CN104529936A - High-sensitivity high-selectivity fluorescence probe capable of real-time responding hypochlorous acid and application of high-sensitivity high-selectivity fluorescence probe - Google Patents
High-sensitivity high-selectivity fluorescence probe capable of real-time responding hypochlorous acid and application of high-sensitivity high-selectivity fluorescence probe Download PDFInfo
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- CN104529936A CN104529936A CN201410781552.0A CN201410781552A CN104529936A CN 104529936 A CN104529936 A CN 104529936A CN 201410781552 A CN201410781552 A CN 201410781552A CN 104529936 A CN104529936 A CN 104529936A
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- hypochlorous acid
- fluorescence probe
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- hypochlorite
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- OVJLMQOPYWHKRH-UHFFFAOYSA-N Oc1c(C2Sc3ccccc3N2)cccc1 Chemical compound Oc1c(C2Sc3ccccc3N2)cccc1 OVJLMQOPYWHKRH-UHFFFAOYSA-N 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- 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
-
- 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
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
Abstract
The invention relates to a high-sensitivity high-selectivity fluorescence probe capable of real-time responding hypochlorous acid and application of the high-sensitivity high-selectivity fluorescence probe. The fluorescence probe is a kind of 2-benzothiazoline phenol compounds specifically and can be used as the fluorescence probe to be used for detection of hypochlorous acid/hypochlorite. By utilizing the fluorescence probe, at least one of the technical effects can be realized, for example, hypochlorous acid/hypochlorite can be identified with high sensitivity and high selectivity, response to hypochlorous acid/hypochlorite can be realized instantly, real-time detection to hypochlorous acid/hypochlorite can be realized, the fluorescence probe is stable in character and can be stored and used for long term, detection to hypochlorous acid/hypochlorite is easy under the condition of physiological level, and the fluorescence probe has strong antijamming capability.
Description
Technical field
The present invention relates to 2-[4-morpholinodithio quinoline phenol compound as hypochlorous acid fluorescent probe, it can carry out real-time highly sensitive highly selective identification application to hypochlorous acid under physiological level condition, or it can measure the concentration of hypochlorous acid/hypochlorite in biological sample and water.
Background technology
Hypochlorous acid (HClO) or hypochlorite (ClO
-) be extremely important one in reactive oxygen species, it all plays a part key from resisting in vivo in drinking water disinfection that pathogenic agent intrudes into our daily life.In vivo, when pathogenic agent is invaded, in phagosome, myeloperoxidase (MPO) catalyzing hydrogen peroxide and chlorion produce the normal operation that hypochlorite carrys out eliminating pathogen maintenance organism.In addition, hypochlorite can also the chemical transformation of the various biomolecules such as Function protein matter, DNA and RNS.In our daily life, hypochlorite is widely used as sterilizing agent and SYNTHETIC OPTICAL WHITNER due to its strong oxidizing property, such as supplies the sterilization of water, the sterilization etc. of swimming pool, and therefore, hypochlorite is full of in the environment of our life.
But, be no matter the ClO in body
-excessive generation is still from external excess ingestion ClO
-all the significant threat to HUMAN HEALTH: due to ClO
-high reaction activity and without specific aim, as ClO excessive in body
-during generation, its meeting attack host cell as destruction pathogenic agent microorganism, causes the infringement of host tissue, causes a series of diseases be associated, such as kidney disease, arteriosclerosis, inflammation even cancer.In addition, as ClO in environment
-and after resultant taken in by human body, also can bring a series of untoward reaction.Such as, can cause with the oxymuriate that generates residual in the water after chlorine disinfectant or in other environment and chlorite and have a stomach upset, more seriously, there is the organic disinfection byproduct (DBP) (DBPS) the such as trichloromethane and chloroacetic potential threat that produce severe toxicity.Therefore, no matter be in viable cell or environment, we need to develop one can rapid detection ClO
-simple efficient means.
Up to the present, at numerous ClO such as volumetry, colorimetry, electrochemical detection method, chromatography and fluorescence probe method
-in detection method, fluorescence probe method becomes the focus that researchist pays close attention to because having simple to operate, highly sensitive and can realize the advantages such as real-time in-situ imaging analysis.Unfortunately, at present still there is numerous defect in the fluorescent probe of report, as low in sensitivity, poor selectivity, response speed slow and synthesis is complicated etc.In order to disclose ClO further
-physiological function and pathogenesis, development highly sensitive, highly selective, synthesis are simple and can the fluorescent probe of real-time response be those skilled in the art's urgent problems.
