CN114989188A - Fluorescent probe for detecting active amine and application thereof - Google Patents

Fluorescent probe for detecting active amine and application thereof Download PDF

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CN114989188A
CN114989188A CN202210605309.8A CN202210605309A CN114989188A CN 114989188 A CN114989188 A CN 114989188A CN 202210605309 A CN202210605309 A CN 202210605309A CN 114989188 A CN114989188 A CN 114989188A
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fluorescent probe
amine
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CN114989188B (en
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林伟英
唐永和
迟涵文
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Guangxi University
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    • C07—ORGANIC CHEMISTRY
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    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
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    • 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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    • 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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Abstract

The invention provides a fluorescent probe for detecting amine, which has a chemical structural formula as follows:
Figure 851742DEST_PATH_IMAGE001
. The fluorescent probe can detect active amine generated in a solution and in a biological decay process. The fluorescence of the fluorescent probe for detecting active amine provided by the invention is obviously enhanced after the active amine is added, and the result and the phenomenon thereof lay the theoretical foundation for the application of the test paper for rapidly detecting the food spoilage. Accordingly, the degree of food spoilage can be assessed by detecting active amines using the probes of the invention via fluorescence imaging techniques.

Description

Fluorescent probe for detecting active amine and application thereof
Technical Field
The invention belongs to the technical field of analytical chemistry, and particularly relates to a fluorescent probe for detecting active amine and application thereof.
Background
Biologically active amines are the most important class of biogenic amines produced by the bacterial decarboxylation of lysine in rotten animal tissues. They are often found in rancid, high protein foods, such as meat and fish. Once formed, the biologically active amine is released into the surrounding environment and generates an unpleasant odor in the atmosphere. Biologically active primary diamines are readily incorporated into the human body by ingestion, inhalation or skin contact and pose serious health risks including food poisoning, respiratory and gastrointestinal damage. Therefore, in order to maintain food safety, it is necessary to develop an appropriate technique for measuring bioactive amines in meat and fish in order to detect whether food is spoiled.
Various analytical methods for the detection of biologically active amines have been developed, including gas chromatography-mass spectrometry (GC-MS), electrochemistry, spectrophotometry, and High Performance Liquid Chromatography (HPLC). However, these methods are limited by problems of cumbersome sample preparation, time consuming procedures, and expensive instruments. The chromophore-based fluorescent probe has the characteristics of simplicity and convenience in operation, high sensitivity and strong specificity, and is beneficial to detection of biogenic amine. Researchers have proposed several different explanations for the interaction mechanism of chromophores and amines, including schiff base formation, deprotonation, aminolysis, nucleophilic addition, amine exchange and cyclization, among others. These approaches enrich the methods for monitoring biological diamines, however, these probes still have several limitations: a small number of the probes work in a fluorescence 'off' mode, have relatively low sensitivity and even are false positive reactions; the design of the probe is based on the alkalinity and nucleophilicity of biogenic amine, so that the probe is easily interfered by other amines; these probes having complicated structures require cumbersome preparation processes. Therefore, the development of a small-molecule organic fluorescent probe with a simple structure for rapid and highly selective detection of biological diamine in food is urgently needed.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides the fluorescent probe for detecting the bioactive amine, which has the characteristics of high response speed and strong anti-interference capability.
It is another object of the present invention to provide a rapid detection of the above fluorescent probe in food spoilage processes.
In order to achieve the purpose, the invention adopts the following technical scheme.
A fluorescent probe for detecting amine, 2',7' -dichloro-3-oxo-3H-spiro [ isobenzofuran-1, 9' -xanthine ] -3',6' -diacetic acid diester, CHW-Cl for short, has a chemical structural formula shown in formula (I):
Figure 950512DEST_PATH_IMAGE001
the formula (I).
The amine is an amine compound except amino acid. Preferably, the amine is selected from putrescine, cadaverine, spermine, spermidine, tyramine, phenethylamine, histamine or tryptamine; most preferred is cadaverine.
