A biotin-labeled ebselen probe and its preparation method and application

A technology of biotin labeling and ebselen, which is applied in the field of biotin-labeled ebselen probes and its preparation, can solve the problems of inaccurate exploration of ebselen proteins, and achieve fast labeling speed and structure Precise, simple preparation method results

Active Publication Date: 2021-02-23
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The design and synthesis of ebselen biotinylated probes will play a very important role in the exploration of the proteins that ebselen can covalently target, but there are already designed and synthesized ebselen analogues of biotin Chemical probes cannot more accurately explore the proteins that ebselen can covalently target

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  • A biotin-labeled ebselen probe and its preparation method and application
  • A biotin-labeled ebselen probe and its preparation method and application
  • A biotin-labeled ebselen probe and its preparation method and application

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Embodiment

[0046]Embodiment A kind of preparation method of biotin-labeled ebselen probe

[0047] The preparation method of the biotin-labeled ebselen probe comprises the following steps:

[0048] (1) O-iodobenzoyl chloride (1.33g) and p-phenylenediamine (1.08g) were dissolved in CH 2 Cl 2 (10 mL each), and triethylamine (1.04 mL) was added to the p-phenylenediamine solution, and then the o-iodobenzoyl chloride solution was added dropwise to the p-phenylenediamine solution in an ice bath, and reacted overnight at room temperature , the reaction was washed with water, and after separation, the aqueous phase was washed with CH 2 Cl 2 Carry out extraction twice, organic phase merges, after drying, spin dry, separate with chromatographic column (eluent: V 石油醚 :V 二氯甲烷 =40:1), the obtained solid is compound I.

[0049] ESI-MS: calculated for [M+H] + =338.9988,found338.9969.

[0050] (2) Dissolve tert-butoxycarbonyl 6-aminocaproic acid (1.02g), EDCI·HCl (0.93g) and HOBT (0.65g) in CH 2...

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Abstract

The invention belongs to the technical field of protein detection, and in particular relates to a biotin-labeled ebselen probe and a preparation method and application thereof. The structural formula of the probe of the present invention is as follows: The ebselen biotin probe prepared by the present invention has a stable structure, simple synthesis, can quickly label small molecules of thiols and proteins that can be covalently targeted by ebselen, and can The targeted protein was enriched by biotin, and then identified by mass spectrometry. The probe of the invention has a profound impact on exploring the mechanism of action of ebselen.

Description

technical field [0001] The invention belongs to the technical field of protein detection, and in particular relates to a biotin-labeled ebselen probe and a preparation method and application thereof. Background technique [0002] Ebselen (Ebselen) is an organic selenium compound small molecular antioxidant, which can remove excessive peroxides in the body and block the chain reaction of free radicals, so it can treat many diseases, such as cardiovascular diseases , arthritis, stroke, atherosclerosis and cancer. In addition, ebselen is also recognized as a glutathione peroxidase activity (GPx) mimic, which can catalyze some important reactions to protect cellular components from free radical and oxidative damage. It has also been shown that ebselen is an excellent substrate for mammalian thioredoxin (TrxR) and acts as a dehydroascorbate (DHA) reductase mimic. However, the molecular mechanism of ebselen's action is still unclear, and deciphering the cellular mechanism of ebs...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D517/08G01N33/68
CPCC07D495/04G01N30/02G01N33/68
Inventor 唐波姜中尧陈蓁蓁石倩李清岭
Owner SHANDONG NORMAL UNIV
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