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GPR120 (G-protein Coupled Receptor 120) small-molecule fluorescent probe and application of GPR120 small-molecule fluorescent probe

A fluorescent probe, small molecule technology, used in the field of medicine

Active Publication Date: 2017-05-24
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, for GPR120, there is no report about its small molecule fluorescent probe

Method used

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  • GPR120 (G-protein Coupled Receptor 120) small-molecule fluorescent probe and application of GPR120 small-molecule fluorescent probe
  • GPR120 (G-protein Coupled Receptor 120) small-molecule fluorescent probe and application of GPR120 small-molecule fluorescent probe
  • GPR120 (G-protein Coupled Receptor 120) small-molecule fluorescent probe and application of GPR120 small-molecule fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1: Preparation of Naphthalimide Fluorophore Probes (L1-L3):

[0060]

[0061] The specific synthetic route is as follows:

[0062]

[0063] Preparation of Intermediate 1

[0064] In a 100 mL round-bottomed flask, add p-hydroxyphenylpropionic acid (1.5 g, 9.03 mmol) and anhydrous methanol (35 mL), stir to dissolve, add a catalytic amount of concentrated sulfuric acid (15 drops) dropwise, and stir at 60 ° C for 6 After 1 hour, it was lowered to room temperature, the reaction solution was spun out, water and dichloromethane were added for extraction, the organic layers were combined, washed with saturated brine, and anhydrous MgSO 4 It was dried overnight, filtered, concentrated and purified by column chromatography to obtain 1.54 g of a colorless and transparent oil with a yield of 95%. 1 H NMR (400MHz, DMSO): δ9.15(s, 1H), 6.99(d, J=8.4Hz, 2H), 6.65(d, J=8.5Hz, 2H), 3.57(s, 3H), 2.73( t, J=7.6Hz, 2H), 2.54 (t, J=7.6Hz, 2H); EI-MS: ([M] + ): 180.1.

[0...

Embodiment 2

[0090] Example 2: Preparation of coumarin-based fluorophore probes (L4-L7):

[0091]

[0092] The specific synthetic route is as follows:

[0093]

[0094] Preparation of Intermediate 7

[0095] In a 100mL round bottom flask, add 4-(diethylamino) salicylaldehyde (1.5g, 7.76mmol) and 40mL of absolute ethanol, then add diethyl malonate (1.24g, 7.76mmol), stir to make Dissolve morpholine (68 mg, 0.78 mmol) and acetic acid (20 μL) in 2 mL of absolute ethanol to obtain a mixed solution, then add the mixed solution to the above reaction solution, reflux and stir for 24 h, cool the reaction solution at ice temperature, and The reaction solution was spin-dried to obtain intermediate 7, which was directly used in the next step without purification.

[0096] Preparation of intermediate 8

[0097] Dissolve intermediate 7 (400mg, 1.38mmol) in a small amount of methanol solution, add 25mL of 2M NaOH solution, stir at room temperature for 24 hours, adjust the pH with 1M HCl to make t...

experiment example 1

[0139] Experimental Example 1: Optical Activity Measurement

[0140] Table 1: Optical properties of probe molecules

[0141]

[0142]

[0143] Note: All the above optical properties were measured in Tris-HCl buffer pH=7.4.

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Abstract

The invention relates to a GPR120 (G-protein Coupled Receptor 120) small-molecule fluorescent probe and application of the GPR120 small-molecule fluorescent probe. The general structural formula of the fluorescent probe is shown as a formula (I), wherein R represents various types of fluorophores and n represents that the number of carbon is 1 to 6. The fluorescent probe provided by the invention can be used for marking cells or tissues which have a high GPR120 expression level, and has good pharmaceutical activity; fluorescent light is remarkably enhanced when the polarity of the surrounding environment is reduced and the fluorescent probe can be used as a tool medicine for researching pharmacological and physiological characteristics of the GPR120. Furthermore, a preparation method of the compound is mature, reaction conditions are moderate, raw materials are cheap and easy to obtain and operation and post-treatment are convenient. The formula (I) is shown as the description.

Description

technical field [0001] The invention belongs to the technical field of medicine, in particular to a GPR120 small molecule fluorescent probe and its application. Background technique [0002] As an important member of the G protein-coupled receptor family, GPR120 is a receptor for long-chain unsaturated free fatty acids (FFAs) (Hirasawa et al. 2005). The mRNA of GPR120 is expressed in a variety of tissues, among which the expression level of GPR120 is higher in the small intestine, lung, colon, adipose and other tissues (Hirasawa et al. 2005). At the cellular level, GPR120 mRNA is expressed in taste bud cells (Matsumura et al. 2007), adipocytes (Gotoh et al. 2007), macrophages (Oh, Det al. 2010), and enteroendocrine cells (Hirasawa et al. 2005 ) was abundantly expressed in various cell lines. This indicates that the expression and distribution levels of GPR120 in tissues and cells may be closely related to many physiological diseases, such as obesity, diet, diabetes and so ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D221/14C07D311/16G01N21/64
CPCC07D221/14C07D311/16C09K11/06C09K2211/1022C09K2211/1029C09K2211/1088G01N21/643G01N21/6486
Inventor 杜吕佩李敏勇刘家翔
Owner SHANDONG UNIV
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