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Cytomembrane targeting H2S fluorescence probe as well as preparation method and application thereof

A fluorescent probe, H2S technology, used in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve the effects of efficient and sensitive analysis and detection, simple and easy preparation methods, and significant changes in fluorescence intensity

Inactive Publication Date: 2017-12-12
WUHAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

None of the existing fluorescent probes can detect the part of H released from inside the cell to the outside of the cell. 2 S for detection

Method used

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  • Cytomembrane targeting H2S fluorescence probe as well as preparation method and application thereof
  • Cytomembrane targeting H2S fluorescence probe as well as preparation method and application thereof
  • Cytomembrane targeting H2S fluorescence probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Intermediate 4-amino-6-sulfonic acid-1,8-naphthalene dicarboxylic anhydride ( figure 1 Synthesis of compound B) in:

[0030] To 0.204g 4-amino-1,8-naphthalene dicarboxylic anhydride ( figure 1 Add 4mL of 50% fuming sulfuric acid to the compound A), stir and react at 100°C for 1 hour, after cooling to room temperature, add 50mL of ice water, then add 7g of sodium chloride for stirring, and filter after forming a suspension The precipitate was collected, washed successively with 2 mL of water, 30 mL of ethanol, and 30 mL of ether, and dried in vacuo to obtain 0.235 g of orange-red powder solid Compound B with a yield of 74%. The intermediate was soluble in water, methanol, and dimethyl sulfoxide; insoluble in ethanol.

Embodiment 2

[0032] Intermediate 4-amino-6-sulfonic acid-N-hexadecyl-1,8-naphthalimide ( figure 1 Synthesis of compound C) in:

[0033] (1) The good solvent of compound B is preferred as the reaction medium. Dissolve 0.300g of Compound B in 15mL of water, add 10 drops of triethanolamine dropwise, then add 10mL of water suspension dispersed with 0.724g of hexadecylamine, and react in an oil bath at 100°C for 18 hours. After the reaction is completed, cool to room temperature. Compound C is obtained.

[0034] (2) Methanol is a good solvent for compound B and raw material hexadecylamine. Dissolve 0.300g of compound B in 15mL of methanol, add 10 drops of triethanolamine dropwise, then add 10mL of methanol solution containing 0.724g of hexadecylamine, react in an oil bath at 90°C for 18 hours, cool to room temperature after the reaction, and collect the precipitate by filtration , washed with anhydrous ether, the resulting precipitate was characterized as an impurity, not compound C.

[003...

Embodiment 3

[0037] Target product 3-sulfonic acid (sodium)-5-azido-N-hexadecyl-1,8-naphthalimide ( figure 1 Compound D) in the synthesis:

[0038] Dissolve 150mg of Compound C in 15mL of water, place it in an ice-salt bath after dissolving, add dropwise 1mL of an aqueous solution containing 154mg of sodium nitrite, add 3mL of concentrated hydrochloric acid within 15 seconds after completion, stop stirring, and place it in an ice-salt bath for 4 After the reaction was completed, the brown precipitate was collected by filtration and washed with 1 mL of ice water. The collected solid was dispersed in anhydrous methanol at -50°C to form a suspension, and a methanol solution containing 181 mg of sodium azide in 15 mL was added within 10 minutes. The reaction was stirred at -50°C for 6 hours, filtered with a G4 sand core funnel, the filtrate was evaporated to dryness at room temperature, and the resulting solid was purified by silica gel column chromatography, and the eluent was dichloromethan...

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Abstract

The invention discloses a fluorescence probe for hydrogen sulfide detection and a preparation method thereof. The preparation method comprises the following steps: firstly, enabling fuming sulfuric acid to react with 4-amino-1,8-naphthalic anhydride, and enabling an obtained product to be subjected to reflux with cetylamine in a turbid liquid manner in ethyl alcohol as a solvent which hardly dissolves the obtained product, wherein the obtained product is still a turbid liquid; collecting and dissolving solid in water, enabling the solid to react with sodium nitrite in ice-batch, enabling solid, which is separated out, to suspend in methanol, dropwise adding the methanol solution of sodium azide at about a low temperature of 40 DEG C, reacting for hours at the low temperature to obtain 3-(sodium) sulfonate-5-nitrine-1,8-naphthalimide. The probe has a property of being able to carrying out target marking on a cytomembrane surface and characteristic solubility, can enable the probe to be only embedded in cytomembrane instead of striding over the cytomembrane to enter a cell, and can be used for detecting endogenous H2S. The probe per se has relatively weak fluorescence, can selectively react with the H2S in a physiological condition to generate a derivative with relatively strong fluorescence, and is not interfered by a living organism, common matter in the environment and a biological medium background.

Description

technical field [0001] The invention relates to a method for detecting H in cells by fluorescence imaging 2 The cell membrane targeting fluorescent probe released by S and its preparation method and application belong to the technical field of biological detection. Background technique [0002] h 2 S is the newly discovered third endogenous gas signal molecule, which participates in the regulation of nervous system, cardiovascular system, metabolism, digestive system, red blood cell function, genitourinary system, and can also scavenge reactive oxygen and reactive nitrogen species , indispensable in life activities. Currently available for detection of H 2 The methods of S include: colorimetry, electrochemical analysis, chromatographic analysis, metal sulfide precipitation and other methods, but these methods cannot realize the detection of H in living cells and tissues like fluorescent probe detection. 2 Spatiotemporal distribution and fast detection of S. In recent ye...

Claims

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Application Information

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IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1029G01N21/6428
Inventor 王红付瑜佳郭小峰
Owner WUHAN UNIV
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