CN108033973B - Preparation method of BODIPY compound as biological recognition detection material - Google Patents
Preparation method of BODIPY compound as biological recognition detection material Download PDFInfo
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- CN108033973B CN108033973B CN201711482185.4A CN201711482185A CN108033973B CN 108033973 B CN108033973 B CN 108033973B CN 201711482185 A CN201711482185 A CN 201711482185A CN 108033973 B CN108033973 B CN 108033973B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 238000001514 detection method Methods 0.000 title description 7
- 239000000463 material Substances 0.000 title description 2
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 18
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 15
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000002841 Lewis acid Substances 0.000 claims abstract 3
- 150000007517 lewis acids Chemical class 0.000 claims abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229960000583 acetic acid Drugs 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 239000012362 glacial acetic acid Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001408 amides Chemical class 0.000 abstract description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 2
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- 229910001437 manganese ion Inorganic materials 0.000 description 30
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 25
- 239000000523 sample Substances 0.000 description 21
- 239000011572 manganese Substances 0.000 description 10
- 150000002500 ions Chemical class 0.000 description 9
- 229910021645 metal ion Inorganic materials 0.000 description 4
- WLZRMCYVCSSEQC-UHFFFAOYSA-N cadmium(2+) Chemical compound [Cd+2] WLZRMCYVCSSEQC-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- USARTISFYYMSBD-UHFFFAOYSA-N N1C=CC=C1.N1C=CC=C1.F[B] Chemical compound N1C=CC=C1.N1C=CC=C1.F[B] USARTISFYYMSBD-UHFFFAOYSA-N 0.000 description 1
- 208000028389 Nerve injury Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 238000012742 biochemical analysis Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical class O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 238000012921 fluorescence analysis Methods 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000006371 metabolic abnormality Effects 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000008764 nerve damage Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 238000010206 sensitivity analysis Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- 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 Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
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- 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
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- 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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- 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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- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- Chemical Kinetics & Catalysis (AREA)
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- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Abstract
The application discloses a preparation method of a BODIPY compound, the BODIPY compound is synthesized by adopting a BODIPY fluorescent dye and 4-N, N-diacetyl amide alcohol benzaldehyde, and Lewis acid such as Mg (ClO)4)2When in catalysis, the obtained fluoroboric pyrrole fluorescent dye can react with two molecules of 4-N, N-diacetyl amide alcohol benzaldehyde, and the obtained product has two coordination sites, so that the sensitivity is higher and can reach 1.0 multiplied by 10‑6mol/L。
Description
Technical Field
The application relates to a novel near-red-light BODIPY dimethyl derivative and a preparation method thereof, belongs to the content of a fluorescent probe, and can be used as a fluorescent probe for manganese ion response.
Background
In recent years, among many detection and identification methods in modern biotechnology and life science research, a fluorescence analysis method has irreplaceable effects in the field of biochemical analysis due to the advantages of high sensitivity, good selectivity, low detection limit and the like. Therefore, the selective detection and identification of important ions, especially heavy metal ions, in ecological environment and biological systems by using artificially designed and synthesized fluorescent probes is receiving wide attention from many scientific researchers. Manganese ions are widely used in industry, and are essential trace elements for maintaining human health. Although manganese ions play an important role in the human body and other biological systems, metabolic abnormalities of manganese ions also cause a series of diseases. For example, manganese ion metabolism disorder can lead to delayed coagulation, hypercholesterolemia, nerve damage and other conditions. Therefore, it is important to detect manganese ions rapidly, simply and selectively in ecological environment and biological system.
Fluorescent probes for manganese ion detection, recently fluorescein series and rhodamine series probes have been reported for the detection of manganese ion content in organisms (Adhikari S, Ghosh A, Sahana A, et al. Taliling Ligand environmental restriction Development of Colorimetric and Fluorescence Indicator for Biological Mn (II) Imaging [ J ]. Analytical Chemistry 2015,88 (2)). However, these fluorescent probes have small stokes shift, poor light stability and low quantum yield of NIR fluorophores, and the fluorescence is greatly influenced by the environment, has certain low toxicity, and is difficult to accurately detect manganese ions in cells.
Disclosure of Invention
The technical problem that this application required to solve is: provides a manganese ion probe with good water solubility, high sensitivity and high selectivity so as to overcome the defects of the prior art.
