Rapid high-selectivity hypobromous acid fluorescence probe, and preparation method and application thereof

A fluorescent probe and sulfonic acid group technology, applied in the field of fluorescent probes, can solve the problems of lack of fluorescent probes, low concentration, short oxidation reaction time, etc., and achieve the effects of strong anti-interference ability, good stability and sensitive response.

CN110878085AActive Publication Date: 2020-03-13BIOLOGY INST OF SHANDONG ACAD OF SCI
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
Publication Date
2020-03-13

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Abstract

The invention relates to a rapid high-selectivity hypobromous acid fluorescence probe, and a preparation method and an application thereof. The fluorescence probe is a 1-(2-aminoethyl)piperidine compound, and can be used for measuring, detecting or screening hypobromite and carrying out living cell fluorescence imaging as a hypobromite fluorescence probe. The probe can realize at least one of high-selectivity identification of hypobromite, rapid response to hypobromite, ultra-sensitive analysis of hypobromite and detection of hypobromite under physiological level conditions, and also has the advantages of strong anti-interference capability, simplicity in synthesis, and stable properties.
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Description

technical field

[0001] The invention belongs to the field of fluorescent probes, in particular to a fluorescent probe of 1-(2-aminoethyl)piperidine compounds and its application in measuring, detecting or screening hypobromous acid and live cell fluorescence imaging methods; The invention also provides a method for preparing the fluorescent probe. Background technique

[0002] Hypobromous acid (HBrO) is an integral part of biological host defense systems and has chemical and physical properties very similar to hypochlorous acid. Endogenous hypobromous acid is produced by H 2 o 2 with Br － It is formed by the reaction catalyzed by eosinophil peroxidase (EPO). In the body, hypobromous acid is a strong oxidizing agent with effective antibacterial activity, however, excessively produced hypobromous acid can damage organisms and cause tissue damage, and can lead to many diseases such as arthritis, cardiovascular disease, cancer and Asthma etc. The correlation of EPO in the ...

Examples

Embodiment 1

[0047] Embodiment 1: the synthesis of formula (II) compound

[0048] The synthetic design route is as follows:

[0049]

Embodiment approach 1

[0050] Embodiment 1: Dissolve 431.5mg (1.5mmol) of N-butyl-4-chloro-1,8-naphthalimide in 8mL of ethylene glycol methyl ether, and then add 301.5mg (1.5mmol) of 1-(2 -aminoethyl)piperidine dihydrochloride, then N,N-diisopropylethylamine was added to reflux for 10h, and then rotary evaporation was carried out by a rotary evaporator to obtain a crude product. If want to obtain purer product, can carry out chromatographic column separation to obtain pure product, obtain pure product 284mg, productive rate is 50%.

Embodiment approach 2

[0051] Embodiment 2: Dissolve 431.5mg (1.5mmol) of N-butyl-4-chloro-1,8-naphthalimide in 8mL of ethylene glycol methyl ether, and then add 603mg (3mmol) of 1-(2-ammonia Ethyl) piperidine dihydrochloride, then reflux for 10h, and then use a rotary evaporator to carry out rotary evaporation to obtain a crude product. If want to obtain purer product, can carry out chromatographic column separation to obtain pure product, obtain pure product 370mg, productive rate is 65%.