CN105669533A - Rate hydrogen sulfide chemical dosimeter and preparation method and application thereof - Google Patents
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- CN105669533A CN105669533A CN201610099281.XA CN201610099281A CN105669533A CN 105669533 A CN105669533 A CN 105669533A CN 201610099281 A CN201610099281 A CN 201610099281A CN 105669533 A CN105669533 A CN 105669533A
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- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 229910000037 hydrogen sulfide Inorganic materials 0.000 title claims abstract description 48
- 239000000126 substance Substances 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 28
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 16
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 claims abstract description 9
- -1 styryl pyridinium Chemical compound 0.000 claims abstract description 7
- 230000004962 physiological condition Effects 0.000 claims abstract description 5
- 238000010992 reflux Methods 0.000 claims abstract description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 13
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 claims description 11
- 238000001514 detection method Methods 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000007853 buffer solution Substances 0.000 claims description 6
- 230000003834 intracellular effect Effects 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 150000003384 small molecules Chemical class 0.000 abstract description 2
- UMZDENILBZKMFY-UHFFFAOYSA-N 1,2-dimethylpyridin-1-ium Chemical compound CC1=CC=CC=[N+]1C UMZDENILBZKMFY-UHFFFAOYSA-N 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 238000002835 absorbance Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- LGZXYFMMLRYXLK-UHFFFAOYSA-N mercury(2+);sulfide Chemical compound [S-2].[Hg+2] LGZXYFMMLRYXLK-UHFFFAOYSA-N 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 2
- VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 201000010374 Down Syndrome Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010044688 Trisomy 21 Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 238000005935 nucleophilic addition reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000011506 response to oxidative stress Effects 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 230000019086 sulfide ion homeostasis Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
-
- 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
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
- G01N31/16—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using titration
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Analytical Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Molecular Biology (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Abstract
The invention discloses a rate hydrogen sulfide chemical dosimeter and a preparation method and application thereof. The rate hydrogen sulfide chemical dosimeter is iodized 1-methyl-2-(4-nitro)styryl pyridinium with the structural formula shown in the description. The preparation method of the rate hydrogen sulfide chemical dosimeter comprises the steps that iodized 1,2-dimethyl pyridinium and 4-nitrobenzaldehyde are added into a normal butanol solution according to the certain proportion, then, piperazine is added, a reaction is performed on the reflux condition to obtain the rate hydrogen sulfide chemical dosimeter. The rate hydrogen sulfide chemical dosimeter has the good rate chemical dosimeter characteristics, hydrogen sulfide can be rapidly and accurately detected on the physiological conditions, the selectivity of hydrogen sulfide is high, and the antijamming capability of other biological active small molecules is high. The rate hydrogen sulfide chemical dosimeter is simple in synthesis method, high in yield and suitable for industrial production.
Description
Technical field
The invention belongs to detection technique field, be specifically related to a kind of ratio hydrogen sulfide chemical dosimeter and preparation method thereof and detect the application of hydrogen sulfide in physiological conditions.
Background technology
Hydrogen sulfide (H2S) be a kind of colourless, there is the gas of typical rotten egg abnormal smells from the patient, for centuries, be considered as the chemical pollutant of a kind of toxicity always. In the last few years, substantial amounts of experimentation showed, H2S is the gas signal compound that the third organism endogenous being found after NO, CO produces, and it plays an important role in adjustment intraor extracellular oxidation-reduction potential and other and the signal process of human health and disease association. As modulated blood pressure, reconcile neurotransmitter, regulate inflammatory reaction, it is suppressed that response to oxidative stress etc. Additionally, H in cell2The change of S level is also believed to relevant with some diseases, such as Down's syndrome, Alzheimer's disease disease, diabetes and liver cirrhosis. Therefore, to H under development physiological condition2Academic research and clinical practice are significant by the effective ways of S detection.
The ratio hydrogen sulfide chemical dosimeter great majority developed at present are all using the increase of signal intensity or reduction as response signal. This have self unsurmountable shortcoming based on the chemical dosimeter of optical signal absolute intensity change under single wavelength, namely the impact of many factors it is vulnerable to when quantitative analysis, such as absolute concentration and distribution, the pH value of system to be tested, temperature and polarity, the stability etc. of detecting instrument, and make the accuracy of analysis result decline.
Summary of the invention
For above-mentioned the deficiencies in the prior art, the invention provides a kind of ratio hydrogen sulfide chemical dosimeter and its preparation method and application, this chemical dosimeter novel structure, other ion interference abilities anti-are strong, and detection is quickly, accurately.
