CN114989184A - Fluorescent dye of pyranoquinoline hybridized coumarins - Google Patents

Fluorescent dye of pyranoquinoline hybridized coumarins Download PDF

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CN114989184A
CN114989184A CN202210540797.9A CN202210540797A CN114989184A CN 114989184 A CN114989184 A CN 114989184A CN 202210540797 A CN202210540797 A CN 202210540797A CN 114989184 A CN114989184 A CN 114989184A
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dye
fluorescent dye
fluorescent
pyranoquinoline
hybridized
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CN114989184B (en
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刘兴江
田如梦
牛培鑫
张文英
李禹函
魏柳荷
孙爱灵
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Zhengzhou University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D491/12—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 three hetero rings
    • C07D491/14—Ortho-condensed systems
    • C07D491/153—Ortho-condensed systems the condensed system containing two rings with oxygen as ring hetero atom and one ring with nitrogen as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D491/22—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 four or more hetero rings
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/02—Coumarine dyes
    • 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
    • C09K11/06—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"
    • 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
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/542—Dye sensitized solar cells

Abstract

The invention discloses a fluorescent dye of pyranoquinoline hybridized coumarin, belonging to the technical field of bioluminescence imaging. The structure of the dye is as follows:

Description

Fluorescent dye of pyranoquinoline hybridized coumarin
Technical Field
The invention belongs to the technical field of biological fluorescence imaging, and particularly relates to a fluorescent dye of pyranoquinoline hybridized coumarin and a preparation method thereof.
Background
The fluorescent dye has wide application in the fields of life science and material science such as material science, medical diagnosis, fluorescent probes and the like. For decades, a variety of classical fluorescent dyes such as rhodamine, coumarin, naphthalimide and the like have been developed, and the development of new fluorescent dyes is crucial to the progress of fluorescence technology. Coumarin is a classic fluorescent dye, and a large number of multifunctional coumarin-based fluorescent dyes with adjustable optical properties are developed due to the fact that the structure of coumarin is easy to modify; the coumarin dye has the advantages of excellent photophysical properties, low toxicity, low cost and the like, and is widely applied to the fields of light-emitting diodes, solar cells, fluorescent probes and the like. Therefore, the development of novel fluorescent dyes is of great importance.
In recent years, the hybridization of different fluorescent dyes is an effective strategy for constructing novel fluorescent dyes, and based on the strategy, the novel coumarin fluorescent dyes can be constructed by hybridizing coumarin matrixes with other fluorescent dyes. Pyranoline fluorochromes are a new class of fluorochromes, and photophysical properties of pyranoline fluorochromes were first reported by Talukdar et al in 2012 (chem. Pyranoquinoline and coumarin hybridized fluorescent dye has not been reported. The invention prepares the pyranoquinoline hybridized coumarin fluorescent dye through heterocyclic Diels-Alder reaction for the first time, and has important significance for the development of coumarin fluorescent dye.
Disclosure of Invention
The invention aims to provide a fluorescent dye of pyranoquinoline hybrid coumarins.
The molecular structure of the fluorescent dye is as follows:
