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A heptamethine fluorescent dye and its application in precise diagnosis and treatment of tumors

A fluorescent dye, tumor technology, applied in the field of near-infrared fluorescent dyes, can solve problems such as changing the specificity and affinity of target molecules

Active Publication Date: 2019-08-16
NANJING NUOYUAN MEDICAL DEVICES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have their limitations for tumor imaging, because the targeted fragments can only detect some specific tumor cells, these cells have clear surface molecular characteristics, and they are only a small part of the diverse tumor cells
Moreover, chemical binding may alter the specificity and affinity of the target molecule

Method used

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  • A heptamethine fluorescent dye and its application in precise diagnosis and treatment of tumors
  • A heptamethine fluorescent dye and its application in precise diagnosis and treatment of tumors
  • A heptamethine fluorescent dye and its application in precise diagnosis and treatment of tumors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] The preparation of compound I of the present invention

[0044] 1. Add phenylhydrazine p-sulfonic acid (5g) to methanol solution of methyl isopropyl ketone (8.55 / 15ml), heat the solution to 117°C, stir for 5h, and evaporate the solvent. Then 50 ml of diethyl ether was added to the oily product to obtain a pink powder, namely compound (3). Then, brown red powder (6g) is added in sodium hydroxide (1.5 grams) solution, solvent is methanol (10 milliliters) and isopropanol (10 milliliters), after this solution is stirred at 82 ℃ for 15 minutes, is cooled to room temperature , a large amount of No. (3) compound was separated and used for the next step of purification. m / z=261.27, NMR spectrum (500 MHz, chloroform) δ7.90 (d, 2H) 7.49 (s, H) 2.10 (s, 3H) 1.44 (s, 6H)

[0045] 2. Compound 3 (6 g) and 1-(bromomethyl)benzene (4.77 ml) were dissolved in 36 ml of toluene. The mixture was stirred and refluxed under nitrogen for 5 h, when the mixture was cooled, the solvent was rem...

Embodiment 2

[0050] Absorption of ICG-03 dye by different cell lines and human tumor-bearing nude mouse models

[0051] The logarithmic growth phase of U87 (glioma cells), MCF7 (breast cancer cells), HepG2 (human liver cancer cells), A549 (human lung cancer cells), MDA-MB-231 (human breast cancer cell lines), Panc1 (Human pancreatic cancer cell line) and L02 (human normal liver cells) were digested with trypsin, and the cells were transferred to laser confocal culture dishes, and the cell density was about 3×10 5 piece / cm 2 . Afterwards, the confocal culture dish was placed in a constant temperature cell culture incubator (37°C, 5% O 2 ) for 24 hours. After the cells adhered to the wall, 0.2 mL of ICG-03 solution filtered through a filter membrane was added and incubated for 2 hours. Cells were then washed twice with cold PBS solution (pH 7.4) for dual-channel fluorescence imaging by confocal laser microscopy.

[0052] Observing the fluorescence intensity of ICG-03 in tumor cells appa...

Embodiment 3

[0056] Compound Safety Test

[0057] In order to investigate the toxic and side effects of drugs on normal tissues, tissue sections and pathological studies are required. 30 rats aged 6 weeks, with a body weight of 200±10g, were intraperitoneally injected with ICG-03 dye 10mg / kg, and the rats were sacrificed four weeks later. Observe whether there are any changes in rat heart, liver, spleen, lung and kidney, fix the tissues in 10% formalin, and do HE staining on sections. There are no significant changes in rat heart, liver, spleen, lung and kidney, and histopathology is not significantly different from that of normal control rats. The dose is about 100 times the dose used in mouse imaging detection. The weight of the mouse is 20g. The dose is 0.1 mg / kg, which proves the safety of this dose. The results show that the dye has no toxicity to animals and cells, and shows good potential for clinical tumor detection and diagnosis.

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Abstract

The invention relates to tumor-specific heptamethine cyanine near-infrared fluorescent dye and application thereof; the near-infrared fluorescent dye is ICG-03, may be spontaneously absorbed and accumulated by various human tumor cells, may specifically gather at tumor parts other than normal cells, and accordingly may serve for accurately diagnosing tumors. Molecules described herein have better optical features than ICG, are suitable for photodynamic therapy and tumor imaging, and are good in stability. The heptamethine cyanine near-infrared fluorescent dye of the invention is suitable for the accurate diagnosis and treatment of tumors.

Description

technical field [0001] The invention relates to the field of near-infrared fluorescent dyes, in particular to a heptamethine fluorescent dye near-infrared fluorescent dye, which can be used for targeted photodynamic therapy of tumors. The invention also discloses its synthesis method and its application in precise diagnosis and treatment of tumors. Background technique [0002] At present, cancer has become the biggest culprit that endangers the health of our residents and seriously threatens human health. The clinical methods used to treat tumors include surgery, chemical drug therapy, and radiotherapy. Among them, photothermal photodynamic therapy technology is an emerging treatment technology without side effects. It uses a kind of photothermal reagent with good photothermal conversion efficiency to release part of the energy in the form of heat under the irradiation of near-infrared light. And generate active oxygen molecules. Compared with traditional treatment metho...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/16C09K11/06A61K49/00A61K41/00A61K47/60A61K47/54A61P35/00
CPCA61K41/0052A61K41/0057A61K49/0034C09B23/16C09K11/06C09K2211/1029A61K2300/00
Inventor 顾月清马祎韩智豪
Owner NANJING NUOYUAN MEDICAL DEVICES CO LTD
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