CN111606854B - For detecting H2Isolongifolane colorimetric probe of S and preparation method thereof - Google Patents
For detecting H2Isolongifolane colorimetric probe of S and preparation method thereof Download PDFInfo
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- CN111606854B CN111606854B CN202010526756.5A CN202010526756A CN111606854B CN 111606854 B CN111606854 B CN 111606854B CN 202010526756 A CN202010526756 A CN 202010526756A CN 111606854 B CN111606854 B CN 111606854B
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- isolongifolanone
- methanobenzo
- octahydro
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- 239000000523 sample Substances 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims abstract description 20
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 16
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 15
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 15
- 238000001514 detection method Methods 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims 1
- VCOCESNMLNDPLX-BTXGZQJSSA-N (3s,6s)-2,2,8,8-tetramethyl-octahydro-1h-2,4a-methanonapthalene-10-one Chemical compound O=C1CCC(C)(C)[C@@]2(C3)C1C(C)(C)[C@H]3CC2 VCOCESNMLNDPLX-BTXGZQJSSA-N 0.000 abstract description 20
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 abstract description 9
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract description 6
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract description 6
- HMRWHLXCRJQBMQ-BQELKBSMSA-N isolongifolane Chemical compound C1CCC(C)(C)[C@@]2(C3)C1C(C)(C)[C@H]3CC2 HMRWHLXCRJQBMQ-BQELKBSMSA-N 0.000 abstract description 6
- 229930002169 isolongifolane Natural products 0.000 abstract description 6
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 150000002473 indoazoles Chemical class 0.000 abstract description 3
- 150000004192 longifolene derivatives Chemical class 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 7
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- -1 indazole compound Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000005882 aldol condensation reaction Methods 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000011664 signaling Effects 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
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- 239000007853 buffer solution Substances 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
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- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
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- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
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Abstract
The invention disclosesFor detecting H2S isolongifolane colorimetric probe and a preparation method thereof. According to the invention, a natural renewable resource longifolene derivative isolongifolanone is used as a raw material, and is condensed with 4-nitrobenzaldehyde to generate 7- (4' -nitrobenzylidene) isolongifolanone; condensing 7- (4' -nitrobenzylidene) isolongifolanone with hydrazine hydrate and dichloro dicyano benzoquinone for cyclization to obtain 5,5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g]Indazoles, which compounds are specific for H2S is acted, the color is changed from colorless to yellow brown, and the S can be used for detecting H2And (3) an S concentration colorimetric type probe.
Description
Technical Field
The invention belongs to the technical field of fine organic synthesis, and relates to H detection2S isolongifolane colorimetric probe and preparation method and application thereof.
Background
Hydrogen sulfide is a colorless, highly toxic acid gas, is highly corrosive and irritating, and can damage the respiratory system and central nervous system of human body. Recent studies have shown that: hydrogen sulfide is also an important endogenous gas signaling molecule in the human body, and has various physiological functions, including inhibition of insulin signaling, regulation of inflammation, tumor resistance, regulation of ion channels, protection of the cardiovascular system, oxidation resistance, relaxation of vascular smooth muscle and the like. At present, methods for detecting hydrogen sulfide mainly comprise high performance liquid chromatography, iodometry, gas chromatography, electrochemical analysis and the like. However, these conventional detection methods have the disadvantages of complicated pretreatment, expensive equipment, complex operation, time-consuming detection, etc., and are not suitable for real-time detection of field samples. The colorimetric probe has the advantages of simple operation, low cost, high sensitivity, fast response time and the like, and is gradually an important means for detecting hydrogen sulfide. Therefore, the development and design of colorimetric hydrogen sulfide probes are of great significance.
Disclosure of Invention
Aiming at the defects in the prior art, the technical problem to be solved by the invention is to provide a method for detecting H2S isolongifolane colorimetric probe, specificity and H2S acts to change the color of the compound from colorless to yellow brown, and can be used for treating H2And (5) detecting the concentration of S. Another technical problem to be solved by the present invention is to provide the above-mentioned detection method H2A preparation method of an isolongifolane colorimetric type probe of S. The invention also aims to provide the detection H2The application of the isolongifolane colorimetric probe of S.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
detection of H2The isolongifolane colorimetric probe of S is as follows: 5,5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g ]]Indazoles, of the formula:
the preparation method of the 5,5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g ] indazole comprises the following steps:
1) subjecting isolongifolanone and 4-nitrobenzaldehyde to aldol condensation to obtain 7- (4' -nitrobenzylidene) isolongifolanone;
2) condensation reaction of 7- (4' -nitrobenzylidene) isolongifolanone with hydrazine hydrate and dichlorodicyanobenzoquinone gives 5,5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g ] indazole.