The preparation method of the fluorescent probe comprises the following steps:
(1) heating 4-chlororesorcinol and phthalic anhydride in peroxyacetic acid for reaction, adding the reaction mixture into ice water after the reaction is finished, filtering to obtain a precipitate, washing and drying to obtain the 2',7' -dichlorofluorescein:
Figure 231102DEST_PATH_IMAGE002
；
(2) adding 4-dimethylamino pyridine and pyridine into a dichloromethane suspension of 2',7' -dichlorofluorescein, dropwise adding acyl chloride for reaction, and after the reaction is finished, separating and purifying to obtain the fluorescent probe:
Figure 807576DEST_PATH_IMAGE003
。
in the step (1), the temperature of the heating reaction is 90 ℃; the heating time is 24 h.
In the step (2), the separation and purification steps are as follows: diluting the reaction mixture with water, extracting with dichloromethane, washing the organic phase with saturated ammonium chloride solution and saturated sodium chloride solution successively, drying the organic phase with anhydrous magnesium sulfate, filtering, and removing the solvent under reduced pressure; dissolving the residue with a small amount of dichloromethane, adding neutral silica gel powder with the same volume as the residue, adsorbing, removing the solvent, and filling the obtained powder into a column; and (3) taking cyclohexane and ethyl acetate in a volume ratio of 10:4 as a chromatographic solution, passing through a silica gel column, and removing the chromatographic solution in vacuum to obtain the fluorescent probe.
An application of the fluorescent probe in detecting active amine in solution and food.
The mechanism of the invention is as follows:
two acetate groups of 2',7' -dichloro-3-oxo-3H-spiro [ isobenzofuran-1, 9' -xanthine ] -3',6' -diacetic acid diester are attacked by active amine, added and then eliminated to release hydroxyl, five-membered ring is opened, pi electron transfer occurs to form a large conjugated system, and strong fluorescence is generated:
Figure 687939DEST_PATH_IMAGE004
。
the invention has the following advantages:
the active amine fluorescent probe provided by the invention belongs to a small molecule fluorescent probe, and few reports are reported for the small molecule fluorescent probe identified by active amine at present, and particularly, the fluorescent probe for rapidly detecting the active amine generated by biological putrefaction is more rarely reported. When the active amine fluorescence probe provided by the invention is added with the active amine, the fluorescence is obviously enhanced, and the result and the phenomenon lay the theoretical basis for the application of the rapid detection test paper for the food spoilage.
Drawings
FIG. 1 shows the hydrogen spectrum of probe CHW-Cl;
FIG. 2 is a carbon spectrum of probe CHW-Cl;
FIG. 3 shows a titration experiment of the effect of probe CHW-Cl on cadaverine (1, 5-pentanediamine); wherein the excitation wavelength is 480 nm; concentration of the probe: 10 mu M;
FIG. 4 shows the kinetics of the interaction of the probe CHW-Cl with cadaverine; wherein the excitation wavelength is 430 nm; concentration of the probe: 10 mu M. Cadaverine concentration was 275 μ M, test time: 100 min;
FIG. 5 shows the selectivity of the probe CHW-Cl in absolute ethanol; wherein the excitation wavelength is 480 nm; concentration of the probe: 10 muM, the concentration of selective ions is 10 mM, and the concentration of active amine (cadaverine) is 100 muM;
FIG. 6 is a photograph of multiple segments of the same banana fruit after being reacted with probe CHW-Cl at different time periods;
FIG. 7 is a photograph of the same live loach after death and after the same live loach was exposed to dry test paper soaked in a CHW-Cl solution as a probe for the same live loach for different periods of time.
Detailed Description
The present invention will be further described with reference to the following examples and drawings, but the present invention is not limited to the following examples.
EXAMPLE 1 Synthesis of fluorescent Probe
Synthesis of 2',7' -dichloro-3-oxo-3H-spiro [ isobenzofuran-1, 9' -xanthine ] -3',6' -diacetic acid diester:
Figure 250114DEST_PATH_IMAGE005
4-Chlororesorcinol (14.4 g, 99.6 mmol) and phthalic anhydride (7.3 g, 49.3 mmol) were dissolved in peroxyacetic acid (50 mL) and the resulting solution was heated at 90 ℃ for 24 hours; cooling to room temperature, slowly adding the reaction mixture into 1L of ice water, stirring, filtering, washing the precipitate with ice water, and drying to obtain 2',7' -dichlorofluorescein, wherein the 2',7' -dichlorofluorescein is directly added into the next step without purification;
4-dimethylaminopyridine (15. mu. mol, 0.1 eq) and pyridine (0.33 mmol, 2.2 eq) were added to a suspension of 2',7' -dichlorofluorescein (0.15 mmol, 1 eq) and dichloromethane (2.0 mL); acid chloride (0.33 mmol, 2.2 eq) was added dropwise and the resulting solution was stirred for 1 hour; diluting with water, extracting with dichloromethane, washing the organic phase with saturated ammonium chloride aqueous solution and saturated saline solution, drying the organic phase with anhydrous magnesium sulfate, filtering, and removing the solvent under reduced pressure; fully dissolving the residue with a small amount of dichloromethane, adding neutral silica gel powder with volume approximately equal to that of the residue, fully stirring, removing the solvent in vacuum to obtain a crude product, namely powder of silica gel powder, and then loading the crude product on a column by a dry method; purifying by silica gel column chromatography (cyclohexane: ethyl acetate =10:4, volume ratio) to obtain a product, namely the fluorescent probe;
