WO2021035654A1 - Procédé de préparation d'une sonde de baïcaline fluorescente ratiométrique à réseau métal-organique dopé double - Google Patents

Procédé de préparation d'une sonde de baïcaline fluorescente ratiométrique à réseau métal-organique dopé double Download PDF

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WO2021035654A1
WO2021035654A1 PCT/CN2019/103465 CN2019103465W WO2021035654A1 WO 2021035654 A1 WO2021035654 A1 WO 2021035654A1 CN 2019103465 W CN2019103465 W CN 2019103465W WO 2021035654 A1 WO2021035654 A1 WO 2021035654A1
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bpqds
agncs
mof
baicalin
dispersion
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桂日军
姜晓文
金辉
孙玉娇
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青岛大学
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    • 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"
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y20/00—Nanooptics, e.g. quantum optics or photonic crystals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B25/00—Phosphorus; Compounds thereof
    • C01B25/02—Preparation of phosphorus
    • C—CHEMISTRY; METALLURGY
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/58—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing copper, silver or gold
    • C—CHEMISTRY; METALLURGY
    • 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
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/70—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing phosphorus
    • 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"
    • 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
    • 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"
    • G01N2021/6432—Quenching

Definitions

  • the invention belongs to the technical field of preparation of metal organic framework composite materials and ratio fluorescent probes, and specifically relates to a method for preparing ratio fluorescent bacitin probes based on silver nanoclusters/black phosphorous quantum dots double-doped metal organic framework composites ,
  • the probe prepared by it can be used for the highly sensitive and selective quantitative detection of bacitrin.
  • Baicalin is a flavonoid compound extracted from the dried rhizome of the plant Scutellaria baicalensis Georgi. Baicin has significant biological activity, and has the effects of antibacterial, anti-inflammatory, cholesterol-lowering, anti-thrombosis, relieving asthma, purging fire and detoxification, hemostasis, and antispasmodic. Bacitin is a specific inhibitor of mammalian liver salivase, which has the effect of regulating certain diseases, and also has a strong anti-cancer response physiological effect. Baicin also has certain side effects on the human body, which are mainly reflected in the bitter cold injures the stomach, and those with spleen and stomach deficiency and cold are not suitable for consumption.
  • Baicin is very low in toxicity and will not have obvious adverse reactions to the human body at general doses. Certain patients may have stomach discomfort, diarrhea and other reactions. People with allergies may have vesicular drug eruption. When apeline glycoside injection preparations are used in large doses, the human body will experience low-grade fever, muscle aches, and decreased white blood cells. Illegal addition of an excessive amount of bacitrin in drugs can cause damage to the human body, which is very necessary for accurate detection.
  • the analytical methods for detecting bacitrin mainly include electrochemical methods, chromatography and so on.
  • Sheng et al. have prepared a cobalt nanoparticle-doped aminated graphene-modified electrode for the electrochemical detection of bacitin (Kai Sheng, Lu Wang, Huichao Li, Lina Zou, Baoxian Ye. Green synthesized Co nanoparticles doped amino-graphene modified electrode and its application towards determination of baicalin. Talanta, 2017, 164, 249-256); Wang et al.
  • the current analytical method for detecting is mainly chromatography, but this method generally suffers from problems such as long time-consuming, complicated operation, harsh conditions, and high cost.
  • chemical and biosensor detection methods such as electrochemical sensors have excellent performance such as easy operation, high sensitivity, and good selectivity.
  • the detection of baclidin is mainly an electrochemical sensor method, in which the detection of baclidin relies on a single electrochemical signal output.
  • the intensity of a single signal is susceptible to interference from factors such as background, reagents, systems, and environmental conditions, causing fluctuations in the measurement results.
  • the dual signal ratio processing to obtain the ratio value of the signal strength can have a self-calibration function, which effectively eliminates the interference of self and background signals, thereby improving the accuracy and reliability of the detection results.
  • the present invention reports a ratio fluorescent probe based on silver nanoclusters AgNCs/black phosphorous quantum dots BPQDs double-doped metal-organic framework MOF complex AgNCs/BPQDs/MOF for detecting bacitin.
  • bacitrin is added, and bacitrin generates hydrogen peroxide under the catalysis of catalase, which causes the fluorescence of AgNCs in the complex to be quenched.
  • the fluorescence of BPQDs has little effect.
  • the purpose of the present invention is to overcome the shortcomings of the above-mentioned prior art, and design a simple method, low cost, high sensitivity and high selectivity based on silver nanocluster/black phosphor quantum dot double doped metal organic framework composite Preparation method of ratio fluorescent bacitin probe.
  • the present invention relates to a preparation process of a ratio fluorescent bacitin probe based on a silver nanocluster/black phosphorous quantum dot double-doped metal-organic framework composite including the following steps:
  • BPQDs black phosphorous quantum dots
  • the concentrations of AgNCs/BPQDs/MOF complex, catalase and bacitin are 1-10 mg mL -1 , 5-10 mU L -1 and 0.01-100 ⁇ g mL -1 , respectively.
  • the linear detection range of bacitin concentration is It is 0.01 ⁇ 100 ⁇ g mL -1 , and the detection limit is 1 ⁇ 10ng mL -1 .
  • the effect of the present invention is: a ratio fluorescent probe based on a metal organic framework AgNCs/BPQDs/MOF complex doped with silver nanoclusters/black phosphorus quantum dots is reported, which is used for quantitative detection of bacitin.
