CN108530446A - A kind of fluorescence probe of identification benzenethiol - Google Patents
A kind of fluorescence probe of identification benzenethiol Download PDFInfo
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- CN108530446A CN108530446A CN201810609532.3A CN201810609532A CN108530446A CN 108530446 A CN108530446 A CN 108530446A CN 201810609532 A CN201810609532 A CN 201810609532A CN 108530446 A CN108530446 A CN 108530446A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
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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"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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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
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
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Abstract
The invention discloses a kind of fluorescence probe that can quickly identify benzenethiol (PhSH) and its applications, belong to chemical analysis detection technique field, molecular structural formula is as follows：The probe is selectively good, high sensitivity, strong antijamming capability, while having red emission and big Stokes shift.And long wavelength emission (feux rouges or near infrared light) has good penetration into tissue, smaller background interference；Big Stokes shift can reduce the interference of self-absorption and autofluorescence to improve the sensitivity of detection simultaneously.These excellent performances show that the fluorescence probe has important application value in the fields such as environment and biology.
Description
Technical field
The invention belongs to chemical analysis detection technique fields, and in particular to a kind of preparation of detection benzenethiol fluorescence probe,
And application of the probe in detecting benzenethiol.
Background technology
Benzenethiol, also known as sulfydryl benzene are a kind of important industrial chemicals, are widely used in pesticide, high molecular material and medicine
The building-up process of object.And benzenethiol has foul smell, is a kind of deadly poisonous compound.Studies have shown that the lethal concentration of 50 of fish
(LC50) it is 0.1-0.4mM, the half lethal dose (LD50) to mouse is 46.2mg/kg (oral), 2.15mg/kg is (subcutaneous to note
It penetrates).People is exposed in the atmosphere of benzenethiol, has strong impulse effect to eyes, mucous membrane respiratory tract and skin, can draw after sucking
Rise larynx, bronchial spasm, oedema and chemical pneumonia, pulmonary edema and it is lethal.Poisoning manifestations have burn feeling, cough, pant, larynx
Inflammation, shortness of breath, headache, Nausea and vomiting.Therefore, the method that exploitation detects benzenethiol is meaningful.
Fluorescence detection is because of high sensitivity, detection speed is fast, high resolution due to become a kind of important detection method.Recent years,
Have some document reports about benzenethiol fluorescence probe, but most of benzenethiol fluorescence visit response speed it is slow (>10min), it sends out
Ejected wave length (in blue light and yellow region) or Stokes shift it is small (<100nm).Long wavelength emission (feux rouges or near-infrared
Light) there is good penetration into tissue, smaller background interference, and big Stokes shift can reduce self-absorption and spontaneous
The interference of fluorescence is to improve the sensitivity of detection.Currently, having long wavelength emission, big Stokes shift and quickly corresponding simultaneously
Benzenethiol fluorescence probe be rarely reported.Therefore, developing has the characteristics that above benzenethiol fluorescence probe has prodigious meaning
Justice.
Invention content
In order to overcome the deficiencies of the prior art, the present invention is intended to provide a kind of high sensitivity, selectivity are good, can have simultaneously
Red emission and big Stokes shift and the fluorescence probe for quickly detecting benzenethiol.
Fluorescence probe in the present invention, molecular structure are as follows：
Fluorescence probe in the present invention is reacted by 4 steps to be prepared, and synthetic route is as follows：
Specific synthetic method is as follows：(a) compound 1 is dissolved in glycol monoethyl ether at room temperature, continues to be heated to 115
DEG C until reaction solution become clarify, hydrazine hydrate (80%) is then added dropwise dropwise into above-mentioned mixed liquor, after being added dropwise to complete continue 115
Mixed liquor is continued into heating reflux reaction 3 hours at a temperature of DEG C, waits after the completion of reacting, is cooled to room temperature, a large amount of crocus are precipitated
Precipitation, filtration washing obtain compound 2；(b) compound 2 is dissolved in 3- methyl -2- butanone, dense sulphur is then slowly added dropwise
Acid, reaction mixture return stirring under nitrogen protection wait for that after completion of the reaction decompression rotation is evaporated remaining 3- methyl -2- fourths
Ketone obtains crude product, and carrying out separating-purifying with silica gel column layer obtains light yellow solid product 3；(c) compound 3 and para hydroxybenzene
Formaldehyde is dissolved in toluene, is stirred and evenly mixed and is then added dropwise in glacial acetic acid and piperidines to above-mentioned mixed liquor successively, after being added dropwise, is mixed
Close liquid return stirring under nitrogen protection, after completion of the reaction, vacuum distillation removes toluene, obtains crude product, with silica gel column layer into
Row separating-purifying obtains red solid product 4；(d) compound 4 and 2,4-dinitrofluorobenzene are dissolved in acetone, are added anhydrous
Potassium carbonate, return stirring obtain crude product after completion of the reaction, and carrying out separating-purifying with silica gel column layer obtains the production of crocus solid
Product 5, i.e. probe molecule.