wherein, 1 H NMR (500 MHz，DMSO-d 6 ) δ 8.07 (d, J = 10.0 Hz, 1H), δ 7.83 (dt, J = 25.0 Hz, J =10.0 Hz, 2H), δ 7.59 (s, J = 0 Hz, 2H), δ 7.50 (d, J = 10.0 Hz, 2H), δ 7.07 (s, J = 0 Hz, 2H), δ 2.36 (s, J =0, 6H)；
13 C NMR (126 MHz, DMSO-d 6 ) δ 168.46, 151.69, 149.80, 148.70, 136.59, 131.34, 129.05, 126.00, 125.86, 124.54, 122.33, 118.26, 113.74, 40.50, 40.33, 40.17, 40.00, 39.83, 39.66, 39.50, 20.85.；
1 h NMR as shown in FIG. 1; 13 c NMR is shown in FIG. 2.
Example 2 response of fluorescent probes to various concentrations of cadaverine
5 mL of a 1 mM cadaverine absolute ethanol solution and 1 mM of the mother solution of the fluorescent probe prepared in example 1 were prepared for use. Preparing a probe with the concentration of 10 mu M, respectively interacting with cadaverine (0-275 mu M) with different concentrations, and performing fluorescence detection (lambda) ex = 480 nm), calculating fluorescence intensity in each system, and establishing a standard curve of fluorescence intensity and cadaverine concentration. As shown in FIG. 3, in the range of the tested concentration, the fluorescence intensity of the reaction system gradually increases linearly with the increase of the cadaverine concentration, and the LOD is calculated to be 52.26 nM.
Example 3 kinetics of response of fluorescent probes to saturating concentrations of cadaverine
5 mL of absolute ethanol solution with the concentration of 1 mM cadaverine and 1 mM of the mother liquor of the fluorescent probe for detecting active amine are prepared for standby. Preparing a probe and a cadaverine solution, wherein the concentrations of the probe and the cadaverine solution are respectively as follows: carrying out probe 10 mu M; cadaverine concentration: 275. mu.M. Performing fluorescence detection (lambda) ex And (5) = 480 nm), testing once every 5 min for 100 min, calculating the fluorescence intensity changing along with time in each system, and establishing a standard curve of the fluorescence intensity and the action time. As shown in FIG. 4, the reaction was carried out for about 90 min, and the fluorescence intensity of the reaction system reached a saturation state.
Example 4 selectivity of fluorescent probes for different ions
5 mL of 10 mM absolute ethanol solution of each selective sample and 1 mM of the fluorescence probe stock solution prepared in example 1 were prepared for use. mu.L of the probe stock solution and 20. mu.L of each selective sample solution were added thereto, and the mixture was shaken well and subjected to fluorescence detection (. lamda.) ex = 480 nm), a matrix of fluorescence intensities and respective selectivity samples was establishedThe results are shown in FIG. 5, where the ions added 1-18 are: hydrogen peroxide, aniline, ethylenediamine, putrescine, cadaverine, n-propylamine, formaldehyde, isoleucine, sodium bisulfite, histidine, serine, phenylalanine, cysteine, leucine, glycine, arginine, lysine and proline. The change of fluorescence emission spectrum of the solution is detected after 60 min, and as can be found from fig. 5, most of amino acids and oxidizing substances have almost no influence on the fluorescence of the compound fluorescein-Cl, and the addition of ethylenediamine, putrescine, cadaverine and n-propylamine obviously enhances the fluorescence of the compound fluorescein-Cl.
Application example 1 fluorescent probes to interact with bananas of varying degrees of decay
Preparing the fluorescent probe mother liquor with the concentration of 50 mu M for detecting the active amine for later use. Taking a complete fresh banana, peeling off the peel, taking out four small pieces, respectively putting the four small pieces into four sample bottles, sequentially adding 1 mL of probe mother liquor after 0 h, 5 h and 24h, covering the probe mother liquor, placing the probe mother liquor for fifteen minutes, placing the probe mother liquor in a dark box type ultraviolet analyzer to observe the fluorescence brightness, and taking a picture and recording, as shown in figure 6.
Application example 2 fluorescent Probe to loaches of different rotting degrees
Preparing the fluorescent probe mother liquor with the concentration of 50 mu M for detecting the active amine, cutting the fluorescent probe mother liquor into four filter paper strips with equal size by using qualitative filter paper (quickly), soaking the filter paper strips into the probe mother liquor, and drying the filter paper strips for later use. Taking four living loaches which grow well, killing the loaches, putting the loaches into four clean conical bottles with plugs respectively, hanging well-organized filter paper strips after 0 h, 5 h and 24h in sequence, covering the plugs, placing the loaches for 15 min, placing the loaches in a dark box type ultraviolet analyzer, observing fluorescence brightness, and taking a picture and recording, as shown in fig. 7.

