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Preparation and Application of Pyran-coumarin-Based Fluorescent Probe for Carbon Monoxide

A carbon monoxide, fluorescent probe technology, applied in the field of fluorescent probes, can solve problems such as long response time, short analysis wavelength, and reduced probe sensitivity

Active Publication Date: 2021-12-14
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are some problems with these probes: (1) These fluorescent probes have short analysis wavelengths, so they are easily interfered by autofluorescent signals generated by biomolecules in vivo, thereby reducing the sensitivity of the probes; (2) these fluorescent probes The probe has a relatively long response time, and the response time is more than 10 minutes
However, no pyran-coumarin-based probes have been used to detect CO, so it is necessary to design and synthesize a pyran-coumarin-based probe to detect CO.

Method used

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  • Preparation and Application of Pyran-coumarin-Based Fluorescent Probe for Carbon Monoxide
  • Preparation and Application of Pyran-coumarin-Based Fluorescent Probe for Carbon Monoxide
  • Preparation and Application of Pyran-coumarin-Based Fluorescent Probe for Carbon Monoxide

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Experimental program
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Embodiment 1

[0025] Synthesis of fluorescent probes

[0026] Synthetic route such as figure 1 . Synthesis of compound CP-OH: In a 100mL round bottom flask, 3-acetyl-7-diethylaminocoumarin (0.39g, 1.5mmol) and 2-(2,4-dihydroxybenzoyl ) benzoic acid (0.39g, 1.5mmol) was dissolved in 8mL of methanesulfonic acid, and the reaction mixture was stirred at 90°C for 12h to stop the reaction, then the reaction mixture was cooled to room temperature, poured into a beaker containing 50g of ice water, and immediately Add 0.8mL of 70% perchloric acid, a blue-green solid precipitates immediately, stand still for 2h, filter, wash the solid with 10mL of ice water, dry, the crude product is mixed with CH at a volume ratio of 20:1 2 Cl 2 / CH 3 OH eluent was subjected to column chromatography to obtain a blue-green solid compound (0.52 g, yield 60%), which was compound CP-OH.

[0027] Synthesis of CO fluorescent probe (CP-CO): In a 100mL round bottom flask, the compound CP-OH (0.58g, 1.0mmol), allyl chlo...

Embodiment 2

[0029] Fluorescent probe and CO solution preparation

[0030] Preparation of probe solution: Weigh a certain amount of probe and dissolve it in dimethyl sulfoxide to make 1×10 -4 M probe solution. At the same time, weigh a certain amount of PdCl 2 Dissolved in twice distilled water to make 1×10 -4 stock solution of M. Preparation of CO solution: Dissolve a certain amount of CORM-3 in twice-distilled water, transfer it to a 500mL volumetric flask, add water to the mark, and obtain a concentration of 1.0×10 -3 mol L -1 CORM-3. Divide 1.0×10 -3 mol L -1 The CORM-3 solution was gradually diluted to obtain 2.0 x 10 -4 -1.0×10 -5 mol L -1 CORM-3 aqueous solution. Mix 1.0 mL of probe stock solution, 1.0 mL of PdCl 2 The stock solution and 1.0mL of CORM-3 aqueous solution were added to a 10mL volumetric flask, and after constant volume with buffer solution, a concentration of 1.0×10 - 5 mol L -1 fluorescent probe and PdCl 2 , 2.0×10 -5 -1.0×10 -6 mol L -1 CO mixed w...

Embodiment 3

[0032] Measurement of Fluorescence Spectrum of Fluorescent Probe Interaction with CO

[0033] figure 2 For the fluorescence spectrum of the fluorescent probe interacting with CO, the fluorescent probe and Pd 2+ The concentration of CO is 10 μM, and the CO concentration is: 0, 1.0, 2.0, 3.0, 4.0, 5.0, 6.0, 7.0, 8.0, 9.0, 10, 12, 15, 20 μM. The excitation wavelength is fixed at 600nm, and the emission wavelength range is 620-780nm. The slit width is 5.0 nm / 5.0 nm, and the fluorescence measurement instrument used is a Hitachi F4600 fluorescence spectrophotometer. From figure 2 It can be seen that due to the quenching effect of allyl formate, the addition of the fluorescent probe to Pd 2+ After that, there is no obvious near-infrared emission peak at the near-infrared (670nm); while adding Pd 2+ After and CO, an obvious near-infrared emission peak appeared at 670 nm. This is because Pd 2+ First reduced to Pd by CO 0 , which subsequently mediates the Tsuji-Trost reaction,...

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Abstract

The present invention relates to the preparation and application of carbon monoxide (CO) fluorescent probe based on pyran-coumarin, the structural formula of this fluorescent probe is: the present invention provides 3-acetyl-7-diethylaminocoumarin 2-(2,4-dihydroxybenzoyl) benzoic acid, allyl chloroformate, etc. are the preparation method for synthesizing the fluorescent probe as raw materials; the fluorescent probe is a near-infrared carbon monoxide fluorescent probe ; Firstly, the fluorescent probe showed high sensitivity to CO, and the fluorescence of the probe was significantly enhanced after reacting with CO; secondly, the fluorescent probe showed high selectivity to CO, and was not affected by other reactive oxygen species and reactive nitrogen species. , active sulfur and biological thiol interference; and, the fluorescent probe reacts rapidly with CO, and the response time is within 50s; in addition, the fluorescent probe is applied to the detection of carbon monoxide content in living cells.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, in particular to the preparation and application of a carbon monoxide near-infrared fluorescent probe based on a pyran-coumarin dye. Background technique [0002] Carbon monoxide (CO) is a signaling molecule catalyzed and synthesized by heme oxygenase in various cells in the body (L.K. Weaver, N. Engl. J. Med., 2009, 360, 1217-1225). Studies in recent years have shown that CO, as a gas transport substance, plays an important role in various physiological and pathological processes (F.Wattel, R.Favory, S.Lancel, R.Neviere, D.Mathieu, Bull.Acad.Natl. Med., 2006, 190, 1961-1975; L. Y. Wu, R. Wang, Pharmacol. Rev., 2005, 57, 585-630). CO is involved in various physiological processes such as vasodilation, anti-apoptosis, anti-inflammation and neurotransmission (D.R.Premkumar, M.A.Smith, P.L.Richey, R.B.petersen, R.Castellani, R.K.Kutty, J. Neurochem., 1995,65,1399 -1402; R.A. Schroeder, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/10C09K11/06G01N21/64
CPCC07D493/10C09K11/06G01N21/6428C09K2211/1088
Inventor 李春艳江文丽
Owner XIANGTAN UNIV
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