations of mercury ions, and the volume was adjusted to 10mL using the corresponding phosphate buffer solutions so that the concentration of the probe in the test solution was 1.0. mu.M and the concentration of mercury ions was 0 to 1.5. mu.M, and fluorescence detection was performed (λ ex ═ 520nm, λ em ═ 581 nm). And obtaining the fluorescence intensity in each system, and establishing a standard curve of the fluorescence intensity and the concentration of mercury ions. As shown in FIG. 5, the fluorescence intensity at 581nm gradually increased with the increase in the concentration of mercury ions, and the fluorescence intensity of the reaction system reached a saturation state when the concentration of mercury ions reached 1.0. mu.M. In addition, at low concentrations, a good linear relationship (R) is present between the fluorescence intensity and the concentration of mercury ions (0-0.3. mu.M)20.99), the detection limit of the probe TPL1 on mercury ions can reach 5.7 nM.
Example 5 selectivity of Compound TPL1 to common coexisting ions
A test mother liquor solution of dimethyl sulfoxide (DMSO) of the fluorescent probe TPL1 for detecting mercury ions, which is provided by the invention, is prepared at a concentration of 1mM for later use. Solutions of various ions, small molecules, at a concentration of 10mM were prepared for future use. Measuring 10 mu L of the mother liquor, respectively dripping the mother liquor into phosphate buffer solutions of different ions or small molecules to be detected, and fixing the volume to 10mL by using the corresponding phosphate buffer solutions so that the concentration of the probe in the test liquor is 1.0 mu M and the concentration of the ions or small molecules to be detected is 2.0 mu M, and carrying out fluorescence detection (lambda ex is 520nm, lambda em is 581 nm). And obtaining the fluorescence intensity in each system, and establishing a histogram of the fluorescence intensity and each ion. As shown in FIG. 6, other ions had little effect on the fluorescence of probe TPL 1.
Claims (3)
1. The fluorescent probe for detecting mercury ions is characterized in that: the molecular formula is C40H34N4O3S, TPL1 for short, and the structural formula is shown as formula (I);
2. the method for preparing the fluorescent probe for detecting mercury ions according to claim 1, which comprises the following steps:
1) dissolving 4g of 3'- (diethylamino) -6' -iodo-3H-spiro [ isobenzofuran-1, 9 '-xanthen ] -3-one, 80mg of cuprous iodide, 0.16g of bis (triphenylphosphine) palladium dichloride and 20mL of triethylamine in 60mL of tetrahydrofuran, adding 1.3g of 4-ethynylanisole, reacting at room temperature for 4 hours, filtering the reaction solution with diatomite, spin-drying the solvent, washing with ethanol, and drying to obtain a compound, namely 3' - (diethylamino) -6'- ((4-methoxyphenyl) ethynyl) -3H-spiro [ isobenzofuran-1, 9' -xanthen ] -3-one;
2) dissolving 25g of a compound 3'- (diethylamino) -6' - ((4-methoxyphenyl) ethynyl) -3H-spiro [ isobenzofuran-1, 9 '-xanthen ] -3-one in 1L of methanol, adding 40mL of hydrazine hydrate, heating and refluxing for 24 hours, adding 1.5L of water to the reaction solution to precipitate a large amount of white solid, filtering, and drying in vacuum to obtain an off-white solid compound 2-amino-3' - (diethylamino) -6'- ((4-methoxyphenyl) ethynyl) spiro [ isoindoline-1, 9' -xanthen ] -3-one;
3) after 1.14g of 2-amino-3 '- (diethylamino) -6' - ((4-methoxyphenyl) ethynyl) spiro [ isoindoline-1, 9 '-xanthen ] -3-one and 0.4mL of phenyl isothiocyanate were dissolved in 20mL of anhydrous DMF and stirred at room temperature for 48 hours, 500mL of water was added to the reaction solution, extracted with ethyl acetate, and the organic layers were combined and dried over anhydrous sodium sulfate to give 1.3g of 1- (3' - (diethylamino) -6'- ((4-methoxyphenyl) ethynyl) -3-oxospiro [ isoindoline-1, 9' -xanthen ] -2-yl) -3-phenylthiourea: TPL 1.
3. The use of the fluorescent probe for detecting mercury ions according to claim 1; the method is characterized in that:
1) adding the compound shown in the formula (I) with the same concentration into buffer solutions with different concentrations of mercury ions, and preparing standard solutions containing the compound shown in the formula (I) with at least 5 different mercury ion contents;
the buffer solution is phosphate buffer solution, Tris-HCl buffer solution, HEPES buffer solution or boric acid-sodium borate buffer solution;
the pH value of the standard solution is 5-11;
the concentration of the compound shown in the formula (I) in the standard solution is 1 nM-1 muM;
the content of mercury ions in the standard solution is 0.1 nM-1 mM;
2) respectively measuring the fluorescence emission spectra of the standard solution with excitation wavelength of 520nm, mercury ion concentration as abscissa and I581Establishing a standard curve for the ordinate;
I581representing the fluorescence emission peak intensity value of the standard solution at the wavelength of 581 nm;
3) adding the compound shown in the formula (I) into a sample to be tested, and controlling the concentration of the compound to be equal to the concentration of the compound shown in the formula (I) in the standard solution; and (3) measuring the fluorescence emission spectrum of the sample under the excitation light with the excitation wavelength of 520nm, namely calculating the mercury ion content of the sample to be measured according to the standard curve.
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| Title |
|---|
| A highly selective colorimetric fluorescent probe for detection of Hg2+ and its application on test strips;Geng Yang et.al;《RSC Advanced》;20190313;第9卷;8529-8536 * |
| A new rhodamine probe with large stokes shift for Hg2+ detection and its application in real sample analysis;Shuxin Chen et.al;《Tetrahedron Letters》;20200525;第61卷;5 pages * |
| Recognition Preference of Rhodamine-Thiospirolactams for Mercury(II) in Aqueous Solution;Wei Huang et.al;《Inorganic Chemistry》;20091231;第48卷;5061-5072 * |
| TBET-based ratiometric fluorescent probe for Hg2+ with large pseudo-Stokes shift and emission shift in aqueous media and intracellular colorimetric imaging in live Hela cells;Xiaofeng Yang et.al;《Biosensors and Bioelectronic》;20181231;21 pages * |
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