CN112239462B - Cyanide receptor compound based on coumarin and carboxylic indole, preparation method and application thereof - Google Patents
Cyanide receptor compound based on coumarin and carboxylic indole, preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a coumarin and carboxylic indole-based cyanide receptor compound, a preparation method and application thereof. The cyanide receptor compound is iodinated E-3, 3-dimethyl-N-ethyl-6-carboxylic acid-2- (7- (diethylamino) coumarin) indole. The compound takes a C = C double bond as a reactive binding site, takes iodinated 7- (diethylamino) coumarin-3-formaldehyde as a fluorescent signal reporting group, and when a receptor meets cyanide ions, the cyanide ions can perform addition reaction with the C = C double bond of the receptor to cause proton transfer and charge transfer in the receptor molecules, so that the receptor molecules generate color and fluorescence changes. The cyanide receptor compounds of the present invention can be in pure H2The cyanide ions are selectively identified in the O system in a single way, and the detection sensitivity is high.
Description
Technical Field
The invention belongs to the technical field of anion detection, relates to a cyanide receptor compound based on coumarin and carboxylic acid indole, a preparation method and application thereof, and particularly relates to a cyanide receptor compound based on iodinated E-3, 3-dimethyl-N-ethyl-6-carboxylic acid-2- (7- (diethylamino) coumarin) indole, a preparation method and application thereof in detection of CN-The use of (1).
Background
Cyanide is one of the strongest, fastest acting toxic drugs known. The cyanide is mainly inorganic cyanide such as hydrocyanic acid, potassium cyanide, etcAnd organic cyanides such as acetonitrile and acrylonitrile. In daily life, cassava, bitter almonds and the like contain cyanide, and automobile exhaust and cigarette smoke also contain hydrogen cyanide. Cyanide is very easily absorbed by human body and can enter human body through oral cavity, respiratory tract or skin. Cyanide enters the stomach and can be immediately hydrolyzed into cyanohydric acid to be absorbed under the dissociation of gastric acid. After the substance enters blood circulation, Fe of cytochrome oxidase in blood3+Combining with cyanide to produce cyaniding ferricytochrome oxidase, losing the ability to transfer electrons, interrupting the respiratory chain and dying the cell chamber. Since cyanide has a greater solubility in lipids, the central nervous system is first of all endangered, in particular the respiratory center is more sensitive. For the reasons stated above, CN in the environment-The detection of (2) has attracted great attention.
In the field of ion detection, colorimetric methods or fluorescent methods are receiving much attention due to their simple operation, easy availability of instruments, and the like. At present, various receptors for colorimetric or fluorescent detection of cyanide ions are disclosed in the literature, but the receptors are often complex in structure and difficult to synthesize, so that the application of the method in detection and identification of cyanide ions is restricted. The cyanide receptor compounds disclosed in Chinese patent applications 201510849223X and 2015108492225 are all in DMSO/H2Cyanide detection is carried out in an O system, and the water solubility is poor.
Disclosure of Invention
Aiming at the problem that the existing cyanide receptor compound fluorescent probe has poor water solubility, the invention provides a cyanide receptor compound based on coumarin and carboxylic indole.
The technical solution of the invention is as follows:
a coumarin and carboxylic acid indole-based cyanide receptor compound, namely E-3, 3-dimethyl-N-ethyl-6-carboxylic acid-2- (7- (diethylamino) coumarin) indole iodide, of the formula:
the invention also provides a preparation method of the cyanide receptor compound based on coumarin and carboxylic indole, which comprises the following steps:
using ethanol as a reaction solvent, using iodinated 7- (diethylamino) coumarin-3-formaldehyde and carboxylic indole as substrates, and reacting at 70-80%oAnd C, carrying out reflux reaction, carrying out suction filtration after the reaction is finished, and washing by using normal hexane to obtain the iodide E-3, 3-dimethyl-N-ethyl-6-carboxylic acid-2- (7- (diethylamino) coumarin) indole.
Preferably, the molar ratio of the iodinated 7- (diethylamino) coumarin-3-carbaldehyde to the carboxylic indole is 1: 1.
preferably, the reflux reaction time is 10-13 h.
