CN116478553B - Red fluorescent dye based on pyran quinoline structure - Google Patents
Red fluorescent dye based on pyran quinoline structure Download PDFInfo
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- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 30
- PVDZKJZSOKXQRY-UHFFFAOYSA-N 2h-pyran;quinoline Chemical group C1OC=CC=C1.N1=CC=CC2=CC=CC=C21 PVDZKJZSOKXQRY-UHFFFAOYSA-N 0.000 title claims description 11
- 239000000975 dye Substances 0.000 abstract description 17
- 238000003384 imaging method Methods 0.000 abstract description 6
- HGFMFKSDOFFKRV-UHFFFAOYSA-N 8h-pyrano[2,3-h]quinoline Chemical group C1=CC=NC2=C(C=CCO3)C3=CC=C21 HGFMFKSDOFFKRV-UHFFFAOYSA-N 0.000 abstract description 4
- 238000005415 bioluminescence Methods 0.000 abstract description 3
- 230000029918 bioluminescence Effects 0.000 abstract description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- 241000252212 Danio rerio Species 0.000 description 7
- 238000010992 reflux Methods 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 238000010186 staining Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 1
- AXKGIPZJYUNAIW-UHFFFAOYSA-N (4-aminophenyl)methanol Chemical compound NC1=CC=C(CO)C=C1 AXKGIPZJYUNAIW-UHFFFAOYSA-N 0.000 description 1
- XXFUZSHTIOFGNV-UHFFFAOYSA-N 1-bromoprop-1-yne Chemical compound CC#CBr XXFUZSHTIOFGNV-UHFFFAOYSA-N 0.000 description 1
- ZMZSYUSDGRJZNT-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)acetonitrile Chemical compound C1=CC=C2SC(CC#N)=NC2=C1 ZMZSYUSDGRJZNT-UHFFFAOYSA-N 0.000 description 1
- GBJXKRIRSDZFGG-UHFFFAOYSA-N 2-(2-methylchromen-4-ylidene)propanedinitrile Chemical compound C1=CC=C2OC(C)=CC(=C(C#N)C#N)C2=C1 GBJXKRIRSDZFGG-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 1
- XDCOYBQVEVSNNB-UHFFFAOYSA-N 4-[(7-naphthalen-2-yl-1-benzothiophen-2-yl)methylamino]butanoic acid Chemical compound OC(=O)CCCNCc1cc2cccc(-c3ccc4ccccc4c3)c2s1 XDCOYBQVEVSNNB-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- TZYWCYJVHRLUCT-VABKMULXSA-N N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal Chemical compound CC(C)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1 TZYWCYJVHRLUCT-VABKMULXSA-N 0.000 description 1
- TZCCKCLHNUSAMQ-DUGSHLAESA-N NC(=O)C[C@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](Cc2ccc(F)cc2)NC(=O)[C@H](Cc3c[nH]c4ccccc34)NC(=O)Cc5cccs5)C(=O)N Chemical compound NC(=O)C[C@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](Cc2ccc(F)cc2)NC(=O)[C@H](Cc3c[nH]c4ccccc34)NC(=O)Cc5cccs5)C(=O)N TZCCKCLHNUSAMQ-DUGSHLAESA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000012984 biological imaging Methods 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 238000010351 charge transfer process Methods 0.000 description 1
- 238000003501 co-culture Methods 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 238000002073 fluorescence micrograph Methods 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- DZFWNZJKBJOGFQ-UHFFFAOYSA-N julolidine Chemical group C1CCC2=CC=CC3=C2N1CCC3 DZFWNZJKBJOGFQ-UHFFFAOYSA-N 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 238000002428 photodynamic therapy Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002379 progesterone receptor modulator Substances 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 108700024526 zebrafish sox32 Proteins 0.000 description 1
Abstract
The invention discloses a red fluorescent dye based on a pyranoquinoline structure, which belongs to the technical field of bioluminescence imaging, and has the following structure:
Description
Technical Field
The invention belongs to the technical field of bioluminescence imaging, and particularly relates to a red fluorescent dye based on a pyranoquinoline structure and application of the red fluorescent dye in bioluminescence imaging seeds.
