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Fluorescent probe for detecting CO (carbon monoxide) in cells and preparation method and application of fluorescent probe

A fluorescent probe and cell technology, applied in the field of detection, can solve problems such as long reaction time, achieve fast detection speed, simple synthesis, and improved selectivity

Active Publication Date: 2016-06-01
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The response groups of the above two probes are all cyclopalladium compounds formed by benzylamine. Although the selectivity is good, the reaction time is long (1h or 30min).

Method used

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  • Fluorescent probe for detecting CO (carbon monoxide) in cells and preparation method and application of fluorescent probe
  • Fluorescent probe for detecting CO (carbon monoxide) in cells and preparation method and application of fluorescent probe
  • Fluorescent probe for detecting CO (carbon monoxide) in cells and preparation method and application of fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] (1) Dissolve p-nitrobenzoyl chloride (7g) and 2,4-dimethylpyrrole (7g) in CH 2 Cl 2 (20mL), heated to reflux for 1h. After cooling, triethylamine (3.5 g) and toluene (30 ml) were added. After 15 minutes of reaction, boron trifluoride diethyl ether (3g) was added, the temperature was raised to 50° C. for 3 hours, spin-dried, and separated by chromatographic column (eluent: V 石油醚 :V 二氯甲烷 =5:1), spin-dried to obtain orange solid nitrophenyl BODIPY.

[0045] NMR and mass spectrometry characterization:

[0046] 1 HNMR (400MHz, CDCl 3 ):δ=1.36(s,6H),2.57(s,6H),6.02(s,2H),7.54(d,J=8Hz,2H),8.39(d,J=8Hz,2H)

[0047] ESI-MS: calculated for [M-H] - =368.1, found 368.1.

[0048] (2) Dissolve nitrophenyl BODIPY (5g), ammonium formate (50g) in CH 2 Cl 2 (10mL), then add Pd / C1 2 (1g), stirred at room temperature for 2 hours, filtered, and the filtrate was spin-dried to obtain aminophenyl BODIPY.

[0049] NMR and mass spectrometry characterization:

[0050] 1 HNMR (400MH...

Embodiment 2

[0060] (1) Dissolve p-nitrobenzoyl chloride (0.14g) and 2,4-dimethylpyrrole (0.14g) in CH 2 Cl 2 (2mL), heated to reflux for 1h. After cooling, triethylamine (0.35 g) and toluene (3 ml) were added. After 15 minutes of reaction, add boron trifluoride diethyl ether (0.3 g), heat up to 50° C. for 3 hours, spin dry, and separate with a chromatographic column (eluent: V 石油醚 :V 二氯甲烷 =5:1), spin-dried to obtain orange solid nitrophenyl BODIPY.

[0061] NMR and mass spectrometry characterization:

[0062] 1 HNMR (400MHz, CDCl 3 ):δ=1.36(s,6H),2.57(s,6H),6.02(s,2H),7.54(d,J=8Hz,2H),8.39(d,J=8Hz,2H)

[0063] ESI-MS: calculated for [M-H] - =368.1, found 368.1.

[0064] (2) Dissolve nitrophenyl BODIPY (10g) and ammonium formate (100g) in CH 2 Cl 2 (20mL), then add Pd / C1 2 (2g), stirred at room temperature for 2 hours, filtered, and the filtrate was spin-dried to obtain aminophenyl BODIPY.

[0065] NMR and mass spectrometry characterization:

[0066] 1 HNMR (400MHz, CDCl 3 ...

Embodiment 3

[0076] The present invention is the same as Example 1, except that 2,4-dimethylpyrrole is changed to 2,3,4-trimethylpyrrole.

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Abstract

The invention discloses a fluorescent probe for detecting CO (carbon monoxide) in cells and a preparation method and application of the fluorescent probe. The fluorescent probe for detecting the CO in the cells is shown as the structural formula below, wherein R refers to H, -CH3, -CH2CH3 or -COOEt. According to the invention, a novel cyclopalladation radical group shown in the description below is synthesized and capable of responding to the CO more rapidly and sensitively, and after the novel cyclopalladation radical group is combined with BODIPY, selectivity for the CO is improved and the CO can be detected more rapidly and sensitively. The preparation method includes enabling paranitrobenzoyl chloride, dimethyl pyrrole and boron trifluoride diethyl etherate or the paranitrobenzoyl chloride, dimethyl pyrrole derivatives and the boron trifluoride diethyl etherate to react to generate nitrophenyl BODIPY, reducing nitro in the nitrophenyl BODIPY to amino, adding nitrite and 3,5-dimethylphenol to undergo diazotization, and adding palladium salt to cyclopalladation so as to obtain a target product, namely, the fluorescent probe for detecting the CO in the cells (ACP-CO). The preparation method is simple in synthesis method and applicable to industrial production.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to a BODIPY fluorescent probe, its synthesis method and its application in detecting intracellular CO, belonging to the detection technical field. Background technique [0002] Over the years, carbon monoxide (CO) easily combines with hemoglobin to form carboxyhemoglobin, which makes hemoglobin lose its ability and function to carry oxygen, causing tissue suffocation and death in severe cases. CO has long been considered a poisonous gas. In the 1970s, it was discovered that the body can produce CO endogenously, which is mainly produced in the body by the enzymatic decomposition of heme by heme oxidase. CO and other gas signal small molecules NO, H 2 Like S, it plays an important role in both physiological and pathological aspects of body regulation. The main physiological role of CO is to protect against tissue damage during myocardial ischemia and reperfusion. Compared with the traditiona...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F15/00G01N21/64C12Q1/02
CPCC07F15/006C09K11/06C09K2211/185C12Q1/02G01N21/6428
Inventor 唐波王栩李勇解希雷李萌萌
Owner SHANDONG NORMAL UNIV
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