In order to solve the above problems, the technical solution of the present application is as follows: the BODIPY manganese ion fluorescent probe is provided, and the structural formula is as follows:
in order to solve the BODIPY fluorescent probe, the technical problems to be solved by the application are as follows: provides a method for synthesizing the manganese ion probe. The method comprises the following steps:
dissolving BODIPY fluorescent dye and 4-N, N-diacetanolbenzaldehyde in a mixed solution of toluene and N, N-dimethylformamide at room temperature, adding piperidine and glacial acetic acid, and adding a small amount of Mg (ClO)4)2Heating and refluxing, tracking by TLC until the raw materials completely react, evaporating the solvent under reduced pressure, carrying out column chromatography, and distilling under reduced pressure to remove the solvent to obtain a reddish brown product.
By adopting the technical scheme, the BODIPY probe is synthesized by the BODIPY fluorescent dye and 4-N, N-diacetyl amide alcohol benzaldehyde, and the 4-N, N-diacetyl amide alcohol benzaldehyde has good water solubility, so that the BODIPY probe can be used for detecting Mn in an aqueous solution2+Exhibit a high degree of selectivity and sensitivity.
Drawings
FIG. 1 is a schematic diagram of the synthesis of a BODIPY manganese ion probe
FIG. 2 is a graph showing the statistics of the fluorescence change of BODIPY manganese ion probe in metal ion solutions of different concentrations, wherein 1 represents blank, and 2 represents Fe3+And 3 represents Zn2+And 4 represents Cu2+And 5 represents Mn2+
The beneficial effect that this application obtained is as follows:
1. BODIPY fluorescent Probe pairs described herein for Mn2+Has high selectivity and can specifically detect Mn ions.
2. The fluorescent probe has two sites capable of being combined with metal ions, and has higher sensitivity which can reach 1.0 multiplied by 10-6mol/L。
3. This application uses small amounts of Mg (ClO)4)2As a co-catalyst, the reaction is made very chemoselective, one molecule of the fluoroboron dipyrrole can react with two molecules of the substituted benzaldehyde, so that the product has two molecules of chelating sites, and moreover, the reaction achieves a yield of up to 95%.
Detailed Description
Example 1
At room temperature, respectively weighing BODIPY fluorescent dye (0.50mmol) and 4-N, N-diacetamidoalcohol benzaldehyde (1.5mmol), dissolving in a mixed solution of 30 ml of toluene and 30 ml of N, N-dimethylformamide, adding 0.1ml of piperidine and 0.1ml of glacial acetic acid as catalysts, and adding Mg (ClO)4)2(0.1mmol), refluxing under heating, TLC tracing to the completion of the reaction of the starting materials, evaporating the solvent under reduced pressure, column chromatography (CH2Cl2/CH3OH, 100: 1, v/v), distilling off the solvent under reduced pressure to obtain a reddish brown product, which is subjected to nuclear magnetic resonance1The H NMR spectrum is used for characterization,1h NMR (d6-DMSO, 400M) data were as follows: 1.71(s, 3H),2.01(br,4H), 2.05(s, 3H),3.39(t, 8H), 3.73(s,3H),3.79(t,8H),4.24(s,8H),5.62(d,1H),6.54(d,4H),6.61(d,1H),6.72(d,2H)6.99(d,2H),7.12(d,4H), 7.19(d,2H), 8.01(t, 4H).
(yield 95%, melting point: 178-179.5 ℃ C.).
Application example 1
In a buffer solution with pH 7.5, the concentration is 1.0 × 10-6Adding 5.0 × 10 mol/L BODIPY manganese ion probe solution-6FeCl in mol/L3、ZnCl2、CuCl2、MnCl2The change in fluorescence spectrum was measured (see FIG. 2). It was found that when the same equivalent of each metal ion was added, the manganese ion significantly enhanced the fluorescence of the probe, and the other heavy metal ions increased the fluorescence of the probeThe intensity had a weak effect. As can be seen from FIG. 2, Mn is a relative ion to other metal ions2+The fluorescence intensity of the BODIPY manganese ion probe is influenced more obviously. When Mn is present2+When the cadmium ion probe coexists with various other ions, the BODIPY manganese ion probe still shows obvious fluorescence enhancement, which indicates that other ions have no influence on the recognition behavior of the cadmium ion recognized by the BODIPY manganese ion probe. Visible BODIPY manganese ion probe pair Fe3+，Zn2+，Cu2+Plasma insensitivity to Mn only2+Exhibit excellent selective fluorescence-enhanced recognition. In addition, experiments also find that the BODIPY manganese ion probe has better selectivity for identifying cadmium ions in a mixed solvent.
