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A dual function probe for endoplasmic reticulum localization imaging/light-induced ferroptosis

A light-induced, endoplasmic reticulum technology, used in fluorescence/phosphorescence, microbial assay/inspection, luminescent materials, etc., can solve the problem of lack of good monitoring methods, compounds without organelle targeting, and difficulty in direct observation of lipid peroxidation changes. wait until the problem

Active Publication Date: 2022-07-26
JIANGXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

The reason is that most of the ferroptosis inducers (such as Erastin) discovered so far act on the related signaling pathways in the process of lipid peroxidation, and these compounds do not have specific organelle targets, so they can only indirectly affect intracellular lipids. peroxidation process
In addition, there is no good monitoring method, making it difficult to directly observe the lipid peroxidation process of intracellular subcellular organelles

Method used

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  • A dual function probe for endoplasmic reticulum localization imaging/light-induced ferroptosis
  • A dual function probe for endoplasmic reticulum localization imaging/light-induced ferroptosis
  • A dual function probe for endoplasmic reticulum localization imaging/light-induced ferroptosis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051]

[0052] In a 100mL reactor, add (E)-2-(4-(4-(diphenylamino)styryl)pyridin-2-yl)quinazolin-4(3H)-one 4.92g (10mmol) , add 50 mL of toluene as a solvent, stir and mix evenly, add 1.38 mL (10 mmol) of triethylamine and boron trifluoride·diethyl ether complex, heat under reflux, react for 30 h, pour the reaction solution into water after the reaction, wait for After separation, extraction was performed with dichloromethane, and the organic phase was concentrated using a rotary evaporator to remove the solvent. The target product is obtained by separation by column chromatography. The yield was 45%. The following are the NMR and MS experimental data of the product:

[0053] 1 H NMR (400 MHz, DMSO-d 6 ) δ =8.94 (d, J = 5.9 Hz, 1H), 8.68 (s, 1H), 8.30 – 8.16 (m, 2H), 8.11 (d, J = 16.3 Hz, 1H), 7.94 – 7.78 (m, 2H) ), 7.66(dd, J = 19.8, 7.8 Hz, 3H), 7.48 (d, J = 16.3 Hz, 1H), 7.39 (t, J = 7.7 Hz, 4H), 7.15 (dd, J = 17.6, 7.5 Hz , 6H), 6.96 (d, J = 8.5 Hz, 2H) ppm.

[...

Embodiment 2

[0074]

[0075] In a 100 mL reactor, add (E)-6-(dimethylamino)-2-(4-(4-(diphenylamino)styryl)pyridin-2-yl)quinazoline-4( 3H)-ketone 5.35g (10mmol), add 50mL of toluene as a solvent, stir and mix well, add triethylamine 1.38mL (10mmol) and boron trifluoride·diethyl ether complex, heat under reflux, react for 30h, the reaction ends Then, the reaction solution was poured into water, and after the layers were separated, the mixture was extracted with dichloromethane, and the organic phase was concentrated using a rotary evaporator to remove the solvent. The target product is obtained by separation by column chromatography. The yield was 45%. The following are the NMR and MS experimental data of the product:

[0076] 1 H NMR (400 MHz, Chloroform-d) δ= 9.00 (d, J = 8.5 Hz, 1H), 8.56 (d, J = 1.8 Hz, 1H), 7.86 (s, 1H), 7.52 (d, J = 2.3 Hz, 1H), 7.46 (d, J = 8.1 Hz, 1H), 7.45 – 7.39 (m, 2H), 7.39 – 7.34 (m, 1H), 7.32 – 7.25 (m, 4H), 7.29 –7.19 (m, 1H), 7.17 – 7.08 (m, 7H), 7.04...

Embodiment 3

[0086]

[0087] In a 100 mL reactor, add (E)-2-(4-(4-(diphenylamino)styryl)pyridin-2-yl)benzo[g]quinazolin-4(3H)-one 5.43 g (10 mmol), 50 mL of toluene was added as a solvent, after stirring and mixing uniformly, 1.38 mL (10 mmol) of triethylamine and boron trifluoride·diethyl ether complex were added, and the mixture was heated to reflux for 30 h. Pour into water, wait for separation, extract with dichloromethane, and use a rotary evaporator to concentrate the organic phase to remove the solvent. The target product is obtained by separation by column chromatography. The yield was 45%. The following are the NMR and MS experimental data of the product:

[0088] 1 H NMR (400 MHz, Chloroform-d) δ= 9.00 (d, J = 8.5 Hz, 1H), 8.57 (d, J = 1.9 Hz, 1H), 8.50 (dd, J = 2.0, 0.7 Hz, 1H), 8.27 (d, J = 1.9 Hz, 1H), 7.94 (ddd, J = 7.8, 2.0, 1.2 Hz, 1H), 7.85 (s, J = 8.4 Hz, 1H), 7.61 – 7.47(m, 2H), 7.46 – 7.39 (m, 2H), 7.39 – 7.33 (m, 1H), 7.33 – 7.24 (m, 4H), 7.29 – 7.18 (m, 1H), 7...

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Abstract

The invention discloses an endoplasmic reticulum localization imaging / light-induced ferroptosis dual function probe. The preparation method is as follows: adding a certain amount of ligands containing quinazolinone-pyridine structure in a non-polar solvent, adding corresponding Boride, adjust the reaction solution to alkaline with triethylamine, after reflux reaction, cooling, standing, layering, extraction, the organic phase is separated by column chromatography with the mixture obtained after concentration, and finally pure product is obtained. The probe structure is mainly based on quinazolinone-BF 2 The structure is the core structure, and triphenylamine, carbazole or its derivatives are used as modified groups, and it has the function of organelle imaging, and can induce tumor cell ferroptosis under visible light-induced conditions. The present invention is the first case of endoplasmic reticulum localization imaging / light-induced ferroptosis dual-function probe. The biggest feature is that this type of probe can monitor live cells in real time, and can achieve fixed-point induction of tumor cell iron through light induction and imaging. death, to achieve the purpose of imaging-guided treatment.

Description

technical field [0001] The invention relates to the fields of fluorescent probes, biological imaging, photodynamic therapy and the like, in particular to an endoplasmic reticulum localization imaging / light-induced ferroptosis dual function probe. Background technique [0002] Ferroptosis is a cell death process caused by iron-dependent abnormal accumulation of intracellular lipid peroxidation, which is morphologically, biochemically and genetically distinct from other forms of cell death. Ferroptosis has been found to inhibit tumor growth and increase the sensitivity of various tumors to chemotherapy and immunotherapy. Inducing ferroptosis in cancer cells is becoming a new strategy for the treatment of tumors, especially for the treatment of highly drug-resistant and metastatic malignant tumors. . [0003] Whether the accumulation of lipid peroxidation products in specific organelles plays a key role in the induction of ferroptosis, and how the damage and morphology of diff...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64C12Q1/02A61K41/00A61P35/00
CPCC07F5/022C09K11/06G01N21/6428G01N21/6447G01N21/6458G01N33/5005A61K41/0057A61P35/00C09K2211/107
Inventor 宋智彬邢致明
Owner JIANGXI NORMAL UNIV
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