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WO2023015795A1 - Sonde fluorescente de polysulfane ratiométrique, son procédé de préparation et son utilisation - Google Patents

Sonde fluorescente de polysulfane ratiométrique, son procédé de préparation et son utilisation Download PDF

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WO2023015795A1
WO2023015795A1 PCT/CN2021/137297 CN2021137297W WO2023015795A1 WO 2023015795 A1 WO2023015795 A1 WO 2023015795A1 CN 2021137297 W CN2021137297 W CN 2021137297W WO 2023015795 A1 WO2023015795 A1 WO 2023015795A1
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fluorescent probe
ratiometric
compound
preparation
hydrogen polysulfide
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Chinese (zh)
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龚萍
向春柏
蔡林涛
向晶晶
张鹏飞
罗媛
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Shenzhen Institute of Advanced Technology of CAS
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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"
    • 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
    • G01N21/6447—Fluorescence; Phosphorescence by visual observation
    • 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
    • G01N21/645—Specially adapted constructive features of fluorimeters
    • G01N21/6456—Spatial resolved fluorescence measurements; Imaging
    • G01N21/6458—Fluorescence microscopy
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
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    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • 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
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    • 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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Definitions

  • the invention relates to the technical field of molecular probes, in particular to a ratio-type hydrogen polysulfide fluorescent probe and its preparation method and application.
  • Reactive sulfur species are sulfur-containing molecules that have important regulatory functions in biological systems.
  • hydrogen sulfide (H 2 S) is an important endogenous gas transporter, which has been widely studied due to its participation in various physiological activities.
  • hydrogen polysulfide (H 2 S n ) has not attracted much attention.
  • some recent evidence suggests that hydrogen polysulfide is involved in an increasing number of physiological activities related to hydrogen sulfide. For example, polyhydrogen sulfide is more likely than hydrogen sulfide to activate TRAP1 channels and induce Ca influx in astrocytes.
  • ratiometric probes are plagued by aggregation-induced quenching (ACQ) in vivo, resulting in massive weak fluorescence and disruption of autofluorescence. Therefore, it is of great significance to develop ratiometric hydrogen polysulfide probes with high fluorescence intensity, fast response and high accuracy.
  • ACQ aggregation-induced quenching
  • the present invention proposes a ratiometric hydrogen polysulfide fluorescent probe and its preparation method and application.
  • the structural formula of the fluorescent probe is shown in formula (I).
  • the fluorescent probe uses 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-methylene)malononitrile to react with a precursor compound to obtain a precursor with aggregation-induced luminescent properties body, and then attached to the electrophilic recognition group 2-fluoro-5-nitrobenzoate.
  • the present invention provides a ratiometric hydrogen polysulfide fluorescent probe, the structural formula of which is shown in formula (I):
  • R is, , , any of the.
  • the present invention also provides the preparation method of the ratio-type hydrogen polysulfide fluorescent probe, the fluorescent probe uses 2-(3-cyano-4,5,5-trimethylfuran-2(5H)- Methyl) malononitrile reacts with 4-(diethylamino) salicylaldehyde to obtain a precursor with aggregation-induced luminescent properties, and then connects the electrophilic recognition group 2-fluoro-5-nitrobenzoate.
  • the precursor compound is When, the intermediate compound is
  • the precursor compound is When, the intermediate compound is ;
  • the precursor compound is When, the intermediate compound is .
  • the basic compound is piperidine or pyridine; the first organic solvent is absolute ethanol, and the second organic solvent is anhydrous dichloromethane.
  • the reaction temperature of the step (1) is 60-100°C; the reaction time is 5-12 hours, preferably 10-12 hours.
  • the reaction temperature can ensure that the intermediate compound yield reaches 85%. If the reaction time is too short, the 85% yield of the fluorescent probe cannot be realized, and if the reaction time is too long, by-products will be generated.
  • the molar ratio of the precursor compound, the 2-fluoro-5-nitrobenzoic acid, the dicyclohexylcarbodiimide and the 4-dimethylaminopyridine is 1:(1-2.5 ): (1-2): (0.1-0.5), preferably 1:2:1.5:0.2; the intermediate compound, the 2-(3-cyano-4,5,5-trimethylfuran-
  • the molar ratio of 2(5H)-methylene)malononitrile to the basic compound is 1:1:0.5.
