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Nanoprobe for detecting hypoxic cells and preparation method and uses of nanoprobe

A nanoprobe, TPE-4NE-O technology, applied in chemical instruments and methods, preparation of amino compounds from amines, preparations for in vivo tests, etc., can solve the problem of poor tumor penetration ability, complex synthesis steps, and poor water solubility. and other problems, to achieve the effect of simple and reliable preparation method, small polydispersity coefficient and uniform particle size

Active Publication Date: 2020-12-25
CHINA PHARM UNIV
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  • Abstract
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Problems solved by technology

[0003] In recent years, with the development of functional molecules and nanomaterials, there are many ways to image hypoxic tumors, such as positron emission tomography, magnetic resonance imaging, fluorescence imaging, photoacoustic tomography, etc., in which activated fluorescent probes It has shown excellent analytical performance in these detection methods and has attracted the attention of many researchers. However, since most hypoxic tumor cells are located in the deep position of solid tumors, and most of the current fluorescent probes have poor tumor penetration ability, At the same time, there are problems such as complex synthesis steps, poor water solubility, and potential systemic toxicity, which greatly limit its further development. Therefore, it is urgent to develop a fluorescent probe with good water solubility and strong tumor penetration ability through a simple method. Enabling identification of solid tumors

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  • Nanoprobe for detecting hypoxic cells and preparation method and uses of nanoprobe
  • Nanoprobe for detecting hypoxic cells and preparation method and uses of nanoprobe
  • Nanoprobe for detecting hypoxic cells and preparation method and uses of nanoprobe

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Experimental program
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Effect test

Embodiment 1

[0054] Synthesis of embodiment 1 fluorescent probe molecule TPE-4NE-O:

[0055] Synthesis of TPE-4NE: Weigh 2.0g of bis(4-(diethylamino)phenyl)methanone and 1.21g of zinc powder in a double-neck flask, then vacuumize and fill with argon, add 50mL of anhydrous tetrahydrofuran, and After the solution was cooled to -20°C, slowly add 680 μL of titanium tetrachloride into the solution using a syringe, continue stirring for 30 minutes, transfer the solution to room temperature and continue stirring for 1 hour, then reflux and stir overnight, after the reaction solution cooled to room temperature, add 20mL 10%K 2 CO 3 Quench the reaction with an aqueous solution, remove insoluble matter by suction filtration, collect the filtrate, extract with dichloromethane three times, combine the organic layers, concentrate in vacuo, and separate by column chromatography to obtain TPE-4NE; 1 HNMR (300MHz, CDCl 3 ), δ(CDCl 3 ,ppm):7.24-6.16(m,16H),4.16-2.22(m,16H),1.15-1.09(m,24H).HRMS,m / z cal...

Embodiment 2

[0057] Embodiment 2 does not contain the preparation of the nanoprobe of PEG modification:

[0058] Weigh 5 mg of TPE-4NE-O and dissolve it in 5 mL of LPBS, stir at 400 rpm for 3 minutes, and then filter through a 0.45 μm microporous membrane to remove the aggregates in the solution to obtain the PEG-free nanoprobe solution TPE-4NE-O NPs were stored in a refrigerator at 4°C for later use.

[0059] The appearance and particle size distribution of the prepared nanoprobes (TPE-4NE-O NPs) were characterized by transmission electron microscopy. Transmission electron microscope pictures as figure 1 , the particle size of the prepared nanoprobes is about 50nm, and the appearance is regular spherical; the particle size is relatively consistent, indicating that the prepared nanoprobes have good uniformity.

Embodiment 3

[0060] Example 3 Preparation of DSPE-PEG-modified nanoprobes bonded with folic acid:

[0061] Weigh 5mg TPE-4NE-O and 1.5mg FA-DSPE-PEG respectively 2000 , dissolved them together in 5mL PBS, stirred at 400rpm for 3min, and then filtered through a 0.45μm microporous membrane to remove the aggregates in the solution to obtain the folic acid-bonded DSPE-PEG-modified nanoprobe FA-DSPE / TPE-4NE-O NPs, store it in a refrigerator at 4°C until use.

[0062] The appearance and particle size distribution of the prepared nanoparticles were characterized by transmission electron microscope and Malvern particle size analyzer. Transmission electron microscope pictures as figure 2 , the particle size of the prepared nanoprobe is about 200nm, and the appearance is regular spherical; the particle size distribution results are as follows image 3 , the hydrated particle size of nanoprobes presents a typical normal distribution, and the polydispersity coefficient is 0.134, indicating that t...

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Abstract

The present invention provides a nanoprobe for detecting hypoxic cells and a preparation method and uses of the nanoprobe. The nanoprobe is formed by self-assembly of fluorescent molecules; the fluorescent molecules are formed by condensing and oxidizing bis (4 (diethylamino) phenyl) ketone; the nanoprobe can realize fluorescence imaging of a hypoxia degree of cells by detecting the content of CYP450 enzyme in the cells; in a hypoxia environment, the nanoprobe is converted into the fluorescent molecules with strong proton adsorption capacity, so that deep penetration of tumors is realized; andthe nanoprobe has advantages of a simple synthesis method, strong water solubility, low toxicity, strong anti-interference capability, high sensitivity and strong deep penetration capability of tumors.

Description

technical field [0001] The invention relates to a nanoprobe and its preparation method and application, in particular to a nanoprobe for detecting anoxic cells and its preparation method and application. Background technique [0002] Early detection of tumors is crucial to improving the cure rate of tumors, and high-sensitivity tumor imaging has very important guiding significance for doctors to perform fine surgical resection. Due to the rapid division and proliferation of tumor cells and the abnormal development of blood vessels, solid tumors are often in a state of hypoxia. The literature shows that even solid tumors with a diameter of only 1-2 mm can suffer from hypoxia. Therefore, hypoxia, as an abnormal indicator of solid tumors, can be used to image solid tumors. Since tumor hypoxia is often associated with malignant invasion and metastasis, treatment resistance and poor prognosis, the imaging of hypoxic tumor cells has very important clinical value. [0003] In re...

Claims

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Application Information

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IPC IPC(8): A61K49/00A61K47/22C09K11/06C07C291/04
CPCA61K49/0021A61K49/0093A61K47/22C09K11/06C07C291/04C07C209/68C09K2211/1007C07C211/50Y02P20/55
Inventor 曲玮冯锋张仲涛王如意柳文媛
Owner CHINA PHARM UNIV
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