Figure BDA0003648206400000021
the fluorescent dye of the invention is prepared by the following synthetic route:
Figure BDA0003648206400000022
the fluorescent dye has long emission wavelength, high fluorescence quantum yield and large molar extinction coefficient. Lambda [ alpha ] abs Representing the maximum absorption wavelength, λ abs Represents the maximum emission wavelength, Δ ss represents the Stokes shift, ε represents the molar extinction coefficient, Φ represents the fluorescence quantum yield, τ represents the fluorescence lifetime. The photophysical properties of the fluorescent dye of the invention in dichloromethane are shown in the table below.
TABLE 1 photophysical properties of pyranoquinoline hybridized coumarins in dichloromethane
Figure BDA0003648206400000023
The fluorescent dye has good light stability. At 20mW/cm 2 The light degradation rate is less than 5 percent after the xenon lamp is irradiated for 1 hour.
The fluorescent dye has low cytotoxicity. After the HeLa cells and the probes are cultured for 24 hours at 37 ℃ by an MTT method, the survival rates within 25.0 mu M are all above 85 percent.
The fluorescent dye can well dye HeLa cells. Intense fluorescent signals were emitted intracellularly by co-culturing with HeLa cells with a dye (5.0. mu.M).
The fluorescent dye can be used for dyeing and imaging zebra fish. After incubation with zebrafish by probe (5.0 μ M), a strong fluorescent signal was emitted from the zebrafish.
Drawings
FIG. 1 is a normalized UV-VIS absorption spectrum of dyes 4a-e of the present invention in methylene chloride. The abscissa is wavelength and the ordinate is absorbance.
FIG. 2 is a normalized fluorescence spectrum of the dyes 4a-e of the present invention in methylene chloride. The abscissa is wavelength and the ordinate is fluorescence intensity.
FIG. 3 shows the photophysical properties of the dyes 4a-e according to the invention. Lambda [ alpha ] abs Is the maximum absorption wavelength, λ em Is the maximum emission wavelength, Δ ss Is the Stokes shift,. epsilon./M -1 cm -1 Is the molar extinction coefficient,. phiIs the fluorescence quantum yield, and τ/ns is the fluorescence lifetime.
FIG. 4 shows the photostability test of the fluorescent dye according to the present invention. At 20mW/cm 2 The photodegradation rate of the dyes 4a, 4b, 4e after 1h of irradiation under xenon lamp.
FIG. 5 is a toxicity test of the dye 4a of the present invention on HeLa cells. The abscissa is probe concentration and the ordinate is cell viability.
FIG. 6 is a fluorescent image of cells with the fluorescent dye 4a (5.0. mu.M) of the present invention.
FIG. 7 is a fluorescent image of the staining of zebrafish with the fluorescent dye 4a (5.0. mu.M) of the present invention.
Detailed description of the preferred embodiment
Example 1: synthesis of dye 4a
Compound 2(10.0mmol) and 3a (10.0mmol) were dissolved in 10mL DMF, cuprous iodide was added as a catalyst, and the mixture was stirred under reflux for 5 hours, after the reaction was completed, the solvent was removed under vacuum, and purification by column chromatography gave 4a in 45% yield. HRMS (ESI) m/z calcd. for C 24 H 22 N 2 O 3 [M+H] + 387.1630；found 387.1708. 1 H NMR(400MHz,CDCl 3 )δ8.39(s,1H),8.23(d,J＝8.9Hz,1H),7.86(d,J＝9.0Hz,1H),7.72(d,J＝9.0Hz,1H),6.49(dd,J＝8.9,2.5Hz,1H),6.31(d,J＝1.1Hz,1H),6.22(d,J＝2.5Hz,1H),5.30(d,J＝1.2Hz,2H),3.42(q,J＝7.1Hz,4H),2.51(s,3H),1.22(t,J＝7.1Hz,6H). 13 C NMR(100MHz,CDCl 3 )δ160.8,159.6,153.4,151.8,150.1,149.7,127.1,125.3,125.1,124.8,123.5,116.4,114.5,113.6,110.2,107.1,98.1,68.5,44.7,19.2,12.7.
Example 2: synthesis of dye 4b
