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Fluorescent switch system, preparation method and application

A fluorescent switch and system technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of cumbersome preparation of fluorescent switch systems

Active Publication Date: 2020-07-21
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to overcome the cumbersome preparation of the polythiophene / diarylethene fluorescent switch system existing in the prior art, and to provide a polythiophene derivative cation / perfluorocyclopentene type diarylethene anion electrostatic composite The fluorescent switch system, preparation method and application of the compound, the fluorescent switch system of the polythiophene derivative cation / perfluorocyclopentene type diarylethene anion electrostatic complex has strong cell penetration rate and is selective in cell imaging Mark the function of specified cells, and the preparation method is simple and universal

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  • Fluorescent switch system, preparation method and application
  • Fluorescent switch system, preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0062] A formula (I 1 ) / (II) poly 3-(2-(6-bromotrimethylaminohexyloxy)ethyl)thiophene / 1,2-bis(5-p-carboxyphenyl-2-methylthiophene- 3-yl) sodium perfluorocyclopentene fluorescent switch system.

[0063] Its preparation method comprises the following steps:

[0064] (1) poly 3-(2-(6-bromotrimethylaminohexyloxy) ethyl) thiophene (structural formula such as formula (Ⅰ) 1 ) Synthesis shown in ).

[0065] m is 100

[0066] 3-Hydroxyethanethiophene (663μL, 6mmol) was added to the DMF solution of NaH (206mg, 6mmol) under the protection of nitrogen. After stirring for 30min, 1,6-dibromohexane (4.6 mL, 10mmol). After stirring for 12 h, it was quenched with water. The resulting mixture was treated with CH 2 Cl 2 Extracted 3 times, the organic phase was washed with brine, and washed with MgSO 4 dry. After removing the solvent, the product was eluted in a silica gel column with petroleum ether and ethyl acetate at a volume ratio of 40:1 to obtain 3-(2-(6-bromohexyloxy)ethyl)thi...

Embodiment 2

[0081] A formula (I 2 ) / (II) poly 3-(4-bromotrimethylaminobutyl)thiophene / 1,2-bis(5-p-carboxyphenyl-2-methylthiophen-3-yl)perfluorocyclic ring Pentenyl sodium fluorescent switch system.

[0082] Its preparation method comprises the following steps:

[0083] (1) poly 3-(2-(6-bromotrimethylaminobutyl))thiophene (structural formula such as formula (Ⅰ) 2 ) Synthesis shown in ).

[0084] m=100

[0085] It differs from Example 1 in that:

[0086] Thiophene (208.0mg, 2.5mmol), Pd(OAc) 2 (28.0mg, 0.125mmol), 1,4-dibromobutane (10.0mmol), potassium carbonate (7.5mmol, 3eq), pivalic acid (5.1mg, 0.05mmol) were added to 3.0mL of anhydrous tert-amyl alcohol, After being filled with nitrogen, it was heated to 100°C and stirred for 24h. Afterwards, the solvent was removed by rotary evaporation, and 3-(4-bromobutyl)thiophene (248.0 mg, 45%) was purified through a silica gel column with ethyl acetate / hexane=10:90 (v:v) as the eluent. 1 HNMR (400 MHz, DMSO-d6, ppm): 7.59 (s, 1H), 6.7...

Embodiment 3

[0091] A formula (I 3 ) / (II) poly 3-(2-(6-bromotrimethylaminoethoxy)ethyl)thiophene / 1,2-bis(5-p-carboxyphenyl-2-methylthiophene- 3-yl) sodium perfluorocyclopentene fluorescent switch system.

[0092] Its preparation method comprises the following steps:

[0093] (1) Preparation of poly 3-(2-(6-bromotrimethylaminoethoxy)ethyl)thiophene.

[0094] m is 150

[0095] It differs from Example 1 in that:

[0096] 3-Hydroxyethanethiophene (663μL, 6mmol) was added to the DMF solution of NaH (206mg, 6mmol) under the protection of nitrogen, and after stirring for 30min, 1,2-dibromoethane (1.5 mL, 10mmol). After stirring for 12 h, it was quenched with water. The resulting mixture was treated with CH 2 Cl 2 Extracted 3 times, the organic phase was washed with brine, and washed with MgSO 4 dry. After removing the solvent, the product was eluted in a silica gel column with petroleum ether and ethyl acetate at a volume ratio of 40:1 to obtain 3-(2-(2-bromoethoxy)ethyl)thiophene (53...

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Abstract

The invention relates to the field of fluorescent switch systems for cell imaging research and discloses a fluorescent switch system of polythiophene derivative cation / perfluor cyclopentene type diarylethene anion, a preparation method and application. The polythiophene derivative cation and the perfluor cyclopentene type diarylethene anion are subjected to stirring and electrostatic compounding in a solution to form a polythiophene derivative cation / perfluor cyclopentene type diarylethene anion fluorescent switch system, the fluorescent switch system can be adopted for imaging of HeLa cells and MCF-7 cells, fluorescence of the fluorescent switch system can be reduced in the presence of ultraviolet light, the fluorescence of the fluorescent switch system can be recovered in the presence ofvisible light, and thus fluorescent on / off can be achieved.

Description

technical field [0001] The invention relates to the field of fluorescent switch systems used in cell imaging research, in particular to a fluorescent switch system, preparation method and application of a polythiophene derivative cation / perfluorocyclopentene type diarylethene anion electrostatic complex. Background technique [0002] Fluorescence imaging technology has a wide range of applications in the biological field, and can be used for cell imaging, tissue imaging and life process research. However, traditional fluorescence imaging techniques are susceptible to interference from background fluorescence and difficult to distinguish from the autofluorescence of the sample. The emergence of fluorescent switch technology solves this problem. By regulating the fluorescence of the labeled molecule to be on or off, the position of the labeled molecule can be clearly distinguished from the background and autofluorescence. Based on the fluorescent switch technology, super-reso...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06B82Y30/00B82Y40/00G01N21/64
CPCB82Y30/00B82Y40/00C09K11/06C09K2211/1007C09K2211/1092C09K2211/1458G01N21/6428G01N21/6486
Inventor 王树彭可吕凤婷刘礼兵
Owner INST OF CHEM CHINESE ACAD OF SCI
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