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Preparation and application of solid 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: 2021-09-24
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Synthesis of solid state fluorescent probes

[0028] Synthetic route figure 1 .

[0029] Synthesis method of solid state fluorophore HPQ-MQ-OH: 0.35 g 1-ethyl-2-methylquinoline (1 mmol), 0.30 g 3- (7-chloro-4-oxygen-3,4-dihydroquinazole) Pyloline) -4-hydroxybenzaldehyde (1 mmol), 20.0 ml of acetonitrile sequentially added to a 100 ml round bottom flask. Then, 0.2 ml of piperidine was added with a microformor, and the reflux reaction was stirred at 80 ° C for 15 h, and the solvent was evaporated. The solid product was dissolved with dichloromethane, extracted three times with saturated brine, dried the lower organic phase, filtered, evaporated, solid products in CH 2 CL 2 / CH 3 OH = 100: 7 (volume ratio) was column chromatography to the eluent, resulting in 0.22 g of reddish brown solid product (HPQ-MQ-OH), and the yield was 50%.

[0030] Synthesis of HPQ-MQ-MQ-MQ-MQ-MQ-MQ-MQ-MQ-MQ-MQ-MQ-CO: 0.25 g of HPQ-MQ-OH (1 mmol) is dissolved under 10 ml of dry CH under ice bath and ...

Embodiment 2

[0032] Solid state fluorescent probe and CO solution formulated

[0033] Preparation of the probe solution: Weigh a certain amount of probe in dimethyl sulfoxide, formulated into 1 × 10 -4 M The probe solution. At the same time, we can weigh a certain amount of PDCL. 2 Dissolve in secondary distilled water, equipped with 1 × 10 -4 M solution. Handling of CO solution: dissolve a certain amount of CORM-3 in secondary distilled water, transferred to a 500 mL volumetric flask, add water to the scale, to give a concentration of 1.0 × 10 -3 M's CORM-3. Will 1.0 × 10 -3 M's CORM-3 solution gradually dilute, get 1.0 × 10 -6 -1.0 × 10 -3 Mol·L -1 CORM-3 aqueous solution. 1.0ml probe solution, 1.0ml of PDCl 2 The solution and 1.0 ml of CORM-3 aqueous solution were added to 10 ml of volumetric flask, and the concentration was 1.0 × 10 after the buffer solution was allowed to obtain a concentration of 1.0 × 10. -5 Fluorescent probe and PDCl 2 , 1.0 × 10 -7 -1.0 × 10 -4 M The CO mixed to be te...

Embodiment 3

[0035] Determination of fluorescence spectrum of solid fluorescence probes and CO effects

[0036] figure 2 Fluorescence spectrum, solid fluorescent probe and PD for solid state fluorescence probes and CO 2+ The concentration was 10 μm, and the Co concentration was: 0, 0.1, 0.5, 1, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100 μm. The excitation wavelength is fixed to 550 nm, and the emission wavelength ranges from 620 to 670 nm. The slit width was 5.0 nm / 5.0 nm, and the fluorescent assay used was a daiser F4600 fluorescence spectrophotometer. From figure 2 It can be seen that the probe itself emits weak fluorescence due to the quenching effect of allyl carbone. Add PD 2+ After Co, a significant emission peak appeared at 650 nm. This is because PD 2+ First by Co reduction as a PD 0 The Tsuji-Trost reaction is then mediated, resulting in the breakage of the allyl carbone, releases fluorophore, resulting in a fluorescent signal. And as the Co concentration increases, the fluorescenc...

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Abstract

The invention relates to preparation and application of a solid-state fluorescent probe for detecting carbon monoxide (CO), the structural formula of the fluorescent probe is shown in the specification. The invention provides a preparation method for synthesizing the solid-state fluorescent probe by taking 3-(7-chloro-4-oxo-3, 4-dihydroquinazoline)-4-hydroxybenzaldehyde, 1-ethyl-2-methylquinoline, allyl chloroformate and the like as raw materials. Firstly, the solid-state fluorescent probe is relatively long in wavelength, emits strong fluorescence at 650nm, is insoluble in water and has anti-diffusion capability; secondly, the fluorescent probe shows very high sensitivity to CO, and fluorescence is remarkably enhanced after the probe reacts with CO; moreover, the solid-state fluorescent probe shows very high selectivity on CO, and is not interfered by other active oxygen, active nitrogen, active sulfur, biological mercaptan and common ions; in addition, the solid-state fluorescent probe can quickly act with CO, and the response time is within 100s; and finally, the solid-state fluorescent probe is applied to detection of the content of carbon monoxide in living cells and can be used for fluorescence imaging of CO.

Description

Technical field [0001] The present invention belongs to the field of fluorescent probe, and more particularly to the preparation and application of solid fluorescent probes for detecting carbon monoxide. Background technique [0002] Carbon monoxide (CO) is a colorless gas that is conventionally considered to be toxic substances due to its strong affinity for hemoglobin (l.k.weaver, n.engl.j.med., 2009, 360, 1217-1225). However, in recent years, scientific evidence suggests that CO is with nitric oxide (NO), hydrogen sulfide (H 2 S), it is an essential gas delivery quality of the human body, play an important role in a variety of physiological and pathological processes (F.Wattel, R.Favory, S.lance, R. Neviere, D.Mathieu, Bull.acad .Natl.med., 2006, 190, 1961-1975; LYWU, R.WANG, Pharmacol.Rev., 2005, 57, 585-630). For example: CO is involved in blood vessels, anti-apoptosis, anti-inflammatory and neuroplastic transmission. In addition, CO metabolism is related to many diseases, s...

Claims

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Application Information

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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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