There is the fluorescence probe of the present invention following mechanism, fluorescence probe unstressed configuration itself to be reacted with benzenethiol, cause 2,4-
Dinitrobenzene ring portion separates, and generates dyestuff 6, emits red fluorescent.The response process of probe molecule is as follows：
The fluorescence probe of the present invention has big Stokes shift, and absorption maximum is in 450nm, maximum after being acted on benzenethiol
Transmitting is in 590nm, stoke shift 140nm.
The fluorescence probe of the present invention is selectively good.The PBS bufferings that the test system of probe molecule is the 10mM that pH is 7.4 are molten
Liquid includes 1.0mM CTAB, is tested at 25 DEG C.Probe molecule itself is in fluorescent quenching state, and 15 times of equivalent benzenethiols are being added
Later, fluorescence intensity increases 5 times at maximum emission wavelength 590nm.And be added its detectable substance (Cys, Hcy, Phe, Trp,
Leu、NO3 -、SO3 2-、S2O3 2-、NO2 -、Ca2+、K+、PO4 3-、SO4 2-、SCN-、Na+、Mg2+、H2O2、Fe3+、S2-、ClO-、Mn2+) after,
Fluorescence is only almost without increase.
The fluorescence probe strong antijamming capability of the present invention, other detectable substances (Cys, Hcy, Phe, Trp, Leu, NO3 -、SO3 2-、
S2O3 2-、NO2 -、Ca2+、K+、PO4 3-、SO4 2-、SCN-、Na+、Mg2+、H2O2、Fe3+、S2-、ClO-、Mn2+) presence do not influence to detect
The effect of benzenethiol.
After the benzenethiol effect of 15 times of equivalents is added, fluorescence enhances the fluorescence probe of the present invention immediately, reaches in 5min
Maximum value.
The fluorescence probe of the present invention can be to carrying out quantitative detection in benzenethiol.
The fluorescence probe of the present invention can be applied in the test of actual water sample, in tap water and mineral water in this explanation
The rate of recovery for adding benzenethiol carries out product.
The present invention fluorescence probe have lower cytotoxicity, within 20 μM, cultivate for 24 hours, survival rate 95% with
On.In addition, the probe has good cell membrane penetration, the benzenethiol of intracellular external source can be detected.
Probe molecule of the present invention is to the launch wavelength after benzenethiol (PhSH) response in near-infrared, stoke shift
Greatly, it has good selectivity and anti-interference ability, and the sensitivity having had, there is wider application range, the fluorescence
Probe has practical application value in biology with fields such as chemistry.
Description of the drawings
Fig. 1 is the fluorescence probe (10.0 μM) of the present invention at PBS buffer solutions (10mM, pH=7.4,1.0mM CTAB)
In, the fluorescence spectrum after being acted on various concentration benzenethiol (PhSH) changes, and abscissa is wavelength, and ordinate is fluorescence intensity.
Fig. 2 is the fluorescence probe (10.0 μM) of the present invention in PBS buffer solutions (10mM, pH=7.4,1.0mM CTAB)
With the linear relationship of fluorescence intensity at any time at 590nm in benzenethiol (PhSH) mechanism, abscissa is the time, and ordinate is
Fluorescence intensity.
Fig. 3 is the selectivity of the fluorescence probe of the present invention, and fluorescence probe is at (10.0 μM) in PBS buffer solutions (10mM, pH
=7.4,1.0mM CTAB) and PhSH, Cys, Hcy, Phe, Trp, Leu, NO3 -、SO3 2-、S2O3 2-、NO2 -、Ca2+、K+、PO4 3-、
SO4 2-、SCN-、Na+、Mg2+、H2O2、Fe3+、S2-、ClO-、Mn2+Fluorescence spectrum after effect, abscissa are wavelength, and ordinate is
Fluorescence intensity.
