CN110818734A - Fluorescent probe with double-ratio recognition function for hydrogen peroxide and hypochlorous acid - Google Patents

Fluorescent probe with double-ratio recognition function for hydrogen peroxide and hypochlorous acid Download PDF

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CN110818734A
CN110818734A CN201911014656.8A CN201911014656A CN110818734A CN 110818734 A CN110818734 A CN 110818734A CN 201911014656 A CN201911014656 A CN 201911014656A CN 110818734 A CN110818734 A CN 110818734A
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hydrogen peroxide
hypochlorous acid
fluorescent probe
probe
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宋相志
乐秀秀
廖立德
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Central South University
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    • C—CHEMISTRY; METALLURGY
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    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/02—Boron compounds
    • C07F5/04—Esters of boric acids
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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
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    • 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"
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    • G—PHYSICS
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    • 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
    • G01N2021/6417—Spectrofluorimetric devices

Abstract

The invention discloses a fluorescent probe capable of identifying hydrogen peroxide and hypochlorous acid by double ratios, which has the structural formula as follows:
Figure DDA0002244306610000011
the probe has the advantages of simple synthetic route, high sensitivity, good selectivity, strong anti-interference capability, large Stokes displacement and the like, is a fluorescent probe capable of rapidly monitoring hypochlorous acid and hydrogen peroxide in vitro or in living cells or performing cell imaging, and has good biological application prospect.

