CN103275698A - Ratio-dependent bisulfite ion fluorescent probes and preparation method thereof - Google Patents
Ratio-dependent bisulfite ion fluorescent probes and preparation method thereof Download PDFInfo
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- CN103275698A CN103275698A CN2013102138064A CN201310213806A CN103275698A CN 103275698 A CN103275698 A CN 103275698A CN 2013102138064 A CN2013102138064 A CN 2013102138064A CN 201310213806 A CN201310213806 A CN 201310213806A CN 103275698 A CN103275698 A CN 103275698A
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- sulfurous acid
- acid hydrogen
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Abstract
The invention relates to preparation and application methods of ratio-dependent bisulfite ion fluorescent probes, belonging to the technical field of anion detection. The probe molecules have recognition specificity for bisulfite ions in a neutral aquatic environment, generate fluorescence ratio variations, have very high sensitivity, and meanwhile, cause obvious color and fluorescent color variations. The fluorescent probes do not generate obvious variations for other ions, free radicals or molecules. The invention implements recognition specificity of the probe molecules for the bisulfite ions, provides the fluorescent probes with color comparison sensing function, and thus, has wide application prospects in the fields of biology and ion detection.
Description
Technical field
A kind of ratio type of the present invention sulfurous acid hydrogen radical ion fluorescent probe and preparation method belong to the technical field that negatively charged ion detects.
Background technology
Hydrosulphite is a kind of important industrial raw material, also can be used for cooking sanitas in preparation, transportation and the storage link of food, medicine.Can suck sulfurous gas and can change into sodium bisulfite and sodium pyrosulfate in human body, have scientific research to show, sodium bisulfite and sodium pyrosulfate not only can cause the anaphylaxis that some is individual, but also can cause lung cancer, cardiovascular disorder and sacred disease.The sulfurous acid hydrogen radical ion that how can monitor effectively in the body is extremely important.
The method of traditional detection sulfurous acid hydrogen radical ion is a lot, problems such as that but these method ubiquities and detected inadequately rapidly, detect is expensive, complicated operation, interference are big, not only need loaded down with trivial details operation, but also need the instrument of relative complex and those skilled in the art just can obtain reliable analytical results.The obvious like this requirement that does not reach the desired quick field evaluation of modern monitoring.Fluorescent spectrometry has been because advantages such as it is easy, sensitivity have represented remarkable performance in trace detection, received increasing concern at the identification sensory field of molecule or ion.In the last few years, detect ion with chemical sensor and become a new research focus gradually.This sensor responds the specificity that determinand has height, can avoid the interference of other ion effectively.Fluorescence chemical sensor can change this corresponding optical signalling that is converted into intuitively and colour-change, not only greatly reduce the dependence to complex instrument, simplification significantly simultaneously trace routine, reduced the detection cost.
Many chemical sensitisation molecules that detect at sulfurous acid hydrogen radical ion have been reported recently, these sensors all are the nucleophilicities of having utilized sulfite ion, mainly be divided into two classes: a class is to be action site with the aldehyde radical, and a class is to be action site with the levulinic acid group.But this two classes chemical sensitisation molecule also has certain limitation.Such as: the former need just can react under sour environment (pH is about 4), and is subjected to the influence of other sulfur-containing molecules or ion bigger; The latter is longer action time, is subjected to simultaneously the destruction on the recurring structure of influencing of biological enzyme in the body easily.Therefore, the fluorescence chemical sensor molecules that detects sulfurous acid hydrogen radical ion in the organism is very important to design and develop a kind of new can being applicable to.
Summary of the invention
A kind of ratio type of the present invention sulfurous acid hydrogen radical ion fluorescent probe and preparation method, purpose is to overcome the deficiencies in the prior art, provides a kind of product that obtains with benzindole quinoline and aromatic aldehyde condensation as the sulfurous acid hydrogen radical ion fluorescent probe of probe molecule and preparation method's technical scheme.
A kind of ratio type of the present invention sulfurous acid hydrogen radical ion fluorescent probe, it is characterized in that it being an a kind of class sulfurous acid hydrogen radical ion fluorescent probe that obtains with benzindole quinoline and aromatic aldehyde condensation, the used aromatic aldehyde of such fluorescent probe comprises that to trifluoromethylated benzaldehyde, paranitrobenzaldehyde, 4-chloro-benzaldehyde, aubepine, paradimethy laminobenzaldehyde and phenyl aldehyde, its general structure is:
Such fluorescent probe is used for detection analysis and the spike of the sulfurous acid hydrogen radical ion of water environment system and biomass cells system.
