CN108516980A - A kind of preparation and application of the rhodamine hypochlorous acid fluorescence probe that can target lysosome - Google Patents

A kind of preparation and application of the rhodamine hypochlorous acid fluorescence probe that can target lysosome Download PDF

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CN108516980A
CN108516980A CN201810504857.5A CN201810504857A CN108516980A CN 108516980 A CN108516980 A CN 108516980A CN 201810504857 A CN201810504857 A CN 201810504857A CN 108516980 A CN108516980 A CN 108516980A
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probe
hypochlorous acid
lysosome
rhodamine
application
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申世立
曹晓群
黄晓晴
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Shandong First Medical University and Shandong Academy of Medical Sciences
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Taishan Medical University
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    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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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"
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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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    • 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
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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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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
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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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • 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"
    • G01N2021/6439—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" with indicators, stains, dyes, tags, labels, marks

Abstract

A kind of seeking group the invention discloses rhodamine hypochlorous acid fluorescence probe probe that can target lysosome using morpholine structure as lysosome, in the presence of having hypochlorous acid, rhodamine group is converted to open loop structure, hyperfluorescence is sent out at 582nm, fluorescence intensity becomes strong with the increase of hypochlorous acid concentration.This probe has to hypochlorous selectivity good, high sensitivity, fast response time, and can target lysosome.