Fig. 4 is the anti-interference of the fluorescence probe of the present invention, benzenethiol (PhSH) and analyte (Cys, Hcy, Phe, Trp,
Leu、NO3 -、SO3 2-、S2O3 2-、NO2 -、Ca2+、K+、PO4 3-、SO4 2-、SCN-、Na+、Mg2+、H2O2、Fe3+、S2-、ClO-、Mn2+) altogether
When depositing, with fluorescence probe (10.0 μM) in PBS buffer solutions (10mM, pH=7.4,1.0mM CTAB) with benzenethiol
(PhSH) the fluorescence intensity ratio (I/I after acting on0) block diagram.
Fig. 5 is the fluorescence probe (10.0 μM) of the present invention at PBS buffer solutions (10mM, pH=7.4,1.0mM CTAB)
In, probe with fluorescence intensity changes with time at 590nm in benzenethiol (PhSH) mechanism, abscissa is the time, indulge sit
It is designated as fluorescence intensity.
Fig. 6 is that the fluorescence probe of the present invention detects the copolymerization coke cell imaging of the intracellular benzenethiols of Hela (PhSH).A1-A3
(150.0 μM) cultivation 15min of benzenethiol (PhSH) are first used at 37 DEG C for cell, then use (10.0 μM) cultivation 15min of probe
Imaging effect.B1-B3 is the imaging effect that probe (10.0 μM) cultivates 15min at 37 DEG C in the cell.
Fig. 7 is toxicity test of the fluorescence probe to cell of the present invention.In probe molecule concentration 2.0 × 10-5mol/L
When, cell survival rate is 95% or more.
Example is embodied
Embodiment 1：The synthesis of compound 2
Compound 1 (3.32g, 10.0mmol) is dissolved in 50mL glycol monoethyl ethers, is heated to 115 DEG C until reaction solution becomes clear
Clearly, 3.0mL hydrazine hydrates (80%) are then added dropwise dropwise into above-mentioned mixed liquor, is added dropwise to complete rear mixed liquor and continues to be heated to reflux instead
It answers 3 hours, waits after the completion of reacting, be cooled to room temperature, a large amount of crocus precipitations are precipitated, filtration washing obtains compound 2.Yield：
2.32g；Yield：81.9%.
Embodiment 2：The synthesis of compound 3
Intermediate 2 (1.98g, 7mmol) is dissolved in 3- methyl -2- butanone (100mL), the 3mL concentrated sulfuric acids are then slowly added dropwise,
Reaction mixture return stirring 4 hours under nitrogen protection wait for that after completion of the reaction 3- methyl -2- butanone is evaporated off in decompression rotation,
Crude product is obtained, isolating and purifying (petroleum ether/dichloromethane=1/10, v/v) with silica gel column layer obtains light yellow solid product 3.
Yield：1.13g；Yield：48.5%.
Embodiment 3：The synthesis of compound 4
Compound 3 (1.0g, 3mmol) and parahydroxyben-zaldehyde (0.37g, 3mmol) are dissolved in the toluene of 20mL dryings, stirring
Then mixing is added dropwise in glacial acetic acid (0.02mL) and piperidines (0.05mL) to above-mentioned mixed liquor successively, after being added dropwise, mixed liquor
Return stirring 6 hours under nitrogen protection, decompression rotation is evaporated toluene, obtain crude product, use column chromatography purifying (ethyl alcohol/
Dichloromethane=1/50, v/v) obtain red solid product 4.Yield：0.68g；Yield：51.7%.
Embodiment 4：The synthesis of probe 5
Compound 4 (0.483g, 1mmol), 2,4-dinitrofluorobenzene (0.279g, 1.5mmol) are dissolved in the acetone of 20mL dryings,
Anhydrous potassium carbonate (0.276g, 2mmol) is added, return stirring 4 hours filters reaction solution to obtain filtrate, and decompression rotation is steamed
Dry solvent, obtains crude product, purifies (petroleum ether/dichloromethane=1 with chromatography:10, v/v) crocus solid product is obtained
5 i.e. probe molecule (0.212g, 35.2%).