The preparation method of above-mentioned a kind of ratio type sulfurous acid hydrogen radical ion fluorescent probe, it is characterized in that be a kind of product that obtains with benzindole quinoline and aromatic aldehyde condensation as the preparation method of the sulfurous acid hydrogen radical ion fluorescent probe of probe molecule, its synthetic route is:
Its synthetic method is: be solvent with the anhydrous acetonitrile, adding mol ratio is benzindole and the methyl iodide back flow reaction 1h of 1:3, obtain pure intermediate with the anhydrous acetonitrile recrystallization behind the cold filtration, be solvent with the dehydrated alcohol, adding mol ratio is intermediate and the aromatic aldehyde back flow reaction 12h of 1:1, reaction back cold filtration gets crude product, and crude product obtains a pure class ratio type sulfurous acid hydrogen radical ion fluorescent probe molecule with the dehydrated alcohol recrystallization, and its synthesis step is:
1) intermediate is synthetic
Under the nitrogen protection, in round-bottomed flask, adding mol ratio is 2,2 of 1:3; 3-trimethylammonium-4,5-benzindole and methyl iodide and acetonitrile, reflux 1h, cold filtration; the cold diethyl ether washing obtains white solid after the drying, productive rate 90%, and the acetonitrile recrystallization obtains pure intermediate.
2) probe molecule is synthetic
Under the nitrogen protection, in round-bottomed flask, add intermediate and aromatic aldehyde and the dehydrated alcohol of equimolar amount, reflux 12h, cold filtration obtains solid after the drying, productive rate 70 ~ 90%, the acetonitrile recrystallization obtains pure probe molecule.
A kind of ratio type of the present invention sulfurous acid hydrogen radical ion fluorescent probe and preparation method's advantage is: the synthetic of (1) fluorescent probe only needs two-step reaction, and aftertreatment is simple, and raw material is easy to get, and cost is low; (2) good water solubility can detect the bisulfite root in the aqueous solution; (3) this probe has outstanding detection sensitivity, after having an effect with the bisulfite root, produce the variation of three kinds of optical properties (color, light splitting, fluorescence) simultaneously, change based on its specificity and obvious color, this probe can be used as the specificity indicator that shows that bisulfite exists in the aqueous solution, can carry out scene visual colorimetry detection qualitatively in real time.Therefore, the present invention is a kind of simple, quick, sensitive bisulfite root detection reagent.Its performance will describe in detail in an embodiment by reference to the accompanying drawings.
Description of drawings
Fig. 1 is the sulfurous acid hydrogen radical ion fluorescent probe that the present invention relates to.
Fig. 2 is fluorescent probe
1In PBS buffered soln (10 mM, pH=7.4), the sulfurous acid hydrogen radical ion fluorescence intensity is schemed over time.Concentration and probe concentration is 1 * 10
-5M, sulfurous acid hydrogen radical ion 2 equivalents.Excitation wavelength is 355nm, and slit width is 5 nm/5 nm.X-coordinate is the time, and ordinate zou is the fluorescence intensity ratio at 465nm and 571nm place.
Fig. 3 is fluorescent probe in the invention
1In PBS buffered soln (10 mM, pH=7.4) to the fluorometric titration graphic representation of sulfurous acid hydrogen radical ion.Concentration and probe concentration is 1 * 10
-5M, sulfurous acid hydrogen radical ion concentration is the 0-10 equivalent.Excitation wavelength is 355nm, and slit width is 5 nm/5 nm.X-coordinate is wavelength, and ordinate zou is fluorescence intensity.
Fig. 4 is the graph of a relation of 465 nm place fluorescence intensities shown in Figure 2 and sulfurous acid hydrogen radical ion concentration in the invention.X-coordinate is sulfurous acid hydrogen radical ion concentration, and ordinate zou is fluorescence intensity.
Fig. 5 is the invention middle probe
1In PBS buffered soln (10 mM, pH=7.4), add various negatively charged ion (HSO
3 –, 2 equivalents, CN
–, F
–, Cl
–, Br
–, I
–, AcO
–, ClO
4 –, ClO
–, NO
3 –, NO
2 –, N
3 –, HS
–, SCN
–, SO
4 2 –, CO
3 2 –, PO
4 3 –, HPO
4 2 –And H
2PO
4 –. 5 equivalents), free radical (O, HO and NO, 5 equivalents) and molecule (EtSH and HOCH
2CH
2SH, 5 equivalents, Cys and GSH, 100 equivalents) fluorescence spectrum figure.White is for adding the fluorescence intensity of different chaff interferences, and black be again the fluorescence intensity of adding sulfurous acid hydrogen radical ion in the chaff interference.