For achieving the above object, the technical solution used in the present invention is as follows:
A kind of ratio hydrogen sulfide chemical dosimeter iodate 1-methyl-2-(4-nitro) styryl pyridinium iodate 1-methyl-2-(4-nitro) styryl pyridinium, its chemical structural formula is as follows:
The preparation method of described ratio hydrogen sulfide chemical dosimeter iodate 1-methyl-2-(4-nitro) styryl pyridinium, comprises the following steps:
(1) iodate 1,2-lutidines salt and 4-nitrobenzaldehyde are joined in butanol solution by a certain percentage;
(2) add piperazine, under reflux conditions react, obtain iodate 1-methyl-2-(4-nitro) styryl pyridinium.
Preferably, iodate 1,2-lutidines salt and 4-nitrobenzaldehyde 1:2-1:2.5 in molar ratio in described step (1);
Preferably, the 4-nitrobenzaldehyde in described step (1) is 0.302:20-0.378:25 with the mass volume ratio of butanol solution;
Preferably, the 4-nitrobenzaldehyde in described step (1) is 0.378:0.025-0.302:0.01 with the mass ratio of the piperazine in described step (2);
Preferably, in described step (2), reflux time is 30-50 minute.
The synthesis equation of the ratio hydrogen sulfide chemical dosimeter of the present invention, as follows:
Further, the invention discloses above-mentioned ratio hydrogen sulfide chemical dosimeter and detect the application in intracellular hydrogen sulfide in physiological conditions.
A kind of method detecting intracellular hydrogen sulfide, step is:
(1) above-mentioned ratio hydrogen sulfide chemical dosimeter is dissolved in dimethylformamide (DMF) solvent, is made into storing solution and stores stand-by;
(2) PBS that the storing solution in step (1) adds containing cell tissue is tested.
Preferably, described in step (2), the pH of PBS is 7.4.
The invention have the benefit that
(1) the ratio hydrogen sulfide chemical dosimeter of the present invention and hydrogen sulfide generation nucleophilic addition, its 339nm place absorbance reduces, and 244nm place occurs that new absworption peak and absorbance strengthen, A244nm/A339nmWith the linear relationship that concentration of hydrogen sulfide is good, there is good ratio chemistry Dosimeter Characteristics, it is achieved in physiological conditions to intracellular hydrogen sulfide quick, accurately detect.
(2) the ratio hydrogen sulfide chemical dosimeter of the present invention is high to hydrogen sulfide selective, and the capacity of resisting disturbance of other biological active small molecular is strong.
(3) the ratio hydrogen sulfide chemical dosimeter synthetic method of the present invention is simple, and productivity is higher, is suitable to industrialized production.
Accompanying drawing explanation
Fig. 1 is the H carried out in the PBS buffer solution (pH7.4) containing 10 μMs of ratio hydrogen sulfide chemical dosimeters2In S ultraviolet titration experiments figure, figure, abscissa is wavelength, and vertical coordinate is absorbance;
Fig. 2 is A244nm/A339nmWith H2The linear relationship chart of S concentration, in figure, abscissa is H2S concentration, vertical coordinate is A244nm/A339nmRatio;
Fig. 3 is that ratio hydrogen sulfide chemical dosimeter is relative to the micromolecular selectivity experiment of Typical reactive in organism.
Detailed description of the invention
Below in conjunction with drawings and Examples, the present invention is further described.
Embodiment 1
Weighing 0.235g iodate 1,2-lutidines salt and 0.310g4-nitrobenzaldehyde in 50ml round-bottomed flask, add 20ml n-butyl alcohol, add 0.01g piperazine, mixed solution heating, to backflow, reacts 40min. TLC detection reaction is cooled to room temperature, has a large amount of solid to precipitate out after completing, and reduce pressure sucking filtration, and n-butyl alcohol recrystallization obtains 0.230g Chinese red solid. Productivity is 62.5%.
Fusing point test: mp:239-242 DEG C
Infrared spectrum measurement: TR (KBr, cm-1) 3346,2997,1635,1616,1567,1516,1457,1349
Nuclear magnetic resonance hydrogen spectruming determining:1HNMR (400MHZ, DMSO): δ (ppm): 9.02 (d, J=6.0Hz, 1H), 8.60 (m, 2H), 8.36 (d, J=8.8Hz, 2H), 8.16 (d, J=8.8Hz, 2H), 8.08 (d, J=16Hz, 1H), 8.03 (m, 1H), 7.86 (d, J=16Hz, 1H), 4.45 (s, 3H).
