Preparation and application of hydrogen sulfide fluorescent probe based on isophorone-xanthene

A fluorescent probe, hydrogen sulfide technology, applied in the field of fluorescent probes

Active Publication Date: 2022-04-05
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, until now, no isophorone-xanthene dyes have been used as fluorescent probes for the detection of H 2 S

Method used

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  • Preparation and application of hydrogen sulfide fluorescent probe based on isophorone-xanthene
  • Preparation and application of hydrogen sulfide fluorescent probe based on isophorone-xanthene
  • Preparation and application of hydrogen sulfide fluorescent probe based on isophorone-xanthene

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Synthesis of fluorescent probes

[0027] Synthetic route such as figure 1 . DCP-OH (96mg, 0.25mmol), 2,4-dinitrofluorobenzene (46.5mg, 0.25mmol), and 0.5mL of triethylamine were added to a 100mL round-bottomed flask, and then 7mL of acetone was added to dissolve it dissolve. The reaction was stirred under reflux at 65 °C for 0.5 h. After the reaction was complete, the solvent was removed under reduced pressure. 10 mL of 5% HCl solution was added to the resulting mixture, the precipitate was filtered, washed several times with water, and then purified by recrystallization in acetone to obtain the dark green solid product DCP-HS (82 mg, yield 60%), which was obtained as fluorescent probes described above. 1 H NMR (400MHz, CHCl 3 )δ8.66(s,1H),8.36(d,J=8.0Hz,1H),7.16–7.08(m,3H),6.83–6.73(m,3H),2.74(d,J=8.0Hz,4H ),1.6(s,4H).1.05(m,6H). 13 C NMR (100MHz, CDCl 3 )δ168.72, 155.44, 154.37, 153.45, 141.91, 141.72, 128.83, 122.37, 119.14, 116.22, 114.14, 113.43, 108.00, 42...

Embodiment 2

[0029] Fluorescent probes and H 2 S solution preparation

[0030] Preparation of probe solution: Weigh a certain amount of probe and dissolve it in dimethyl sulfoxide to make 2×10 -4 M stock solution. Add 500 μL of the spare solution of the probe into a 10 mL volumetric flask, and after constant volume with PBS buffer solution, a concentration of 1.0×10 -5 mol / L fluorescent probe solution. H 2 S was prepared at the following concentrations (1.0, 2.0, 3.0, 4.0, 5.0, 6.0, 7.0, 8.0, 9.0, 10.0 μM), respectively.

Embodiment 3

[0032] Fluorescent probes with H 2 Determination of Fluorescence Spectrum of S Effect

[0033] figure 2 as a fluorescent probe with H 2 The fluorescence spectrum of S interaction, the concentration of fluorescent probe is 10μM, H 2 The concentration of S was 1.0, 2.0, 3.0, 4.0, 5.0, 6.0, 7.0, 8.0, 9.0, 10.0 μM in turn. The excitation wavelength used in the experiment is 570nm, and the emission wavelength range is 590-900nm. The slit width is 10.0 nm / 10.0 nm, and the fluorescence measurement instrument used is a Hitachi F4600 fluorescence spectrophotometer. From figure 2 It can be seen that adding H 2 Before S, the probe itself has almost no emission peak due to the quenching effect of the dinitrophenyl ether group; 2 With the addition of S, the thiolysis of the dinitrophenyl ether group returns to the electron-donating hydroxyl group, and the emission peak at 770nm is greatly enhanced, and with the H 2 With the increase of S concentration, the fluorescence intensity ...

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Abstract

The present invention relates to a kind of hydrogen sulfide (H 2 S) preparation and application of near-infrared fluorescent probe, the structural formula of the probe is: the present invention provides isophorone-xanthene dye, 2,4-dinitrofluorobenzene, etc. as raw materials to synthesize the fluorescent probe The preparation method of the needle; the fluorescent probe is a hydrogen sulfide fluorescent probe with a large Stokes shift and near-infrared emission; first, the fluorescent probe is sensitive to H 2 S showed good sensitivity, with a linear range of 1μM‑10μM and a detection limit of 0.3μM; secondly, the fluorescent probe was sensitive to H 2 S exhibits high selectivity and is not affected by other ions, reactive oxygen species, and biothiols; and, the fluorescent probe interacts with H 2 S acts quickly, and the response time is within 10 minutes; in addition, this fluorescent probe can also be applied to H in living cells. 2 Detection of S content.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, in particular to the preparation and application of hydrogen sulfide fluorescent probes based on isophorone-xanthene dyes. Background technique [0002] Hydrogen sulfide (H 2 S) is an important endogenous gas signal molecule in the system, involved in various physiological and pathological processes (Wang, R. Antioxid. Redox Signaling, 2003, 5, 493-501.). It has been recognized as a physiological gastransmitter with potent cytoprotective effects in various organ systems, including modulation in the cardiovascular system and modulation of the central nervous, respiratory and gastrointestinal systems (H. Kimura, Antioxid .Redox Signaling, 2010, 12, 1111; N. Skovgaard, A. Gouliaev, M. Aalling, U. Simonsen, Curr. Pharm, Biotechnol. 2011, 12, 1385; R. Wang, Physiol. Rev. 2012, 92, 791; G. Tang, G. Yang, B. Jiang, Y. Ju, L. Wu, R. Wang, Antioxid. Redox Signaling, 2013, 19, 1634.). At the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/78C09K11/06G01N21/64
CPCC07D311/78C09K11/06G01N21/6428C09K2211/1007C09K2211/1014C09K2211/1088
Inventor 李春艳闫灵徐芬
Owner XIANGTAN UNIV
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