Sensitivity analysis of BODIPY manganese ion probe:
with the addition of manganese ions, the fluorescence emission intensity of the BODIPY manganese ion probe at 583nm is obviously enhanced, and when 1.5 equivalent of Mn is added2+(15. mu.M), the fluorescence intensity was increased by 10-fold. Because the BODIPY manganese ions and the Mn ions are complexed to form a good electron acceptor, PET blocking occurs, and the fluorescence of the BODIPY manganese ion probe is enhanced. (conditions for this spectrometry: a neutral buffer aqueous solution at 25 ℃ C., the concentration of Compound (1) was 5. mu.M, Mn2+ at various concentrations, 0, 0.12, 0.2, 0.4, 1.0, 2.0, 4.0, 7.0, 10.0, 20.0, 30.0and 50.0 eq.).
Therefore, the method has a good linear relation on the ultraviolet and fluorescence identification of Mn ions. The influence of the manganese ions on the wavelength of the absorption spectrum is obvious, and the absorbance of the probe is increased along with the increase of the added concentration of the manganese ions. The concentration of manganese ion is 0-5.0 x 10-6mol·L-1In the range of 1.0X 10 as the concentration of manganese ions increases-6mol·L-1The absorbance of the probe at 580nm also gradually increases, and the maximum absorption wavelength gradually decreases after 600 nm. With Mn2+After the concentration of (B) reaches 1: 2, Mn is further increased2+The absorption strength of the concentrated solution remains substantially unchanged. These spectral behaviors show Mn2+A1: 2 complex was formed with the probe.
Claims (3)
1. A preparation method of BODIPY compounds is characterized in that: the reaction route is shown as the following formula,
the specific reaction steps are as follows: respectively weighing a BODIPY fluorescent dye and 4-N, N-diacetanolbenzaldehyde at room temperature, dissolving the BODIPY fluorescent dye and the 4-N, N-diacetanolbenzaldehyde in a mixed solution of toluene and N, N-dimethylformamide, adding piperidine and glacial acetic acid as catalysts, adding Lewis acid, heating for refluxing, tracking by TLC until the raw materials completely react, evaporating the solvent under reduced pressure, performing column chromatography, and distilling under reduced pressure to remove the solvent to obtain a reddish brown product, wherein the Lewis acid is Mg (ClO)4)2。
2. A method of preparing the BODIPY compound of claim 1, wherein: the molar ratio of the BODIPY fluorescent dye to the 4-N, N-diacetamidoalcohol benzaldehyde is 1: 2-1:5.
3. A method of preparing BODIPY compounds of claim 2, comprising: the molar ratio of the BODIPY fluorescent dye to the 4-N, N-diacetamidoalcohol benzaldehyde is 1: 3.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101817838A (en) * | 2009-02-26 | 2010-09-01 | 上海市七宝中学 | Cadmium ion probe and synthesis method thereof |
| WO2016133913A1 (en) * | 2015-02-16 | 2016-08-25 | Seed Research And Development Llc | Fluorescently labeled molecules containing modified tryptophan |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101817838A (en) * | 2009-02-26 | 2010-09-01 | 上海市七宝中学 | Cadmium ion probe and synthesis method thereof |
| WO2016133913A1 (en) * | 2015-02-16 | 2016-08-25 | Seed Research And Development Llc | Fluorescently labeled molecules containing modified tryptophan |
Non-Patent Citations (1)
| Title |
|---|
| Red-Emission Fluorescent Probe Sensing Cadmium and Pyrophosphate Selectively in Aqueous Solution;Xuhong Qian et al.;《Org. Lett.》;20110620;第13卷(第14期);supporting information第S2页 * |
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Effective date of registration: 20230627 Address after: No. 4-2, Building 4, No.1 Jiangxia Road, Nan'an District, Chongqing 400000 Patentee after: Chongqing Huangjia Biotechnology Co.,Ltd. Address before: 400714 room 201-204, second floor, No. 62, Yunhe Road, Beibei District, Chongqing Patentee before: Chongqing Huangjia Tongyi Technology Co.,Ltd. |