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Fluorescent probe and preparation method thereof

A fluorescent probe and compound technology, applied in the field of biomedicine, can solve problems such as the impact of diagnostic accuracy, and achieve accurate diagnosis, good tissue penetration, biocompatibility and biodegradability.

Active Publication Date: 2020-09-11
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The invention provides a fluorescent probe and its preparation method, which solves the problem that the accuracy of diagnosis is affected because the existing fluorescent probe cannot directly pass through the blood-brain barrier and enter the brain

Method used

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  • Fluorescent probe and preparation method thereof
  • Fluorescent probe and preparation method thereof
  • Fluorescent probe and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Present embodiment is the preparation of formula (I) compound (PROP, compound 6):

[0043]

[0044] (1) Accurately weigh 0.143 g of compound 1 and 0.214 g of compound 2 and mix, add 10 ml of anhydrous acetonitrile as a solvent, and react at 70° C. for 24 h to obtain compound 3 (compound of formula II).

[0045](2) Weigh 0.181g of compound 4 and 0.202g of 1,3-dibromobutane, add 10ml of anhydrous DMF as a reaction solvent after mixing, and use 200ul of triethylamine as a catalyst, react at room temperature for 12h to obtain compound 5 (formula III compounds).

[0046] (3) Mix 0.303 g of compound 5 and 0.358 g of compound 3, add 200 ul of triethylamine as a solvent, and stir at room temperature for 24 hours to obtain compound 6 (compound of formula I).

[0047] Depend on Figure 1~4 According to the H NMR spectrum and NMR mass spectrometry results, Compound 3, Compound 5, and Compound 6 were successfully prepared in this example.

Embodiment 2

[0049] This embodiment is the synthesis of fluorescent probe (TPP)

[0050] 1. Through the EDC / NHS technology, 3 mg of transferrin and 0.9 mg of small molecule PROP were coupled at 4°C for 48 hours, and then dialyzed with a dialysis bag for 36 hours to remove free small molecules and collected in the dialysis bag The sample is the TPP obtained from the reaction, which is stored in a 4°C refrigerator for later use, and the above experiments must be completed under dark conditions.

[0051] 2. Prepare 1mg / ml PROP mother solution, and dilute it into 15 different concentrations, the minimum concentration is 0mg / ml, then measure its absorption spectrum in the range of 600-900nm with a UV spectrophotometer, and make a standard curve according to the absorption spectrum ; Measure the absorption spectra of different dosage ratio samples, calculate the PROP concentration in the sample by the standard curve, and then according to the drug loading=(the quality of PROP in the nanoparticle...

Embodiment 3

[0053] This embodiment is TPP toxicity detection

[0054] Select the U87 cells in the logarithmic growth phase, digest and centrifuge, discard the supernatant and resuspend the cells, collect the single cell suspension, perform cell counting, calculate and dilute to an appropriate concentration with complete medium, inoculate in a 96-well plate, and 37°C, 5% CO 2 After culturing for 24 hours under the condition of 95% relative humidity, discard the medium, wash with PBS three times, add different concentrations of free PROP and TPP nanoparticles for cell culture, after incubation for 4 hours, discard the medium, add CCK-8 The fresh medium of the reagent was incubated for 4 hours, the absorption of the sample at 450 nm was detected with a multi-functional microplate reader, and the cell survival rate was calculated by the MTT method.

[0055] From Figure 5 It can be seen that the PROP and TPP small molecule probes have low toxicity and basically no damage to cells, which mee...

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Abstract

The invention relates to the technical field of biological medicines, in particular to a fluorescent probe and a preparation method thereof. The invention discloses a fluorescent probe. The fluorescent probe comprises a compound shown as a formula (I) and transferrin, the compound shown in the formula (I) and transferrin are combined through a condensation reaction of amino and carboxyl. Accordingto the fluorescent probe provided by the invention, transferrin is preferably used as a transport ligand; a compound represented by formula (I) is used as an imaging agent. Transferrin and a compoundshown as a formula (I) are subjected to self-assembly; the fluorescent probe taking the all-iron transporter as the carrier to couple with small molecules is obtained; the fluorescent probe can be combined with a blood brain barrier and an overexpressed receptor TFR on brain glioma through mediation of a ligand-receptor to realize effective targeted delivery of an imaging agent, so that the imaging agent reaches brain glioma tissues to perform fluorescence imaging, and early accurate diagnosis and postoperative tracking can be performed on a brain glioma patient.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to a fluorescent probe and a preparation method thereof. Background technique [0002] Glioma is a tumor derived from the neuroepithelium, accounting for 40% to 50% of brain tumors. It is the most common intracranial malignant tumor, with an annual incidence of 3 to 8 people per 100,000 population, and the annual new cases exceed 14000 cases. Age group 10-20 years old and 40-50 years old are the peak period of onset, and the treatment methods are mainly surgical treatment, supplemented by radiotherapy and chemotherapy, and the therapeutic effect is limited. Therefore, in order to obtain accurate and timely treatment for patients with glioma, better early diagnosis methods and postoperative follow-up methods are needed. However, because gliomas mainly occur in the neuroectoderm of the brain, and their location is rather special, most of the existing fluorescent probes cannot di...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K14/79C07K1/107C07K1/34C07D417/06C09K11/06A61K49/00
CPCC07K14/79C07D417/06C09K11/06A61K49/0021A61K49/0056C09K2211/1029C09K2211/1037
Inventor 卞旺青卢宇靖龙威何燕张焜张智陈泽丰王亚坤陈霓平黄艺斌
Owner GUANGDONG UNIV OF TECH
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