Further, the invention provides an application of the cyanide receptor compound based on coumarin and carboxylic indole in cyanide ion detection.
Compared with the prior art, the invention has the advantages that:
(1) the compound is simple to synthesize, and the raw materials are easy to obtain;
(2) the compound can be used for detecting CN in pure water solution-；
(3) CN can be detected quickly by naked eyes-；
(4) The compound is less cytotoxic.
Drawings
FIG. 1 is a mechanism diagram of detection of cyanide ions by receptor compound iodinated E-3, 3-dimethyl-N-ethyl-6-carboxylic acid-2- (7- (diethylamino) coumarin) indole.
FIG. 2 shows a cyanide receptor compound (2X 10) according to the present invention-5mol/L) in pure H2UV-Vis spectrum of the interaction with various anions (50equiv.) in the O system.
FIG. 3 shows a cyanide receptor compound (2X 10) according to the present invention-5mol/L) in pure H2Fluorescence spectra of O system when interacting with various anions (50 equiv.).
FIG. 4 shows a cyanide receptor compound (2X 10) according to the present invention-5mol/L) in pure H2When other ions are contained in the O system, to CN-The ultraviolet-visible spectrum and the fluorescence spectrum without influence on the detection of (2).
FIG. 5 shows a cyanide receptor compound (2X 10) according to the present invention-5mol/L) in pure H2Titration of CN with O System-Fluorescence spectrum of the ion.
FIG. 6 shows the cytotoxicity of the cyanide receptor compound of the present invention, with abscissa 1 showing 0. mu.M for sensor CID, 0.1. mu.M for 2, 1. mu.M for 3, 10. mu.M for 4, 30. mu.M for 5, and 50. mu.M for 6.
Detailed Description
The invention will be further described in the following by means of specific examples and figures.
The synthetic route of the receptor compound, namely the iodized E-3, 3-dimethyl-N-ethyl-6-carboxylic acid-2- (7- (diethylamino) coumarin) indole, is as follows:
the cyanide receptor compound contains C = C double bond, and the receptor compound generates nucleophilic addition reaction of cyanide ions in the presence of cyanide, so that conjugation of receptor molecules is interrupted, the color of a solution of the receptor molecules is faded, and strong green fluorescence is emitted. Therefore, the mechanism of detecting cyanide ions by using the receptor compound, namely, iodinated E-3, 3-dimethyl-N-ethyl-6-carboxylic acid-2- (7- (diethylamino) coumarin) indole, is shown in figure 1.
The cyanide receptor compound takes a C = C double bond as a reactive binding site, and takes iodinated 7- (diethylamino) coumarin-3-formaldehyde as a fluorescent signal reporting group. When the acceptor molecule meets the cyanide ion, the cyanide ion can generate addition reaction with the C = C double bond of the acceptor molecule, thereby leading proton transfer and charge transfer to be generated in the acceptor molecule, leading the acceptor molecule to generate color and fluorescence change, and further achieving the colorimetric-fluorescence double-channel detection of CN-The purpose of (1).
Anion recognition assay for (I) receptor
1. Study of anion recognition Properties of receptor
Separately, 0.5mL of the acceptor was removed as pure H2O solution (2X 10)-4mol/L) in a series of 10mL colorimetric tubes, and then respectively transferring 9mL of pure H2O in the colorimetric tube added with the receptor, and then F is respectively added-, Cl-, Br-, I−, AcO-, H2PO4 -, HSO4 -, ClO4 -, CN-, N3 -And SCN-H of (A)2O solution (0.01 mol/L) 0.5 mL. The receptor concentration was 2X10 at this time-5mol/L, anion concentration is 50 times of acceptor concentration, after mixing evenly, standing for 30 minutes, and observing the response of each acceptor to anions.