Summary of the invention
A kind of highly sensitive, highly selective and prepare the hypochlorous fluorescent probe of simple real-time response are badly in need of in this area, thus effectively can detect and particularly can detect hypochlorous acid under physiological level condition.For this reason, the present invention has synthesized the hypochlorous acid fluorescent probe of a class novelty, and its synthesis is simple, good stability and/or highly sensitive and/or selectivity is high, and/or can identify hypochlorous acid fast.Probe of the present invention can carry out hypochlorous mensuration under physiological level condition.
Specifically, the invention provides a kind of hypochlorous acid fluorescent probe, it is 2-[4-morpholinodithio quinoline phenol compound, and its structure is as follows:
Preferably, fluorescent probe of the present invention is:
In the preparation method of hypochlorous acid fluorescent probe of the present invention, temperature of reaction is 60 ~ 140 DEG C; Reaction times is 1h ~ 24h; Reaction solvent is one or both in the organic reagents such as methyl alcohol, ethanol, Virahol, propyl carbinol, acetonitrile, toluene and dimethylbenzene; The mol ratio of near amino thiophenols compounds and salicylic aldehyde compounds is 1:1 to 1:5, is preferably 1:2.
Present invention also offers the detection preparation for detecting hypochlorous acid concentration in sample (such as blood sample) or test kit, it comprises probe of the present invention.Preferably, detection preparation of the present invention or test kit also comprise the working instructions of product.Also preferably, test kit of the present invention also comprises the buffer reagent for measuring hypochlorous acid concentration in sample.
Present invention also offers the method detecting hypochlorous acid concentration in sample (such as blood sample), it comprises the step that probe of the present invention contacts with sample to be tested.
Present invention also offers the purposes of probe of the present invention in the preparation for the preparation of the middle hypochlorous acid concentration of detection sample (such as blood sample).
Present invention also offers the purposes of probe of the present invention in the test kit for the preparation of the middle hypochlorous acid concentration of detection sample (such as blood sample).
Fluorescent probe of the present invention can carry out instantaneous reaction with hypochlorous acid, and its result result in the remarkable enhancing change of solution fluorescence spectrum, thus can realize hypochlorous real-time qualitative and detection by quantitative.
Specifically, hypochlorous acid fluorescent probe of the present invention respectively with hydrogen peroxide, tertbutanol peroxide, potassium superoxide, hydroxyl free radical, tertbutanol peroxide free radical and the effect of sodium nitrite isoreactivity chalcogenide all can not cause the obvious change of fluorescence spectrum, thus achieve hypochlorous Selective recognition, and then optionally for getting rid of hydrogen peroxide, tertbutanol peroxide, potassium superoxide, hydroxyl free radical, the interference that the existence of these active oxygen compounds of group such as tertbutanol peroxide free radical and sodium nitrite measures hypochlorous qualitative and quantitative.
Hypochlorous acid fluorescent probe of the present invention better water-soluble, thus to hypochlorous detection under physiological level condition can be conducive to.
Selectively, the good stability of hypochlorous acid fluorescent probe of the present invention, and then use can be preserved for a long time.
Further, hypochlorous acid fluorescent probe of the present invention is the hypochlorous fluorescent probe of highly sensitive highly selective real-time response, and synthesis is simple, is conducive to business-like applying.
Accompanying drawing explanation
Fig. 1 a and Fig. 1 b is the impact of different concns NaClO (0 ~ 1000 μM) on probe (5 μMs) fluorescence spectrum.
Fig. 2 is the impact of different analyte (200 μMs) on probe (5 μMs) fluorescence spectrum.
Fig. 3 is the impact of different analyte (200 μMs) on probe (5 μMs) fluorescence spectrum quantitative analysis NaClO (200 μMs).
Fig. 4 is that probe (5 μMs) is to the test result of NaClO (200 μMs) time of response.
Embodiment:
The invention provides the synthetic route of above-mentioned highly sensitive highly selective real-time response hypochlorous acid fluorescent probe, method and spectrum property thereof.
