CN108218772A - It is a kind of to be used to detect fluorescence probe of hydrogen polysulfide and preparation method thereof and dedicated test kit - Google Patents
It is a kind of to be used to detect fluorescence probe of hydrogen polysulfide and preparation method thereof and dedicated test kit Download PDFInfo
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- CN108218772A CN108218772A CN201810242770.5A CN201810242770A CN108218772A CN 108218772 A CN108218772 A CN 108218772A CN 201810242770 A CN201810242770 A CN 201810242770A CN 108218772 A CN108218772 A CN 108218772A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
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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
- 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
Abstract
The present invention proposes a kind of for detecting fluorescence probe of hydrogen polysulfide and preparation method thereof and dedicated test kit,A kind of fluorescence probe for being used to detect hydrogen polysulfide,The fluorescence probe is 2 butyl 6 nitro 1H benzos [de] isoquinolin 1,3 (2H) diketone,The present invention is based on hydrogen polysulfides reduction reaction occurs with nitro,Using 4 nitros as specificly-response group,Using 1,8 naphthalimide fluorogens,Naphthalimide fluorogen itself has good photoluminescent property,Devise a kind of naphthalimide fluorescent probe,The kit of the design can then show yellowish and send out strong fluorescence after being reacted with hydrogen polysulfide,High sensitivity,The variation of color can be observed at >=10 μM for hydrogen polysulfide concentration,The chromogenic reaction only occurs under the conditions of existing for hydrogen polysulfide,Other common inorganic salts,Active nitrogen,Active oxygen,Amino acid,Vitamin,Biological sulfydryl species do not generate interference.
Description
Technical field
The present invention relates to chemical analysis, bioassay technique field, particularly relate to a kind of for detecting the glimmering of hydrogen polysulfide
Light probe and preparation method thereof and dedicated test kit.
Background technology
Active sulfur species (Reactive sulfur species, RSS) are the total of a kind of sulfur-bearing biomolecule in organism
Claim, be one of endogeneous activity species in organism.For example, sulfane sulphur, hydrogen sulfide, glutathione, hydrogen polysulfide etc..Wherein,
Direct oxidation form of the hydrogen polysulfide as hydrogen sulfide has inoxidizability, cytoprotective and oxidation-reduction quality.More vulcanizations
Hydrogen adjusts cell function by intracellular a series of redox signal.It is reported that some physiology participated in by hydrogen sulfide
Activity is actually mediated by hydrogen polysulfide.Therefore, it is right in order to obtain the more chemical property of hydrogen polysulfide and biological property
Its detection in biosystem is essential.
Invention content
The purpose of the present invention is to provide it is a kind of for detect fluorescence probe and preparation method thereof of hydrogen polysulfide with it is special
Detection kit.
The technical proposal of the invention is realized in this way：A kind of fluorescence probe for being used to detect hydrogen polysulfide, the fluorescence are visited
Needle is 2- butyl -6- nitro -1H- benzos [de] isoquinolin -1,3 (2H)-diketone, and structural formula is as shown in formula I：
The present invention proposes a kind of preparation method for the fluorescence probe for being used to detect hydrogen polysulfide, includes the following steps：
Under the conditions of existing for catalyst, in 30 DEG C~90 DEG C, by the 4- nitro-1,8-naphthalic acids acid anhydride described in formula II with
N-butylamine mixing carries out reduction reaction, reacts 1~24 hour, obtains compound shown in formula I,
Preferably, the catalyst is at least one of organic base and inorganic base；The organic base is triethylamine and pyrrole
At least one of pyridine；The inorganic base is at least one of potassium carbonate, sodium hydroxide, sodium carbonate and sodium bicarbonate.
Preferably, the molar ratio of the 4- nitro-1,8-naphthalic acids acid anhydride, n-butylamine and catalyst is 1：0.5~
5：0.5~5.
Preferably, the molar ratio of the 4- nitro-1,8-naphthalic acids acid anhydride, n-butylamine and catalyst is 1:1~4:1
~4.