Background
The fluorescent dye has wide application in the life science fields of medical diagnosis, photodynamic therapy, fluorescence sensing and the like, so that the development of the novel fluorescent dye with good performance has important significance. The red/near infrared fluorescent dye has the advantages of good penetrability, small background interference, small damage to tissues and the like, and is widely applied to the field of biological imaging; fluorescent dyes with large stokes shifts can reduce self-absorption and increase their sensitivity. The fluorescent probe developed based on fluorescent dye has the advantages of good selectivity, high sensitivity, convenient operation, real-time nondestructive detection and the like, and becomes an important tool in the technical field of analysis and detection. Therefore, it is interesting to develop new fluorescent dyes with red/near infrared emission and large stokes shift.
Pyran quinoline derivatives are heterocyclic compounds that are hybridized to the pyran and quinoline rings, which can be synthesized by Diels-Alder reaction of the heterocyclic ring. The current research is mainly focused on the synthesis method and biological activity. It is often used as a progesterone receptor modulator, glucocorticoid modulator and transcriptional activity modulator. From structural analysis, the pyran quinoline parent has a larger conjugated structure. The quinoline ring is an electron-deficient part, the pyran ring is an electron-donating part, and the pyran ring has the characteristic of a donor-acceptor D-A fluorescent dye, and the pyran quinoline is a potential chromophore. In 2012, tauukdar et al reported for the first time that the photophysical properties of pyran quinoline fluorescent dyes were (λmax＝377nm,λem＝422nm)(D.Kand,A.M.Kalle,S.J.Varma and P.Talukdar,Chem.Commun.,2012,48,2722-2724);2014 years, lin et al introduced diethylamino on the pyran quinoline matrix to red shift the wavelength to λ em =483 nm, and found that the emission peak was λ em =545 nm under acidic conditions due to protonation of the quinoline ring (w.huang, w.lin and x.guard, tetrahedron lett.,2014,55,116-119); in 2017, we have developed methylated pyranoquinoline fluorescent dyes that can be red shifted to red fluorescence (λ em =622 nm) by introducing julolidine groups to pyranoquinoline dyes such that the emission wavelength is red shifted to the yellow region (λem＝560nm)(X.Liu,Y.Su,H.Tian,L.Yang,H.Zhang,X.SongandJ.W.Foley,Anal.Chem.,2017,89,7038-7045);2018 (X.Liu, Y.Li, X.Ren, Q.Yang, Y.Su, L.He andX.Song, chem.Commun.,2018,54,1509-1512).
Based on this, we believe that the emission wavelength of the pyran quinoline fluorescent dye can be further increased and its stokes shift increased by increasing the molecular conjugate plane and increasing the charge transfer process within the molecule. In the invention, the pyran quinoline dye of a large conjugated system is constructed through conjugated double bonds for the first time, so that the emission wavelength is red shifted to far-red light.
Disclosure of Invention
The invention aims to provide a red fluorescent dye based on a pyran quinoline structure.
The fluorescent dye has the following molecular structure:
The fluorescent dye is prepared by the following synthetic route:
(a) Bromopropyne, potassium carbonate, N-dimethylformamide, 25 ℃ for 10h; (b) P-aminobenzyl alcohol, cuprous iodide, N-dimethylformamide, 110 ℃ for 6h; (c) manganese dioxide, methylene chloride, 25 ℃ for 5h; (d) piperidine, acetonitrile, reflux, 6h.
The fluorescent dyes of the present invention have long emission wavelengths and stokes shifts. Fluorescent dyes exhibit long emission wavelengths in different solvents and all emission wavelengths reach the red region. The maximum absorption peak (lambda abs), maximum emission peak (lambda abs), stokes shift (deltass), molar extinction coefficient (epsilon), quantum yield (phi f) and fluorescence lifetime (tau) in different solvents are shown in the following table.
The fluorescent dye has lower cytotoxicity. After the HeLa cells and the probes are incubated for 24 hours at 37 ℃, the survival rate within 15.0 mu M is more than 90 percent.
The fluorescent dye can be used for well staining HeLa cells. Cells were stained red for fluorescence by co-culture with HeLa cells with dye (5.0. Mu.M).
The fluorescent dye can be used for imaging zebra fish. After incubation with zebra fish by probe (5.0. Mu.M), zebra fish were stained with red fluorescence.
The probe has good light stability. The photodegradation rate is less than 5% when irradiated under a xenon lamp of 20mW/cm 2 for 1 hour.
Drawings
Fig. 1 is a graph of normalized uv-vis absorption spectra of dye 5a in different solvents. The abscissa is wavelength and the ordinate is absorbance.
FIG. 2 is a normalized fluorescence spectrum of dye 5a in different solvents. The abscissa is wavelength and the ordinate is fluorescence intensity.
Fig. 3 is a normalized uv-vis absorption spectrum of fluorescent dye 5b in different solvents. The abscissa is wavelength and the ordinate is absorbance.