Hypochlorous acid fluorescent probe of the present invention is a class 2-[4-morpholinodithio quinoline phenol compound, and it has following general structure
In above formula: R
1, R
2, R
3, R
4, R
5, R
6, R
7and R
8for hydrogen atom, straight or branched alkyl, straight or branched alkoxyl group, sulfonic group, ester group, carboxyl; R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8can be identical or different.
Synthetic route and the method for such hypochlorous acid fluorescent probe are as follows:
Particularly, fluorescent probe of the present invention can be prepared by the following method, the near amino thiophenols compounds (such as near amino thiophenols) of certain mol proportion (such as 1:1 ~ 1:5) and salicylic aldehyde compounds (such as salicylic aldehyde) are dissolved in organic reagent (mixed solvent of such as propyl carbinol and toluene), then thermostatically heating for some time (such as 10h) under high temperature (such as 120 DEG C), revolving after reaction terminates boils off except organic solvent, finally debris is carried out pillar layer separation and obtains sterling fluorescent probe.
Therefore, present invention also offers near amino thiophenols compounds for the preparation of the purposes detected in hypochlorous fluorescent probe.
Present invention also offers salicylic aldehyde compounds for the preparation of the purposes detected in hypochlorous fluorescent probe.
The notable feature of hypochlorous acid fluorescent probe of the present invention is can instantaneous highly sensitive highly selective identification hypochlorous acid/hypochlorite, and/or accurately can carry out quantitative analysis to hypochlorous acid/hypochlorite under the existence of other high-strength hydrogen peroxides, tertbutanol peroxide, potassium superoxide, hydroxyl free radical, tertbutanol peroxide free radical and sodium nitrite isoreactivity chalcogenide.
Below will by illustrating in greater detail the present invention by following examples.Following examples are only illustrative, should be understood that the present invention not by the restriction of following embodiment.
Embodiment 1
122mg (1.0mmol) salicylic aldehyde, 125mg (1.0mmol) near amino thiophenols are dissolved in the mixed solvent of 15mL propyl carbinol and toluene (volume ratio is 7:3) by (scheme 1), then under the constant temperature of 120 DEG C, react 10h.Then revolved by reaction soln and boil off except propyl carbinol and toluene obtain thick product, use dichloromethane system to carry out pillar layer separation, obtain white pure product 144mg, productive rate is 63 ﹪.
183mg (1.5mmol) salicylic aldehyde, 125mg (1.0mmol) near amino thiophenols are dissolved in the mixed solvent of 15mL propyl carbinol and toluene (volume ratio is 7:3) by (scheme 2), then under the constant temperature of 120 DEG C, react 10h.Then revolved by reaction soln and boil off except propyl carbinol and toluene obtain thick product, use dichloromethane system to carry out pillar layer separation, obtain white pure product 172mg, productive rate is 75 ﹪.
244mg (2.0mmol) salicylic aldehyde, 125mg (1.0mmol) near amino thiophenols are dissolved in the mixed solvent of 15mL propyl carbinol and toluene (volume ratio is 7:3) by (scheme 3), then under the constant temperature of 120 DEG C, react 10h.Then revolved by reaction soln and boil off except propyl carbinol and toluene obtain thick product, use dichloromethane system to carry out pillar layer separation, obtain white pure product 188mg, productive rate is 82 ﹪.
366mg (3.0mmol) salicylic aldehyde, 125mg (1.0mmol) near amino thiophenols are dissolved in the mixed solvent of 15mL propyl carbinol and toluene (volume ratio is 7:3) by (scheme 4), then under the constant temperature of 120 DEG C, react 10h.Then revolved by reaction soln and boil off except propyl carbinol and toluene obtain thick product, use dichloromethane system to carry out pillar layer separation, obtain white pure product 213mg, productive rate is 93 ﹪.
488mg (4.0mmol) salicylic aldehyde, 125mg (1.0mmol) near amino thiophenols are dissolved in the mixed solvent of 15mL propyl carbinol and toluene (volume ratio is 7:3) by (scheme 5), then under the constant temperature of 120 DEG C, react 10h.Then revolved by reaction soln and boil off except propyl carbinol and toluene obtain thick product, use dichloromethane system to carry out pillar layer separation, obtain white pure product 218mg, productive rate is 95 ﹪.