  • blue fluorescent BPQDs and MOF precursors were reacted to prepare BPQDs/MOF complexes, and then red fluorescent AgNCs were added to continue the reaction, and BPQDs and AgNCs were gradually embedded in the MOF structure.
  • BPQDs are encapsulated in MOF, while AgNCs are adsorbed in MOF pores.
  • Baicin is added to the aqueous dispersion of AgNCs/BPQDs/MOF compound with catalase added.
  • Baicin is catalyzed by catalase to generate hydrogen peroxide.
  • the oxidation of hydrogen peroxide leads to the fluorescence of AgNCs.
  • Quenched, BPQDs are encapsulated in MOF, which has little effect on their fluorescence.
  • MOF metal-oxide-semiconductor
  • the ratio of the fluorescence emission peak intensity I BPQDs /I AgNCs and the linear relationship between the concentration of baclidin were fitted to construct a ratio fluorescent baclidin probe.
  • the method of the present invention is easy to operate, has strong anti-interference ability of ratio fluorescent signal, high sensitivity and good selectivity, and can be used as a novel ratio fluorescent probe for the highly sensitive and selective detection of bacein. .
  • Figure 1 is a schematic diagram of the preparation of a ratio fluorescent probe based on a silver nanocluster/black phosphorous quantum dot double-doped metal-organic framework composite and the principle diagram of bacitin detection;
  • Figure 2 (a) is the measurement of the fluorescence emission spectra of the ratio fluorescent probe system under different bacitin concentrations
  • Figure 2(b) shows the ratio of fluorescence emission peak intensity I BPQDs /I AgNCs corresponding to different bacitin concentrations , i.e. I 530 /I 630 , fitting the linear relationship between different ratio values and bacitin concentrations.
  • This embodiment relates to a method for preparing a ratio fluorescent bacein probe based on a silver nanocluster/black phosphorous quantum dot double-doped metal-organic framework complex.
  • the preparation process and the principle diagram of the ratio fluorescent detection of bacein are shown in Figure 1 As shown, the specific process steps are as follows:
  • BPQDs Preparation of BPQDs: Weigh 10 mg of black phosphorus crystals and add 30 mL of nitrogen methyl pyrrolidone, sonicate for 30 minutes to form a dispersion, transfer the dispersion to a micro high pressure reactor, heat to 140°C under nitrogen protection, and continue stirring for 12 hours . The reaction mixture was centrifuged at 3500 rpm for 15 minutes to remove larger-sized products, and then centrifuged at 13000 rpm for 15 minutes to obtain a precipitate. The precipitate was washed three times with ethanol and distilled water, and dried in vacuum to obtain BPQDs, which were stored in the dark and nitrogen for use. The average size of BPQDs was 2 nm.
  • Preparation of AgNCs Weigh 40 mg of lipoic acid powder into 20 mL of distilled water, stir well, add 0.1 mL of freshly prepared sodium borohydride with a concentration of 2 mol L -1 , and stir quickly for 30 minutes to form a homogeneous mixture. Add 0.4 mL of silver nitrate with a concentration of 0.05 mol L -1 to the mixed solution, and then add 0.3 mL of sodium borohydride with a concentration of 2 mol L -1 dropwise, keep the rapid stirring reaction for 90 minutes, and prepare the product AgNCs dispersion. When stored at 4°C, the average size of AgNCs is 10 nm.
  • Preparation of AgNCs/BPQDs/MOF complex Weigh 2 mg of BPQDs and add 10 mL of 2-methylimidazole ethanol solution with a concentration of 1 g L -1 , stir for 10 min to form a mixed solution, and add 10 mL of 2 g L -1 of hexahydrate nitric acid The zinc aqueous solution was stirred for 30 min to prepare a brown precipitate, which was washed three times with ethanol and distilled water, and centrifuged at 3500 rpm for 15 min to prepare an aqueous dispersion of the BPQDs/MOF complex.
  • the concentrations of AgNCs/BPQDs/MOF complex, catalase and bacitin are 1 mg mL -1 , 5 mU L -1 and 0.1-50 ⁇ g mL -1 , respectively.
  • the linear detection range of bacitin concentration is 0.1-50 ⁇ g mL -1 , the detection limit is 4ng mL -1 .
  • Example 2 This example relates to the preparation process of the ratio fluorescent bacein probe based on the silver nanocluster/black phosphorus quantum dot double-doped metal-organic framework composite and the schematic diagram of the principle of ratio fluorescent detection of bacein, BPQDs and The process steps for preparing AgNCs are the same as in Example 1, wherein the average size of BPQDs is 3 nm, and the average size of AgNCs is 12 nm. Other specific process steps are as follows:
  • Preparation of AgNCs/BPQDs/MOF complex Weigh 2 mg of BPQDs and add 10 mL of 2-methylimidazole ethanol solution with a concentration of 2 g L -1 , stir for 10 min to form a mixed solution, and add 10 mL of 3 g L -1 of hexahydrate nitric acid The zinc aqueous solution was stirred for 30 min to prepare a brown precipitate, which was washed three times with ethanol and distilled water, and centrifuged at 3500 rpm for 15 min to prepare an aqueous dispersion of the BPQDs/MOF complex.
  • the concentrations of AgNCs/BPQDs/MOF complex, catalase and bacitin are 2 mg mL -1 , 7 mU L -1 and 0.1-100 ⁇ g mL -1 , respectively.
  • the linear detection range of bacitin concentration is 0.1-100 ⁇ g mL -1 , the detection limit is 5ng mL -1 .
  • Example 3 This example relates to the preparation process of the ratio fluorescent bacitin probe based on the silver nanocluster/black phosphorus quantum dot double-doped metal-organic framework complex and the schematic diagram of the principle of ratio fluorescent detection of bacein, BPQDs and The process steps for preparing AgNCs are the same as in Example 1, wherein the average size of BPQDs is 5 nm, and the average size of AgNCs is 15 nm. Other specific process steps are as follows:
  • Preparation of AgNCs/BPQDs/MOF complex Weigh 2 mg of BPQDs and add 10 mL of 2-methylimidazole ethanol solution with a concentration of 4 g L -1 , stir for 10 min to form a mixed solution, and add 10 mL of 5 g L -1 of hexahydrate nitric acid The zinc aqueous solution was stirred for 30 min to prepare a brown precipitate, which was washed three times with ethanol and distilled water, and centrifuged at 3500 rpm for 15 min to prepare an aqueous dispersion of the BPQDs/MOF complex.
  • the concentrations of AgNCs/BPQDs/MOF complex, catalase and bacitin are 5 mg mL -1 , 10 mU L -1 and 0.01-50 ⁇ g mL -1 , respectively.
  • the linear detection range of bacitin concentration is 0.01-50 ⁇ g mL -1 , the detection limit is 2ng mL -1 .

