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Fluorescent diagnosis and treatment reagent development for diagnosing and treating non-small cell lung cancer (NSCLC) and application of cells thereof

A technology of fluorescent probes, fluoropyrrole, which is applied in the field of fluorescent probes, can solve the problems of lack of tumor positioning groups, shortages, etc., and achieve the effect of improving the utilization rate of drugs

Inactive Publication Date: 2016-07-06
BINZHOU MEDICAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it lacks a tumor targeting group, so it can only be administered at the cellular level, and there is a lack of data on the use of probes throughout the body

Method used

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  • Fluorescent diagnosis and treatment reagent development for diagnosing and treating non-small cell lung cancer (NSCLC) and application of cells thereof
  • Fluorescent diagnosis and treatment reagent development for diagnosing and treating non-small cell lung cancer (NSCLC) and application of cells thereof
  • Fluorescent diagnosis and treatment reagent development for diagnosing and treating non-small cell lung cancer (NSCLC) and application of cells thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Preparation of a compound of formula:

[0050] Under the protection of argon, D-biotin (1.215g, 5mmol) was dissolved in 90mL N,N-dimethylformamide, 4-dimethylaminopyridine (0.61g, 5mmol), 1-(3-bis Methylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.93g, 6mmol) and 1-hydroxybenzotriazole (0.067g, 0.5mmol) were added to the solution and reacted for 30 minutes, then the fluorophore ( 0.529g, 1mmol), after reacting at room temperature for 24 hours, wash with water and ethyl acetate (1:1 / v / v), obtain the ethyl acetate layer and spin dry the solvent with a rotary evaporator, and dissolve the obtained solid in dichloromethane , separated by silica gel column chromatography (200-300 mesh). The eluent was dichloromethane and methanol (50:1 / v / v), and the green fraction was collected.

[0051]Under the protection of argon, dissolve gefitinib (0.116g, 0.26mmol) in 100mL of dichloromethane and add bis(trichloromethyl)carbonate (1.539g, 5.2mmol) N,N-Diisopropylethylamine (1.00...

Embodiment 2

[0055] Compound of preparation formula two:

[0056] Under the protection of argon, dissolve (2) (0.194g, 0.31mmol) in 100mL of dichloromethane and add bis(trichloromethyl)carbonate (1.835g, 6.2mmol) Add N,N-diisopropylethylamine (1.200 g, 9.3 mmol) dropwise, and react at room temperature for 3 hours after the dropwise addition. After the reaction was completed, the solvent was evaporated to dryness on a rotary evaporator, and the obtained solid was dissolved in dichloromethane, and added dropwise to a solution containing N,N-diisopropylethylamine (0.040g, 0.31mmol) and fluorophore (0.132g, 0.25 mmol) in 50 mL of dichloromethane solution, reacted at room temperature for 36 hours. After the reaction, wash with water and dichloromethane (1:1 / v / v), spin dry the solvent with a rotary evaporator after obtaining the dichloromethane layer, dissolve the resulting solid in dichloromethane, and use aluminum oxide column chromatography (200-300 mesh) separation. The eluent was dichlor...

Embodiment 3

[0060] The prepared compound of formula one is used as a probe in the water system to simulate the physiological environment to detect the drug sustained release kinetics. Physiological conditions were simulated, and the following experiments were all carried out under the condition of pH=7.4 (HEPES buffer solution, the concentration was 40 mM). The compound of formula 2 is used at 10 μM, and the concentration of glutathione is 5 mM. like figure 1 As shown, the probe can achieve the purpose of drug sustained release.

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Abstract

The invention relates to a fluorescent probe for quickly diagnosing and accurately treating non-small cell lung cancer (NSCLC), particularly fluorine boron pyrrole compounds and application thereof. The fluorine boron pyrrole compounds are disclosed as General Formula I, and are used as the fluorescent probe for diagnosing and treating NSCLC. The fluorophore and lung cancer cells are used for locating the label of the ligand, and the probe can specifically select the NSCLC cells. The overexpressed glutathione in the lung cancer cells breaks the disulfide bond in the probe, the drugs can be slowly released in the cancer cells to generate the target treatment effect, and meanwhile, near-infrared fluorescence can be emitted, thereby generating the double effects of diagnosis and treatment. The fluorescent probe can trace the alveolar epithelial cells with pathological changes at high sensitivity, and can release the drugs to the cancer tissues in a more accurate mode, thereby lowering the general untoward effects of the drugs and enhancing the living quality of the patient. The research has important biomedical meanings for the diagnosis and treatment modes of NSCLC and the research of the drug-resistance mechanism of the NSCLC cell strain.

Description

technical field [0001] The invention relates to a fluorescent probe for rapid diagnosis and precise treatment of non-small cell lung cancer, specifically a fluoropyrrole compound and its application. Background technique [0002] Malignant tumors have always been the number one killer that threatens human health. In my country, lung cancer has become the most common cancer. The pathological basis of lung cancer comes from the malignant proliferation of alveolar epithelial cells. Among lung cancer cases, non-small cell lung cancer (NSCLC) patients account for more than 80%. The main screening methods for the diagnosis of NSCLC are blood tumor markers of lung cancer and high-resolution computed tomography (HRCT) in imaging; the diagnosis depends on the clinical manifestations of patients combined with pathological tissue biopsy. These diagnostic methods are based on the histological changes of lung cancer pathological development to a certain extent. With the increase of pati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64A61K47/48A61K31/5377A61P35/00A61P11/00
CPCA61K31/5377C07F5/022C09K11/06C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1092G01N21/6428
Inventor 吕长俊宋新宇陈令新于法标
Owner BINZHOU MEDICAL COLLEGE
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