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Hydrogen sulfide fluorescent probe with active oxygen dependency as well as preparation method and application thereof

A fluorescent probe, hydrogen sulfide technology, applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., can solve the problem of unreported fluorescent probe molecules, achieve large Stokes shift, good selectivity, The effect of high response sensitivity

Active Publication Date: 2018-06-01
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, for H alone 2 Fluorescent probe molecules for S detection have been widely reported, but for H 2 o 2 -H 2 Fluorescent probe molecules that respond to S interactions have not been reported

Method used

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  • Hydrogen sulfide fluorescent probe with active oxygen dependency as well as preparation method and application thereof
  • Hydrogen sulfide fluorescent probe with active oxygen dependency as well as preparation method and application thereof
  • Hydrogen sulfide fluorescent probe with active oxygen dependency as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] In this example, the synthesis and response test of the handle molecule NB-PMP with benzothiadiazole as the mother nucleus is carried out first, and then the synthesis, response and cell imaging application of the probe molecule are carried out, such as figure 1 shown.

[0052] Step 1: Synthesis and performance testing of NB-PMP

[0053] NB-PMP was prepared by a two-step method, such as figure 2 As shown, then the handle molecule NB-PMP with benzothiadiazole as the mother nucleus is tested by fluorescence and ultraviolet light for H 2 S and H 2 o 2 Response situation.

[0054] The preparation method comprises the following steps:

[0055] (1) Synthesis of 4,7-dibromo-5-nitrobenzo[c][1,2,5]thiadiazole (NB-Br)

[0056] Under mechanical stirring, fuming nitric acid (1.9 g, 30 mmol) was slowly added dropwise into trifluoromethanesulfonic acid (13.3 mL, 150 mmol), and reacted at 0° C. for 10 minutes. Subsequently, 4,7-dibromobenzothiadiazole (4.4 g, 15 mmol) was adde...

Embodiment 2

[0085] The synthesis of (1) 4,7-dibromo-5-nitrobenzo[c][1,2,5]thiadiazole (NB-Br) in step 1 is the same as in Example 1.

[0086] (2) Synthesis of 4-(4-methoxyphenoxy)-7-bromo-5-nitrobenzo[c][1,2,5]thiadiazole (NB-PMP)

[0087] Dissolve NB-Br (340mg, 1mmol) and 4-methoxyphenol (250mg, 2mmol) in dry N,N-dimethylformamide DMF (30mL), add potassium carbonate (276mg, 2mmol), 50 °C for 8 hours. After the reaction, the reaction solution was concentrated under reduced pressure. Add 50 mL of ethyl acetate to the concentrated solution, then wash with water (50 mL) and saturated sodium chloride (50 mL) successively, collect the organic phase, wash with anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure. Separation by column chromatography (petroleum ether: ethyl acetate = 4:1, v / v) gave 246 mg of a yellow solid with a yield of 65%.

[0088] The performance test of NB-PMP meets the requirements.

[0089] Step 2: Synthesis and performance testing of the probe molecule TM...

Embodiment 3

[0096] The synthesis of (1) 4,7-dibromo-5-nitrobenzo[c][1,2,5]thiadiazole (NB-Br) in step 1 is the same as in Example 1.

[0097] (2) Synthesis of 4-(4-methoxyphenoxy)-7-bromo-5-nitrobenzo[c][1,2,5]thiadiazole (NB-PMP)

[0098] Dissolve NB-Br (340mg, 1mmol) and 4-methoxyphenol (250mg, 2mmol) in dry DMSO (30mL), add triethylamine (0.27mL, 2mmol), and react at 60°C 4 hours. After the reaction, the reaction solution was concentrated under reduced pressure. Add 50 mL of ethyl acetate to the concentrated solution, then wash with water (50 mL) and saturated sodium chloride (50 mL) successively, collect the organic phase, wash with anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure. Separation by column chromatography (petroleum ether: ethyl acetate = 4:1, v / v) gave 234 mg of a yellow solid with a yield of 62%.

[0099] Its performance testing composite requirements.

[0100] Step 2: Synthesis and performance testing of TMR-BTD probe molecules

[0101] (1) Synthesi...

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PUM

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Abstract

The invention discloses a hydrogen sulfide fluorescent probe with active oxygen dependency as well as a preparation method and application thereof. The hydrogen sulfide fluorescent probe is formed byconnecting a handing molecule using diazosulfide as a mother nucleus and a positioning molecule using rhodamine as a mother nucleus through acetylenic bonds. The preparation method comprises the following steps of firstly preparing NB-PMP; performing coupling reaction on the NB-PMP and 5-alkynyl-TMRH to obtain precursor molecules; then, catalyzing the precursor molecules through cupric salt; performing hydrolysis ring opening to obtain the hydrogen sulfide fluorescent probe. The hydrogen sulfide fluorescent probe has the advantages that through the BTD handle fragment response molecule, the H2O2 dependent hydrogen sulfide fluorescent amplitude increase response can be realized. In addition, the prepared hydrogen sulfide fluorescent probe has the advantages of great stokes displacement, high response sensitivity, high selectivity and the like. Meanwhile, low-concentration H2S in mitochondria in the cell level can be detected; wide application prospects are realized in a mitochondria-targeted hydrogen sulfide / hydrogen peroxide imaging aspect in living cells.

Description

technical field [0001] The invention belongs to the field of biological analysis and detection, and in particular relates to an active oxygen-dependent hydrogen sulfide fluorescent probe and its preparation method and application. Background technique [0002] Hydrogen sulfide (H 2 S) is the third gas signal molecule confirmed after nitric oxide (NO) and carbon monoxide (CO). itself as an endogenous molecule, H 2 The research on the regulation of physiological functions of S has attracted extensive attention. In addition, more and more studies have shown that some physiological and pathological processes of organisms can be regulated through various interactions between S and other two signaling molecules. For example, in biochemistry, H 2 S and NO have a potential synergistic effect on vascular regulation. In terms of chemistry, under special conditions, they can form a series of biologically active species, such as nitrosothiols (SNOs), nitroxyl ions (HNO - ), and sul...

Claims

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Application Information

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IPC IPC(8): C07D417/10C09K11/06G01N21/64
CPCG01N21/6486C09K11/06C07D417/10C09K2211/1088C09K2211/1037
Inventor 冯福德孙剑
Owner NANJING UNIV