1h-NMR (400MHz, DMSO-d
6) δ (* 10
-6): 7.03 (t, J=6Hz, 1H), 7.10 (d, J=8Hz, 1H), 7.40-7.47 (m, 2H), 7.55 (t, J=8Hz, 1H), 8.07 (d, J=8Hz, 1H), 8.14 (d, J=8Hz, 1H), 8.18 (d, J=8Hz, 1H), 11.62 (s, 1H);
13c-NMR (100MHz, DMSO-d
6) δ (* 10
-6): 117.44,118.79,120.23,122.47,122.59,125.56,126.94,128.99,132.95,134.71,151.90,156.75,165.71.ESI-MS calculated value C
13h
10nOS [M-H]
-228; Measured value 228.
Embodiment 2
The present inventor has carried out following test: (a) different concns NaClO (0 ~ 1000 μM) is on the impact of probe (5 μMs) fluorescence spectrum; Linear relationship between the fluorescence intensity at (b) 468nm place and the NaClO concentration (0 ~ 600 μM) added.Said determination is the mixed system (5:5 at acetonitrile and water, v/v, 5mM PBS, pH=7.4) in carry out, the probe used is compound prepared in embodiment 1, and all spectrum tests all at 25 DEG C the NaClO effect that adds record after 2 minutes.Result is see Fig. 1.
As can be seen from Figure 1, along with the increase of NaClO concentration in probe solution, fluorescence spectrum rises gradually, and in the NaClO concentration range of 0 ~ 600 μM, concentration and the fluorescence intensity of NaClO are linear.Therefore, quantitative analysis can be carried out to the NaClO in biological sample and water by means of probe of the present invention.
Embodiment 3
Different analyte (200 μMs) is on the impact of probe (5 μMs) fluorescence spectrum.Analyte comprises: hydrogen peroxide H
2o
2, tertbutanol peroxide TBHP, potassium superoxide KO
2, hydroxyl free radical OH, tertbutanol peroxide free radical TBHP, sodium nitrite NaONOO, clorox NaClO.All tests are the mixed system (5:5 at acetonitrile and water, v/v, 5mMPBS, pH=7.4) in carry out, the probe used is compound prepared in embodiment 1, and all spectrum tests all at 25 DEG C the analyte effect that adds record after 2 minutes.Particularly, the probe storing solution (1mM) pipetting 50 μ L is put in 10mL colorimetric cylinder, then 5mL acetonitrile is added, pipetting the above-mentioned analyte storing solution (10mM) of 200 μ L again adds in colorimetric cylinder, then PBS solution (the pH=7.4 of 0.5mL is pipetted, 100mM), finally 10mL is settled to ultrapure water.Shake up, leave standstill 2 minutes, can measure.Result as shown in Figure 2.
As can be seen from Figure 2, probe has very high selectivity to hypochlorite, can react with hypochlorite in specific manner, after reaction, fluorescence spectrum has remarkable enhancing, and after the Typical reactive chalcogenide such as hydrogen peroxide existed in organism and probe effect, fluorescence intensity considerable change does not occur.
Embodiment 4
Different analyte (200 μMs) is on the impact of probe (5 μMs) fluorescence spectrum quantitative analysis clorox (200 μMs).Analyte comprises: hydrogen peroxide H
2o
2, tertbutanol peroxide TBHP, potassium superoxide KO
2, hydroxyl free radical OH, tertbutanol peroxide free radical TBHP and sodium nitrite NaONOO.All tests are the mixed system (5:5 at acetonitrile and water, v/v, 5mM PBS, pH=7.4) in carry out, the probe used is compound prepared in embodiment 1, and all spectrum tests all at 25 DEG C the analyte effect that adds record after 2 minutes.Result as shown in Figure 3.
As can be seen from Figure 3, the Typical reactive chalcogenides such as the hydrogen peroxide existed in organism can not obviously disturb probe to the qualitative and quantitative analysis of clorox.
Embodiment 5
Probe (5 μMs) is to the test result of NaClO (200 μMs) time of response.First, the probe storing solution (1mM) pipetting 50 μ L is put in 10mL colorimetric cylinder, then 5mL acetonitrile is added, add the PBS solution (pH=7.4,100mM) of 0.5mL to it, then pipette the NaClO storing solution (10mM) of respective volume, finally be settled to 10mL with ultrapure water, shake up fast, timing measures, and wherein used probe is compound prepared in embodiment 1.Result as shown in Figure 4.