Description

Fluorescent probe with double-ratio recognition function for hydrogen peroxide and hypochlorous acid
Technical Field
The invention belongs to the technical field of chemical analysis and detection, and particularly relates to a fluorescent probe capable of identifying hydrogen peroxide and hypochlorous acid by double ratios and application thereof.
Background
Reactive Oxygen Species (ROS) are the second signal molecule, O, within and between cells2 -、·OH、1O2、HClO、H2O2Isoreactive Reactive Oxygen Species (ROS) are very important active substances, and play an important role in cell signaling, differentiation, migration, cellular immunity, and defense of the body against pathogens. Wherein hydrogen peroxide (H)2O2) And hypochlorous acid (HClO) as a typical Reactive Oxygen Species (ROS) plays an important role in both physiological and pathological processes. Different active oxygen passes through different parts of the human bodyHypochlorous acid can catalyze hydrogen peroxide and chloride ion production by the enzyme Myeloperoxidase (MPO). The right amount of hypochlorous acid helps the organism destroy bacteria, but the excessive amount of hypochlorous acid is very harmful to human body, resulting in many diseases such as cardiovascular disease, arthritis, arteriosclerosis, cancer, etc. Therefore, monitoring the change in the concentration of hypochlorous acid in a living body is indispensable. There are many conventional methods for detecting hypochlorous acid and hydrogen peroxide, such as colorimetry, iodometry, coulometry, chemiluminescence, and the like. However, these methods are complicated and many of them must be carried out in organic media or organic/aqueous media, which limits their biological applications. The fluorescent probe is an ideal detection means for overcoming the defects, and has the advantages of convenient detection, quick response time, high sensitivity, low detection limit, small damage to cells and the like.
Disclosure of Invention
One of the objectives of the present invention is to develop a method for identifying H with double ratio2O2And HClO, the probe has high sensitivity, good selectivity, strong anti-interference capability and ratio type, can quickly monitor hypochlorous acid and hydrogen peroxide in vitro or living cells or can image cells, and has the following structure of PTZC-1:
Figure BDA0002244306590000011
the synthetic route is as follows:
the specific synthesis method comprises the following steps: a, compound PTZ-E (790.0mg,2.0mmol) was dissolved in 5mL of methanol, sodium hydroxide (240.0mg,72.6mmol) was added under reflux for 1h, then the solvent was spun off, the crude product was dissolved in 10mL of dichloromethane, Ph was adjusted to 3.0 with hydrochloric acid, washed 3 times with saturated sodium chloride, dried over anhydrous sodium sulfate, and the solvent was spun off to give product PTZ-COOH (672mg, 91%). b, dissolving the compound HB-CHO-1(152.2mg,1.0mmol) and 4-bromomethylbenzeneboronic acid pinacol ester (296.3mg,1.0mmol) and potassium carbonate (414.2mg,3.0mmol) in 15mL of anhydrous acetonitrile, reacting at 85 ℃ for 5h, pouring the reaction system into 20mL of water, extracting with dichloromethane to obtain an orange organic phase, drying with anhydrous sodium sulfate, and performing spin-dry column chromatography to obtain a white solid (312.2mg, yield 85%). c, compound TDB-1(128.1mg,0.4mmol), HC (64.5mg,0.5mmol) and piperidine (11.0. mu.L, 0.1mmol) were dissolved in 15mL of ethanol and reacted at room temperature for 5h, after which time dry column chromatography gave a yellow solid (132.2mg, 79% yield). d, taking the compound PTZ-COOH (37.0mg,0.1mmol) and the compound HCB-1(48mg,0.1mmol), EDCI (14.5mg,0.15mmol) and DMAP (2.0mg,0.015mmol) and dissolving in 15mL of anhydrous dichloromethane, reacting for 5h at room temperature, and performing spin-dry column chromatography to obtain a red solid (57.2mg, 69% yield).
The mechanism of the probe of the present invention is as follows:
Figure BDA0002244306590000031
in the presence of hypochlorous acid (HClO), thioether bonds in molecules of the probe PTZC-1 are oxidized into sulfoxide, the red fluorescence (the maximum emission wavelength of 640nm) of the probe PTZC-1 per se is blue-shifted to green fluorescence (the maximum emission wavelength of 520nm) of P1, P1 continues in the presence of hydrogen peroxide, boric acid ester can be oxidized into phenol oxide by hydrogen peroxide, generated oxyanions attack nitrile groups, cyclization reaction is caused, coumarin precursors are released, a cyclized coumarin C18 is further formed, blue fluorescence (the maximum emission wavelength of 409nm) of C18 and P3 (the maximum emission wavelength of 520nm) of blue fluorescence occur, and therefore specific continuous detection of hypochlorous acid and hydrogen peroxide is achieved. Probe PTZC-1 in hydrogen peroxide (H)2O2) In the presence of the hydrogen peroxide, the boric acid ester can be oxidized into phenol oxygen by the hydrogen peroxide, and generated oxygen anions can attack nitrile groups to cause cyclization reaction and release coumarin precursors, so that cyclized coumarin C18 is formed, P2 is released, blue fluorescence of C18 and red fluorescence of P2 (the maximum emission wavelength is 409nm and 640nm) appear, and continuous detection of hydrogen peroxide and hypochlorous acid is achieved.
The fluorescent probes of the present invention have a ratio of fluorescence emission to secondary fluorescence emissionChloric acid (HClO) emits red fluorescence at 640nm before acting, green fluorescence is generated after acting, and the emission peak is 520 nm. With hydrogen peroxide (H)2O2) The emission peak of the red fluorescence is respectively 640nm and 409nm, the red fluorescence is unchanged and the blue fluorescence is generated after the action.
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FIG. 1 shows a fluorescent probe (5.0X 10) of the present invention-6mol/L) PBS buffer solution (10.0mM, stabilizing 50% CH) at pH 7.43CN) on the surface of the glass, ultraviolet absorption changes after response to hypochlorous acid and hydrogen peroxide are respectively shown in a graph, wherein the abscissa is wavelength, and the ordinate is absorption intensity.