Description

A kind of preparation of the rhodamine hypochlorous acid fluorescence probe that lysosome can be targeted and Using
Technical field
The present invention relates to a kind of synthesis and its application of novel HOCl fluorescence probes, it is molten which can be applied to detection cell The variation of HOCl concentration in enzyme body.
Background technology
Hypochlorous acid is a kind of weak acid, is activating oxide important in organism, in the redox equilibrium in cell It plays an important role.When hypochlorous acid is excessive, many diseases in organism can be caused, such as：Alzheimer's disease, rheumatism joint Inflammation, cancer etc..Play an important roll to the real-time monitoring of hypochlorous acid concentration, therefore detects the hypochlorous acid in organism at current The heat subject of scholar's research.
Fluorescence probe become detection intracellular reactive small-molecule substance important tool, the selectivity that it has had, High sensitivity, and sample size is seldom, it is small to cytotoxicity.Therefore fluorescence probe is increasingly becoming the research heat of researcher Point.
However, the report of hypochlorous acid fluorescence probe to lysosome targeting positioning and few now.
In addition, the needs for the probe reported ability in the organic solvent of high level and the mixed liquor of buffer solution It realizes to hypochlorous detection [5 (2017) 525-530 of Qiao L. et al, J. Mater. Chem. B; Li K. et al, Chem. Commun. 53 (2017) 5539-5541; Tang Z. et al, RSC Adv. 5 (2015) 99664-99668;263 (2018) 252-257 of Shen S.L. et al, Sens. Actuators B], however these Probe is not appropriate for the detection with intracellular environment HOCl.
On this basis, inventor has invented the hypochlorous acid fluorescence probe based on rhodamine, and introduces morpholine ring work For the seeking group of lysosome, a kind of highly sensitive, highly selective hypochlorous acid fluorescence probe has been synthesized.The probe can almost answer For hypochlorous measurement in pure aquatic system, there is lysosome target function, and can apply to hypochlorous acid concentration in lysosome Detection.
Invention content
The purpose of the present invention is to provide a kind of preparations and application of the rhodamine fluorescence probe of targeting lysosome.
The invention discloses a kind of Rhodamine Derivatives class fluorescence probes of targeting lysosome（LR1）, chemical constitution is such as Under：
The variation of hypochlorous acid concentration in lysosome can be detected using hypochlorous acid fluorescence probe of the present invention, and can carry out cell Imaging.
The preparation method of hypochlorous acid fluorescence probe of the present invention, as shown in Figure 1.
The PBS buffer solutions for preparing hypochlorous acid probe of the present invention, be separately added into a certain amount of active oxygen, metal from Then son carries out spectrofluorimetry to sample.As a result show that probe is more preferable to hypochlorous selectivity, as shown in Figure 2.
In the presence of HOCl, rhodamine spirane structure open loop, probe sends out hyperfluorescence at 582nm, and glimmering Luminous intensity becomes strong with the increase of hypochlorous acid concentration, as shown in Figure 3.
Fluorescence probe of the present invention can not only detect the hypochlorous acid in solution, can also detect in lysosome The variation of hypochlorous acid concentration, as shown in Figure 4.
There is probe of the present invention good lysosome to target ability, as shown in Figure 5.
Description of the drawings
Fig. 1 is the preparation route of probe of the present invention.
Fig. 2 is selectivity of the probe of the present invention to common ion in organism.
Fig. 3 is the fluorescence spectra that probe of the present invention changes with hypochlorous acid concentration's variation.
Fig. 4 is detection of the probe application of the present invention in intracellular HOCl.
Fig. 5 is probe targeting lysosome experiment of the present invention.
Specific implementation method
Embodiment 1：The synthetic route of probe is shown in Fig. 1.
By compound 1（2 mmol）It is dissolved in 7 mL SOCl2In, 6 hours of stirring at normal temperature, solvent is then removed under reduced pressure, obtains Yellow solid 2（It is unpurified, it is directly used in and reacts in next step）.
By compound 2（2 mmol）It is dissolved in 50 mL dry methylene chlorides, is separately added into triethylamine（6 mmol）And chemical combination Object 3（1 mmol）, then about 6 h of stirring at normal temperature washes reaction solution, solvent is removed under reduced pressure, then carries out in anhydrous sodium sulfate drying Column chromatographic isolation and purification obtains probe LR1 of the present invention.
With1H NMR、13C NMR and HRMS characterize it, and data are as follows：
1H NMR (400 MHz, d 6-DMSO), δ (ppm): 1.09 (t, 6H, J = 6.8 Hz, CH3), 2.36 (s, 4H, CH2), 3.24 (br, 4H, CH2), 3.32 (br, 4H, CH2), 3.50 (br, 4H, CH2), 3.58 (br, 4H, CH2), 3.70 (br, 2H,CH2), 5.35 (s, 2H, NH2), 6.20 (d, 1H, J = 8.8 Hz, ArH), 6.25 (d, 1H, J = 8.8 Hz, ArH), 6.38 (d, 2H, J = 8.8 Hz, ArH), 6.66 (dd, 1H, J = 8.8 Hz, J = 2.4 Hz, ArH), 6.75 (d, 1H, J = 2.4 Hz, ArH), 7.04 (d, 1H,J = 6.4 Hz, ArH), 7.39 (br, 4H, ArH), 7.51 (m, 2H, ArH), 7.89 (d, 1H, J = 6.8 Hz, ArH).
13C NMR (100 MHz, d 6-DMSO), δ (ppm): 181.9, 169.4, 153.1, 152.9, 152.1, 149.6, 149.2, 140.0, 136.3, 134.8, 132.5, 129.2, 128.2, 127.9, 127.5, 126.5, 124.2, 123.3, 112.1, 108.7, 108.0, 103.5, 102.4, 97.8, 72.8, 66.6, 62.5, 53.6, 48.0, 44.2, 12.9.
HRMS m/z: calcd for C40H45N6O3S [M+H]+: 689.3274; found: 689.3278.
Embodiment 2：Probe of the present invention is to hypochlorous selectivity.
Prepare the PBS buffer solutions of 1 μM of probe（Containing 0.5% ethyl alcohol, pH 5.00）.Be separately added into again common metal from Son, anion, activating oxide.The result shows that the selectivity that probe of the present invention has had hypochlorous acid, such as Fig. 2 institutes Show.(1): blank, (2): H2O2, (3): t-BuOOH, (4): t-BuO•, (5): 1O2, (6): -O2, (7): ON, (8): •OH, (9): ONOO-, (10): Br-, (11): Cl-, (12): I-, (13): CO3 2-, (14): SO4 2-, (15): NO3 -, (16): Na+, (17): K+, (18): Ca2+, (19): Mg2+, (20): Zn2+, (21): Cu2+, (22): Hg2+, (23): HOCl. Conditions: [HOCl] = 3 µM, [Other ROS/RNS] = 10 µM, [Anions] = 50 µM, [Cations] = 5 µM.。
Embodiment 3：The detection that probe of the present invention changes hypochlorous acid concentration in solution.
Prepare the PBS buffer solutions of 1 μM of probe（Containing 0.5% ethyl alcohol, pH 5.00）.Add respectively into above-mentioned buffer solution Enter 0 μM, 0.125 μM, 0.25 μM, 0.375 μM, 0.5 μM, 0.625 μM, 0.75 μM, 0.875 μM, 1.0 μM, 1.25 μM, 1.5 μM, 1.75 μM, 2.0 μM, 2.25 μM, 2.5 μM, the hypochlorite solution of 2.75 eq, 3.0 eq, then Spectrofluorimetry is carried out, as a result shows that fluorescence intensity becomes strong with the increase of hypochlorous acid concentration, as shown in Figure 3.
Embodiment 4：It is detection of the probe application of the present invention in intracellular HOCl.
Experimental group：First cell is stimulated with 1 μ g/mL LPS 6 hours, then add 1 μ g/mL PMA and continue 30 points of culture 1 μM of probe LR1 of the present invention is then added in clock in serum free medium, cultivates 30 minutes；Cell washes 3 with PBS respectively Time, fluorescence imaging is carried out using laser confocal microscope, collects the fluorescence of 550-700 nm.
Control group：1 μM of probe is added in serum free medium, cultivates 30 minutes；Cell is washed 3 times with PBS respectively, then Fluorescence imaging is carried out, the fluorescence of 550-700 nm is collected, as a result sees Fig. 4.
Embodiment 5：
First cell is stimulated with 1 μ g/mL LPS 6 hours, then add 1 μ g/mL PMA and continue culture 30 minutes, then in nothing 1 μM of probe of the present invention is added in blood serum medium, cultivates 30 minutes；Add lysosome marker Lyso Tracker Deep Red continue to be incubated 30 minutes.Cell is washed 3 times with PBS respectively, and fluorescence imaging is carried out using laser confocal microscope, Collect probe of the present invention（LR1）With the fluorescence photo of Lyso Tracker Deep Red.Then it is overlapped analysis, sees Fig. 5.