Further preferably, the molar ratio of the 4- nitro-1,8-naphthalic acids acid anhydride, n-butylamine and catalyst is 1:1:
1 or 1:4:4.
Preferably, the reduction reaction carries out in organic solvent, and the organic solvent is n,N-Dimethylformamide, three
At least one of ethamine, ethyl alcohol and acetonitrile.
The present invention also proposes a kind of dedicated test kit, comprising compound and solvent shown in claim 1 Chinese style I,
A concentration of 1mM of compound shown in formula I,
Solvent is ethyl alcohol or dimethyl sulfoxide (DMSO).
Preferably, the buffer solution containing catalyst is further included,
The buffer solution is the phosphate buffer that pH value is 6.5~8.5, and the phosphate is selected from Na2HPO4、NaH2PO4
And KH2PO4At least one of；The phosphatic a concentration of 0.01~0.5M；The catalyst is cetyl trimethyl
Ammonium, a concentration of 0.01~0.1mM.
Application of the hydrogen polysulfide detection kit provided by the invention in hydrogen polysulfide content is measured, is especially being detected
It generates the application in hydrogen polysulfide content into the cell in biosystem, all belongs to the scope of protection of the present invention.
The method for measuring hydrogen polysulfide content, includes the following steps：
1) standard curve is made：
A) using 435nm as excitation wavelength, the solution for measuring a series of hydrogen polysulfide standard items of various concentrations is emitting
Wavelength is the fluorescence intensity at 540nm, is denoted as F；And measure reagent blank is the fluorescence intensity at 540nm in launch wavelength, is remembered
For F0, using the concentration C of hydrogen polysulfide as abscissa, fluorescence intensity change value Δ F is ordinate, draws standard curve；
Wherein, Δ F=F-F0；A series of solution of the hydrogen polysulfide standard items of various concentrations is by the hydrogen polysulfide
The Standard Stock solutions mixing of reagent stock liquid 1, reagent stock liquid 2 and hydrogen polysulfide in detection kit and obtain；
2) content of hydrogen polysulfide in sample to be tested is detected：
The step 1) the hydrogen polysulfide standard items are replaced with into sample to be tested, are examined according to described step 1) the method
It is the fluorescence intensity at 540nm that the sample to be tested, which is surveyed, in launch wavelength, is denoted as F ', the F ' is substituted into obtained by the step 1)
Standard curve, and then obtain the content of hydrogen polysulfide in the sample to be tested.
In above-mentioned detection method, in a series of solution of the hydrogen polysulfide standard items of various concentrations, more vulcanizations
The concentration of hydrogen is followed successively by 0,1,5,7,10,20,30,40,50,60,80 and 100 μM.
A series of volume of the solution of the hydrogen polysulfide standard items of various concentrations is 2mL.
In the Standard Stock solutions of the hydrogen polysulfide, solvent is water；It is more in the Standard Stock solutions of the hydrogen polysulfide
A concentration of 10mM of hydrogen sulfide.
The volume ratio of reagent stock liquid 1 and the reagent stock liquid 2 in the hydrogen polysulfide detection kit is 2mL：
10μL。
Hydrogen polysulfide detection kit provided by the invention, has the characteristics that：
1) the kit water white transparency of 2- butyl -6- nitro -1H- benzos [de] isoquinolin -1,3 (2H)-diketone is included, and
Unstressed configuration；And it can then show yellowish after being reacted with hydrogen polysulfide and send out strong fluorescence.
2) reaction speed is fast, can develop the color in 20 minutes.
3) high sensitivity, hydrogen polysulfide concentration can observe with the naked eye apparent yellowish generation at >=10 μM.
4) chromogenic reaction only occurs under the conditions of existing for hydrogen polysulfide, other common inorganic salts, active nitrogen, activity
Oxygen, amino acid, vitamin, biological sulfydryl species do not generate interference.
5) there are long fluorescence emission wavelengths (540nm), can be detected with fluorescent spectrometry, determination limit can be used for up to 26nM
Cell generates the detection of hydrogen polysulfide content under physiological condition.
