CN115894413B - Method for detecting fluoride ions by using fluorescent probe - Google Patents
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- -1 fluoride ions Chemical class 0.000 title claims abstract description 33
- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 13
- 239000000523 sample Substances 0.000 claims description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 19
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 14
- 230000004044 response Effects 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 5
- 239000001301 oxygen Substances 0.000 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 230000035945 sensitivity Effects 0.000 abstract description 3
- 210000004027 cell Anatomy 0.000 description 14
- 238000000862 absorption spectrum Methods 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000002189 fluorescence spectrum Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 229910020366 ClO 4 Inorganic materials 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000001218 confocal laser scanning microscopy Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000012447 hatching Effects 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011775 sodium fluoride Substances 0.000 description 2
- 235000013024 sodium fluoride Nutrition 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 206010016818 Fluorosis Diseases 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 208000014151 Stomatognathic disease Diseases 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
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- 229940125904 compound 1 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 208000004042 dental fluorosis Diseases 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
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- 230000002349 favourable effect Effects 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
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- 239000003960 organic solvent Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000006049 ring expansion reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention discloses a method for detecting fluoride ions by using a fluorescent probe, and belongs to the technical field of analytical chemistry. The fluorescent probe contains an asymmetric five-membered oxygen heterocyclic ring cyclized perylene tetracarboxylic acid ester electron-accepting unit and a hydroxyl electron-donating unit. The fluorescent probe provided by the invention is simple to synthesize, convenient to use, capable of reacting with fluoride ions specifically, good in selectivity and sensitivity to fluoride ions, and capable of being used for detecting fluoride ions in living cells.
Description
Technical Field
The invention belongs to the technical field of analytical chemistry, and relates to a method for detecting fluoride ions by using a fluorescent probe.
Background
In the ecological environment and in the living body, fluoride ions play an extremely important role. The amount of fluoride ion is not large or small, and a proper amount of fluoride ion is favorable for preventing and treating dental diseases such as decayed teeth, decayed teeth and the like, and is widely used for treating osteoporosis and the like, but if the amount of fluoride ion exceeds a certain limit in a human body, diseases such as fluorosis, urinary tract calculus and the like are caused, and even cancers are caused. Therefore, the research of the method for detecting the content of the fluoride ions in the environment and life is increasingly attracting attention, and the fluorescent probe method for detecting the fluoride ions has the advantages of high efficiency, good selectivity and the like. Perylene bisimides (PDIs) fluorescent probes have excellent thermal and light stability, high fluorescence quantum yields, and excellent chemical inertness. But PDIs have poor solubility properties, which limit their wide range of applications. Structurally similar to PDIs, perylene tetracarboxylic acid esters (PTBACs) have four electron-deficient ester chains attached to the perylene core and thus have excellent solubility in organic solvents while exhibiting excellent fluorescence intensity. PTBAC can effectively improve the optical, electrical and chemical properties of the compounds along the perylene nucleus ring expansion, and is a good perylene compound derivatization method. In various fluorogenic fluorescent probes reported in recent decades, N-H groups are used as recognition groups, for example, compounds such as urea, thiourea, imidazole, indole, pyrrole, amine and imide containing N-H groups are used to form hydrogen bonds with fluorogenic ions, so that intermolecular proton transfer occurs, and absorption and fluorescence spectrum change are caused. In comparison, although hydroxyl (O-H) is also a good proton donating group, even more acidic than amino, there are few reports of using O-H groups as recognition groups.
Disclosure of Invention
In view of the above prior art, the present invention provides a method for detecting fluoride ions using a fluorescent probe and application of the probe compound to imaging applications for detecting fluoride ions in living cells.
The chemical structural formula of the fluorescent probe compound provided by the invention is as follows:
the invention has the beneficial effects that:
the invention relates to a method for detecting fluoride ions by using a fluorescent probe, which comprises an electron-donating unit of asymmetric five-membered oxygen heterocyclic ring cyclization perylene tetracarboxylic acid ester and an electron-donating unit of hydroxyl, wherein the fluorescent probe can be used for detecting fluoride ions with high sensitivity due to strong acidity of phenolic hydroxyl and intermolecular hydrogen bonding between hydroxyl and fluoride ions under the action of intramolecular hydrogen bonding between phenolic hydroxyl and ortho-position protons of perylene nuclei, and the mechanism of identifying fluoride ions by the probe is mainly an intermolecular proton transfer mechanism.
