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Tumour targeting fluorescent probe and application in tumour NO test

A fluorescent probe and tumor-targeting technology, applied in fluorescence/phosphorescence, microbial measurement/inspection, bacteria, etc., can solve the problems of difficult time and space distribution and expression, lack of tumor targeting, etc., and achieve synthesis cost Low, long fluorescence retention time, good practical effect

Inactive Publication Date: 2008-09-24
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most NO fluorescent probes, such as the commercially available diaminofluoresceins (DAFs) and diaminorhodamines (DARs), lack good tumor targeting although they can detect NO sensitively.
At the same time, the reaction between these fluorescent probes and NO requires the participation of oxygen molecules, and many solid tumor tissues are in a hypoxic state, so when these fluorescent probes are applied to tumor NO imaging, there will be no obvious fluorescence changes.
These limitations make it difficult for most classical fluorescent probes to be applied in vivo to accurately measure the temporal and spatial distribution and expression of NO during tumor development.

Method used

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  • Tumour targeting fluorescent probe and application in tumour NO test
  • Tumour targeting fluorescent probe and application in tumour NO test
  • Tumour targeting fluorescent probe and application in tumour NO test

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1: the synthetic route of probe 1 and probe 2:

[0052] (1) Synthesis of 2-(2-hydroxyphenyl)-benzimidazole: mix equimolar (5~15mmol) salicylaldehyde, sodium bisulfite and 25mL absolute ethanol, stir at room temperature for 3~6h, and then Dissolve equimolar o-phenylenediamine in 25mL DMF, add dropwise to the previous solution and heat to reflux for 2-3h. After the reaction is completed, pour the reactant into 10 times cold water, precipitate out, filter with suction, dry, and recrystallize twice with absolute ethanol;

[0053] (2) Synthesis of 2-(2-hydroxy-5-nitro)-benzimidazole: Dissolve 0.01~0.05g of 2-(2-hydroxyphenyl)-benzimidazole in 10 times the amount of concentrated sulfuric acid and use Cool to -10°C in an ice-salt bath, add dropwise the pre-prepared and cooled mixed acid (concentrated HNO 3 1.0~5.0g; concentrated H 2 SO 4 1.2 to 6.0 g), and keep the temperature at -10°C for 30 to 60 minutes, pour the reactant into ice, filter the precipitate, was...

Embodiment 2

[0060] Example 2: Study on tumor targeting of probe 1 in mice bearing S180 sarcoma

[0061] Inoculate S180 sarcoma cells (at a concentration of 10 6 cells / ml) to the armpit of Balb / c mice (male, 6-8 weeks, 18-22 g), and 200 μl of S180 cells were subcutaneously injected into the armpit of each mouse. One week after inoculation, take 200 μl of the PBS suspension of probe 1 (concentration is 10 9 Top10 / ml), injected into the tail vein of S180 tumor-bearing mice. Two days after the tail vein injection, the mice were sacrificed, and the main organs (heart, liver, spleen, lung, kidney, brain, blood) and tumor tissues were taken, homogenized and dissolved in 800 μl DMSO, and the organ fluorescence distribution of probe 1 was measured , to determine whether it has tumor targeting, when measuring, the excitation light is 330nm, and the fluorescence intensity value at 505nm is measured. Results for each organ are shown as fluorescence intensity per gram of tissue. The results can be...

Embodiment 3

[0064] Example 3: Fluorescence change of probe 2 reacting with NO

[0065] Suspend Probe 2 in 1×PBS to a final concentration of 10 9 Top10 / ml, take 200μl and react with 1.8mM NO for 1, 5min, measure the change of fluorescence intensity of the suspension, the excitation wavelength is 330nm, see the results Figure 4 , and the fluorescence intensities were normalized. The results of fluorescence photos before and after the reaction between probe 2 and NO can be found in Figure 5 .

[0066] from Figure 4It can be seen from the figure that the background fluorescence intensity of probe 2 is very low. After reacting with NO, the fluorescence intensity rapidly (within 1 minute) increases significantly. After five minutes of reaction, the fluorescence intensity tends to be stable. . The rapid and obvious fluorescence enhancement after reacting with NO indicated that probe 2 could be used as a fluorescent probe for NO detection for the determination of NO. Figure 5 The fluore...

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Abstract

The invention provides a tumor-targeted fluorescent probe, and application of the fluorescent probe in tumor NO detection, which belongs to the biotechnology field. The invention in particular relates to a fluorescent probe which can be targeted to a tumor tissue based on specificity. The fluorescent probe can form a complex with double-charge copper ions, and can be applied for the fluorescent imaging detection of the level of NO in the tumor. The fluorescent probe is the Top10 bacterial strain of colibacillus modified with N-(3-(2- phenyl imidazolyl)-4-hydroxy phenyl) maleimide. The fluorescent probe can be targeted to the tumor tissue quickly in a mammal body. In addition, the complex formed by the fluorescent probe and the double-charge copper ions can react with NO released in the tumor tissue, thus significantly improving the fluorescence intensity. In this way, the fluorescent probe can be used for the fluoroscopic detection of NO in the tumor tissue of a living body and the fluorescent imaging of the living body.

Description

a technical field [0001] The invention belongs to the field of biotechnology, and in particular relates to a molecular probe for tumor-targeted fluorescence imaging and its application in tumor NO detection. Two background technology [0002] Nitric oxide (Nitric Oxide, NO) is a highly reactive molecule that plays a variety of physiological functions in the body. The main functions of NO are as follows: regulating blood vessels, regulating nerves, and regulating cytotoxicity at relatively high concentrations. NO plays an important role in the process of tumor formation, development and metastasis, and it can both promote and inhibit tumors. Chronic inflammation or sustained exposure to induced moderate to high concentrations of NO is thought to promote neoplastic transformation. Because NO or NO-derived highly reactive groups can induce oxidation or nitrosylation, thereby causing DNA damage in a direct or indirect manner (such as nitrosative deamination of nucleic acid bas...

Claims

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Application Information

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IPC IPC(8): C12N1/20G01N21/64C12Q1/02
Inventor 张峻峰洪浩张佳妮欧阳杰陈江宁沈超赵勇
Owner NANJING UNIV
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