In the step 1), the isolongifolanone and 4-nitrobenzaldehyde are subjected to aldol condensation to obtain 7- (4' -nitrobenzylidene) isolongifolanone, and the specific preparation method is as follows:
(1) sequentially adding 0.8mol of isolongifolanone, 1.5-3L of tert-butyl alcohol, 0.5mol of potassium tert-butoxide and 0.8-1.0 mol of 4-nitrobenzaldehyde into a three-neck flask provided with a stirrer, a thermometer and a reflux condenser, and reacting at 80-90 ℃;
(2) extracting the reactant by using 4-4.5L ethyl acetate for 3 times, combining organic phases, and washing the organic phases for a plurality of times by using saturated saline solution until the reaction mixture is neutral; drying the organic phase by anhydrous sodium sulfate, filtering, concentrating and recovering a solvent 7- (4' -nitrobenzylidene) isolongifolanone crude product;
(3) recrystallizing the crude product of the 7- (4 '-nitrobenzylidene) isolongifolanone with ethanol to obtain a pure product of the 7- (4' -nitrobenzylidene) isolongifolanone.
In the step 2), 7- (4' -nitrobenzylidene) isolongifolanone reacts with hydrazine hydrate and dichlorodicyanoquinone to obtain 5,5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g ] indazole, and the specific preparation method comprises the following steps:
(1) sequentially adding 0.8mol of 7- (4' -nitrobenzylidene) isolongifolanone, 4-4.8 mol of hydrazine hydrate and 4.5-5.0L of ethanol into a three-neck flask with a stirrer, a thermometer and a reflux condenser, heating and carrying out reflux reaction for 10h, carrying out GC tracking detection, and stopping the reaction until the conversion rate reaches 95%;
(2) after the reaction mixture is cooled to room temperature, removing ethanol by rotary evaporation, adding 4L of 1, 4-dioxane and 0.8-0.85 mol of dichloro dicyanobenzoquinone, heating and refluxing, reacting for 8h, adding 2L of potassium hydroxide solution and 5L of dichloromethane, stirring for 30 min at room temperature, extracting with dichloromethane for three times, washing the combined organic layers with deionized water to neutrality, drying with anhydrous sodium sulfate, filtering, concentrating to obtain an oily liquid, and performing silica gel column chromatography (ethyl acetate/petroleum ether ═ 1/3) and recrystallization to obtain 5,5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g ] indazole.
The compound 5,5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g ]]Indazole-specific and H2The color of the product changes from colorless to yellow brown under the action of S ions.
The 5,5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g ] indazole is used as a colorimetric probe to detect hydrogen sulfide.
The 5,5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g ] indazole is applied to detection of hydrogen sulfide.
Has the advantages that: compared with the existing research results, the invention utilizes the natural renewable resource longifolene derivative isolongifolanone as the raw material to prepare the 5,5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g]Indazoles; can be specific with H2S function as assay H2And (3) an S concentration colorimetric type probe.
Drawings
FIG. 1 is 5,5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g ]]Indazole with varying concentrations of H2(ii) a graph of the ultraviolet absorption spectrum result of the S action;
FIG. 2 is a graph showing the results of ultraviolet absorption spectra of 5,5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g ] indazole added with different ions.
Detailed Description
The present invention will be further described with reference to the following specific examples.
Example 1
The synthesis method of the 5,5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g ] indazole compound comprises the following steps:
the method comprises the following specific steps:
1) preparation of 7- (4' -nitrobenzylidene) isolongifolanone:
adding 2.2g of isolongifolanone, 30mL of tert-butyl alcohol, 0.28g of potassium tert-butoxide and 1.51g of p-nitrobenzaldehyde into a three-neck flask provided with a stirrer, a thermometer and a reflux condenser in sequence, heating to reflux at 80-90 ℃ for reaction, and reacting for about 4 hours until the conversion rate of the isolongifolanone reaches more than 95% (GC tracking detection). Extracting the reaction with 20mL ethyl acetate for 3 times, combining organic phases, and washing with saturated saline for several times until the reaction is neutral; drying the organic phase by anhydrous sodium sulfate, filtering, concentrating and recovering the solvent to obtain a crude product of 7- (4' -nitrobenzylidene) isolongifolanone, and recrystallizing by using ethanol to obtain a light yellow blocky solid, wherein the yield is 88.5 percent, and the purity is 96 percent.