Embodiment
The present invention is described further below by example:
The synthetic method of probe molecule:
1) intermediate is synthetic
Under the nitrogen protection, in the 100mL round-bottomed flask, add 2; 2; 3-trimethylammonium-4,5-benzindole 6g(28.7mmol), methyl iodide 8.4g(60mmol) and acetonitrile 20mL; reflux 1h; cold filtration, a small amount of cold diethyl ether washing obtains white solid 9g after the drying; productive rate 90%, the acetonitrile recrystallization obtains pure intermediate.
2) probe molecule
1Synthetic
Under the nitrogen protection; in the 50mL round-bottomed flask; add intermediate 1.053g (3mmol); to trifluoromethylated benzaldehyde 0.52g (3mmol) and dehydrated alcohol 10 mL; reflux 12h, cold filtration obtains orange/yellow solid 1.4g after the drying; productive rate 90%, the acetonitrile recrystallization obtains pure probe molecule.
Probe molecule
2Synthetic
Synthetic described in enforcement mode 1.With paranitrobenzaldehyde 0.453g(3mmol) replace trifluoromethylated benzaldehyde.Get orange solids 1.3g, productive rate 90% after the drying.
Probe molecule
3Synthetic
Synthetic described in enforcement mode 1.With 4-chloro-benzaldehyde 0.42g(3mmol) replace trifluoromethylated benzaldehyde.Get orange/yellow solid 1.1g, productive rate 80% after the drying.
Probe molecule
4Synthetic
Synthetic described in enforcement mode 1.With aubepine 0.41g(3mmol) replace trifluoromethylated benzaldehyde.Get orange red solid 1.0g, productive rate 70% after the drying.
Embodiment 5
Probe molecule
5Synthetic
Synthetic described in enforcement mode 1.With paradimethy laminobenzaldehyde 0.45g(3mmol) replace trifluoromethylated benzaldehyde.Get garnet solid 1.0g, productive rate 70% after the drying.
Probe molecule
6Synthetic
Synthetic described in enforcement mode 1.With phenyl aldehyde 0.32g(3mmol) replace trifluoromethylated benzaldehyde.Get yellow solid 1.0g, productive rate 77% after the drying.
Embodiment 7
1 * 10
-5The M probe molecule
1PBS buffered soln (10 mM, pH=7.4), add the sulfurous acid hydrogen radical ion of 2 equivalents, detect that the probe fluorescence intensity of solution changes (Fig. 2) under the different time.Find that fluorescence intensity reaches stable behind 4min, so the optimum detection time is 4 min.
1 * 10
-5The M probe molecule
1PBS buffered soln (10 mM, pH=7.4), add the sulfurous acid hydrogen radical ion aqueous solution of 0 ~ 10 equivalent respectively, detect fluorescence intensity of solution and change (Fig. 3).Discovery is along with the increase of sulfurous acid hydrogen radical ion, and the emission peak at 580nm place descends gradually, and new emission peak has appearred in 465nm, simultaneously, launching site occurred waiting at the 450nm place.Be that reaction reaches balance substantially, even add more sulfurous acid hydrogen radical ion, does not also cause the variation (Fig. 4) of fluorescence intensity when sulfurous acid hydrogen radical ion reaches 2 equivalents.
1 * 10
-5The M probe molecule
1PBS buffered soln (10 mM, pH=7.4), add interfering ion, free radical, the molecule (Fig. 5) of 5 equivalents respectively.Discovery has only sulfurous acid hydrogen radical ion that the fluorescence of probe molecule is obviously strengthened, and illustrates that probe molecule is very good to the selectivity of sulfurous acid hydrogen radical ion.
Claims (2)
1. ratio type sulfurous acid hydrogen radical ion fluorescent probe, it is characterized in that it being an a kind of class sulfurous acid hydrogen radical ion fluorescent probe that obtains with benzindole quinoline and aromatic aldehyde condensation, the used aromatic aldehyde of such fluorescent probe comprises that to trifluoromethylated benzaldehyde, paranitrobenzaldehyde, 4-chloro-benzaldehyde, aubepine, paradimethy laminobenzaldehyde and phenyl aldehyde, its general structure is:
Such fluorescent probe is used for detection analysis and the spike of the sulfurous acid hydrogen radical ion of water environment system and biomass cells system.