The present invention is based on hydrogen polysulfides reduction reaction occurs with nitro, using 4- nitros as specificly-response group, adopts
With 1,8- naphthalimide fluorogens, naphthalimide fluorogen itself has good photoluminescent property：It is higher stability, larger
Stokes displacements and stronger fluorescent emission.Group of the n-butylamine as targeting endoplasmic reticulum, it is glimmering to devise a kind of naphthalimide
Light probe.Experiment finds that the fluorescence intensity of the probe in itself is very weak, after adding in hydrogen polysulfide, based on Intramolecular electron transfer
Mechanism, probe are opened, and solution fluorescence significantly increases and color becomes yellowish by almost colourless, shows that this method can be used for
The detection of hydrogen polysulfide.In order to verify the practicability of this method, and applied to the quantitative determination of hydrogen polysulfide in organism,
Using the principle, it is prepared for hydrogen polysulfide detection kit.The present invention have it is easy to operate, it is at low cost, it is rapidly and efficiently sensitive etc.
Advantage, easy to spread and application.The kit is a kind of function admirable, hydrogen polysulfide detection device easy to use, can be become
The related fields such as modern biology, physiology and medicine provide strong research tool.
Description of the drawings
In order to illustrate more clearly about the embodiment of the present invention or technical scheme of the prior art, to embodiment or will show below
There is attached drawing needed in technology description to be briefly described, it should be apparent that, the accompanying drawings in the following description is only this
Some embodiments of invention, for those of ordinary skill in the art, without having to pay creative labor, may be used also
To obtain other attached drawings according to these attached drawings.
Fig. 1 is the chemical equation of compound shown in formula I of the present invention.
Fig. 2 is the fluorescence spectrum that hydrogen polysulfide detection kit is reacted with the hydrogen polysulfide of various concentration.
Fig. 3 is fluorescence emission spectrum of the hydrogen polysulfide detection kit for various interference species reactions.
Fig. 4 is the absorbance change and fluorescence intensity change that hydrogen polysulfide detection kit detects hydrogen polysulfide.
Fig. 5 is the hydrogen polysulfide in hydrogen polysulfide detection kit detection cell.
Fig. 6 is hydrogen polysulfide in hydrogen polysulfide detection kit detection and localization endoplasmic reticulum.
Fig. 7 is hydrogen spectrogram (600MHz, the CDCl of formula I3,298K)。
Fig. 8 is carbon spectrogram (150MHz, the CDCl of formula I3,298K)。
Specific embodiment
Below by specific embodiment, the present invention will be described, but the present invention is not limited thereto.
Experimental method described in following embodiments is conventional method unless otherwise specified；The reagent and biological material
Material, unless otherwise specified, commercially obtains.
2- butyl -6- shown in embodiment 1, formula I nitro -1H- benzos [de] isoquinolin -1,3 (2H)-diketone
It is prepared according to chemical reaction flow figure shown in FIG. 1, operating procedure is as follows：By 4- nitro -1,8- naphthalene diformazans
Acid anhydrides (60.75mg, 0.25mmol) is dissolved in ethyl alcohol (10mL), adds in n-butylamine (36.57mg, 0.5mmol), catalyst three
Ethamine (50 μ L) reacts 6 hours in reaction solution, and at 80 DEG C.Reaction finishes, and after cooling, reduced pressure solvent, which obtains, slightly to be produced
Product, with methylene chloride/methanol (15：1, v/v) make eluent, column chromatography purification crude product obtains product 47.3mg.
The structural characterization data result of the product is as follows：
1H NMR(600MHz,CDCl3,298K):δ 8.80 (d, J=8.7Hz, 1H), 8.70 (d, J=7.3Hz, 1H),
8.66 (d, J=7.9Hz, 1H), 8.38 (d, J=7.9Hz, 1H), 7.97 (t, J=8.0Hz, 1H), 4.17 (t, J=7.6Hz,
2H), 1.71 (m, 2H), 1.44 (m, 2H), 0.98 (t, J=7.4Hz, 3H)；
13C NMR(150MHz,CDCl3,298K):δ163.2,162.4,149.5,132.3,129.9,129.7,129.2,
129.0,127.0,123.8,123.6,123.1,40.6,30.1,20.3,13.8.
