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Preparation and application of a solid-state fluorescent probe for detecting carbon monoxide

A solid-state fluorescence and carbon monoxide technology, applied in the field of fluorescent probes, can solve the problems of short wavelength and limited application of solid-state fluorescent probes

Active Publication Date: 2022-05-10
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the short wavelengths of these solid-state fluorescent probes limit their application in living organisms

Method used

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  • Preparation and application of a solid-state fluorescent probe for detecting carbon monoxide
  • Preparation and application of a solid-state fluorescent probe for detecting carbon monoxide
  • Preparation and application of a solid-state fluorescent probe for detecting carbon monoxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Synthesis of solid-state fluorescent probes

[0029] Synthetic route such as figure 1 .

[0030] The synthesis method of solid-state fluorophore HPQ-MQ-OH: 0.35g 1-ethyl-2-methylquinoline (1mmol), 0.30g3-(6-chloro-3,4-dihydro-4-oxo- 2-Quinazolinyl)-4-hydroxybenzaldehyde (1 mmol) and 20.0 mL of acetonitrile were successively added into a 100 mL round bottom flask. Then, under the protection of nitrogen, 0.2 mL of piperidine was added with a micro injector, and the reaction was stirred and refluxed at 80°C for 15 h, and the solvent was removed by distillation under reduced pressure. The solid product was dissolved in dichloromethane, extracted three times with saturated brine, the lower organic phase was dried, filtered and evaporated, and the solid product was extracted with CH 2 Cl 2 / CH 3 OH=100:7 (volume ratio) was used as the eluent for column chromatography to obtain 0.22 g of a reddish-brown solid product (HPQ-MQ-OH), with a yield of 50%.

[0031] The synthes...

Embodiment 2

[0033] Preparation of solid-state fluorescent probe and CO solution

[0034] 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 M's solution. Preparation of CO solution: Dissolve a certain amount of CORM-3 in double distilled water, transfer it to a 500mL volumetric flask, add water to the mark, and obtain a concentration of 1.0×10 -3 CORM-3 of M. will be 1.0×10 -3 The CORM-3 solution of M was gradually diluted to obtain 1.0 × 10 -6 -1.0×10 -3 mol L -1 CORM-3 aqueous solution. Mix 1.0 mL of probe solution, 1.0 mL of PdCl 2 Solution and 1.0mL of CORM-3 aqueous solution were added to a 10mL volumetric flask, and after constant volume with buffer solution, the concentration was 1.0×10 -5 M fluorescent probe and PdCl 2 , 1.0×10 -7 -1.0×10 -4 M of CO mixed with the solution to be teste...

Embodiment 3

[0036] Measurement of Fluorescence Spectrum of Solid State Fluorescent Probe Interaction with CO

[0037] figure 2 For the fluorescence spectrum of the solid-state fluorescent probe interacting with CO, the solid-state fluorescent probe and Pd 2+ The concentrations of CO are 10 μM, and the CO concentrations are: 0, 0.1, 0.5, 1, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100 μM. The excitation wavelength is fixed at 550nm, and the emission wavelength range is 620-670nm. 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 the probe itself emits only weak fluorescence due to the quenching effect of allyl formate. Join Pd 2+ After and CO, an obvious emission peak appeared at 650 nm. This is because Pd 2+ First reduced to Pd by CO 0 , which subsequently mediates the Tsuji-Trost reaction, resulting in the cleavage of the allyl formate, releasing the fluorophore, t...

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Abstract

The present invention relates to the preparation and application of a solid-state fluorescent probe for detecting carbon monoxide (CO). The structural formula of the fluorescent probe is: Dihydroquinazoline)-4-hydroxybenzaldehyde, 1-ethyl-2-methylquinoline, allyl chloroformate, etc. are the preparation method for synthesizing the solid-state fluorescent probe as raw materials; first, the solid-state fluorescent The probe has a long wavelength, emits strong fluorescence at 650nm, is insoluble in water and has anti-diffusion ability; secondly, the fluorescent probe shows high sensitivity to CO, and the fluorescence of the probe is significantly enhanced after the reaction of the probe with CO; and , the solid-state fluorescent probe exhibits high selectivity to CO, and is not interfered by other reactive oxygen species, reactive nitrogen species, reactive sulfur, biothiols, and common ions; in addition, the solid-state fluorescent probe reacts rapidly with CO and responds The time is within 100s; finally, the solid-state fluorescent probe is applied to the detection of carbon monoxide content in living cells, and can perform fluorescence imaging of CO.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and in particular relates to the preparation and application of a solid-state fluorescent probe for detecting carbon monoxide. Background technique [0002] Carbon monoxide (CO) is a colorless, odorless gas that has traditionally been considered a toxic substance due to its strong affinity for hemoglobin (L.K. Weaver, N. Engl. J. Med., 2009, 360, 1217-1225). However, in recent years, scientific evidence has shown that CO and nitric oxide (NO), hydrogen sulfide (H 2 Like S), it is an essential gas transmitter for the human body and 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). For example: CO is involved in vasodilation, anti-apoptosis, anti-inflammation and neurotransmission. In addition, abnormal CO m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/10C09K11/06G01N21/64
CPCC07D401/10C09K11/06G01N21/6428C09K2211/1029C09K2211/1044
Inventor 李春艳付贵勤夏雨桑
Owner XIANGTAN UNIV
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