PH and anoxia dual-response tumor cell location naphthalimide rate fluorescent probe and synthesis method thereof

A ratiometric fluorescent probe, tumor cell technology, applied in the field of naphthalimide ratio fluorescent probes for localizing tumor cells with dual response to pH and hypoxia and their synthesis, which can solve the problems of limited accuracy of localizing tumor cells, etc. achieve the effect of improving accuracy

Inactive Publication Date: 2017-06-30
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the reported fluorescent probes can only detect the hypoxic environment or the pH alone, and locate tumor cells through

Method used

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  • PH and anoxia dual-response tumor cell location naphthalimide rate fluorescent probe and synthesis method thereof
  • PH and anoxia dual-response tumor cell location naphthalimide rate fluorescent probe and synthesis method thereof
  • PH and anoxia dual-response tumor cell location naphthalimide rate fluorescent probe and synthesis method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1 (synthesis of probe)

[0041] The reaction scheme is as follows:

[0042]

[0043] 1.1 Synthesis of compound 1:

[0044] Put 5.54g of A and 40mL of n-butylamine into a 250mL flask, add 100mL of absolute ethanol, reflux at 120°C for 3h. After cooling to room temperature, 8.0 g of white solid was obtained by suction filtration.

[0045] 1.2 Synthesis of Compound 2:

[0046]2.0 g of compound 1 and 3.2 mL of N-(2-aminoethyl)morpholine were added to a 100 mL flask and 0.01 mg of copper sulfate pentahydrate and 40 mL of ethoxyethanol were added. Under the protection of nitrogen, it was refluxed at 120°C for 8 h, spin-dried, and purified by column chromatography (DCM:methanol=10:1) to obtain 1.3 g of a yellow solid.

[0047] The H NMR spectrum of compound 2 is shown in Figure 7 .

[0048] 1.3 Synthesis of compound 3:

[0049] 130 mg NaH was dissolved in 2 mL THF, cooled to 0° C. under argon protection, 50 mg of compound 2 was dissolved in 3 mL THF and a...

Embodiment 2

[0050] Embodiment 2 (the ultraviolet-visible absorption spectrum of compound 2 and compound 3)

[0051] A DMSO solution with a concentration of 1 mM Compound 2 and Compound 3 was prepared. Take 3mL0.01M PBS buffer solution and add 30μL DMSO solution as blank control. Also take 3mL of the same PBS solution and add the prepared compound 2 and compound 3 solutions respectively, and test respectively to get figure 1 UV absorption curves of compound 2 and compound 3. Depend on figure 1 It can be seen that the isoabsorptive point of compound 2 and compound 3 is 389 nm.

Embodiment 3

[0052] Embodiment 3 (pH titration of compound 2)

[0053] from figure 1 The excitation wavelengths for obtaining compound 2 were 449 nm. Take 3 mL of 0.01M PBS (pH7.4) buffer solution and add 30 μL of 1 mM compound 2 and compound 3 solutions respectively, and titrate with 0.1M HCl and NaOH solutions. The fluorescence intensities of compound 2 at pH 3.0, 4.0, 5.0, 6.0, 7.0, 8.0, 9.0, and 10.0 were collected respectively. Compound 2 measured results see figure 2 . Depend on figure 2 It can be seen that the titration transition of compound 2 is 4.0-7.0.

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Abstract

The invention relates to the technical field of location and detection of tumor cells, particularly to a PH and anoxia dual-response tumor cell location naphthalimide rate fluorescent probe. The probe takes naphthalimide as a parent to introduce active groups of nitrobenzyl and morpholine for detecting anoxia and pH respectively, and the experiment proves that the effect of detecting nitroreductase of the probe under the acid condition is better than that under the neutral condition, therefore, the probe eliminates the limit that the conventional anoxia probe can only detect the nitroreductase, the imaging accuracy of the tumor cell is greatly improved, a new idea is provided for the treatment and detection of tumors, and the application prospect is quite broad.

Description

technical field [0001] The invention relates to the technical field of localization and detection of tumor cells, specifically, a naphthylimine ratiometric fluorescent probe for localizing tumor cells with pH and hypoxia dual responses. and Naphthalene imine-based ratiometric fluorescent probes for nitroreductases. Background technique [0002] According to relevant organizations, about 8 million people died of cancer in 2004, and about 9 million people died of cancer in 2013. It is estimated that the number of people who will die of cancer will exceed 13 million by 2030. Obviously, cancer has become a major threat to human health. disease. Researchers hypothesized that hypoxic regions exist in tumors as early as 1955, and numerous subsequent experiments showed that tumor cells have lower oxygen concentrations than normal cells. Since tumor hypoxia is closely related to the malignant phenotype of tumor cells, the resistance to cancer therapy, and the mortality of cancer pa...

Claims

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Application Information

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IPC IPC(8): C07D221/14C07D405/12C07D409/12C07D401/12C09K11/06G01N21/64A61K49/00
CPCA61K49/0021C07D221/14C07D401/12C07D405/12C07D409/12C09K11/06C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1088C09K2211/1092G01N21/643G01N21/6486
Inventor 程探宇何兆帅刘国华李标丑亚杰张寒李良赵军伟
Owner SHANGHAI NORMAL UNIVERSITY
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