Near infrared BODIPY (Boron Dipyrromethene Compounds) hydroxyl radical probes and synthesis method and usage thereof

A near-infrared and compound technology, which is applied in chemical instruments and methods, compounds of group 5/15 elements of the periodic table, material inspection products, etc., to achieve rapid and efficient detection of hydroxyl radicals

Inactive Publication Date: 2013-10-09
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Pou and his subject combined a class of probes based on nitroxide. After being oxidized by nitroxide, the fluorescence intensity is greatly enhanced, but there is no selectivity.

Method used

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  • Near infrared BODIPY (Boron Dipyrromethene Compounds) hydroxyl radical probes and synthesis method and usage thereof
  • Near infrared BODIPY (Boron Dipyrromethene Compounds) hydroxyl radical probes and synthesis method and usage thereof
  • Near infrared BODIPY (Boron Dipyrromethene Compounds) hydroxyl radical probes and synthesis method and usage thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1. Synthesis of Compounds B1-B4:

[0031]

[0032] In a 250 mL round bottom flask, add (2 mmol) corresponding aldehyde, (4 mmol) 2,4-dimethylpyrrole, 0.01 mL of trifluoroacetic acid and 100 mL of anhydrous dichloromethane, and stir overnight at room temperature. Then add (2 mmol) DDQ for oxidation, react for 1 h, add 3 mL of triethylamine and boron trifluoride ether solution in turn, react for 5 h, add water to quench the reaction. After the reaction is finished, extract with dichloromethane, spin dry under reduced pressure, perform column chromatography, and use dichloromethane to petroleum ether as a developer of 1:2 to pass through the column to obtain the corresponding BODIPY product.

[0033] B1C 19 h 19 BF 2 N 2 (324.16) yellow solid, 38.6% yield, 1 H NMR (CDCl 3 , 500MHz): 7.45(t, J=5Hz, 3H), 7.27(s, 2H), 6.95(s, 2H), 2.53(s, 6H), 1.34(s, 6H).

[0034] B2C 51 h 83 BF 2 N 2 o 2 (804.65) red solid, 62.2% yield, 1 H NMR (CDCl 3 , 500MHz): 6....

Embodiment 2

[0037] Example 2. Synthesis of Compounds B5-B8:

[0038]

[0039] In a 100mL two-necked flask, add (0.16mmol) simple BODIPY compounds B1-B4, (0.32mmol) 2-(diphenylphosphine)benzaldehyde, 0.4mL anhydrous piperidine, 0.4mL glacial acetic acid and 50mL anhydrous Water acetonitrile, under the protection of argon, using a water separator, heated to 90 ° C, the reaction process was monitored by TLC, until all the raw material points B1-B4 disappeared. After the reaction was completed, it was cooled to room temperature. After the reaction, a large amount of solids were precipitated, which were directly sucked and filtered to obtain a solid as the product. The filtrate was extracted with water and saturated brine respectively, dried over anhydrous sodium sulfate, and the crude product was obtained under reduced pressure. The target compounds B5-B8 were obtained by column chromatography. NMR spectrum see attached Figure 1-Figure 4 .

Embodiment 3

[0040] Example 3. Synthesis of Compounds B9 and B10:

[0041]

[0042] In a 100mL round bottom flask, add (0.02mmol) compound B5 or B6, dissolve it in tetrahydrofuran, then add (0.2mmol) hydrogen peroxide, then add (0.12mmol) cobalt acetate, react for 30 minutes, and the reaction process is analyzed by TLC Monitor until all raw material points disappear. The filtrate was extracted with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain the pure product. NMR spectrum see attached Figure 5 and Figure 6 . The crystal structure of probe B9 is attached Figure 7 , the test data of probe B9 single crystal is shown in Table 1.

[0043] Table 1 Single crystal data of probe B9

[0044]

[0045]

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Abstract

The invention discloses a kind of near infrared boron dipyrromethene compounds (BODIPY) based on duplex thiophene pyrrole groups. The near infrared boron dipyrromethene compounds have the following structure: FORMULA, wherein the group at meso site is changed to obtain a series of hydroxyl radical probes. The BODIPY hydroxyl radical probes based on 3,5-(diphenyl phosphate styryl) are synthesized for the first time in the invention, the 3,5 site groups of the BODIPY are introduced into the group, so that the absorption spectrum red shift of the probe reaches 630nm, the emission peak reaches 650nm and is located within the range (650-900nm) of a biological window, and meanwhile, the fluorescence quantum efficiency of the probe is high. Moreover, the kind of probes can be used for efficiently and quickly detecting hydroxyl radicals and can be successfully applied in biological imaging. Therefore, the probes have a brilliant application prospect of detecting the hydroxyl radicals in biological systems.

Description

technical field [0001] The invention relates to a series of near-infrared BODIPY compounds based on boron dipyrromethene, their synthesis method and their application in cell imaging. Background technique [0002] Reactive oxygen species (ROS) include superoxide radicals (O 2 · - ), Hydroxyl radicals (HO·), alkane peroxide radicals (ROO·), hydrogen peroxide (H 2 o 2 ), singlet oxygen ( 1 o 2 ), hypochlorous acid / hypochlorite (HOCl / - OCl). Reactive nitrogen (RNS), including nitric oxide (NO), nitric peroxide (ONOO - ), nitrogen dioxide free radicals (NO 2 ) and nitrate (NO 3 - ). [See: (a) B. Halliwell and J.M.C. Gutteridge, Free Radicals in Biology and Medicine, Oxford University Press, Oxford, 2007, pp.1-677. (b) L.L. Smith, Free Radical Biol. Med., 2004, 37 , 318-324.] ROS / RNS are very important to human health and disease, and it becomes more important to study their role in biology. However, an important obstacle to detecting ROS / RNS in living cells is thei...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/572C07F9/6558C09K11/06G01N21/64G01N33/52
Inventor 沈珍渠星宇边永军
Owner NANJING UNIV
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