2)5, 5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g ] indazole compound:
adding 7- (4' -nitrobenzylidene) isolongifolanone 4.24g, hydrazine hydrate (80%) 4.51g and anhydrous ethanol 80mL into a three-neck flask with a stirrer, a thermometer and a reflux condenser in sequence, and heating to reflux reaction at 80-90 ℃ for 10 h; after the reaction liquid is cooled, adding 20mL of acetonitrile, and removing the solvent and the excessive hydrazine hydrate in the reaction liquid by rotary evaporation; after rotary evaporation, 70mL of dried 1, 4-dioxane and 3.00g of 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone are sequentially added, and the mixture is heated to reflux reaction for 8 hours; then cooling to room temperature, adding 30mL of potassium hydroxide (20%) aqueous solution and 80mL of dichloromethane, stirring for 30 minutes at room temperature, extracting with dichloromethane, combining organic phases, washing with deionized water for several times until the mixture is neutral; the organic phase was dried over anhydrous sodium sulfate, filtered, concentrated to recover the solvent to give an oily crude product, which was subjected to silica gel column chromatography (ethyl acetate/petroleum ether ═ 1/3) and recrystallization to give a yellow solid in a yield of 72.5% and a purity of the desired product of 97.3% (GC).1H NMR(400 MHz，DMSO-d6)δ：12.80(s，1H)，8.28(d，J＝8.5Hz，2H)，7.95(d，J＝8.5Hz，2H)， 2.69(d，J＝15.2Hz，1H)，2.40(d，J＝15.3Hz，1H)，2.26(s，1H)，1.82(dd，J＝12.3， 8.7Hz，1H)，1.64-1.75(m，2H)，1.58(d，J＝9.9Hz，1H)，1.47(td，J＝12.4，6.3Hz， 1H)，1.27(s，3H)，1.13-1.25(m，2H)，1.06(s，3H)，0.76(s，3H)，0.67(s，3H).13C NMR(100MHz，DMSO)δ：145.6，144.4，141.3，140.9，126.7，123.9，111.9，55.8， 49.7，47.9，41.7，36.2，35.7，33.8，28.9，27.2，26.4，25.7，24.9，23.3；HRMS(m/z)： [M+H]+calcd for C22H27N3O2：366.2182found 366.2184。
Example 2
Reacting 5,5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g ]]Indazole was dissolved in PBS/DMF (v/v ═ 9/1) buffer to make 1 × 10-5M in solution, likewise with H2S is dissolved in PBS/DMF (v/v-9/1) buffer solution to be prepared into a concentration of 0-1.5 × 10-4A solution of M. Measuring H at different concentrations2S-para-5, 5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g ]]The ultraviolet absorption spectrum of indazole is shown in FIG. 1. The results show that with H in the system2The concentration of S is increased continuously, and the ultraviolet absorption of the solution at 450nm is increased gradually, which shows that the probe can sensitively and quantitatively detect H2S。
Example 3
Reacting 5,5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g ]]Indazole was dissolved in PBS/DMF (v/v ═ 9/1) buffer to make 1 × 10-5M concentration solution was colorless and transparent, and each ion was dissolved in PBS/DMF (v/v ═ 9/1) buffer to prepare 1 × 10-5Solution of M concentration, H2S is prepared into 1 × 10-5M concentration solution. Different ion pairs of 5,5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g ] were detected]The ultraviolet absorption spectrum of indazole is shown in FIG. 2. The results show that the probe solution is addedInto H2The maximum UV absorption wavelength in the post-S UV spectrum shifts from 350nm to 443nm, while other ions such as F are added-，Cl-，Br-，NO2 -，NO3 -， CO3 2-，SO4 2-，SO3 2-，SCN-，PO4 3-，H2PO4 -，ACO-CyS, ATP, Blank, the ultraviolet spectrum of the solution did not change significantly, indicating that the probe can specifically recognize H2S。
Claims (2)
- Use of 5,5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g ] indazole for the preparation of a colorimetric probe for the detection of hydrogen sulfide.
- Use of 5,5,9, 9-tetramethyl-3- (4-nitrophenyl) -2,4,5,6,7,8,9,9 a-octahydro-5 a, 8-methanobenzo [ g ] indazole for the preparation of a medicament for the detection of hydrogen sulfide.
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