By upper combination Fig. 7, Fig. 8 is it is found that the product structure is correct, for the 2- butyl -6- nitro -1H- benzos shown in formula I
[de] isoquinolin -1,3 (2H)-diketone.
Embodiment 2：The spectral quality that compound shown in formula I is reacted with various concentration hydrogen polysulfide
3mg reagents 1 are weighed, are made into 10mL dimethyl sulphoxide solutions as mother liquor (1mM).
The above-mentioned mother liquor of 100 μ L is added drop-wise in the 10mM phosphate buffer solutions containing 100 μM of catalyst (CTAB), so
Add in the hydrogen polysulfide solution of various concentration afterwards, then with the phosphate buffer solution constant volume of 10mM to 10mL.It is reacted at 37 DEG C
After 20min, its ultraviolet-visible absorption spectroscopy and fluorescence emission spectrum are measured.With 435nm deexcitations when fluorescence emission spectrum measures；
The slit width of excitation and transmitting is 5nm；Voltage 700V.
Fig. 2 is the fluorescence spectrum that reagent 1 is reacted with 0-100 μM of hydrogen polysulfide.
Fig. 2 the result shows that, the present invention in reagent 1 have the characteristics that：
1) probe is in the solution in colourless and unstressed configuration, but with the addition of hydrogen polysulfide, the probe is at about 430nm
Absorption is generated, and yellow-green fluorescence is generated at 540nm；
2) intensity of ultravioletvisible absorption and fluorescence intensity increase with the increase of hydrogen polysulfide concentration；
3) when using 10 μM of reagent 1, the concentration of Fluorescence Increasing and hydrogen polysulfide is linearly closed in the range of 0-260 μM
System.
Embodiment 3：Compound shown in formula I and other species response situations
Various substances are separately added into 10 μM of 1 solution of reagent：1Blank,RNS(2-5):150μM NO,50μM
ONOO-,50μM NO2 -,50μM NO3 -；ROS(6-10):50μM1O2,50μM HOCl,50μM HOBr,50μM H2O2,50μM
OH-；RSS(11-17):50μM SO2,50μM H2S2O3,50μM H2S,2nM GSH,50μM Hcy,500μM Cys,GSSG；18
50μM H2S2.After reacting 20min at 37 DEG C, its fluorescence emission spectrum is measured.Fluorescence emission spectrum is deactivated when measuring with 435nm
Hair；The slit width of excitation and transmitting is 10nm；Voltage 700V.
1 mother liquor of reagent (1mM) of 10 μ L is added in the solution for being mixed with above-mentioned various substances in 10mL, adding CTAB makes
Its ultimate density is 100 μM.
Fig. 3 is reagent 1 (10 μM) and the fluorescence emission spectrum obtained during various other material mixings.
The experimental results showed that only hydrogen polysulfide can cause reagent 1 to generate apparent optical signal response, it was demonstrated that the reagent pair
Hydrogen polysulfide has the selectivity of height, and the measure of hydrogen polysulfide is not interfered in the presence of other species.
Embodiment 4：The concentration of the hydrogen polysulfide that cell generates under physiological status is measured with hydrogen polysulfide kit quantification
1) cell culture：
In culture vessel with glass bottom (Corning Inc.), culture medium is used containing 10% (v/v) tire ox MCF-7 cell growths
DMEM (Dulbecco's modified eagle media) liquid of serum, 100U/mL penicillin and 100 μ g/mL streptomysins
Culture medium, 37 DEG C of environment temperature, gas concentration lwevel are controlled 5%.