FIG. 4 is a normalized fluorescence spectrum of dye 5b in different solvents. The abscissa is wavelength and the ordinate is fluorescence intensity.
Fig. 5 is a normalized uv-vis absorption spectrum of dye 5c in different solvents. The abscissa is wavelength and the ordinate is absorbance.
FIG. 6 is a normalized fluorescence spectrum of dye 5c in different solvents. The abscissa is wavelength and the ordinate is fluorescence intensity.
Fig. 7 is a normalized uv-vis absorption spectrum of dye 5d in different solvents. The abscissa is wavelength and the ordinate is absorbance.
FIG. 8 is a normalized fluorescence spectrum of dye 5d in different solvents. The abscissa is wavelength and the ordinate is fluorescence intensity.
FIG. 9 is a series of photophysical properties of fluorescent dyes of the present invention. Lambda abs/nm is the maximum absorption wavelength, lambda em is the maximum emission wavelength, delta ss is the Stokes shift, epsilon/M -1 cm-1 is the molar extinction coefficient, phi is the fluorescence quantum yield, and tau/ns is the fluorescence lifetime.
FIG. 10 is a toxicity test of dye 5c of the present invention on HeLa cells. The abscissa indicates probe concentration, and the ordinate indicates cell viability.
FIG. 11 is a fluorescence image of co-staining of dye 5c (2.0. Mu.M) with Hela cells according to the invention. Imaging was performed after incubation for 15min in the dark at 37 ℃.
FIG. 12 is a fluorescent image of zebra fish staining with fluorescent dye 5c (2.0. Mu.M) of the present invention. Imaging after incubation for 15min at 28 ℃.
Examples of the embodiments
Example 1: synthesis of Compound 5a
Compound 4 (10.0 mmol) and 2- (2-methyl-4H-chromen-4-ylidene) malononitrile (10.0 mmol) were dissolved in 10mL of acetonitrile, 10. Mu.L of piperidine was added, stirred under reflux for 6 hours, after the completion of the reaction, the solvent was removed under vacuum, and purified by column chromatography to give 5a in yield 73％.HRMS(ESI)m/z:calcd.for C34H27N4O2[M+H]+523.2134;found 523.2136.1H NMR(400MHz,CDCl3)δ8.28(s,1H),8.02(s,1H),7.80(d,J＝8.9Hz,1H),7.73(d,J＝7.4Hz,2H),7.52(dd,J＝9.1,2.1Hz,2H),7.35(d,J＝9.1Hz,2H),7.16(d,J＝16.0Hz,1H),7.06(d,J＝16.1Hz,1H),6.87(s,1H),6.52(d,J＝10.1Hz,1H),6.23(d,J＝2.4Hz,1H),5.29(d,J＝9.3Hz,2H),3.43(q,J＝7.1Hz,4H),1.22(d,J＝7.1Hz,6H).13C NMR(100MHz,CDCl3)δ175.50,163.35,154.43,152.09,150.23,148.04,145.04,141.73,141.51,139.85,139.64,137.78,135.66,133.56,128.16,125.31,123.42,122.31,119.24,115.49,112.93,111.29,109.64,106.12,104.47,103.78,101.92,95.84,95.54,92.32,66.50,63.21,43.03,15.87.
Example 5: synthesis of Compound 5b
Compound 4 (10 mmol) and 2- (benzo [ d ] thiazol-2-yl) acetonitrile (10 mmol) were dissolved in 10mL of acetonitrile, 10. Mu.L of piperidine was added, stirred under reflux for 6 hours, after the reaction was completed, the solvent was removed under vacuum, and purification by column chromatography gave 5c in yield 70％.HRMS(ESI)m/z:calcd.for C30H25N4OS[M+H]+489.1749;found 489.1742.1H NMR(400MHz,CDCl3)δ8.29(dt,J＝8.9,7.1Hz,4H),8.09(d,J＝8.0Hz,2H),7.92(d,J＝7.9Hz,1H),7.81(s,1H),7.58–7.50(m,1H),7.47–7.40(m,1H),6.51(dd,J＝9.0,2.4Hz,1H),6.21(d,J＝2.3Hz,1H),5.28(s,2H),3.41(q,J＝7.1Hz,4H),1.22(t,J＝7.1Hz,6H).13C NMR(100MHz,CDCl3)δ163.03,159.71,153.69,151.91,146.10,143.67,135.00,131.35,131.09,129.70,128.73,127.41,126.94,126.81,126.49,125.94,125.71,124.09,123.56,121.67,121.58,117.29,116.83,107.24,104.69,98.00,68.38,58.47,44.68,18.44,12.71.