2. the preparation method of the described a kind of ratio type sulfurous acid hydrogen radical ion fluorescent probe of claim 1, it is characterized in that be a kind of product that obtains with benzindole quinoline and aromatic aldehyde condensation as the preparation method of the sulfurous acid hydrogen radical ion fluorescent probe of probe molecule, its synthetic route is:
Its synthetic method is: be solvent with the anhydrous acetonitrile, adding mol ratio is benzindole and the methyl iodide back flow reaction 1h of 1:3, obtain pure intermediate with the anhydrous acetonitrile recrystallization behind the cold filtration, be solvent with the dehydrated alcohol, adding mol ratio is intermediate and the aromatic aldehyde back flow reaction 12h of 1:1, and reaction back cold filtration gets crude product, crude product obtains a pure class ratio type sulfurous acid hydrogen radical ion fluorescent probe molecule with the dehydrated alcohol recrystallization, and its synthesis step is:
1) intermediate is synthetic
Under the nitrogen protection, in round-bottomed flask, adding mol ratio is 2,2 of 1:3,3-trimethylammonium-4,5-benzindole and methyl iodide and acetonitrile, reflux 1h, cold filtration, the cold diethyl ether washing obtains white solid after the drying, productive rate 90%, and the acetonitrile recrystallization obtains pure intermediate;
2) probe molecule is synthetic
Under the nitrogen protection, in round-bottomed flask, add intermediate and aromatic aldehyde and the dehydrated alcohol of equimolar amount, reflux 12h, cold filtration obtains solid after the drying, productive rate 70 ~ 90%, the acetonitrile recrystallization obtains pure probe molecule.
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| CN103554126A (en) * | 2013-11-15 | 2014-02-05 | 西安石油大学 | Preparation method and application of fluorescein derivative serving as tracer agent for oil field |
| CN104262287A (en) * | 2014-09-02 | 2015-01-07 | 苏州罗兰生物科技有限公司 | Preparation and application of sulfite ratiometric fluorescent probe |
| CN104610955A (en) * | 2014-05-16 | 2015-05-13 | 中南大学 | Synthesis method and application of ratiometric fluorescent molecular probe for simultaneously detecting fluorine ion and sulfite radical |
| CN104945307A (en) * | 2015-05-18 | 2015-09-30 | 北京科技大学 | Benzoindolyl salt material and nonlinear optical crystal thereof, and preparation method and application thereof |
| CN105037359A (en) * | 2015-07-06 | 2015-11-11 | 河南大学 | Compound with hemicyanine-naphthalimide structure, and preparation method and application thereof |
| CN105112049A (en) * | 2015-09-23 | 2015-12-02 | 山东理工大学 | Sulfite ratiometric fluorescence probe and preparation method thereof |
| CN105203512A (en) * | 2015-09-16 | 2015-12-30 | 山西大学 | Carbazole fluorescent probe and preparation method and application thereof |
| CN105348268A (en) * | 2015-09-24 | 2016-02-24 | 四川大学 | Substituted carbazole-indole sulfonate derivative, and preparation method therefor and use thereof |
| CN106518749A (en) * | 2016-11-07 | 2017-03-22 | 湖南师范大学 | Rate type difunctional fluorescence molecular probe for detecting HSO4- ions, SO2 and derivatives thereof |
| CN108129428A (en) * | 2018-01-09 | 2018-06-08 | 山东大学 | A kind of ratio fluorescent probe for detecting bisulfite and its application |
| CN108226106A (en) * | 2017-11-07 | 2018-06-29 | 泰山医学院 | Ratio-type sulfite ion fluorescence probe based on half flower cyanines of indolizine-cyanofuran |
| CN108623575A (en) * | 2017-03-21 | 2018-10-09 | 泰山医学院 | A kind of fluorescence probe that is simple and effectively detecting sulphite |
| CN109856104A (en) * | 2019-04-15 | 2019-06-07 | 齐齐哈尔大学 | A kind of half cyanines derivative pH fluorescence probe of benzindole and preparation method thereof |
| CN110283213A (en) * | 2019-05-31 | 2019-09-27 | 中南民族大学 | Colorimetric probe and synthetic method and the application of detectable bisulfate ion and mercury ion |
| CN110590762A (en) * | 2019-09-24 | 2019-12-20 | 河南牧业经济学院 | Ratio type fluorescent probe for detecting bisulfite and preparation method and application thereof |
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| CN103554126B (en) * | 2013-11-15 | 2016-04-13 | 西安石油大学 | The fluorescein derivative preparation method of oil field tracer agent and application |
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| CN104262287B (en) * | 2014-09-02 | 2016-06-08 | 苏州罗兰生物科技有限公司 | The preparations and applicatio of a kind of inferior sulfate radical ratio fluorescent probe |
| CN104262287A (en) * | 2014-09-02 | 2015-01-07 | 苏州罗兰生物科技有限公司 | Preparation and application of sulfite ratiometric fluorescent probe |
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| CN105348268B (en) * | 2015-09-24 | 2018-11-16 | 四川大学 | Substituted carbazole-indoles sulfonate derivatives and its preparation method and application |
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| CN108129428B (en) * | 2018-01-09 | 2021-07-09 | 山东大学 | Ratiometric fluorescent probe for detecting bisulfite and application thereof |
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Application publication date: 20130904 |