2) making of working curve
1.1mg sodium disulfides are taken, are dissolved in 1mL secondary waters, are made into the Standard Stock solutions of 10mM hydrogen polysulfides；In addition,
In sample bottle, 100 μM and 10 μ L reagent stocks liquid 2 are sequentially added, and the ultimate density of hydrogen polysulfide is made to be followed successively by 0,1,5,
It 7,10,20,30,40,50,60,80,100,120,150,200 and 260 μM, shakes up, reacts 20min in 37 DEG C of shaking tables, negating should
Liquid makees excitation wavelength in 1 centimetre of quartz colorimetric utensil, with 435nm, measures the fluorescence intensity at 540nm, obtains series of standards
The fluorescence intensity F of solution, while measure the fluorescence intensity F of corresponding reagent blank solution0.With the concentration C (μ g/mL) of hydrogen polysulfide
For abscissa, fluorescence intensity change value Δ F (Δ F=F-F0) for ordinate, drawing curve, as Fig. 2A obtains corresponding line
Property regression equation be Δ F=31.0 × [H2S2] (μM) -8.6 (r=0.9935).
Reagent stock liquid 2 is the dimethyl sulphoxide solution of reagent 1 (compound shown in formula I), and the ultimate density of the reagent is
10μM；
3) in cell hydrogen polysulfide content measure
Reagent stock liquid 2 is added in into the cell Jing Guo different disposal, measures the fluorescence intensity at 500-580nm.Each group
The processing mode of cell：A groups：Adherent cell is washed three times with the DMEM culture mediums without fetal calf serum, then adds in 10 μM
37 DEG C of probe is incubated 30 minutes；B groups：It first adds in 50 μM of 37 DEG C of hydrogen sulfides to be incubated 20 minutes, is washed three times with PBS, add in 10 μ
37 DEG C of M probes are incubated 30 minutes；C groups：It first adds in 50 μM of 37 DEG C of N- methylmaleimidos to be incubated 30 minutes, three is washed with PBS
It is secondary, it adds in 10 μM of 37 DEG C of probes and is incubated 30 minutes；D-f groups：It is separately added into 50 μM of sodium hypochlorite, 100 μM of vulcanized sodium, 50 μM chlorine
37 DEG C of the mixed liquor of sour sodium and 100 μM of vulcanized sodium is incubated 30 minutes, is washed three times with PBS respectively, is added 10 μM of 37 DEG C of probes
It is incubated 30 minutes.After the completion of incubation, cell is washed with PBS (pH7.4) and carries out imaging experiment, such as Fig. 5 afterwards three times.
4) hydrogen polysulfide content in kit detection and localization cell
The processing of cell is as follows：A groups：Adherent cell is washed three times with the DMEM culture mediums without fetal calf serum, then
10 μM of 37 DEG C of probes are added in be incubated 30 minutes；B groups：Adherent cell is washed three times with the DMEM culture mediums without fetal calf serum,
Then 37 DEG C of 200nM ER-Tracker Red are added in be incubated 30 minutes.After the completion of incubation, cell is washed with PBS (pH 7.4)
Carry out imaging experiment, such as Fig. 6 afterwards three times.
Fig. 5 detects the cell through different disposal, the changes of contents of intracellular hydrogen polysulfide for kit；N- as shown in Figure 5
Methylmaleimido can inhibit the generation of hydrogen polysulfide, and vulcanized sodium can generate hydrogen polysulfide with active oxygen.Fig. 6 determines for kit
Hydrogen polysulfide in position detection endoplasmic reticulum；It will be appreciated from fig. 6 that the kit of this seminar design can be more in detection and localization endocytoplasmic reticulum
The variation of hydrogen sulfide content.
Finally it should be noted that：Above-described embodiment is only enumerated with reagent 1 as fluorescent reagent, and 1 and phosphoric acid are contained in reaction system
The concentration of salt buffer is respectively 10 μM, 10mM, and catalyst (cetyl trimethyl ammonium) reacts 20min's for 100 μM
Situation.Remaining fluorescent reagent concentration and the result in reaction time are not listed one by one, however it is not intended to limit the present invention.It is any
Those skilled in the art, without departing from the spirit and scope of the present invention, should can with various modification can be adapted with become
More.