  • the yield of the fluorescent probe prepared by adopting the above ratio is high, up to 83%.
  • step (1) a step of post-processing the obtained product is also included, and the post-processing includes the following steps:
  • the concentrate was subjected to column chromatography to obtain the intermediate compound.
  • the present invention also provides the application of the ratio-type hydrogen polysulfide fluorescent probe in the qualitative or quantitative detection of hydrogen polysulfide in organisms.
  • the method includes the following steps: adding the sample to be tested into the ratiometric hydrogen polysulfide fluorescent probe solution, and then visually observing the color change and/or testing the change in ultraviolet absorption.
  • the solution of the ratiometric hydrogen polysulfide fluorescent probe is a mixed solution of the ratiometric hydrogen polysulfide fluorescent probe, water and an organic solvent.
  • the volume ratio of the water to the organic solvent is 99.5:5-99:10.
  • organic solvent is dimethylsulfoxide.
  • the ratiometric hydrogen polysulfide fluorescent probe of the present invention has the characteristics of aggregation-induced luminescence, and can emit strong fluorescence in the aggregated state, avoiding a large number of weak fluorescence and interruption of autofluorescence.
  • the ratiometric hydrogen polysulfide fluorescent probe of the present invention has a short response time and a fast response time of only 2 minutes.
  • the ratiometric hydrogen polysulfide fluorescent probe of the present invention performs self-calibration through the ratio change of the fluorescence intensity of two different emission wavelengths, which can effectively avoid the fluorescence quenching of traditional fluorescent molecules at high concentrations or the fluorescence intensity of a single wavelength is susceptible to The shortcomings of external factors such as concentration, temperature, pH value and instrument interference have effectively improved the accuracy and resolution of detection.
  • the ratiometric hydrogen polysulfide fluorescent probe of the present invention can realize a ratiometric linear response to hydrogen polysulfide in a certain concentration range, and can quantitatively detect hydrogen polysulfide in cells and living bodies.
  • Fig. 1 is the working principle figure of the ratio type hydrogen polysulfide fluorescent probe of the present invention
  • Figure 2 is a graph showing the ratio of the fluorescence intensity at 619 nm to the fluorescence intensity at 751 nm after incubation of 5 ⁇ M TCFPB-H 2 S n in the presence of different concentrations of hydrogen polysulfide for different times;
  • Fig. 3 is a change diagram of the fluorescence emission spectrum after adding different concentrations of hydrogen polysulfide to the 5 ⁇ M TCFPB-H 2 S n solution for incubation;
  • Fig. 4 is a linear graph of the ratio of the fluorescence intensity at 619nm to the fluorescence intensity at 751nm of 5 ⁇ M TCFPB-H 2 S n solution and the concentration of hydrogen polysulfide;
  • Figure 5 is a graph showing the ratio of the fluorescence intensity at 619nm to the fluorescence intensity at 751nm of a 5 ⁇ M TCFPB-H 2 Sn solution as a function of different pH values;
  • Figure 6 is a graph showing the ratio of the fluorescence intensity at 619nm to the fluorescence intensity at 751nm after adding different competitor molecules to 5 ⁇ M TCFPB-H 2 S n solution;
  • Figure 7 is a photo of confocal laser microscopy imaging of 5 ⁇ M TCFPB-H 2 S n and HeLa cells incubated at 37°C for 20 minutes;
  • Fig. 8 is a diagram showing the change of the ratio of the fluorescence intensity of the green channel to the fluorescence intensity of the red channel in cells with different concentrations of polyhydrogen sulfide.
  • the invention provides a ratiometric hydrogen polysulfide fluorescent probe, the structural formula of which is shown in formula (I).
  • R is , , any of the.
  • the present invention also provides the preparation method of the fluorescent probe, the fluorescent probe is 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-methylene)malononitrile React with the precursor compound to obtain a precursor with aggregation-induced luminescent properties, and then connect the electrophilic recognition group 2-fluoro-5-nitrobenzoate, the electrophilic recognition group 2-fluoro-5-nitrobenzene Formate is the hydrogen polysulfide recognition unit.
  • the reaction temperature is 60-100°C; the reaction time is 5-12 hours, preferably 10-12 hours.
  • the basic compound is piperidine or pyridine; the first organic solvent is absolute ethanol.
  • the molar ratio of the precursor compound, the 2-fluoro-5-nitrobenzoic acid, the dicyclohexylcarbodiimide and the 4-dimethylaminopyridine is 1: (1-2.5): ( 1-2):(0.1-0.5), preferably 1:2:1.5:0.2.
  • the precursor compound is When, the intermediate compound is
  • the precursor compound is When, the intermediate compound is ;
  • the precursor compound is When, the intermediate compound is .
  • This embodiment is prepared by a two-step method.
  • the precursor compound is 4-(diethylamino) salicylaldehyde, which is prepared according to the following route:
