Near-infrared fluorescent probe as well as preparation method and application thereof

A fluorescent probe and near-infrared technology, applied in the field of fluorescent probes, can solve the problems of concentrated luminescence, complex fluorescent probe preparation process and high cost, and achieve the effects of good stability, controllable cost and high biocompatibility.

Active Publication Date: 2022-07-15
INST OF AUTOMATION CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The present invention provides a near-infrared fluorescent probe and its preparation method and application to solve the problems of complex preparation process and high cost of existing fluorescent probes, and most of the luminescence is concentrated in the range of visible light

Method used

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  • Near-infrared fluorescent probe as well as preparation method and application thereof
  • Near-infrared fluorescent probe as well as preparation method and application thereof
  • Near-infrared fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Synthesis and Purification of Probe WZB117-IR820

[0053] The synthetic route of WZB117-IR820 in the present embodiment is as follows:

[0054]

[0055] IR820 (2.6 mg, 3.2 μmol) and WZB117 (1.2 mg, 3.2 μmol) were dissolved in 1 mL of N,N-dimethylformamide, then potassium carbonate (1.3 mg, 10.0 μmol) was added, and the reaction solution was heated to 60 The reaction was carried out at °C for 24 hours, and the N,N-dimethylformamide was distilled off under reduced pressure to obtain a crude product, which was purified with a preparative silica gel plate to obtain 1.4 mg of WZB117-IR820 with a yield of 37.5%. MS (ESI): m / z 1160.9 ([M+H]+).

Embodiment 2

[0057] Detection of tumor cells in vitro by probe WZB117-IR820

[0058] 1. Cell Culture

[0059] (1) Prepare the complete medium required for each cell

[0060] Specifically, the basic medium DMEM or 1640 accounts for 80-90%, the fetal bovine serum accounts for 10-20%, and the double-antibody stock solution (penicillin + streptomycin) is added at a volume fraction of 1%. Final concentrations were 100 U / mL and 100 μg / mL, respectively.

[0061] (2) Before starting the experiment, confirm the name, culture medium, passage time, passage and other information of the cell line marked on the 100mm petri dish to ensure that the experiment is correct.

[0062] (3) Use a sterile pipette to aspirate the cell culture medium.

[0063] (4) Rinse the cell surface layer with 3-5 mL of sterile PBS solution, and then suck out the PBS waste solution with a sterile pipette.

[0064] (5) Add 1 mL of 0.25% (w / v) trypsin solution containing 0.04% (w / v) EDTA to the culture medium to digest the cell...

Embodiment 3

[0076] Detection of live tumor cells by probe WZB117-IR820

[0077] (1) Establishment of tumor-bearing mouse model

[0078] Take CAL-fLUC tumor cells, centrifuge at 800 rpm for 5 min, wash the tumor cells three times with sterile PBS, make appropriate dilutions, and count them with a hemocytometer to make the concentration of 1 × 10 7 50 μL of tumor cell suspension was subcutaneously inoculated on the left hind limb of each mouse.

[0079] (2) Targeting verification

[0080] Seven days after tumor inoculation, 0.1 mL of 3 mg / mL WZB117-IR820 solution was intravenously injected, and the fluorescence and nuclear magnetic signal distributions in mice at different time points were monitored by an optical imaging system analyzer with high detection sensitivity.

[0081] For the results of in vivo fluorescence images of mice at different time points after intravenous injection of the probe, please refer to image 3 , the details are as follows:

[0082] With the prolongation of t...

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Abstract

The invention belongs to the technical field of fluorescent probes, particularly relates to a near-infrared fluorescent probe as well as a preparation method and application thereof, and aims to solve the problems that the preparation process of the fluorescent probe is complicated, the cost is relatively high, and light emission is mostly concentrated in a visible light range. The near-infrared fluorescent probe is prepared by the following steps: carrying out nucleophilic substitution reaction on near-infrared dye and WZB117 to obtain a mixture containing the near-infrared fluorescent probe, and purifying the mixture. The near-infrared fluorescent probe can be obtained only through nucleophilic substitution one-step reaction, the preparation technology is simple, the WZB117 and the near-infrared dye are commercially available products, raw materials are easy to obtain, the cost is controllable, and compared with a traditional visible light fluorescent probe, the near-infrared fluorescent probe is higher in penetrability and higher in signal-to-noise ratio.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and particularly relates to a near-infrared fluorescent probe and a preparation method and application thereof. Background technique [0002] At present, tumor has become a global disease that threatens human health. It is very important to develop effective drugs for early tumor screening, micrometastasis and lymph node metastasis monitoring to improve the treatment effect, prolong the postoperative survival period and quality of life of patients. [0003] At present, traditional tumor diagnosis methods mainly rely on the morphological characteristics of tumor tissue and tumor cells for judgment. It is necessary to sample and detect tumor tissue with a certain volume, and it is impossible to detect the existence of tumor cells when the number of tumor cells is small. Early screening and judgment of tumor metastasis or recurrence. [0004] In recent years, with the rapid development ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/60C09B23/08C09K11/06G01N21/64A61K49/00
CPCC07D209/60C09B68/463C09B23/0066C09B23/086C09K11/06G01N21/6486A61K49/0032A61K49/0052C09K2211/1029
Inventor 田捷杜洋唐初张海钟田瑜
Owner INST OF AUTOMATION CHINESE ACAD OF SCI
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