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Fluorescent probe for detecting intracellular hydrogen sulfide based on nitroreduction and application thereof

A fluorescent probe and hydrogen sulfide technology, applied in the field of fluorescent probes for detecting hydrogen sulfide (H2S), can solve the problems of damaging biological samples, slow response of hydrogen sulfide, and inability to detect H2, so as to improve detection accuracy and reduce interference Effect

Active Publication Date: 2014-03-26
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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Problems solved by technology

However, this kind of fluorescent probe has a slow response to hydrogen sulfide and cannot be used for rapid detection of H 2 S
Binghe Wang et al. disclosed a method to detect H 2 The fluorescent probe DNS-Az of S (for the structure see figure 1 , B.Wang et.al, Angew.Chem.Int.Ed., 2011, 50, 9672), but the excitation and emission wavelength of this probe is in the ultraviolet region, which cannot effectively avoid the interference of biological autofluorescence, and ultraviolet light is harmful to biological Body photobleaching has a strong effect and is easy to damage biological samples
The above-mentioned probes are fluorescence-enhanced probes, and there is no change in wavelength, so quantitative detection cannot be realized

Method used

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  • Fluorescent probe for detecting intracellular hydrogen sulfide based on nitroreduction and application thereof
  • Fluorescent probe for detecting intracellular hydrogen sulfide based on nitroreduction and application thereof
  • Fluorescent probe for detecting intracellular hydrogen sulfide based on nitroreduction and application thereof

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Experimental program
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Effect test

Embodiment 1

[0083] Embodiment 1. The synthesis of the compound shown in specific formula I.

[0084] Such as figure 2 As shown, the structure of the probe compound used in the specific formula I of the embodiment is coded Cy-NO 2 express

[0085] Dissolve 0.696g m-nitrophenol and 0.0524-0.173g sodium hydride in 30mL anhydrous DMF, add 0.5g cyanine dye Cy7-Cl, and react at room temperature for 24h under nitrogen protection. After the reaction, the DMF was removed in vacuo, purified by silica gel chromatography, and the eluents were ethyl acetate and methanol to obtain 0.425 g of dark green product with a yield of 73.2%. 1 H NMR (500MHz, CDCl 3 -D 1 )δ(ppm):1.25-2.09(m,20H),2.63-2.65(q,4H),4.17-4.22(q,4H),6.08-6.17(d,2H),7.04-7.98(m,12H) ,8.01-8.09(d,2H). 13 C NMR (500MHz, CDCl 3 -D 1 )δ (ppm): 171.4, 162.2, 159.7, 141.7, 141.1, 131.7, 129.9, 128.8, 125.3, 122.3, 122.2, 117.4, 110.7, 110.5, 110.2, 100.7, 77.3, 77.0, 76.8, 40, 28.4, 40. 27.8, 24.8, 21.0, 12.4, 12.3. LC-MS (API-ES)...

Embodiment 2

[0086] Synthesis of compound shown in embodiment 2 concrete formula II

[0087] Such as figure 2 As shown, the structure of the probe compound used in the embodiment specific formula I is coded mCy-NO 2 express

[0088] Dissolve 0.696g m-nitroaniline in 30mL anhydrous DMF, add triethylamine, stir at room temperature for 15min, then add 0.50g cyanine dye Cy7-Cl, react at 60-90℃ for 24h under nitrogen protection. After the reaction, the DMF was removed in vacuo, and purified by silica gel column chromatography, and the eluents were ethyl acetate and methanol. 0.274 g of dark blue product was obtained, with a yield of 47.3%. 1 HNMR (400MHz, CDCl 3 -D 1 ,0.1%CD 3 COOD-D 4 )δ(ppm):8.00(s,1H),7.30-7.15(m,8H),6.50(s,1H),5.84(s,1H),5.28(s,1H),4.02(m,2H), 2.96(s,2H),2.88(s,2H),2.79(s,1H),1.87-1.58(m,10H). 13 C NMR (100MHz, CDCl 3 -D 1 )δ (ppm): 168.8, 162.6, 142.4, 140.7, 140.1, 128.5, 127.7, 123.8, 122.2, 122.0, 121.5, 120.0, 109.2, 105.54, 96.3, 59.2, 54.6, 45.5, 39.3, 3...

Embodiment 3

[0091] Compound Cy-NO shown in specific formula I 2 Temperature Effects on the Response to Hydrogen Sulfide

[0092] In order to simulate physiological conditions as much as possible, the following detection effect experiments were carried out under the condition of pH=7.4 (HEPES buffer solution, the concentration was 40mM), and the probe concentration was 10μM.

[0093] pH was controlled with HEPES buffer solution. Add 10 μM Cy-NO, the compound shown in specific formula Ⅰ, to the 10ml colorimetric tube 2 , then 40 mM HEPES was added, followed by 350 μM Na 2 S, dilute to 10ml with ultrapure water, shake the solution evenly, and equilibrate at 25, 37, 45, and 60°C for 50 minutes, then add the above working solution into a fluorescent dish to measure the fluorescence spectrum. . Fluorescence intensity changes with temperature as Figure 4 shown. Figure 4 show that Cy-NO 2 and H 2 The reaction rate of S is affected by temperature. For the purpose of in vivo application ...

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Abstract

The invention relates to a fluorescent probe for detecting hydrogen sulfide (H2S), and specifically relates to a fluorescent probe for detecting intracellular hydrogen sulfide based on nitroreduction and an application thereof. The fluorescent probe takes a hemicyanine dye or a cyanine dye as a fluorescent matrix, and m-nitrophenylamine or m-nitrophenol is introduced to the matrix. The fluorescent probe is used for detecting hydrogen sulfide inside and outside a water body or a living body. According to these compounds of the fluorescent probe for detecting hydrogen sulfide, corresponding fluorescence intensity changes in presence of hydrogen sulfide, so that the fluorescent probe can be used for detecting hydrogen sulfide, thereby greatly reducing interference of outer conditions and improving the detection accuracy. In particular, these compounds used as the fluorescent probe can be used for detecting intracellular hydrogen sulfide, thereby having an important significance for lucubrating the dynamic mechanism of hydrogen sulfide which is generated, conveyed, accumulated and the like in the living body and further understanding the physiological and toxicological effects of hydrogen sulfide.

Description

technical field [0001] The invention relates to a method for detecting hydrogen sulfide (H 2 S) A fluorescent probe, specifically a fluorescent probe for detecting intracellular hydrogen sulfide based on nitro reduction and its application. Background technique [0002] For centuries, hydrogen sulfide (H 2 S) Much attention has been paid to environmental toxicity and toxic effects. When the human body is exposed to exogenous hydrogen sulfide, the gas can be rapidly absorbed through the lungs to enter the blood circulation system, and then produce toxic effects in the human body. It is now generally believed that sulfide inhibits oxidases in a similar manner to cyanide and produces physiological toxicity. However, recent studies on endogenous H 2 Research work on S has been devoted to several of its physiological functions. After nitric oxide (NO) and carbon monoxide (CO), H 2 S was identified as a third biologically active gas, known as a gas transmitter or gas mediato...

Claims

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Application Information

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IPC IPC(8): C07D209/12C07D209/14C09K11/07G01N21/64C12Q1/02
CPCC07D209/10C07D209/12C09K11/06C09K2211/1029G01N21/6428G01N21/6486
Inventor 陈令新于法标王锐陈浩
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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