Drawings
FIG. 1 is a molecular structure diagram of a fluorescent probe compound.
FIG. 2 is a fluorescent probe compound 1 H NMR spectrum.
FIG. 3 is a fluorescent probe compound 13 C NMR spectrum.
FIG. 4 is a FT-IR spectrum of a fluorescent probe compound.
FIG. 5 is a graph showing the change in absorbance spectrum when fluorine ions in an amount 0 to 3 times the probe concentration are gradually added to a methylene chloride solution of a fluorescent probe compound (10. Mu.M).
FIG. 6 is a fluorescent light of a fluorescent probe compound (10. Mu.M) in methylene chloride solution (a) when fluorine ions were gradually added in an amount of 0 to 3 times the probe concentrationSpectral change plots (λex=519 nm) and (b) a correspondence between the fluorescence emission peak intensity value at 477nm and the added fluoride ion concentration multiple value; the illustration is to add F under ultraviolet light - Comparison of the changes in fluorescence of the front and rear solutions (λex=365 nm).
FIG. 7 is (a) an absorption spectrum and (b) a fluorescence spectrum when 5 times the amount of different anions of a probe concentration are added to a methylene chloride solution of a fluorescent probe compound (concentration: 10. Mu.M); other anions being Cl - 、Br - 、I - 、SO 4 − 、BF 4 − 、PF 6 − 、ClO 4 − 、H 2 PO 4 − 、HPO 4 2- 、CH 3 COO - 。
FIG. 8 is a graph of fluorescent probe compounds versus A549 intracellular fluoride ion detection; (a) fluorescence photographs of cells incubated with 10u mol/L of a dimethyl sulfoxide solution of the probe at 37℃for 30 minutes, (b) bright field photographs of A549 cells after incubation of the probe, and (C) fluorescence photographs of A549 cells after incubation of the probe after further incubation with 60 umol/L of sodium fluoride for 10 minutes.
Detailed Description
The invention will be further described with reference to the accompanying drawings and examples
EXAMPLE 1 preparation of fluorescent Probe Compounds
The synthetic route is shown in the following formula:
compound 1 (150 mg, 0.2 mmol) and potassium carbonate (150 mg, 1.0 mmol) were dissolved in 15ml N-methylpyrrolidone. At N 2 Stirring for 5h at 60 ℃ under the protection condition. After cooling to room temperature, the mixture was filtered by pouring into HCl (100 ml, 2M), the pellet was rinsed thoroughly with water and dried under vacuum. Purification by gel column chromatography using methylene chloride/ethyl acetate (20/1) as an eluent gave the red solid fluorescent probe compound P1 (136 mg, 86%). 1 H-NMR (CDCl 3 , 300 MHz, δ ppm): 11.09 (s, 1H), 9.73 (d, J = 9.0 Hz, 1H), 8.71 (s, 1H), 8.55 (s, 1H), 8.33 (s, 1H), 8.11 (d, 1H), 4.34-4.43 (m, 8), 1.74 (m, 8H), 1.48 (m, 8H), 0.88-0.99 (m, 12H). 13 C NMR (75 MHz, CDCl3, δ ppm): 169.59, 169.20, 168.81, 153.19, 129.87, 129.08, 128.16, 127.77, 126.94, 126.77, 125.43, 124.15, 123.01, 122.27, 119.10, 116.71, 65.71, 65.61, 65.42, 30.81, 29.67, 19.34, 13.84. FT-IR (KBr, cm −1 ): v = 3365, 3189, 2922, 2854, 1651, 1462, 1410, 1067, 873, 732, 661, 586, 528, 486, 437. HRMS (APCI): m/z = 682.2869(M + -H).
The effect test was carried out on the fluorescent probe compound P1 obtained in example 1:
1. absorption spectral response of probe compounds to fluoride ions
The response of probe P1 to fluoride ion was studied by adding tetrabutylammonium fluoride to methylene chloride solvent. As the fluorine ion concentration increases, the change in the absorption spectrum of the probe is shown in FIG. 5, the maximum absorption peak of the probe is at 450nm, the shoulder peak is at 424nm, and when 0 to 3 times the fluorine ion concentration of the probe P1 is added, the absorption peaks at 450nm and 424nm are weakened, and new absorption peaks appear at 512nm and 562 nm. The probe P1 has two equal absorption points at 460 nm and 519nm, respectively, illustrating the response to F - The probe generated two new species, and the red shift of the observed absorbance indicates that the probe added F - Deprotonation occurs afterwards. And the response time of the probe and the fluoride ions is very fast, and can be completed in almost 1 second, which shows that the probe is identified as an immediate process.
