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Compound and preparation method thereof, fluorescent probe and antitumor drug

A technology of fluorescent probes and compounds, applied in the field of organic synthesis, can solve the problems of unstable non-biodegradability and long-term toxicity, and achieve the effect of photothermal therapy

Active Publication Date: 2020-11-06
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the developed photothermal agents are inhibited from further clinical application due to their instability or non-biodegradability in vivo, accompanied by long-term toxicity.

Method used

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  • Compound and preparation method thereof, fluorescent probe and antitumor drug
  • Compound and preparation method thereof, fluorescent probe and antitumor drug
  • Compound and preparation method thereof, fluorescent probe and antitumor drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Present embodiment is the synthesis of compound (TPHP) shown in formula (VI)

[0050]

[0051]

[0052] (1) Accurately weigh 0.143g of compound 1 and 0.214g of compound 2 and mix, add 10ml of anhydrous acetonitrile as solvent, react at 70°C for 24h to obtain compound 3 (compound of formula II).

[0053] (2) Weigh 0.181g of compound 4 and 0.214g of 1,4-dibromobutane, add 10ml of anhydrous DMF after mixing as a reaction solvent, and 200ul of triethylamine as a catalyst, react at room temperature for 12h to obtain compound 5 ( compound of formula III).

[0054] (3) Mix 0.397 g of compound 5 and 0.358 g of compound 3, add 200 μl of triethylamine as a solvent, and stir at 300 rpm for 24 hours at room temperature to obtain compound 6 (compound of formula IV).

[0055] (4) Mix 0.626g of compound 6 with 0.262g of triphenylphosphine, add 10ml of anhydrous acetonitrile as a solvent, weigh 100mg of sodium carbonate as a catalyst, and react at 120°C for 12h to obtain compoun...

Embodiment 2

[0060] The present embodiment is the optical property of TPHP and photostability determination

[0061] In order to investigate the photothermal performance, different concentrations of TP-PPh 3 (Formula V compound) and TPHP nano micelles were exposed to 808nm (1.0w / cm 2 ) in the laser for 5min. At predetermined time points, the regional maximum temperature of the solution was monitored using an infrared thermal imaging camera, with phosphate buffered saline as a negative control.

[0062] TP-PPh 3 (Such as Figure 4 shown) and TPHP have good photothermal properties, and with the increase of laser density and TP-PPh 3 With the increase of the concentration of TPHP, the temperature of the solution continued to rise, indicating that TP-PPh 3 and TPHP have good photostability, so TP-PPh 3 And TPHP converts the absorbed light energy into heat energy, thereby ablate tumor and realize photothermal therapy.

Embodiment 3

[0064] This embodiment establishes the subcutaneous model for bearing U87 mice

[0065] Prepare 6-8 week-old Balb / c nude mice, digest U87 cells in logarithmic growth phase, resuspend, and count. For the inoculation of mice with subcutaneous tumors, prepare 5 × 10 6 Cells (100 μl) were injected subcutaneously in the lower right lower back of the mouse. The size of the subcutaneous tumor in the mouse to be observed grows to 60mm 3 Around , the mice were divided into TP-PPh 3 Group and TPHP group, with 5 mice in each group, for subsequent imaging experiments.

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Abstract

The invention relates to the technical field of chemical synthesis, in particular to a compound, a preparation method thereof, a fluorescent probe and an antitumor drug. The invention discloses a compound as shown in a formula (I) which is described in the specification. The compound is accurately targeted and recognized through a hyaluronic acid ligand-receptor mediation effect; the overexpressedesterase in tumor cells releases TP-PPh3 by destroying an ester bond between the TP-PPh3 and hyaluronic acid, and fluorescence quenched by aggregation of the TP-PPh3 can be recovered. At mitochondrial respiration period, the proton pump in the membrane transports protons to the space in the mitochondrial membrane to form a mitochondrial transmembrane potential with high negativity, so that triphenylphosphine cations have the mitochondrial targeting capability, a mitochondrial region of a tumor can emit red fluorescence under the irradiation of near-infrared light, and fluorescence imaging ofthe tumor part is realized. When a laser of 650-980nm is used for irradiating tumor tissues, the TP-PPh3 can convert absorbed light energy into heat energy, so that tumors are ablated, and photothermal therapy is realized.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a compound, a preparation method thereof, a fluorescent probe and an antitumor drug. Background technique [0002] Malignant tumors have always been a headache for people because they threaten human health and will become the number one killer of modern society. Traditional tumor treatment options include surgery, chemotherapy, and radiotherapy, but they are stuck in bottlenecks due to their severe side effects and low prognosis. The current emerging photothermal therapy (PTT) has reversed this situation. It uses near-infrared lamps to excite photothermal agents and converts light energy into heat energy to kill cancer cells, providing a new tools to improve tumor treatment outcomes, and photothermal therapy has many advantages, such as high efficiency and less invasiveness. However, most of the developed photothermal agents are inhibited from further clinical applica...

Claims

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Application Information

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IPC IPC(8): C08B37/08C09K11/06A61K31/337A61K41/00A61K47/61A61K47/64A61K49/00A61P35/00G01N21/64
CPCC08B37/0072C09K11/06A61K31/337A61K47/6425A61K47/61A61K41/0052A61K49/0021A61P35/00A61K49/0054G01N21/6402G01N21/6428G01N21/6458C09K2211/1088C09K2211/1037C09K2211/1029C09K2211/1007
Inventor 卞旺青何燕卢宇靖龙威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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