Embodiment 2
Weighing 0.2350g iodate 1,2-lutidines salt and 0.3875g4-nitrobenzaldehyde in 50ml round-bottomed flask, add 25ml n-butyl alcohol, add 0.025g piperazine, mixed solution heating, to backflow, reacts 30min.TLC detection reaction is cooled to room temperature, has a large amount of solid to precipitate out after completing, and reduce pressure sucking filtration, and n-butyl alcohol recrystallization obtains 0.242g Chinese red solid. Productivity is 65.8%.
Fusing point test: mp:239-242 DEG C
Infrared spectrum measurement: TR (KBr, cm-1) 3346,2997,1635,1616,1567,1516,1457,1349
Nuclear magnetic resonance hydrogen spectruming determining:1HNMR (400MHZ, DMSO): δ (ppm): 9.02 (d, J=6.0Hz, 1H), 8.60 (m, 2H), 8.36 (d, J=8.8Hz, 2H), 8.16 (d, J=8.8Hz, 2H), 8.08 (d, J=16Hz, 1H), 8.03 (m, 1H), 7.86 (d, J=16Hz, 1H), 4.45 (s, 3H).
Embodiment 3
Weighing 0.2350g iodate 1,2-lutidines salt and 0.355g4-nitrobenzaldehyde in 50ml round-bottomed flask, add 22ml n-butyl alcohol, add 0.018g piperazine, mixed solution heating, to backflow, reacts 30min. TLC detection reaction is cooled to room temperature, has a large amount of solid to precipitate out after completing, and reduce pressure sucking filtration, and n-butyl alcohol recrystallization obtains 0.235g Chinese red solid. Productivity is 63.9%.
Fusing point test: mp:239-242 DEG C
Infrared spectrum measurement: TR (KBr, cm-1) 3346,2997,1635,1616,1567,1516,1457,1349
Nuclear magnetic resonance hydrogen spectruming determining:1HNMR (400MHZ, DMSO): δ (ppm): 9.02 (d, J=6.0Hz, 1H), 8.60 (m, 2H), 8.36 (d, J=8.8Hz, 2H), 8.16 (d, J=8.8Hz, 2H), 8.08 (d, J=16Hz, 1H), 8.03 (m, 1H), 7.86 (d, J=16Hz, 1H), 4.45 (s, 3H).
Effect experimental 1
The ratio hydrogen sulfide chemical dosimeter obtained in Example 1 is dissolved in DMF solvent and is made into storing solution, drawing a certain amount of storing solution to add in PBS buffer solution (pH7.4), making ratio hydrogen sulfide chemical dosimeter concentration in PBS buffer solution is 10 μMs. Add the Na of different volumes2S (0.01M) aqueous solution, Na2S volume is 0,50 μ L respectively, 100 μ L, 150 μ L, 200 μ L, 300 μ L, 400 μ L, 450 μ L, 500 μ L, 550 μ L, 600 μ L, and 700 μ L carry out Na2S ultraviolet titration is tested, and test effect is as it is shown in figure 1, at Na2In the scope of S volume 0～700 μ L (concentration is 0～700 μM), uv absorption Strength Changes is clearly, and its 339nm place absorbance is gradually lowered, and 244nm place occurs that new absworption peak and absorbance strengthen gradually, and A244nm/A339nmWith H2S concentration (0-700 μM) is in good linear relationship, as shown in Figure 2. Equation of linear regression is: A244nm/A339nm=0.0012c (H2S, μM)+0.1784, R2=0.987. Can illustrate that this ratio hydrogen sulfide chemical dosimeter has good Ratio Features, can be used for H2The detection of S, and detection is accurately, quickly.
Effect experimental 2
The ratio hydrogen sulfide chemical dosimeter obtained in Example 1 is dissolved in DMF solvent and is made into storing solution, drawing a certain amount of storing solution to add in PBS buffer solution (pH7.4), making ratio hydrogen sulfide chemical dosimeter concentration in PBS buffer solution is 10 μMs. It is separately added into inorganic molecule K+、Ca2+、Mg2+、SO4 2-、NO2 -、Cl-, and aminoacid and polypeptide small molecule Glu, Pro, Leu, Cys, GSH, measuring the ratio change of wavelength 244nm and 339nm absorbance, test result is as it is shown on figure 3, ratio hydrogen sulfide chemical dosimeter is to H2S selectivity is high, and other biological bioactive molecule is had stronger capacity of resisting disturbance.