Example 6: synthesis of Compound 5c
Compound 4 (10 mmol) and 2- (3-cyano-4, 5-trimethylfuran-2 (5H) -ylidene) malononitrile (10 mmol) were dissolved in 10mL of acetonitrile, 10. Mu.L of piperidine was added, stirred under reflux for 6 hours, after completion of the reaction, the solvent was removed under vacuum, and purified by column chromatography to give 5c in yield 85％.HRMS(ESI)m/z:calcd.for C32H28N5O2[M+H]+514.2243;found 514.2252.1H NMR(400MHz,CDCl3)δ7.95(s,1H),7.91(s,1H),7.55(d,J＝9.1Hz,2H),6.88(s,1H),6.84(s,1H),6.42(dd,J＝9.1,2.1Hz,2H),6.26(s,1H),4.81(d,J＝2.4Hz,4H),3.49(d,J＝7.1Hz,6H),2.62(t,J＝2.3Hz,2H),1.27(s,6H).13C NMR(100MHz,CDCl3)δ193.61,180.90,176.54,175.04,167.16,160.21,157.32,153.32,152.72,143.16,131.58,131.50,129.44,127.63,113.05,112.45,112.43,112.25,111.66,108.74,108.68,106.91,99.14,96.60,95.02,93.11,58.48,56.41,45.43,27.03,18.44,12.72.
Example 7: synthesis of Compound 5d
Compound 4 (10 mmol) and ethyl 2-cyanoacetate (10 mmol) were dissolved in 10mL of acetonitrile, 10. Mu.L of piperidine was added, stirred under reflux for 6 hours, after the reaction was completed, the solvent was removed under vacuum, and purification by column chromatography gave 5d in yield 81％.HRMS(ESI)m/z:calcd.for C26H26N3O3[M+H]+428.1974;found 428.1977.1H NMR(400MHz,CDCl3)δ8.32(d,J＝7.8Hz,2H),8.29–8.19(m,2H),8.05(d,J＝8.8Hz,1H),7.79(s,1H),6.51(dd,J＝9.0,2.3Hz,1H),6.22(d,J＝2.3Hz,1H),5.27(s,2H),4.40(q,J＝7.1Hz,2H),3.42(q,J＝7.1Hz,4H),1.42(t,J＝7.1Hz,3H),1.22(t,J＝7.1Hz,6H).13C NMR(100MHz,CDCl3)δ162.83,159.76,154.28,152.57,151.92,132.77,131.06,129.86,129.70,127.73,127.39,126.38,125.76,115.98,110.40,107.21,101.73,97.97,68.38,62.69,44.68,31.51,30.13,29.71,14.22,12.71.
Example 8: dye 5c staining of cells
The HeLa cells were incubated with PBS buffer containing dye 5c (5.0. Mu.M) for 15min, and after rinsing 3 times with PBS buffer, the cells were imaged by fluorescence with a confocal laser fluorescence microscope, and a strong red fluorescence signal was observed.
Example 9: dye 5c fluorescent staining of zebra fish
Zebra fish were cultured in E3 embryo medium at 28℃comprising 15mM NaCl、0.5mM MgSO4,1mM CaCl2,0.15mM KH2PO4,0.05mM Na2HPO4,0.7mM NaHCO3 and 1% methylene blue. The pH of the medium was 7.5. Fluorescence imaging observations were performed after 3-day-old zebra fish were selected and incubated with dye 5c (5.0 μm) for 30 minutes. Zebra fish can be observed to be stained with red fluorescence.
Claims (1)
1. The red fluorescent dye based on the pyran quinoline structure is characterized by having the structural formula:
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| CN105504860A (en) * | 2014-10-20 | 2016-04-20 | 中南大学 | Synthesis and applications of pyranoquinoline fluorescent dye |
| CN109400616A (en) * | 2018-11-02 | 2019-03-01 | 广西师范大学 | A kind of Sulfur Dioxide-derivatives fluorescence probe and its preparation method and application |
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| CN105504860A (en) * | 2014-10-20 | 2016-04-20 | 中南大学 | Synthesis and applications of pyranoquinoline fluorescent dye |
| CN109400616A (en) * | 2018-11-02 | 2019-03-01 | 广西师范大学 | A kind of Sulfur Dioxide-derivatives fluorescence probe and its preparation method and application |
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