As can be seen from Figure 4, NaClO and probe reaction after 1 minute fluorescence intensity namely reach maximum value and tend towards stability.The rapidity that this fluorescence intensity strengthens and palpability illustrate that this probe may be used for the real-time detection of clorox completely.
Although with above embodiments describing the present invention, should be understood that, under the prerequisite not deviating from spirit of the present invention, the present invention can further modify and change, and these are modified and variation all belongs within protection scope of the present invention.
Claims (10)
1. compound, it has following structure
In above formula: R
1, R
2, R
3, R
4, R
5, R
6, R
7and R
8independently selected from hydrogen atom, straight or branched alkyl, straight or branched alkoxyl group, sulfonic group, ester group, carboxyl; R
1, R
2, R
3, R
4, R
5, R
6, R
7, R
8can be identical or different.
2. compound according to claim 1, it is
3., for detecting the preparation of hypochlorous acid in sample/hypochlorite content, it comprises the compound according to claim 1 or 2.
4. preparation according to claim 3, wherein said sample is blood sample.
5., for detecting the test kit of hypochlorous acid in sample/hypochlorite content, it comprises the compound according to claim 1 or 2.
6. test kit according to claim 5, wherein said sample is blood sample.
7. the test kit according to any one of claim 5-6, it also comprises working instructions.
8. the test kit according to any one of claim 5-6, it also comprises the buffer reagent for detecting hypochlorous acid in sample/hypochlorite content.
9. according to the compound in claim 1 or 2 for the preparation of the purposes detected in sample in hypochlorous acid/hypochlorite content.
10. purposes according to claim 9, wherein said detection sample is liquid sample.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105441065A (en) * | 2015-11-18 | 2016-03-30 | 浙江理工大学 | Fluorescent probe for detecting hypochlorite ions as well as preparation method and using method thereof |
| CN106596479A (en) * | 2016-11-29 | 2017-04-26 | 福州大学 | Fluorescent sensor used for detection of free chlorine |
| CN108409685A (en) * | 2018-02-09 | 2018-08-17 | 华南理工大学 | With the photoactivation aggregation-induced emission probe of in-situ preparation ability and its preparation and application |
| CN113461637A (en) * | 2021-08-10 | 2021-10-01 | 广东石油化工学院 | Fluorescence probe based on benzothiazole fluorophore and application of fluorescence probe in hypochlorous acid detection |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010036922A1 (en) * | 2008-09-26 | 2010-04-01 | Enzo Life Sciences, Inc. | Profiling reactive oxygen, nitrogen and halogen species |
-
2014
- 2014-12-16 CN CN201410781552.0A patent/CN104529936A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010036922A1 (en) * | 2008-09-26 | 2010-04-01 | Enzo Life Sciences, Inc. | Profiling reactive oxygen, nitrogen and halogen species |
Non-Patent Citations (3)
| Title |
|---|
| ALBERTO DONZELLI，等: "TiIV Complexes of Redox-Active Schiff Bases", 《EUR.J.INORG.CHEM.》 * |
| STEFAN METZ，等: "Synthesis and Structural Characterization of Neutral Hexacoordinate Silicon(IV) Complexes with SiO2N4 Skeletons", 《CHEM. ASIAN J.》 * |
| ZHISHENG WU，等: "Benzothiazoline based chemodosimeters for fluorogenic detection of hypochlorous acid", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105441065A (en) * | 2015-11-18 | 2016-03-30 | 浙江理工大学 | Fluorescent probe for detecting hypochlorite ions as well as preparation method and using method thereof |
| CN106596479A (en) * | 2016-11-29 | 2017-04-26 | 福州大学 | Fluorescent sensor used for detection of free chlorine |
| CN106596479B (en) * | 2016-11-29 | 2019-07-09 | 福州大学 | A kind of fluorescent optical sensor for free chlorine detection |
| CN108409685A (en) * | 2018-02-09 | 2018-08-17 | 华南理工大学 | With the photoactivation aggregation-induced emission probe of in-situ preparation ability and its preparation and application |
| CN108409685B (en) * | 2018-02-09 | 2021-06-08 | 华南理工大学 | Light-activated aggregation-induced emission probe with in-situ generation capability and preparation and application thereof |
| CN113461637A (en) * | 2021-08-10 | 2021-10-01 | 广东石油化工学院 | Fluorescence probe based on benzothiazole fluorophore and application of fluorescence probe in hypochlorous acid detection |
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Application publication date: 20150422 |