2. Fluorescence spectral response of probe compounds to fluoride ions
As shown in FIG. 6a, the fluorescence emission peak of the probe P1 is at 477nm when the concentration of fluorine ions is from 1X10 -5 Up to 3X10 -5 As the mol/L was gradually increased, a new fluorescence emission peak at 600nm was developed with a decrease in fluorescence emission peak intensity at 477 nm. This is because the introduction of the five-membered oxygen heterocycle in the perylene position of the probe increases the conjugated structure of the perylene ring of the probe, and thus the electron donor is from the phenoloxy group to the electron acceptorThe charge transfer capability is enhanced, and the probe has the characteristic of a ratio fluorescent probe, thereby being beneficial to improving the sensitivity of the probe for detecting fluorine ions. FIG. 6b shows that the concentration of fluoride ion is from 0 to 2X 0 −5 In the mol/L range, the fluorescence intensity at 477nm is reduced correspondingly, the linear equation is y= -102.87x+205.23, and the correlation coefficient R is 0.986. The detection limit calculated as three times the standard deviation of the blank signal was 0.53. Mu. Mol/L. Corresponding to the change in fluorescence emission spectrum, it can be seen that the fluorescence color of the probe changes from blue to red upon addition of fluoride ions.
3. Selective analysis of fluorine ions by probe compounds
The interference effect of other common anions on the detection of fluoride ions by the probe was examined, as shown in FIG. 7, the absorption and fluorescence spectra of the probe were measured at the time of Cl addition - 、Br - 、I - 、SO 4 − 、BF 4 − 、PF 6 − 、ClO 4 − 、H 2 PO 4 − 、HPO 4 2- 、CH 3 COO - The method has no change, and the absorption spectrum of the complex after the probe is combined with the fluoride ion is not influenced by other interfering ions, so that the probe has high selectivity in detecting the fluoride ion by the absorption and fluorescence spectrum method. This high selectivity results from the high acidity of the hydroxyl groups attached to the perylene core and F in methylene chloride solution - The high alkalinity is exhibited.
4. Application of probe compound in cell imaging for detecting fluoride ions
The ability of probe P1 to detect fluoride ions in living cells was examined by confocal fluorescence microscopy, A549 human lung cancer cells were incubated with 50umol/L probe in dimethyl sulfoxide solution at 37℃for 30 minutes, and then excited by 460-490 nm blue light channel under confocal fluorescence microscopy, and a fluorescence photograph was taken. After the cells were hatched with the probes, strong intracellular fluorescence was observed (fig. 8 a), which indicates that the probe has good permeability to cell membranes, the morphology of the cells after the hatching of the probes was observed in the bright field, the morphology of the a549 cells was good, no collapse phenomenon was observed, the cells remained healthy after the hatching of the probes, the survival rate was very high (fig. 8 b), and the cells hatched with the probes were continuously hatched at 37 ℃ for 10 minutes with a PBS buffer solution of NaF at a concentration of 60 μmol/L, and the cells hatched with the probes were seen to have weak red fluorescence (fig. 8C), and the above results indicate that the probes can be used to detect the change of fluoride ions in living cells.
Claims (1)
1. A method for detecting fluoride ions using a fluorescent probe, wherein the fluorescent probe compound has the chemical structural formula shown below:
；
the specific steps of the fluoride ion detection are as follows:
step one: the response of probe P1 to fluoride was studied by adding tetrabutylammonium fluoride to methylene chloride solvent;
step two: the fluorescence emission peak of the probe P1 was located at 477nm at a fluoride ion concentration of from 1X10 -5 To 3x10 -5 As the mol/L was gradually increased, a new fluorescence emission peak at 600nm was developed with a decrease in fluorescence emission peak intensity at 477 nm.
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Non-Patent Citations (1)
| Title |
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| Fluorescent pH probes for alkaline pH range based on perylene tetra-(alkoxycarbonyl) derivatives;Fengxia Zhang et al;《Arabian Journal of Chemistry》;第13卷;第5900–5910页 * |
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