  • nuclear magnetic model is Bruker AVANCE 400, the test condition is room temperature, the NMR data is:
  • Mass spectrometry was performed on the purple intermediate compound prepared in Example 1.
  • the equipment model of the mass spectrometer was Orbitrap Fusion Tribrid mass spectrometer, and the test condition was room temperature.
  • the purple compound TCFPB-H 2 S n prepared in Example 1 was analyzed by NMR, and the purple compound TCFPB-H 2 S n is the hydrogen polysulfide fluorescent probe of the present invention.
  • the nuclear magnetic model is Bruker AVANCE 400, and the test condition is room temperature.
  • the resulting product is characterized by nuclear magnetic resonance, and it can be known that the structural formula of the ratiometric hydrogen polysulfide fluorescent probe prepared in this example is:
  • the intermediate compound can be obtained:
  • the structural formula of the ratio type hydrogen polysulfide fluorescent probe prepared by the present embodiment is:
  • the intermediate compound can be obtained:
  • Figure 2 is a diagram of the ratio change of the fluorescence intensity at 619nm to the fluorescence intensity at 751nm after TCFPB-H 2 S n was incubated in a 95% PBS/DMSO mixed solution for different times in the presence of different concentrations of hydrogen polysulfide. It can be seen from Figure 2 , after incubating at 37°C for 2 minutes, the fluorescence intensity basically reached saturation, which indicated that the polyhydrogen sulfide probe responded quickly, only for 2 minutes.
  • Figure 3 is a graph showing the changes in fluorescence emission spectra after adding different concentrations of hydrogen polysulfide to 5 ⁇ M TCFPB-H 2 S n solution and incubating; it can be seen from Figure 3 that with the increase of the concentration of hydrogen polysulfide, the fluorescence intensity at 619nm Gradually enhanced, while the fluorescence intensity at 751nm gradually decreased.
  • Figure 5 is a graph showing the ratio change of the fluorescence intensity at 619nm to the fluorescence intensity at 751nm in PBS/DMSO mixed solutions of different pH values for TCFPB-H 2 S n . It can be seen from Figure 5 that the probe TCFPB-H 2 S n itself has a very good Excellent pH stability, insensitive to pH value, the probe TCFPB-H 2 S n has a good response ability to hydrogen polysulfide in the range of pH 6.0 ⁇ 10.0.
  • Figure 6 is a diagram of the ratio change of the fluorescence intensity at 619nm to the fluorescence intensity at 751nm after adding different competing molecules to the TCFPB-H 2 S n solution.
  • the fluorescence intensity ratio before and after the 2 S n reaction did not change significantly, indicating that TCFPB-H 2 S n can selectively recognize H 2 S n and is not easily interfered by other ions, and has strong specificity.
  • Example 7 The hydrogen polysulfide fluorescent probe of the present invention qualitatively and quantitatively detects hydrogen polysulfide in cells
  • HeLa cells were resuscitated and inoculated in RPMI 1640 medium containing 10% fetal bovine serum, cultured in an incubator at 37°C, 5% CO 2 , and 100% saturated humidity, and then cultured on 18mm coverslips for 24 hours before use.
  • Figure 7 is a laser confocal microscopic image of TCFPB-H 2 S n incubated with HeLa cells at 37°C for 5 minutes.
  • the light channels all showed weak fluorescent signals, but in the HeLa cells added with hydrogen polysulfide, the fluorescent signals of the red light channel gradually weakened, while the fluorescent signals of the green light channel increased significantly.
  • Figure 8 is a diagram of the ratio of the fluorescence intensity of the green channel to the fluorescence intensity of the red channel in cells with different concentrations of polysulfide hydrogen.
  • 2 S n can be used for ratiometric fluorescence imaging of intracellular hydrogen polysulfide.
  • the hydrogen polysulfide fluorescent probe of the invention can not only detect the hydrogen polysulfide qualitatively in cells and living bodies, but also realize quantitative detection.
  • the ratiometric hydrogen polysulfide fluorescent probe obtained in Example 4 and Example 5 was tested for response time, fluorescence titration, pH sensitivity, selectivity, and imaging conditions in human cervical cancer cells, and the obtained Result and embodiment 6 ⁇ 7 are similar.
  • the ratiometric hydrogen polysulfide fluorescent probe provided by the present invention has aggregation-induced luminescent characteristics and ratiometric response characteristics, and has a short response time, is insensitive to pH, and can qualitatively and quantitatively detect intracellular hydrogen polysulfide , and can respond and image cells through the fluorescence intensity ratio of two different emission wavelengths, which can effectively avoid the interference of a single wavelength from external factors such as temperature, pH, concentration and instruments, obtain higher imaging resolution, and prepare raw materials
  • the method is easy to obtain, has simple steps, is easy to operate, has high yield, is suitable for industrial production, and has broad application prospects.