It was found that when H is present in the acceptor compound2When the aqueous solution of the anion is added into the O system, only CN is added-By addition of (2) to make H of the acceptor2The O system changed from blue to colorless. In its corresponding ultraviolet spectrum, CN-By addition of (2) to make H of the acceptor2The O system absorption peak at 584nm disappeared, while a new absorption peak at 425nm appeared. Addition of other anions H to the acceptor2The O system color and the uv spectrum absorption peak had no significant effect (see figure 2). In addition, H of the receptor2The O system has a fluorescence emission peak at 642nm under the excitation of 365nm wavelength ultraviolet light, and shows purple red fluorescence. And CN-Is added to make H of the acceptor2The O system emits green fluorescence (see fig. 3). The addition of other anions had no effect on the fluorescence of the acceptor (see FIG. 4). Therefore, the receptor can identify CN by single-selective colorimetric-fluorescent double channel-。
2. Determination of minimum detection limit of receptor for CN
At 25。C, by UV-visible spectroscopy, according to CN-Titration experiments on the receptor solution (see FIG. 5) and the receptor pair CN was obtained by 3. sigma.B/S calculation-The lowest detection limit of the ions reaches 3.35 multiplied by 10−7 mol/L. This is far below CN in WTO-specified drinking water-Highest content (1.9X 10)−6mol/L). Therefore, the receptor has potential application value in the aspect of detecting cyanide in drinking water.
A large number of experiments prove that the receptor compounds have single selectivity in a pure water systemColorimetric-fluorescent double-channel property of identifying cyanide ions and for CN-The detection sensitivity of (2) is very high.
(II) detection of CN in vivo cell-
With iodine E-3, 3-dimethyl-N-ethyl-6-carboxylic acid-2- (7- (diethylamino) coumarin) indole as a sensor CID, we tested the biocompatibility of CID on B16-F10 cells in vitro in order to explore the potential biological application of the sensor CID. Even if the receptor concentration is not 50. mu.M, the cell viability can still reach more than 85% (see FIG. 6). Therefore, the CID sensor is likely to be applied to the living cell CN-Detection of (3). The specific experimental scheme is as follows:
B16-F10 cells were cultured for 24 h in an incubator containing 5% carbon dioxide and 95% air in RPMI-1640 medium containing 10% fetal bovine serum. Prior to the experiment, cells were placed in 6-well plates, followed by dropwise addition of the receptor solution (10 μ M). Cells were allowed to incubate at 5% CO2And incubated at 37 ℃ for 3 h in a 95% air environment, 3 wells of which were washed 3 times with PBS. Subsequently, 20. mu.M CN -Injected into the three wells and incubated for an additional 20 minutes to allow entry into the recipient cells. The receptor-containing solution and CN were then washed with PBS buffer-Three times, and the floating color was removed. The results of the assay then confirmed red channel fluorescence microscopy (λ) by fluorescence imagingem= 570-620nm)。
The receptor solution enters the cells and is widely distributed throughout the cytoplasmic matrix. Cells containing the receptor were observed under a microscope to show vivid red fluorescence. Whereas cells containing receptors and cyanide appear only in large black patches. This result indicates that the present invention can be used for CN in living cells-The detection of (3).
Example 1
Carboxylic acid indole (0.232 g, 1mmol) and iodinated 7- (diethylamino) coumarin-3-carbaldehyde (0.245 g, 1mmol) were dissolved in ethanol (20mL), stirred and refluxed at 76oC, reacting for 10 hours. After the reaction is finished, the product is recrystallized in an n-hexane-ethanol solvent, and is washed and purified by the n-hexane to obtain dark green powder.
Yield 73%, 1H NMR (500 MHz, DMSO) δ 13.30 (s, 0H), 8.88 (s, 1H), 8.39 (d, J = 12.3 Hz, 1H), 8.15 (d, J = 8.2 Hz, 1H), 7.90 (dd, J = 51.3, 11.9 Hz, 1H), 7.60 (d, J = 9.0 Hz, 1H), 6.94 (d, J = 8.9 Hz, 1H), 6.74 (s, 1H), 4.48 (d, J = 6.9 Hz, 2H), 3.59 (d, J = 6.6 Hz, 2H), 1.81 (s, 3H), 1.46 (t, J = 6.8 Hz, 2H), 1.19 (t, J = 6.6 Hz, 3H).13C NMR (126 MHz, DMSO) δ 166.95, 159.95, 158.38, 154.89, 144.26, 143.79, 133.15, 131.06, 130.89, 124.37, 114.66, 112.73, 112.14, 110.32, 109.43, 97.18, 51.88, 45.47, 40.50, 40.34, 40.17, 40.00, 39.84, 39.67, 39.50, 26.54, 13.31, 13.00.MS m/z [M]+ Calcd for C28H31N2O4 +459.2299, found 459.2278.