Compound 2(10mmol) and 3b (10mmol) were dissolved in 10ml dmf, cuprous iodide was added as a catalyst, and the mixture was stirred under reflux for 5 hours, after the reaction was completed, the solvent was removed under vacuum, and the mixture was purified by column chromatography to obtain 5b in 55% yield. HRMS (ESI) m/z calcd. for C 24 H 19 F 3 N 2 O 3 [M+H] + 441.1348；found 441.1431. 1 H NMR(400MHz,CDCl 3 )δ8.33(s,1H),7.79(d,J＝10.9Hz,1H),6.78(s,1H),6.49(d,J＝8.0Hz,1H),6.20(d,J＝2.3Hz,1H),5.28(s,2H),3.42(q,J＝7.1Hz,4H),1.23(t,J＝7.1Hz,6H). 13 C NMR(100MHz,CDCl 3 )δ171.1,160.8,154.5,153.4,152.4,149.9,146.7,125.5,124.9,124.8,123.4,123.1,116.4,116.3,114.3,113.5,107.5,68.4,60.4,53.4,50.1,49.6,29.7,27.5,21.1,20.8,14.2.
Example 3: synthesis of dye 4c
Compound 2(10.0mmol) and 3a (10.0mmol) were dissolved in 10ml dmf, cuprous iodide was added as a catalyst, and the mixture was stirred under reflux for 5 hours, after the reaction was completed, the solvent was removed under vacuum, and purification by column chromatography gave 4c in 50% yield. HRMS (ESI) m/z calcd. for C 26 H 22 N 2 O 3 [M+H] + 411.1630；found.411.1712. 1 H NMR(400MHz,CDCl 3 )δ7.72–7.62(m,1H),7.31(d,J＝8.7Hz,1H),6.75(d,J＝7.5Hz,2H),6.48–6.39(m,1H),4.87(s,1H),3.26(d,J＝5.4Hz,5H),2.86–2.59(m,4H),2.00(d,J＝3.4Hz,5H),1.26(s,2H). 13 C NMR(100MHz,CDCl 3 )δ160.8,153.4,149.9,125.5,124.9,124.8,123.4,123.1,116.4,116.3,113.5,107.5,60.4,50.1,49.6,27.5,22.0,21.0,19.1,14.2.
Example 4: synthesis of dye 4d
Compound 2(10.0mmol) and 3b (10.0mmol) were dissolved in 10.0mL DMF, cuprous iodide was added as a catalyst, stirred under reflux for 5 hours, after the reaction was finished, the solvent was removed under vacuum, and purified by column chromatography to give 4d in 40% yield. HRMS (ESI) m/z calcd. for C 26 H 19 F 3 N 2 O 3 [M+H] + 465.1348；found.465.1443. 1 H NMR(600MHz,CDCl 3 )δ8.39(s,1H),7.93–7.86(m,3H),7.82(d,J＝10.4Hz,1H),6.82(s,1H),5.30(s,2H),3.30–3.26(m,4H),2.85(t,J＝6.3Hz,2H),2.74(t,J＝6.5Hz,2H),2.02–1.98(m,4H). 13 C NMR(100MHz,CDCl 3 )δ160.8,153.4,149.9,125.5,124.9,124.8,123.4,123.1,116.4,116.3,113.5,107.5,60.4,50.1,49.6,27.5,22.0,21.0,19.1,14.2.
Example 5: synthesis of dye 4e
Compound 2(10.0mmol) and 3c (10.0mmol) were dissolved in 10mL DMF and iodinatedCuprous was used as a catalyst, and stirred under reflux for 5 hours, after the reaction was completed, the solvent was removed under vacuum, and purification by column chromatography gave 4e in 35% yield. 1 H NMR(400MHz,CDCl 3 )δ8.31(d,J＝9.8Hz,1H),8.18(q,J＝8.0Hz,2H),8.06(s,1H),7.59(d,J＝9.3Hz,1H),6.56(d,J＝9.7Hz,1H),6.50(d,J＝8.9Hz,1H),6.23(d,J＝2.5Hz,1H),5.31(s,2H),3.42(q,J＝7.1Hz,4H),1.22(t,J＝7.1Hz,6H). 13 C NMR(100MHz,CDCl 3 )δ160.7,159.1,152.6,150.0,145.7,138.3,133.8,126.6,126.1,124.1,119.9,116.1,112.9,107.0,98.1,68.6,44.6.
Example 6: staining of cells with dye 4a
HeLa cells were incubated with PBS buffer containing dye 4a (5.0. mu.M) for 15min, rinsed 3 times with PBS buffer, and subjected to fluorescence imaging with a confocal laser fluorescence microscope, whereby an intense fluorescence signal was observed.
Example 7: dyeing of zebra fish with dye 4a
Culturing zebrafish in E3 embryo culture medium at 28 deg.C, wherein the culture medium comprises 15mM NaCl and 0.5mM MgSO 4 ,1mM CaCl 2 ,0.15mM KH 2 PO 4 ,0.05mM Na 2 HPO 4 ,0.7mM NaHCO 3 And 1% methylene blue. The pH of the medium was 7.5. 3-day-old zebrafish were selected for fluorescence imaging after 30 min incubation with dye 4a (5.0. mu.M). Intense fluorescent signals can be observed within zebrafish.

Claims (1)

1. The fluorescent dye of pyranoquinoline hybridized coumarin is characterized in that the structural formula is as follows:
Figure FDA0003648206390000011
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Cited By (1)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115960110A (en) * 2023-01-31 2023-04-14 山西大学 Efficient photodynamic photosensitizer and preparation method and application thereof
CN115960110B (en) * 2023-01-31 2024-04-12 山西大学 Efficient photodynamic photosensitizer and preparation method and application thereof

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