Claims (2)

1. the purpose of the present invention is to provide a kind of rhodamine fluorescence probes of targeting lysosome（LR1）Preparation and in cell Interior application, chemical constitution are as follows：
Probe as described in right 1 is containing the application in hypochlorous solution and cell.
2. probe hypochlorous application in detecting Cytolysosome as described in right 1.
CN201810504857.5A 2018-05-24 2018-05-24 A kind of preparation and application of the rhodamine hypochlorous acid fluorescence probe that can target lysosome Pending CN108516980A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109232615A (en) * 2018-11-02 2019-01-18 泰山医学院 Across the key energy transfer hypochlorous acid fluorescence probe of one kind and its lysosome hypochlorous acid detection in apply
CN109851622A (en) * 2019-01-22 2019-06-07 济南大学 A kind of hypochlorite fluorescence probe targeting lysosome

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CN106632363A (en) * 2016-11-07 2017-05-10 山东大学 Mitochondrial targeted ratio type hypochlorous acid fluorescence probe and application thereof
CN106810561A (en) * 2017-01-04 2017-06-09 济南大学 A kind of lysosome targeting hypochlorous acid ratio fluorescent probe and preparation method and application
CN106967078A (en) * 2017-03-17 2017-07-21 济南大学 A kind of lysosome targeting hypochlorous acid fluorescence probe and its preparation and application

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CN106632363A (en) * 2016-11-07 2017-05-10 山东大学 Mitochondrial targeted ratio type hypochlorous acid fluorescence probe and application thereof
CN106810561A (en) * 2017-01-04 2017-06-09 济南大学 A kind of lysosome targeting hypochlorous acid ratio fluorescent probe and preparation method and application
CN106967078A (en) * 2017-03-17 2017-07-21 济南大学 A kind of lysosome targeting hypochlorous acid fluorescence probe and its preparation and application

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109232615A (en) * 2018-11-02 2019-01-18 泰山医学院 Across the key energy transfer hypochlorous acid fluorescence probe of one kind and its lysosome hypochlorous acid detection in apply
CN109851622A (en) * 2019-01-22 2019-06-07 济南大学 A kind of hypochlorite fluorescence probe targeting lysosome
CN109851622B (en) * 2019-01-22 2021-08-31 济南大学 Hypochlorite fluorescent probe targeting lysosome

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