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Photo-induced cell covalent labeled fluorescent molecules as well as preparation method and application thereof

A compound, selected technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem that the chemical reaction functional group has not been developed

Pending Publication Date: 2022-04-12
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the introduction of chemically reactive functional groups with photoinducible activity into fluorescent molecules has not been exploited so far.

Method used

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  • Photo-induced cell covalent labeled fluorescent molecules as well as preparation method and application thereof
  • Photo-induced cell covalent labeled fluorescent molecules as well as preparation method and application thereof
  • Photo-induced cell covalent labeled fluorescent molecules as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 3

[0126] Example 3: 4-(Hydroxymethyl)-N-(3-(4-(5-(4-methylpiperazin-1-yl)-1H,1'H-[2,5'-biphenyl And [d] imidazolium] -2'-yl) phenoxy) propyl) -3-nitrobenzamide (3)

[0127]

[0128] Step 3-1: Compound 3-A (10mg, 0.01873mmol) was dissolved in 1mL DMF, potassium carbonate (13mg, 0.09365mmol) and tert-butyl (3-bromopropyl)carbamate (6.7mg, 0.0282mmol) were added, Reaction overnight at 50°C, spin-dry column chromatography directly after the reaction, the product is a yellow-green solid (10.1mg, 92%).ESI-MS[M-H] - m / z=580.47.[M+H] + m / z=582.46. 1 H NMR (600MHz, DMSO) δ12.55(s, 1H), 8.23(m, 3H), 8.14(d, J=8.7Hz, 2H), 8.00(d, J=8.4Hz, 1H), 7.66(m ,1H),7.44(m,1H),7.12(d,J=8.8Hz,2H),6.94(d,J=8.5Hz,2H),4.08(t,J=6.2Hz,2H),3.11(dd ,J=13.1,6.5Hz,8H),2.52(m,2H),2.25(s,3H),1.91–1.83(m,2H),1.38(s,9H).

[0129] Step 3-2: Dissolve compound 3-B in 2 mL of dichloromethane and add 0.5 mL of trifluoroacetic acid. After reacting for 1 hour at room temperature, spin the system to obtain a solid...

Embodiment 9

[0130] Example 9: N-(2-((2,7-difluoro-3-oxo-9-(o-tolyl)-3H-xanthin-6-yl)amino)ethyl)-4-(hydroxy Methyl)-3-nitrobenzamide (9)

[0131]

[0132] Step 9-1: Dissolve 1-bromo-2,4,5-trifluorobenzene (3.5mL, 30mmol) in anhydrous tetrahydrofuran (THF), add isopropylmagnesium chloride (i-PrMgCl) at -78°C 2,4,5-Trifluorobenzaldehyde (2.9mL, 20mmol ). The resulting mixture was stirred for a further 10 min, then at room temperature for 24 h. Add saturated NH 4 The reaction was quenched with aqueous Cl, and Et 2 O extraction, the organic phase was Na 2 SO 4 Drying and evaporation gave crude product 9-A (6.7 g, 77%) as a brown oil. 1H NMR (500MHz, DMSO) δ7.63–7.43(m, 4H), 6.49(d, J=4.6Hz, 1H), 6.06(d, J=4.5Hz, 1H).

[0133] Step 9-2: CH to 9-A (6.6g, 22.6mmol) 2 Cl 2 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) (117mg, 1.13mmol), KBr (540mg, 4.5mmol), NaHCO 3 (3.8 g, 45.2 mmol), saturated aqueous NaCl solution, the reaction mixture was vigorously stirred, then aqueous NaOCl so...

Embodiment 21

[0140] Example 21: 4-(Hydroxymethyl)-N-(5-((4-(morpholinomethyl)-2-oxo-2H-benzopyran-7-yl)oxy)pentyl )-3-nitrobenzamide (21)

[0141]

[0142] Step 21-1: 4-Bromomethyl-7-methoxycoumarin (1.0 g, 3.7 mmol) was dissolved in anhydrous DCM under N 2 Protection, dropwise addition of BBr at -78°C 3 (9.3mmol), continued stirring at -78°C for 0.5h, and warmed to room temperature overnight. After the reaction was complete, water was added to quench the reaction, filtered, and washed with DCM to obtain 925 mg of the crude product as a pale yellow solid, which was directly used in the next step.

[0143] Step 21-2: Dissolve compound 21-A (410mg, 2.35mmol) in 2-methoxyethanol, add morpholine (410mg, 4.7mmol), and reflux for 6h. After the reaction was complete, it was concentrated and column chromatographed to obtain compound 21-B (610 mg, 99%) as a yellow solid. 1H NMR (500MHz, DMSO) δ10.51(s, 1H), 7.76(d, J=8.7Hz, 1H), 6.79(dd, J=8.7, 2.3Hz, 1H), 6.71(d, J=2.3Hz, 1H),6.24(s,1H),3....

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Abstract

The invention relates to a photoinduced cell covalent labeled fluorescent molecule, and a preparation method and application thereof, in particular to a compound as shown in the following formula (I), or a tautomer, an enantiomer, an enantiomer, a diastereomer, a racemate, a precursor compound, an isotope compound and various forms of salts or hydrates thereof. The compounds can be used for preparing light-induced covalent labeled fluorescent probes and are used for positioning and imaging subcellular organelles in cell biology. The light-induced covalent labeled fluorescent probe has important application potential and outstanding practical value in cell biology research, proteomics research and dynamic change research of biomacromolecules.

Description

technical field [0001] The invention belongs to the technical field of protein interaction research in cell labeling imaging and its analysis, and mainly relates to a light-induced multifunctional covalently labeled fluorescent probe and its application in cell biology imaging and mass spectrometry analysis. Background technique [0002] The ability to probe cellular structures and processes has been greatly enhanced by fluorescent molecular probes, which refer to chemical groups that absorb a specific wavelength of light and emit light at a longer wavelength (fluorescence). Live-cell imaging technology uses these fluorescent molecular probes, such as small molecule organic dyes or quantum dots, to specifically label molecules of interest. Fluorescent probes that can be naturally or artificially linked to proteins are used in fluorescence imaging. Another important point of using fluorescent probes is to ensure that they do not cause damage to the cells when they enter the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/20C07D311/88C07D311/18C07D491/107C07D221/14C07D221/12C07D471/22C07D417/06C07D209/14C07D491/22C09K11/06G01N21/64
Inventor 陈小华冯磊周宾山郭安娣
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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