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A cycloalkyl monosubstituted aminofluorescein compound and its preparation method and application

A technology of cycloalkyl mono- and compound, which is applied in the field of cycloalkyl mono-substituted amino luciferin compound and its preparation, can solve problems such as the influence of luminescent properties, and achieve the effects of good absorption in vivo, easy transmembrane, and long luminescent time

Active Publication Date: 2017-08-11
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Modifications to the structure of luciferin may affect its luminescent properties

Method used

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  • A cycloalkyl monosubstituted aminofluorescein compound and its preparation method and application
  • A cycloalkyl monosubstituted aminofluorescein compound and its preparation method and application
  • A cycloalkyl monosubstituted aminofluorescein compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0041] [Example 1: Preparation of (S)-4-((2-(4-carboxy-4,5-dihydrothiazol-2-yl)benzothiazole-6-(cyclohexyl)amino (L1)]

[0042] Preparation of intermediate 2-cyano 6-cyclohexane alkylated aminobenzothiazole (1-1)

[0043] Dissolve 2-cyano 6-aminobenzothiazole (50mg, 0.28mmol) in 2mL of acetic acid, stir for five minutes, if not dissolved, then add cyclohexanone (1mL, mmol) and stir for 5 minutes, then add cyano Sodium borohydride (62mg, 1mmol) was added, and a large number of bubbles were generated. When the reaction solution presented a clear orange-red solution, ethyl acetate was added to the reaction solution, stirred for five minutes, and then saturated sodium carbonate solution was added in portions until the reaction No bubbles were generated in the solution. The reaction solution was washed with saturated sodium carbonate solution, extracted with ethyl acetate, the ethyl acetate layer was dried with anhydrous sodium sulfate, filtered, and then purified by a silica gel c...

example 3

[0057] [Example 3 Preparation of (S)-4-((2-(4-carboxy-4,5-dihydrothiazol-2-yl)benzothiazole-6-(cyclobutyl)amino (L3)]

[0058] Preparation of intermediate 2-cyano 6-cyclobutylated aminobenzothiazole (3-1)

[0059] Dissolve 2-cyano 6-aminobenzothiazole (50mg, 0.28mmol) in 2mL of acetic acid, stir for five minutes, if not dissolved, then add cyclobutanone (200μL,) and stir for 5 minutes, then add cyanoboron Sodium hydride (62mg, 1mmol) was added, and a large number of bubbles were generated. When the reaction solution presented a clear orange-red solution, ethyl acetate was added to the reaction solution, stirred for five minutes, and then saturated sodium carbonate solution was added in portions until the reaction solution No bubbles were generated in the medium. The reaction solution was washed with saturated sodium carbonate solution, extracted with ethyl acetate, the ethyl acetate layer was dried with anhydrous sodium sulfate, filtered, and then purified by a silica gel colu...

example 5

[0071] 【Example 5: Evaluation of the fat solubility of firefly luciferase substrate】

[0072] Three compounds L1, L2, and L3 with better activity were selected as the target compounds for further in-depth research. The target compound, D-luciferin, and aminoluciferin were calculated for their lipid solubility with Chembiodraw ultra 12.0 software, and CLogP was obtained. The results are shown in the following table:

[0073]

[0074] The results show that the CLogP of the target compound is larger than that of D-luciferin and aminoluciferin, so it has better fat solubility, which may give it a certain advantage in the process of cell transmembrane. [Example 6: Detection of the bioluminescent wavelength properties of the probe compound]

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Abstract

The invention discloses a naphthenic-base mono substituted amino fluorescein compound as well as a preparation method and application thereof. The naphthenic-base mono substituted amino fluorescein compound has a structural general formula (described in the specification) or a free form thereof, wherein n is 0-9, and m is 1-9; when n is equal to m, R is mono substituted groups such as a hydrogen group, methyl, ethyl, propyl and halogen; and when n is not equal to m, R is the hydrogen group. The naphthenic-base mono substituted amino fluorescein compound can be used for detecting distribution and imaging of luciferase in vitro, cells and vivo by detecting the presence and quantity (including enzyme level, cellular level and animal level) of the luciferase by virtue of bioluminescence, can be also used for detecting distribution and imaging of ATP in vitro, cells and vivo by detecting the presence and quantity (including enzyme level, cellular level and animal level) of ATP and can be used for detecting pharmacological action of a medicine in enzyme level, cellular level and animal level as a report signal in the presence of luciferase, ATP and Mg<2+>.

Description

technical field [0001] The invention belongs to the technical field of medicines, in particular to a cycloalkyl monosubstituted amino luciferin compound and its preparation method and application. Background technique [0002] Bioluminescence is a process in which chemical substances in living organisms convert chemical energy into light energy under the catalysis of enzymes. This is a special type of chemiluminescence that does not depend on the absorption of light by the body. The efficiency for light energy is very high, close to 100%. [0003] The structures of luciferase and luciferin in different bioluminescent systems are also different. Currently, only a few species of active substances have been separated and their molecular structures determined, and they have been applied to mammalian imaging studies. Although The luminescent substrate of each luminescent system is different, but the mechanism of bioluminescence is roughly the same: the substrate is catalyzed and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/62C09K11/06G01N21/64A61K49/00
CPCA61K49/0021C07D277/62C09K11/06C09K2211/1018G01N21/643
Inventor 李敏勇杜吕佩吴文晓
Owner SHANDONG UNIV
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