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Fluorescent probe for identifying hydrogen sulfide in lysosome and application thereof

A fluorescent probe, lysosome technology, applied in fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., can solve the problems of reduced detection probability of acidic organelles, low probe selectivity, etc.

Inactive Publication Date: 2015-11-11
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, comprehensive analysis of the current H 2 The S fluorescent probe mainly has the following disadvantages: First, for H in the acidic region 2 The detection of S is still rare, due to acidic organelles causing H 2 Dynamic changes in S, H in acidic organelles especially in lysosomes 2 The detection probability of S is greatly reduced; secondly, H 2 The selectivity of the S probe is not high, especially the interference of the environment in the cell, especially the interference of the acidic environment; based on this, the development of a new type of hydrogen sulfide (H 2 S) fluorescent probe, and give the detection curve to judge H 2 S level, has important practical application value

Method used

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  • Fluorescent probe for identifying hydrogen sulfide in lysosome and application thereof
  • Fluorescent probe for identifying hydrogen sulfide in lysosome and application thereof
  • Fluorescent probe for identifying hydrogen sulfide in lysosome and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 2-(9-(2-ethoxyethyl)-2-(pyridin-4-yl)vinyl)-9hydro-carbazol-3-yl)ethenyl)-1-ethyl-3,3- Synthesis of dimethyl-3hydro-indole-1-iodine (PCAI):

[0033]With 0.37g (1mmol) compound 9-(2-ethoxyethyl ester)-6-(2-(pyridine-4-yl) vinyl)-9 hydrogen-carbazole-3-aldehyde (1) 0.32g ( 1.1 mmol) compound 1-ethyl-2,3,3-trimethyl-3 hydrogen-indole-1-iodide salt (2), dissolved in 20 mL of ethanol. The reaction was refluxed under the protection of nitrogen. After the reaction, part of the ethanol was evaporated by rotary evaporation, and then poured into 20 mL of ether to obtain a red solid, which was washed 3-4 times with ether. The red powder obtained by filtration is PCAI. Yield: 90%.

[0034] 1 HNMR (400MHz, CDCl 3 )δ9.76(s,1H),9.40(s,1H),8.35(dd,J=10.1,5.4Hz,3H),8.11(d,J=15.6Hz,1H),7.90(d,J=8.3 Hz, 1H), 7.78–7.61(m, 4H), 7.60–7.51(m, 4H), 7.49(d, J=7.5Hz, 1H), 7.43(d, J=8.5Hz, 1H), 5.13(d ,J=7.1Hz,2H),4.51(t,J=5.3Hz,2H),3.85(t,J=5.4Hz,2H),3.42(q,J=7.0Hz,2H),1.88(s,5H ), 1.70...

Embodiment 2

[0036] PCAI's Response to Sour Sexual Environment:

[0037] Prepare in advance 1 serving of 10 mL of 10 -3 M probe N,N-dimethylformamide solution of the present invention, then take 10 μ L respectively and add in six identical 5 mL volumetric flasks, dilute to 5 mL with solutions of different pH (pH4.53~pH7.93), and then Fluorescence detection (λ Ex =488nm), the results are shown in figure 1 .

[0038] Conclusion: It shows that the probe responds in the acidic range of lysosome.

Embodiment 3

[0040] PCAI vs H 2 S selectivity:

[0041] Among them: the excitation wavelength is 405nm; the concentration of the probe mother solution: 10 -3 M, the concentration of the selective ion is 4.5x10 -5 M. Take 10 μL of the probe mother solution and dilute it in 5ml, then take 2mL of the above diluted solution, add 40 equivalents of various ions for spectral testing.

[0042] Serial numbers 1 to 13, respectively 1. Blank (PCAI); 2. Cl - ;3.GSH;4.H 2 o 2 ; 5.Hcy; 6.HSO 3 - ; 7.I - ; 8. Mg 2+ 9. NO 2 - ;10.S 2 o 3 2- ;11. SO 3 2- ; 12. SO 4 2 ; 13.Zn 2+ . (See figure 2 ).

[0043] Conclusion: The test results show that the probe PCAI is effective for H 2 S is highly selective. Join H 2 After S, the probe response multiple was about 7 times.

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Abstract

The invention discloses a fluorescent probe for identifying hydrogen sulfide in lysosome. The fluorescent probe is 2-(9-(2-ethoxy ethyl ester)-2-(pyridyl-4-yl)vinyl)-9H-carbazolyl-3-yl)vinyl)-1-ethyl-3,3-dimethyl-3H-indolyl-1-iodine which is called PCAI for short, and the chemical structural formula is disclosed as Formula (I). The invention also discloses application of the fluorescent probe in detecting H2S in lysosome. The experiment proves that the fluorescent probe can identify lysosome and H2S in the lysosome through fluorescence enhancement; and the probe has potential application value in the field of targeted molecular markers of acidic regions of living cells.

Description

technical field [0001] The present invention relates to a kind of recognition hydrogen sulfide (H 2 S) Fluorescent probe and application thereof, especially relate to a kind of specific recognition H in lysosome 2 The invention relates to a carbazole compound fluorescent probe of S and its application; it belongs to the field of small organic molecule fluorescent probes. Background technique [0002] Hydrogen sulfide (H 2 S) plays an important role in various physiological processes, H 2 Abnormal S levels are associated with many types of diseases such as Alzheimer's, cirrhosis, Down's syndrome and diabetes. Recently, H 2 S has been confirmed to be the third type of active small molecule related to major human diseases after carbon monoxide (CO) and nitric oxide (NO) in academia. Based on this, for H 2 The detection of S has also aroused people's great attention. In addition, lysosomes are acidic organelles in cells with a pH range of 4.5-5.5. Lysosomes are also impor...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D401/14G01N21/64
Inventor 林伟英刘勇孟芳芳石起慢
Owner UNIV OF JINAN
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