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Compound, preparation method and application of compound as fluorescent probe

A compound and mixture technology, applied in the field of fluorescent probes, can solve the problems of limited penetration depth of organisms, inability to realize PGP-1 detection and imaging, high detection limit, etc.

Active Publication Date: 2019-06-04
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

From the excitation / emission wavelengths and detection limits of these two probes, it can be seen that these two probes have great deficiencies in the analysis and detection of enzymes, especially commercialized probes, whose excitation wavelengths are in the ultraviolet region. This is very unfavorable for the detection of cells and organisms, and its high detection limit is not conducive to the detection of low-level PGP-1
In addition, the excitation of ultraviolet and visible light has a very limited penetration depth to the organism, and it is impossible to detect and image PGP-1 in the organism.
[0006] So far, no probes that can be used for the detection and imaging of PGP-1 in vivo have been reported

Method used

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  • Compound, preparation method and application of compound as fluorescent probe
  • Compound, preparation method and application of compound as fluorescent probe
  • Compound, preparation method and application of compound as fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0096] Example 1 Compound I Sample 1 # preparation of

[0097] In a 100ml round bottom flask, add IR-780 iodine compound (1mmol) and m-nitrophenol (1mmol) dissolved in 10mL of organic solvent acetonitrile, add 2mol of alkaline activator Na 2 CO 3 , stirred at room temperature for 4 hours, washed three times with water, and dried by rotary evaporation at 40°C to obtain mixture A. Add 2 mol of catalyst SnCl to mixture A 2 , under the protection of nitrogen, reacted at 70°C for 8 hours, washed the mixture three times with water, and dried by rotary evaporation at 40°C to obtain mixture B. BOC-pyroglutamic acid was activated by DIPEA and HATU to obtain activated BOC-pyroglutamic acid. 2 mol of activated BOC-pyroglutamic acid was added to mixture B, reacted at room temperature for 8 hours, washed with water three times, and dried by rotary evaporation at 40°C to obtain mixture C. Slowly add 2ml of trifluoroacetic acid dropwise to mixture C at 0°C, react at room temperature for...

Embodiment 2

[0099] Example 2 Compound I Sample 2 # ~Sample 6 # preparation of

[0100] The specific steps are the same as sample 1 # The difference is that the preparation conditions are changed according to table 1 (unspecified conditions in table 1 are the same as sample 1 in embodiment 1 # The same preparation conditions), to obtain sample 2 # ~Sample 6 # .

[0101] Table 1

[0102]

[0103] sample 2 # ~Sample 6 # NMR characterization results and high-resolution mass spectrometry of the same sample 1 # .

Embodiment 3

[0104] Example 3 Compound I Sample 7 # preparation of

[0105] (1) In a 100 ml round bottom flask, add 2,3,3-trimethylindole, 4-bromobutyric acid and 1,2 dichlorobenzene, heat up to 110 degrees Celsius and react for 12 hours, ethyl acetate precipitates, Suction filtration to obtain a pink precipitate; (2) Add dichloromethane, N,N-dimethylformamide, phosphorus oxychloride to cyclohexanone, react under reflux for 2 hours, pour into water for precipitation, Suction filtration to obtain a yellow precipitate; (3) The precipitate obtained in (1) and (2) was added to the acetic anhydride solvent, and sodium acetate was added at 70 degrees Celsius for 40 minutes and then poured into the aqueous solution for precipitation to obtain a green (4) Add m-nitrophenol and an appropriate amount of catalyst to (3), under nitrogen protection, react overnight at 70 degrees Celsius, wash the mixture three times, and spin dry the solvent; Add amino acid to (4), react at room temperature for 8 hou...

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Abstract

The invention discloses a compound I, a preparation method thereof and application of the compound I as a fluorescent probe. The compound I has near-infrared excitation / emission, the excitation wavelength ranges from 500 nm to 750 nm; and the compound is excited at a maximum absorption wavelength of 670 nm, and the emission wavelength is 700 to 810 nm. In addition, the compound I has an ultra-highsensitivity response to the PGP-1 enzyme. The detection limit for the PGP-1 enzyme at lambda ex / em=670 / 700 nm is 0.18 ng / mL. The compound I is used as a fluorescent probe to realize PGP-1 in vivo detection and fluorescence imaging for the first time. In vitro, cell and in vivo PGP-1 detection and fluorescence imaging can be realized, and all cells and tissues with inflammatory response and canceration can be assayed and imaged.

Description

technical field [0001] The application relates to a compound, its preparation method and its application as a fluorescent probe, belonging to the field of fluorescent probes. Background technique [0002] Most of the naturally occurring or artificially synthesized polypeptide and protein end-capping groups are N-terminal-containing groups that are capped by three types: acetyl, formyl, and pyroglutamyl (pGlu). Among them, hormones, polypeptides, and proteins capped with pyroglutamyl groups, until now, have been found to be enzymatically degraded only by pyroglutamate aminopeptidase during in vivo or in vitro degradation. [0003] Since Doolittle and Armentrout first reported pyroglutamyl peptidase 1 (Pyroglutamyl peptidase 1, abbreviated as PGP-1) in 1968, researchers have conducted in-depth and detailed studies on the structure and function of pyroglutamyl aminopeptidase. The study found that it plays a very important and basic role in the regulation and transmission of ne...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14C09K11/06G01N21/64A61K49/00
CPCA61K49/00C07D405/06C07D405/14C09K11/06G01N21/64
Inventor 吴爱国邹瑞芬龚秋雨
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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