Claims (10)
1. a kind of fluorescence probe for being used to detect hydrogen polysulfide, which is characterized in that the fluorescence probe is 2- butyl -6- nitros -1H-
Benzo [de] isoquinolin -1,3 (2H)-diketone, structural formula is as shown in formula I：
A kind of 2. preparation method of fluorescence probe for being used to detect hydrogen polysulfide as described in claim 1, which is characterized in that packet
Include following steps：
Under the conditions of existing for catalyst, in 30 DEG C~90 DEG C, by the 4- nitro-1,8-naphthalic acids acid anhydride described in formula II and positive fourth
Amine mixing carries out reduction reaction, reacts 1~24 hour, obtains compound shown in formula I,
3. a kind of preparation method of fluorescence probe for being used to detect hydrogen polysulfide as claimed in claim 2, which is characterized in that
The catalyst is at least one of organic base and inorganic base；The organic base is at least one in triethylamine and pyridine
Kind；The inorganic base is at least one of potassium carbonate, sodium hydroxide, sodium carbonate and sodium bicarbonate.
4. a kind of preparation method of fluorescence probe for being used to detect hydrogen polysulfide as claimed in claim 2, which is characterized in that
The molar ratio of the 4- nitros -1,8- naphthalic anhydrides, n-butylamine and catalyst is 1：0.5~5：0.5~5.
5. a kind of preparation method of fluorescence probe for being used to detect hydrogen polysulfide as claimed in claim 4, which is characterized in that
The molar ratio of the 4- nitros -1,8- naphthalic anhydrides, n-butylamine and catalyst is 1:1~4:1~4.
6. a kind of preparation method of fluorescence probe for being used to detect hydrogen polysulfide as claimed in claim 5, which is characterized in that
The molar ratio of the 4- nitros -1,8- naphthalic anhydrides, n-butylamine and catalyst is 1:1:1 or 1:4:4.
7. a kind of preparation method of fluorescence probe for being used to detect hydrogen polysulfide as claimed in claim 2, which is characterized in that
The reduction reaction carries out in organic solvent, the organic solvent for n,N-Dimethylformamide, triethylamine, ethyl alcohol and
At least one of acetonitrile.
8. a kind of dedicated test kit, which is characterized in that comprising compound and solvent shown in claim 1 Chinese style I,
A concentration of 1mM of compound shown in formula I,
Solvent is ethyl alcohol or dimethyl sulfoxide (DMSO).
9. a kind of dedicated test kit as claimed in claim 8, which is characterized in that the buffer solution containing catalyst is further included,
The buffer solution is the phosphate buffer that pH value is 6.5~8.5, and the phosphate is selected from Na2HPO4、NaH2PO4With
KH2PO4At least one of；The phosphatic a concentration of 0.01~0.5M；The catalyst is cetyl trimethyl
Ammonium, a concentration of 0.01~0.1mM.
10. the answering in hydrogen polysulfide content is detected of kit described in compound shown in claim 1 Chinese style I or claim 8
With.
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| CN108226377A (en) * | 2018-01-08 | 2018-06-29 | 浙江新和成特种材料有限公司 | The detection method of sodium polysulfide |
| CN111103243A (en) * | 2019-12-03 | 2020-05-05 | 首都师范大学 | Color developing agent for detecting hydrogen sulfide content, preparation method thereof, and method and device for detecting hydrogen sulfide content by using color developing agent |
| CN111103243B (en) * | 2019-12-03 | 2022-12-27 | 首都师范大学 | Color developing agent for detecting hydrogen sulfide content, preparation method thereof, and method and device for detecting hydrogen sulfide content by using color developing agent |
| CN113899721A (en) * | 2021-09-13 | 2022-01-07 | 中国特种设备检测研究院 | Fluorescent probe, fluorescent probe kit and method for detecting sulfate reducing bacteria |
| CN113698379A (en) * | 2021-10-20 | 2021-11-26 | 中国科学院烟台海岸带研究所 | Fluorescent probe for detecting hydrogen polysulfide and preparation method and application thereof |
| CN114516836A (en) * | 2021-12-31 | 2022-05-20 | 上海工程技术大学 | Fluorescent probe material, preparation method thereof and method for detecting sulfide |
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