Claims (8)

1. A fluorescent probe for detecting amine has a chemical structural formula shown in formula (I):
Figure 338079DEST_PATH_IMAGE001
formula (I).
2. The fluorescent probe of claim 1, wherein the amine is an amine compound other than an amino acid.
3. The fluorescent probe of claim 1, wherein the amine is selected from putrescine, cadaverine, spermine, spermidine, tyramine, phenethylamine, histamine, or tryptamine.
4. A method for preparing the fluorescent probe of claim 1, comprising the steps of:
(1) heating 4-chlororesorcinol and phthalic anhydride in peroxyacetic acid for reaction, adding the reaction mixture into ice water after the reaction is finished, filtering to obtain a precipitate, washing and drying to obtain the 2',7' -dichlorofluorescein:
Figure 634806DEST_PATH_IMAGE002
；
(2) adding 4-dimethylamino pyridine and pyridine into a dichloromethane suspension of 2',7' -dichlorofluorescein, dropwise adding acyl chloride for reaction, and separating and purifying after the reaction is finished to obtain the fluorescent probe:
Figure 958340DEST_PATH_IMAGE003
。
5. the production method according to claim 4, wherein in the step (1), the temperature of the heating reaction is 90 ℃; the heating time is 24 h.
6. The method according to claim 4, wherein in the step (2), the separation and purification steps are: diluting the reaction mixture with water, extracting with dichloromethane, washing the organic phase with saturated ammonium chloride solution and saturated sodium chloride solution successively, drying the organic phase with anhydrous magnesium sulfate, filtering, and removing the solvent under reduced pressure; dissolving the residue with a small amount of dichloromethane, adding neutral silica gel powder with the same volume as the residue, adsorbing, removing the solvent, and filling the obtained powder into a column; and (3) taking cyclohexane and ethyl acetate in a volume ratio of 10:4 as a chromatographic solution, passing through a silica gel column, and removing the chromatographic solution in vacuum to obtain the fluorescent probe.
7. Use of the fluorescent probe of claim 1 for detecting reactive amines in solutions and food products.
8. Use according to claim 7, wherein the active amine is selected from putrescine, cadaverine, spermine, spermidine, tyramine, phenethylamine, histamine or tryptamine.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116124751A (en) * 2023-03-28 2023-05-16 云南大学 Spermine and spermidine detection method suitable for meat food freshness assessment
CN116120257A (en) * 2022-12-12 2023-05-16 渤海大学 Fluorescent probe for indicating freshness of large yellow croaker as well as preparation method and application thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WEN CHYAN，ET AL.: "Electronic and Steric Optimization of Fluorogenic Probes for Biomolecular Imaging" *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116120257A (en) * 2022-12-12 2023-05-16 渤海大学 Fluorescent probe for indicating freshness of large yellow croaker as well as preparation method and application thereof
CN116120257B (en) * 2022-12-12 2024-04-30 渤海大学 Fluorescent probe for indicating freshness of large yellow croaker as well as preparation method and application thereof
CN116124751A (en) * 2023-03-28 2023-05-16 云南大学 Spermine and spermidine detection method suitable for meat food freshness assessment
CN116124751B (en) * 2023-03-28 2024-03-19 云南大学 Spermine and spermidine detection method suitable for meat food freshness assessment

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