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Fluorescent probe for detecting tumor and use

A fluorescent probe, tumor technology, applied in fluorescence/phosphorescence, luminescent materials, measurement devices, etc., can solve the problems of limited application and low synthesis efficiency

Pending Publication Date: 2019-10-29
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Combined with the above-mentioned problems in clinical application, the tumor tracer requires the implantation of radioisotopes in the molecule and the low synthesis efficiency greatly limits its application.

Method used

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  • Fluorescent probe for detecting tumor and use
  • Fluorescent probe for detecting tumor and use
  • Fluorescent probe for detecting tumor and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]

[0041] Preparation of fluorescent probe (I-1) for detecting tumors:

[0042] 160mg of 3-aminoethyluracil and 200mg of fluorophore-containing halogen-substituted compound (A-1)-Cl were dissolved in 5 milliliters of N,N-dimethylformamide, then 202mg of triethylamine was added at room temperature, and the reaction was Heat at 60°C for 12 hours under nitrogen atmosphere. After the reaction was completed, cool to room temperature, add 20 ml of dichloromethane and stir, and then wash the reaction solution with 10 ml of saturated ammonium chloride and 10 ml of saturated brine in sequence. The aqueous phase was back-extracted twice with dichloromethane (2x10), and the organic phase solvent was dried with anhydrous sodium sulfate, spin-dried under reduced pressure, and purified by silica gel chromatography (dichloromethane:methanol=15:1) to obtain the yellow solid target Product (222mg).

[0043] Yield: 70%

[0044] 1 H NMR(400MHz,DMSO)δ11.12(s,1H),9.45(s,1H),8.57(d,1H,...

Embodiment 2

[0047]

[0048] Preparation of fluorescent probe (I-2) for detecting tumors:

[0049] According to the method of Example 1, 3-aminoethyluracil was replaced with 170 mg of 3-aminoethyl-5-methyluracil, and the reaction was heated at 60° C. for 12 hours to finally obtain 250 mg of the target product.

[0050] Yield: 75%

[0051] 1 H NMR(400MHz,DMSO)δ11.12(s,1H),9.45(s,1H),8.57(d,1H,J=8.6Hz,),7.78(br,1H),6.55(d,1H,J =8.6Hz,),4.08(m,2H),3.71(m,2H),2.40(s,3H).

[0052] ESI-MS: (m / z)333.1[M+1] +

Embodiment 3

[0054]

[0055] Preparation of fluorescent probe (I-3) for detecting tumors:

[0056] According to the method of Example 1, 3-aminoethyluracil was replaced with 175mg of 3-aminoethyl-5-fluorouracil, the reaction was heated at 60°C for 12 hours, and finally 235mg of the target product was obtained.

[0057] Yield: 70%

[0058] 1 H NMR (400MHz, DMSO) δ11.12(s, 1H), 9.45(s, 1H), 8.57(d, 1H, J=8.6Hz,), 7.88(d, 1H, J=5.0Hz), 6.55( d,1H,J=8.6Hz,),4.08(m,2H),3.71(m,2H).

[0059] ESI-MS: (m / z)337.1[M+1] +

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Abstract

The invention discloses a fluorescent probe for detecting tumor and use. The fluorescent probe for detecting the tumor has a structure shown in a formula (I) (please see the specification for the formula), and the fluorescent probe can be directly used in a cell system to analyze and detect the expression degree of ENT protein of tumor cells, so as to achieve the purposes of the screening of the tumor cells, the prediction of drug resistance of the tumor cells to chemotherapy drugs, and screening of various antitumor drugs. According to the fluorescent probe, effective means and useful tools are provided for early screening and diagnosis of the tumor, discovery and development of new antitumor drugs, and prediction and evaluation of drug resistance of tumor to the chemotherapy drugs.

Description

technical field [0001] The invention belongs to the field of biological analysis and detection, and in particular relates to a fluorescent probe targeting nucleoside transporter channels and its use in the preparation and detection of tumor reagents. [0002] technical background [0003] The nucleoside transporter distributed on the cell membrane is the main channel responsible for the transport and delivery of nucleoside drugs. It is divided into two categories, namely, equilibrative nucleoside transporter (ENT) and concentration nucleoside transporter (concentrative nucleoside transporter, CNT). Among them, ENT plays a very important role in the process of transporting and delivering nucleoside drugs. The importance of ENT in tumor research is mainly reflected in its widespread expression in a variety of human malignant tumor cells. For example, studies have shown that hENT1 has medium and high levels of expression in human cervical cancer (Hela), human breast cancer (MC...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D413/12C07D403/14C07D401/12C07D239/553C07D239/54C07D493/10C07D405/12C07F5/02G01N21/64G01N33/574
CPCC09K11/06C07D413/12C07D403/14C07D401/12C07D239/553C07D239/54C07D493/10C07D405/12C07F5/022G01N21/6428G01N33/57484C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1048C09K2211/1088C09K2211/1055
Inventor 高清志刘胜男石蕴丽
Owner TIANJIN UNIV
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