The specific embodiment of the present invention is described in conjunction with accompanying drawing although above-mentioned; but the not restriction to invention protection domain; one of ordinary skill in the art should be understood that; on the basis of technical scheme, those skilled in the art need not pay various amendments or deformation that creative work can make still in protection scope of the present invention.
Claims (9)
1. ratio hydrogen sulfide chemical dosimeter iodate 1-methyl-2-(4-nitro) styryl pyridinium iodate 1-methyl-2-(4-nitro) styryl pyridinium, its chemical structural formula is as follows:
2. the preparation method of chemical dosimeter described in claim 1, is characterized in that, comprises the following steps:
(1) iodate 1,2-lutidines salt and 4-nitrobenzaldehyde are joined in butanol solution by a certain percentage;
(2) add piperazine, under reflux conditions react, obtain described chemical dosimeter.
3. preparation method as claimed in claim 2, is characterized in that, iodate 1,2-lutidines salt and 4-nitrobenzaldehyde 1:2-1:2.5 in molar ratio in described step (1).
4. preparation method as claimed in claim 2, is characterized in that, the mass volume ratio of the 4-nitrobenzaldehyde in described step (1) and butanol solution is 0.302:20-0.378:25.
5. preparation method as claimed in claim 2, is characterized in that, in described step (1), 4-nitrobenzaldehyde is 0.378:0.025-0.302:0.01 with the mass ratio of piperazine in described step (2).
6. preparation method as claimed in claim 2, is characterized in that, in described step (2), reflux time is 30-50 minute.
7. described in claim 1, ratio hydrogen sulfide chemical dosimeter detects the application in intracellular hydrogen sulfide in physiological conditions.
8. the method for ratio hydrogen sulfide chemical dosimeter detection intracellular hydrogen sulfide described in claim 1, is characterized in that, step is:
(1) above-mentioned ratio hydrogen sulfide chemical dosimeter is dissolved in dimethylformamide buffer solution, is made into storing solution and stores stand-by;
(2) PBS that the storing solution in step (1) adds containing cell tissue is tested.
9. the method detecting intracellular hydrogen sulfide as claimed in claim 8, is characterized in that, in described step (2), the pH of PBS is 7.4.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106496217A (en) * | 2016-10-31 | 2017-03-15 | 湖南师范大学 | A kind of new detection H2The preparation method and application of S fluorescent molecular probes |
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| CN103173212A (en) * | 2013-03-01 | 2013-06-26 | 浙江大学 | Fluorescent probe for detecting biological hydrogen sulfide as well as preparation and application of fluorescent probe |
| CN105131941A (en) * | 2015-09-23 | 2015-12-09 | 山东理工大学 | Endogenous H2S detecting fluorescence probe and preparation method thereof |
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- 2016-02-23 CN CN201610099281.XA patent/CN105669533B/en not_active Expired - Fee Related
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4142935A1 (en) * | 1991-12-24 | 1993-07-01 | Wolfen Filmfab Ag | Negative photographic material for processing in room light - contg. UV absorber combination with electron acceptor desensitiser, giving synergistic effect |
| CN103173212A (en) * | 2013-03-01 | 2013-06-26 | 浙江大学 | Fluorescent probe for detecting biological hydrogen sulfide as well as preparation and application of fluorescent probe |
| CN105131941A (en) * | 2015-09-23 | 2015-12-09 | 山东理工大学 | Endogenous H2S detecting fluorescence probe and preparation method thereof |
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| GIEBELHAUS IRINA ET AL.: "One-dimensional CuO-SnO2 p-n heterojunctions for enhanced detection of H2S", 《JOURNAL OF MATERIALS CHEMISTRY A: MATERIALS FOR ENERGY AND SUSTAINABILITY》 * |
| M. TAREK M. ZAKI ET AL.: "APPLICATION OF 2-PICOLINE METHIOOIOE FOR THE SPECTROPHOTOMETRIC OETERMINATION OF SOME AROMATIC ALDEHYDES", 《ANALYTICAL LETTERS》 * |
| PENGFEI XU ET AL.: "An ESIPT-based highly selective and sensitive probe for the detection of hydrogen sulfide", 《TETRAHEDRON LETTERS》 * |
| PFOERTNER, KARL HEINZ: "Substituted alkyl sulfonates by addition of sodium hydrogen sulfide to chalcones", 《HELVETICA CHIMICA ACTA》 * |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106496217A (en) * | 2016-10-31 | 2017-03-15 | 湖南师范大学 | A kind of new detection H2The preparation method and application of S fluorescent molecular probes |
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