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Abstract

Procédé de préparation d'une sonde de baïcaline fluorescente ratiométrique à base d'un complexe MOF à réseau métal-organique dopé double de BPQD à point quantique d'AgNC/phosphore noir à nanoagrégat d'argent. Des BPQDs fluorescents bleus sont mis à réagir avec un précurseur MOF pour préparer un complexe BPQD/MOF, des AgNC fluorescents rouges sont ajoutés et la réaction est poursuivie, des BPQD sont encapsulés dans le MOF, et les AgNC sont adsorbés dans des pores MOF. La baïcaline est ajoutée dans une dispersion aqueuse d'un complexe AgNC/BPQD/MOF contenant de la catalase, et la baïcaline génère de l'H2O2 sous l'action de la catalase. L'H2O2 provoque une extinction par fluorescence d'AgNC, mais a peu d'effet sur la fluorescence des BPQD encapsulés dans le MOF. Une relation linéaire entre un rapport d'intensité de pic d'émission fluorescente IBPQD/IAgNC et la concentration de baïcaline est ajustée pour construire une sonde fluorescente ratiométrique pour une détection efficace de la baïcaline.
PCT/CN2019/103465 2019-08-27 2019-08-30 Procédé de préparation d'une sonde de baïcaline fluorescente ratiométrique à réseau métal-organique dopé double WO2021035654A1 (fr)

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