Example 2
Carboxylic acid indole (0.232 g, 1mmol) and iodinated 7- (diethylamino) coumarin-3-carbaldehyde (0.245 g, 1mmol) were dissolved in ethanol (20mL), stirred and refluxed at 76oC, reacting for 11 h. After the reaction is completed, the product is recrystallized in an n-hexane-ethanol solvent, and washed and purified by n-hexane to obtain dark green powder.
Yield: the characterization data of the synthesized product is the same as example 1 at 70%.
Example 3
Carboxylic acid indole (0.232 g, 1mmol) and iodinated 7- (diethylamino) coumarin-3-carbaldehyde (0.245 g, 1mmol) were dissolved in ethanol (20mL), stirred and refluxed at 76oC, reacting for 12 h. After the reaction is finished, the product is recrystallized in an n-hexane-ethanol solvent, and is washed and purified by the n-hexane to obtain dark green powder.
Yield: 74%, characterization data of the synthesized product are the same as in example 1.
Example 4
Carboxylic acid indole (0.232 g, 1mmol) and iodinated 7- (diethylamino) coumarin-3-carbaldehyde (0.245 g, 1mmol) were dissolved in ethanol (20mL), stirred and refluxed at 76oC, reacting for 13 h. After the reaction is completed, the product is recrystallized in an n-hexane-ethanol solvent, and washed and purified by n-hexane to obtain dark green powder.
Yield: 72% characterization data for the synthesized product are the same as in example 1.
Claims (5)
1. A coumarin and carboxylic acid indole-based cyanide receptor compound is iodinated E-3, 3-dimethyl-N-ethyl-6-carboxylic acid-2- (7- (diethylamino) coumarin) indole, and has the following structural formula:
2. the method for preparing the coumarin and carboxylic indole-based cyanide receptor compound according to claim 1, comprising the following steps:
using ethanol as a reaction solvent, using iodinated 7- (diethylamino) coumarin-3-formaldehyde and carboxylic indole as substrates, and reacting at 70-80%oAnd C, carrying out reflux reaction, carrying out suction filtration after the reaction is finished, and washing by using normal hexane to obtain the iodide E-3, 3-dimethyl-N-ethyl-6-carboxylic acid-2- (7- (diethylamino) coumarin) indole.
3. The process according to claim 2, wherein the molar ratio of 7- (diethylamino) coumarin-3-carbaldehyde to carboxylic indole is 1: 1.
4. the preparation method according to claim 2, wherein the reflux reaction time is 10-13 h.
5. Use of the coumarin and carboxylic indole-based cyanide receptor compounds according to claim 1 for cyanide ion detection for non-disease diagnosis.
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Non-Patent Citations (4)
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| Janet Cusido,等.A Photochromic Bioconjugate with Photoactivatable Fluorescence for Superresolution Imaging.《The Journal of Physical Chemistry C》.2016,第120卷第12860-12870页. * |
| Xin Lv,等.Ratiometric fluorescence detection of cyanide based on a hybrid coumarin–hemicyanine dye: the large emission shift and the high selectivity.《Chem. Commun.》.2011,第47卷第12843-12845页. * |
| Yasuhiro Shiraishi，等.Effects of substituents on fluorometric detection of cyanide anions by indolium-coumarin dyads.《Physical Chemistry Chemical Physics》.2015,第17卷(第38期),第25027-25036页. * |
| Yasuhiro Shiraishi，等.Rapid, selective, and sensitive fluorometric detection of cyanide anions in aqueous media by cyanine dyes with indolium–coumarin linkages.《Chem. Commun.》.2014,第50卷第11583-11586页. * |
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