Preparation and application of an open fluorescent probe for detecting carbon monoxide

A fluorescent probe, carbon monoxide technology, applied in the field of fluorescent probes

Active Publication Date: 2022-06-28
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, no fluorescent probes synthesized by HPQ-based novel fluorophores have been used to detect CO, so it is necessary to design and synthesize a new fluorescent probe for detecting CO

Method used

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  • Preparation and application of an open fluorescent probe for detecting carbon monoxide
  • Preparation and application of an open fluorescent probe for detecting carbon monoxide
  • Preparation and application of an open fluorescent probe for detecting carbon monoxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Synthesis of Fluorescent Probes

[0027] Synthetic routes such as figure 1 . Synthesis of compound Ct-OH: In a 100 mL round bottom flask, 3-(6-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-4-hydroxybenzaldehyde (HPQ- CHO) (0.30 g, 1.0 mmol) and 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indole-3-onium (0.35 g, 1.0 mmol) were dissolved in 10 mL of toluene , under the conditions of room temperature and nitrogen protection, firstly add 0.5mL piperidine with a 1mL syringe, then add 0.5mL acetic acid with a 1mL syringe, the reaction mixture was stirred overnight to stop the reaction, and then the reaction solution was mixed with saturated saline and CH 2 Cl 2 Extraction, take the lower organic phase, dry with anhydrous sodium sulfate, filter, and spin dry, the crude product can be CH with a volume ratio of 100:1 to 100:4. 2 Cl 2 / CH 3 OH eluent was used for column chromatography to obtain a green solid compound (0.32 g, yield 50%), which is compound Ct-OH.

[0028] Synthesis of C...

Embodiment 2

[0030] Fluorescent probe and CO solution preparation

[0031] Preparation of probe solution: Weigh a certain amount of probe and dissolve it in dimethyl sulfoxide to make 1×10 -4 M's probe solution. PdCl 2 Preparation of solution: weigh a certain amount of PdCl at the same time 2 Dissolve in double distilled water to make 1×10 -4 M stock 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 mol·L -1 CORM-3. will be 1.0 x 10 -3 mol·L -1 The CORM-3 solution was gradually diluted to obtain 1.0 x 10 -4 -1.0×10 -5 mol·L -1 of CORM-3 in water. Combine 1.0 mL of probe stock solution, 1.0 mL of PdCl 2 The stock solution and 1.0 mL of CORM-3 aqueous solution were added to different 10 mL volumetric flasks, and the volume was adjusted with buffer solution to obtain a concentration of 1.0 × 10 -5 mol·L -1 Fluorescent probe s...

Embodiment 3

[0033] Determination of Fluorescence Spectra of Fluorescent Probe Interaction with CO

[0034] figure 2 Fluorescence spectra for the interaction of fluorescent probes with CO, fluorescent probes and Pd 2+ The concentrations of CO were all 10 μM, and the CO concentrations were: 0, 1.0, 5.0, 10, 15, 20, 25, 30, 40, 50, 60, 80, 90, 100 μM, respectively. The excitation wavelength was fixed at 570 nm, and the fluorescence emission wavelength ranged from 540 to 750 nm. The slit width is 5.0 nm / 5.0 nm, and the fluorescence measuring instrument used is Hitachi F4600 fluorescence spectrophotometer. from figure 2 It can be seen that due to the quenching effect of allyl chloroformate on the hydroxyl group in the novel fluorophore Ct-OH, it can be found that when the fluorescent probe is added to Pd 2+ After that, there is no obvious emission peak at 605 nm; while adding Pd 2+ After CO and CO, a distinct emission peak appeared at 605 nm. This is because Pd 2+ First reduced by CO ...

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Abstract

The present invention relates to the preparation and application of an open-type fluorescent probe for detecting carbon monoxide (CO). The structural formula of the fluorescent probe is: Phthalaldehyde, 3-ethyl-1,1,2-trimethyl-1H-benzo[e]indole-3-ium, allyl chloroformate, etc. are used as raw materials to synthesize the fluorescent probe Methods; We believe that the fluorescent probe has a good spectral response performance. The probe has a wide detection range and a low detection limit, which shows that the probe can detect CO with high sensitivity; the probe has good selectivity for CO, and it is not affected by other active substances when it reacts with CO. Effects such as active oxygen, active nitrogen, active sulfur, and biological thiols; and the response time of the probe is within 120s, and it reacts relatively quickly with CO; the fluorescent probe can monitor changes in intracellular CO content.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, in particular to the preparation and application of an open-type fluorescent probe for detecting carbon monoxide. Background technique [0002] Carbon monoxide (CO) is known to be highly toxic and lethal to humans and animals. However, the latest research shows that CO can be continuously produced through the interaction of heme and heme oxygenase, so it can act as an important gas signaling molecule in our body (L. Wu, R. Wang, Pharmacol. Rev. , 2005, 57, 585-630). To maintain its normal biological functions, such as anti-inflammatory, lowering blood pressure, etc., it is believed that the physiological concentration of carbon monoxide in the physiological environment needs to be strictly regulated (E.Bathoorn, D.-J. Slebos, D. Postma, G. Koeter, A. Oosterhout, M. Toorn, H. Boezen, H. Kerstjens, Eur. Respir. J., 2007, 30, 1131-1137; R. Motterlini, L.E. Otterbein, Nat. Rev. Drug Disc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/10C09K11/06G01N21/64
CPCC07D403/10C09K11/06G01N21/6428G01N21/6486C09K2211/1029C09K2211/1044G01N2021/6432
Inventor 李春艳夏雨桑
Owner XIANGTAN UNIV
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