FIG. 2 shows a fluorescent probe (5.0X 10) of the present invention-6mol/L) PBS buffer solution (10.0mM, stabilizing 50% CH) at pH 7.43CN), wherein graphs (A) and (C) are graphs showing the change of fluorescence spectrum in response to hydrogen peroxide (0-100equiv) at excitation wavelengths of 376nm and 440nm, respectively, and graphs (B) and (D) are graphs showing the change of fluorescence spectrum in response to hypochlorous acid (0-80equiv) at excitation wavelengths of 440nm and 376nm, respectively, with the abscissa showing the wavelength and the ordinate showing the fluorescence intensity, respectively. (E) The graph shows the change in fluorescence spectrum of a probe that first responded with 100 equivalents of hydrogen peroxide and then added with hypochlorous acid (0 to 120equiv) at an excitation wavelength of 376 nm. (F) The graph shows the change of fluorescence spectrum of a probe in response to 80 equivalents of hypochlorous acid and then hydrogen peroxide (0 to 110equiv) under an excitation wavelength of 376nm, with the wavelength on the abscissa and the fluorescence intensity on the ordinate, respectively.
FIG. 3A shows a fluorescent probe (5.0X 10) of the present invention-6mol/L) change in fluorescence intensity in the presence and absence of hydrogen peroxide and in systems of different pH values, with different pH values on the abscissa and fluorescence intensity on the ordinate. (B) Is the fluorescent probe (5.0X 10) of the present invention-6mol/L) in the presence and absence of hypochlorous acid (HClO) in a system with different pH values, the abscissa is the pH value and the ordinate is the fluorescence intensity ratio.
FIG. 4 shows a fluorescent probe (5.0X 10) of the present invention-6mol/L) PBS buffer solution at pH 7.4(10.0mM,containing 50％CH3CN), 80 times equivalent of hypochlorous acid (HClO) and 100 times equivalent of hydrogen peroxide (H) were added to the solution2O2) Then, the fluorescence intensity ratio was plotted with time on the abscissa and the ordinate as the fluorescence intensity ratio.
FIG. 5(A) shows a fluorescent probe (5.0X 10) of the present invention-6mol/L) PBS buffer solution (10.0mM, stabilizing 50% CH) at pH 7.43CN) in presence of (1) NO, (2) ONOO-，(3)·OH，(4)1O2，(5)O2 -，(6)ROO·，(7)t-BuO·，(8)H2O2Selective fluorescence spectra for different substances. (B) Is the fluorescent probe (5.0X 10) of the present invention-6mol/L) PBS buffer solution (10.0mM, stabilizing 50% CH) at pH 7.43CN) in presence of (1) NO, (2) ONOO-，(3)·OH，(4)1O2，(5)O2 -(6) ROO., (7) t-BuO., (8) HOCl, and the like. The ordinate is the change in fluorescence intensity.
FIG. 6 shows the toxicity test of the cell applicability of the fluorescent probe of the present invention, with probe concentration on the abscissa and cell survival rate on the ordinate.
FIG. 7 shows the intracellular detection of hypochlorous acid (HClO) and hydrogen peroxide (H) using the fluorescent probe of the present invention2O2)。
Detailed description of the preferred embodiment
Example 1: synthesis of Probe molecules
Synthesis of Compound PTZ-COOH
Compound PTZ-E (790.0mg,2.0mmol) was dissolved in 5mL of methanol, sodium hydroxide (240.0mg,72.6mmol) was added under reflux for 1h, then the solvent was spun off, the crude product was dissolved in 10mL of dichloromethane, Ph 3.0 was adjusted with hydrochloric acid, washed 3 times with saturated sodium chloride, dried over anhydrous sodium sulfate, and the solvent was spun off to give product PTZ-COOH (672mg, 91%).
After dissolving the compound HB-CHO-1(152.2mg,1.0mmol) and 4-bromomethylbenzeneboronic acid pinacol ester (296.3mg,1.0mmol) and potassium carbonate (414.2mg,3.0mmol) in 15mL of anhydrous acetonitrile and reacting at 85 ℃ for 5 hours, the reaction was poured into 20mL of water, and extraction was performed with dichloromethane to obtain an orange organic phase, which was dried over anhydrous sodium sulfate, and column chromatography was performed to obtain TDB-1(312.2mg, yield 85%) as a white solid.
Compound TDB-1(128.1mg,0.4mmol), HC (64.5mg,0.5mmol) and piperidine (11.0. mu.L, 0.1mmol) were dissolved in 15mL of ethanol and reacted at room temperature for 5h, after which time, by spin-dry column chromatography, HCB-1 was obtained as a yellow solid (132.2mg, 79% yield).
The compound PTZ-COOH (37.0mg,0.1mmol) and the compound HCB-1(48mg,0.1mmol), EDCI (14.5mg,0.15mmol) and DMAP (2.0mg,0.015mmol) were dissolved in 15mL of anhydrous dichloromethane and reacted at room temperature for 5 hours, and spin-dry column chromatography gave PTZC-1(57.2mg, 69% yield) as a red solid.
Example 2: application of the fluorescent Probe of the present invention
Fluorescent probe (5.0X 10)-6mol/L) PBS buffer solution (10.0mM, stabilizing 50% CH) at pH 7.43CN), NO, ONOO-，·OH，1O2，O2 -No significant change in emission peak of probe itself was caused after ROO, t-BuO, when hypochlorous acid (HClO) and hydrogen peroxide (H) were added2O2) Then, a significant change in fluorescence was caused, indicating that the probe had excellent selectivity. And the probe can rapidly detect hypochlorous acid (HClO) and hydrogen peroxide (H)2O2) The probe has good biological application prospect, and the cell imaging experiment can show that the probe can detect endogenous hydrogen peroxide and simultaneously can detect hypochlorous acid generated by catalyzing hydrogen peroxide and chloride ions by myeloperoxidase.

Claims (1)

1. A fluorescent probe capable of identifying hydrogen peroxide and hypochlorous acid by a double ratio has a structural formula of PTZC-1:
Figure FDA0002244306580000011
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CN113387973A (en) * 2021-05-24 2021-09-14 云南师范大学 Double-recognition fluorescent probe molecule and preparation method and application thereof

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CN113135948B (en) * 2021-03-12 2022-06-07 徐州医科大学 For detecting ClO-/ONOO-Ratiometric fluorescent probes, methods of making and uses thereof
CN113387973A (en) * 2021-05-24 2021-09-14 云南师范大学 Double-recognition fluorescent probe molecule and preparation method and application thereof

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