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BODIPY (Boron Dipyrromethene) compound-based lysosome fluorescence probe as well as preparation method and applications thereof

A fluoroboron dipyrrole and compound technology, which is applied to the lysosome fluorescent probe based on fluoroboron dipyrrole compound and its preparation method and application field, and achieves high sensitivity, reduced photo-induced tissue damage, and high fluorescence quantum yield. Effect

Inactive Publication Date: 2013-08-14
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[See: (a) C. Hunte, E. Screpanti, M. Venturi, A. Rimon, E. Padan, H. Michel, Nature 2006, 435, 1197-1202. (b) H. Izumi, T. Torigoe, H . Ishiguchi, H. Uramoto, Y. Yoshida, M. Tanabe, T. Ise, T. Murakami, T. Yoshida, M. Nomoto, K. Kohno, Cancer Treat. Rev. 2003, 29, 541–549. (c) M . Chesler, Physiol. Rev. 2003, 83, 1183–1221. (d) A.M. Paradiso, R.Y. Tsien, T.E. Machen, Nature 1987, 325, 447–450. (e) I. Yuli, A. Oplatka, Science 1987, 235, 340–342. ] While the pH of lysosomes is about 4.5-5.5, most of the existing pH fluorescent probes are not suitable for studying such acidic organelles

Method used

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  • BODIPY (Boron Dipyrromethene) compound-based lysosome fluorescence probe as well as preparation method and applications thereof
  • BODIPY (Boron Dipyrromethene) compound-based lysosome fluorescence probe as well as preparation method and applications thereof
  • BODIPY (Boron Dipyrromethene) compound-based lysosome fluorescence probe as well as preparation method and applications thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthesis of embodiment 1.BODIPY A1:

[0029]

[0030] Benzaldehyde (0.106g, 1mmol) and 2-(2-cyano-2-acetylcarboethoxy)-1H-pyrrole (0.380g, 2mmol) were added to the reaction vessel, and dissolved in 50ml of anhydrous dichloromethane. Use a syringe to extract 0.5ml of trifluoroacetic acid (TFA) catalyst and inject it into the system, put it into the magnetic sub-stirring under the condition of anhydrous and light-proof, reflux for 4 days, and spot plate detection until the pyrrole is completely consumed. Then add 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ: 0.227g, 1mmol) into the reaction solution, stir at room temperature for 30 minutes, then add excess triethylamine ( TEA) 3ml after stirring evenly, add boron trifluoride-ether solution (BF 3 ·Et 2 (0) 6ml, continue to stir and reflux for one hour to obtain a blue solution with strong red fluorescence, and spot plate detection until the uncoordinated product is exhausted, then quench the reaction with water...

Embodiment 2

[0036] The synthesis of embodiment 2.BODIPY A2:

[0037]

[0038] Add p-nitrobenzaldehyde (0.151g, 1mmol) and 2-(2-cyano-2-acetylcarboxylate)-1H-pyrrole (0.380g, 2mmol) to the reaction vessel, dissolve in 50ml of dry dichloromethane middle. Use a syringe to extract 0.5ml of trifluoroacetic acid (TFA) catalyst and inject it into the system, put it into the magnetic sub-stirring under the condition of anhydrous and light-proof, reflux for 7 days, and spot plate detection until the pyrrole is completely consumed. Then add 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ: 0.227g, 1mmol) into the reaction solution, stir at room temperature for 30 minutes, then add excess triethylamine ( TEA) 3ml after stirring evenly, add boron trifluoride-ether solution (BF 3 ·Et 2 (0) 9ml, continue to stir and reflux for one hour to obtain a blue solution, and spot the plate to detect that the uncoordinated product is exhausted, then quench the reaction with water. The reaction mixture was w...

Embodiment 3

[0039] The synthesis of embodiment 3.BODIPY A3:

[0040]

[0041] Add p-dimethylaminobenzaldehyde (0.149g, 1mmol) and 2-(2-cyano-2-acetyl ester group)-1H-pyrrole (0.380g, 2mmol) into the reaction vessel, dissolve in 50ml of anhydrous di In methyl chloride, use a syringe to extract 0.5ml of trifluoroacetic acid (TFA) catalyst and inject it into the system, put it into the magnetic sub-stirring under the condition of anhydrous and dark, and reflux for 7 days, then point the plate to detect until the pyrrole is completely consumed. Then add 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ: 0.227g, 1mmol) into the reaction solution, stir at room temperature for 30 minutes, then add excess triethylamine ( TEA) 3ml after stirring evenly, add boron trifluoride-ether solution (BF 3 ·Et 2 (0) 9ml, continue to stir and reflux for one hour to obtain a blue solution, and spot the plate to detect that the uncoordinated product is exhausted, then quench the reaction with water. The reac...

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Abstract

The invention provides a near infrared BODIPY (Boron Dipyrromethene) compound-based molecular fluorescence probe which has the following structure, wherein the substituent group Ar is one of the following four substituent groups described in the specification. The BODIPY probe with an alpha bit containing a strong electrondrawing group is synthesized for the first time, the absorption spectrum red shift of the fluorescence probe can achieve 606-633nm through the introduced substituent group, and the emission peak can achieve 616-646nm. The BODIPY molecule is a favorable fluorescence, can be used for specifically marking lysosome in biological cells, and can emit light through the self molecules, and the absorption and emission of the BODIPY molecule are close to the near-infrared zone; and in addition, the fluorescence probe has the advantages of high mole extinction coefficient, acute emission peak, high fluorescence quantum yield and the like, and has attractive application prospects on the lysosome marking application.

Description

technical field [0001] The present invention relates to a series of near-infrared BODIPY containing a strong electron-withdrawing group at the alpha position, its preparation method and its application as a fluorescent probe in marking intracellular lysosomes. Background technique [0002] Lysosome is a very important organelle in eukaryotic cells. Its internal environment is weakly acidic (pH4-6). It contains a variety of acid hydrolytic enzymes that can decompose waste substances and debris in cells, and directly participate in the digestion process in cells. . In addition, lysosomes are directly related to cell autophagy, apoptosis, immune defense, and cancer. [0003] In recent years, due to their convenience and sensitivity, synthetic molecular fluorescent probes have been highly valued and widely used to detect different ions in cells. [See: (a) T. Hirano, K. Kikuchi, Y. Urano, T. Higuchi, T. Nagano, Angew. Chem. 2000, 112, 1094–1096; (b) Z. H. Lin, M. Wu, M. Schafe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06C09B23/10G01N33/52
Inventor 沈珍刘汉壮郭秋丽
Owner NANJING UNIV
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