Embodiment 5：Probe molecule detects the application of benzenethiol in actual water sample
By (0.22 μm) filtering of filter membrane of tap water and mineral water, be then configured to PBS buffer solutions (10mM, pH=7.4,
1.0mM CTAB).Probe molecule is dissolved in above-mentioned buffer solution, 10.0 μM of probe molecule solutions are configured to, with this to the spy
Benzenethiol (0.0,4.0,8.0,12.0,16.0 μM) is added in needle solution, as shown in table 1 in tap water and mineral spring water sample
The good rate of recovery (96%-105%) is obtained, shows that the probe can be used for the detection of benzenethiol in actual water sample.
1 fluorescence probe of table detects the rate of recovery of benzenethiol in tap water and mineral water
Embodiment 6：Probe molecule detects the application of benzenethiol in cell
HeLa cell is incubated 15min with the PBS bufferings (10.0mM, pH=7.4) containing benzenethiol (150.0 μM) first, slow with PBS
Fliud flushing rinses 3 times；Again with containing probe (10.0 μM) PBS buffer solution be incubated 15min, with PBS buffer solution rinse 3 times after, with swash
Light confocal fluorescent microscopic carries out cell fluorescence imaging, it can be seen that strong fluorescence signal.In control experiment, HeLa is thin
Born of the same parents are only incubated 15min in the PBS buffer solution (10.0mM, pH=7.4) containing probe (10.0 μM), after being rinsed with PBS buffer solution,
Cell fluorescence imaging is carried out with laser confocal fluorescence microscope, it is observed that faint fluorescence signal.These result tables
Bright, which can detect the benzenethiol in living cells.
Claims (1)
1. a kind of fluorescence probe of identification benzenethiol, structural formula are：
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| CN201810609532.3A CN108530446B (en) | 2018-06-13 | 2018-06-13 | Fluorescent probe for identifying thiophenol |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109180561A (en) * | 2018-11-14 | 2019-01-11 | 中国科学院海洋研究所 | The application of chalcones fluorescence probe thiophenols in detection aqueous solution |
| CN109810107A (en) * | 2019-03-02 | 2019-05-28 | 郑州大学 | A kind of fluorescence probe and preparation method thereof identifying mercaptoamino acid |
| CN109879851A (en) * | 2019-04-11 | 2019-06-14 | 济南大学 | A kind of near infrared fluorescent probe of specific detection benzenethiol |
| CN109913207A (en) * | 2019-04-11 | 2019-06-21 | 济南大学 | A kind of fluorescence probe for the longwave transmissions detecting benzenethiol |
| CN111138431A (en) * | 2020-01-13 | 2020-05-12 | 商丘师范学院 | Reactive fluorescent probe for detecting thiophenol and synthetic method and application thereof |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109180561A (en) * | 2018-11-14 | 2019-01-11 | 中国科学院海洋研究所 | The application of chalcones fluorescence probe thiophenols in detection aqueous solution |
| CN109180561B (en) * | 2018-11-14 | 2021-07-27 | 中国科学院海洋研究所 | Application of chalcone fluorescent probe in detection of thiophenol compounds in aqueous solution |
| CN109810107A (en) * | 2019-03-02 | 2019-05-28 | 郑州大学 | A kind of fluorescence probe and preparation method thereof identifying mercaptoamino acid |
| CN109879851A (en) * | 2019-04-11 | 2019-06-14 | 济南大学 | A kind of near infrared fluorescent probe of specific detection benzenethiol |
| CN109913207A (en) * | 2019-04-11 | 2019-06-21 | 济南大学 | A kind of fluorescence probe for the longwave transmissions detecting benzenethiol |
| CN109879851B (en) * | 2019-04-11 | 2021-08-31 | 济南大学 | Near-infrared fluorescent probe for specifically detecting thiophenol |
| CN111138431A (en) * | 2020-01-13 | 2020-05-12 | 商丘师范学院 | Reactive fluorescent probe for detecting thiophenol and synthetic method and application thereof |
| CN111138431B (en) * | 2020-01-13 | 2022-02-15 | 商丘师范学院 | Reactive fluorescent probe for detecting thiophenol and synthetic method and application thereof |
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