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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Abstract

L'invention concerne une sonde fluorescente de polysulfane ratiométrique, son procédé de préparation et son utilisation. La formule développée de la sonde fluorescente est représentée par la formule (I). La sonde fluorescente est obtenue par réaction de 2-(3-cyano-4,5,5-triméthylfuran-2(5H)-méthylène)malononitrile avec un composé précurseur pour obtenir un précurseur ayant une caractéristique d'émission induite par agrégation, et ensuite la liaison d'un groupe de reconnaissance électrophile 2-fluoro-5-nitrobenzoate. La sonde fluorescente de polysulfane ratiométrique présente des avantages en termes de matières premières synthétiques facilement accessibles, une synthèse simple, un rendement élevé de composé cible, une réponse ratiométrique élevée et similaire, permet d'éviter les défauts que les sondes fluorescentes classiques ne sont pas appropriées pour une détection à fortes concentrations et une émission unique susceptible d'être brouillée par des facteurs externes tels que la concentration, la température, la valeur du pH, et des instruments pendant le processus de détection, a une intensité de fluorescence élevée, une réponse rapide, une haute résolution et une forte capacité anti-interférence, peut être utilisée pour la détection qualitative et quantitative de polysulfane dans des cellules et des corps vivants, et présente de bonnes perspectives d'application.
PCT/CN2021/137297 2021-08-10 2021-12-12 Sonde fluorescente de polysulfane ratiométrique, son procédé de préparation et son utilisation Ceased WO2023015795A1 (fr)

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CN119019464A (zh) * 2024-09-05 2024-11-26 北京工业大学 含Ir金属配合物及其制备方法与应用
CN119899162A (zh) * 2025-01-08 2025-04-29 常州大学 基于氯水杨醛亚氨类荧光探针及其制备方法和应用

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