Triphenylamine-triphenylphosphine compound as well as preparation method and application thereof

A technology of triphenylphosphine and triphenylamine, which is applied in the field of triphenylamine-triphenylphosphine compounds and their preparation, can solve the problem of insufficient anti-cancer effect, achieve excellent luminescent properties and prolong the triplet lifetime

Active Publication Date: 2020-11-10
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the defects and deficiencies that the anticancer effect of relying solely on photodynamic therapy is not significant enough, and to provide a triphenylamine-triphenylphosphine compound capable of photodynamic therapy and mitochondria-mediated cancer at the same time. Apoptosis has dual anti-cancer functions. This synergistic anti-cancer effect not only retains the advantages of photodynamic therapy, but also significantly improves the anti-cancer effect, making up for the shortcomings of photodynamic therapy.

Method used

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  • Triphenylamine-triphenylphosphine compound as well as preparation method and application thereof
  • Triphenylamine-triphenylphosphine compound as well as preparation method and application thereof
  • Triphenylamine-triphenylphosphine compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] A kind of triphenylamine-triphenylphosphine compound name is 4-4-diphenyl ether-4 pyridyl-triphenylamine-(6-bromohexyl)-triphenylphosphine (OPY-TPA-TPP), has the following Show molecular structure:

[0048]

[0049] The preparation method of above-mentioned OPY-TPA-TPP, comprises the steps:

[0050] S1. Mix triphenylphosphine (10mmol, 2.62g) and 1,6-dibromohexane (20mmol, 4.86g) in tetrahydrofuran (100mL) and react at 120°C for 72 hours to obtain a white viscous product Crude product (6-bromohexyl)-triphenylphosphine (1,6-TPP); after washing 3 times with diethyl ether, the viscous product solidified and was recrystallized with three mixed solvents of tetrahydrofuran, methanol and n-hexane to obtain a white Crystalline 1,6-TPP (5mmol, 2.53g, yield 50%) (the NMR results are as figure 1 shown);

[0051] Its reaction equation is as follows:

[0052]

[0053] Mix 4,4,4-tribromotriphenylamine (5mmol, 2.41g) with 4-boronic diphenyl ether (10mmol, 2.14g), tetrakistrip...

Embodiment 2

[0063] A kind of triphenylamine-triphenylphosphine compound name is 4-4-dibromo-4 pyridyl-triphenylamine-(6-bromohexyl)-triphenylphosphine (Br-TPA-TPP), has as follows Molecular Structure:

[0064]

[0065] The preparation method of above-mentioned Br-TPA-TPP, comprises the steps:

[0066] S1. Combine 4,4,4-tribromotriphenylamine (5mmol, 2.41g), 4-pyridineboronic acid (3mmol, 3.69g), tetrakistriphenylphosphopalladium (0.15mmol, 173.3mg) and potassium carbonate (3mmol, 414mg) was mixed in a mixed solution of methanol and tetrahydrofuran with a volume ratio of 1:1, and reacted at 90°C for 24h under nitrogen protection to obtain 4-4-dibromo-4-pyridyl-triphenylamine (Br-TPA-PY) crude product (The NMR results are as Figure 4 shown), purified by column chromatography to obtain a light yellow solid, the solid has a faint blue fluorescence, and the yield is 35%;

[0067] Its reaction equation is as follows:

[0068]

[0069] S2. Dissolve Br-TPA-PY (1mmol, 506mg) and 1,6-tri...

Embodiment 3

[0073] A kind of triphenylamine-triphenylphosphine compound name is 4-pyridyl-triphenylamine-(6-bromohexyl)-triphenylphosphine (TPA-TPP), has molecular structure as shown below:

[0074]

[0075] The preparation method of above-mentioned TPA-TPP, comprises the steps:

[0076] S1. Mix 4-bromotriphenylamine (10mmol, 3.23g) with 4-pyridine boronic acid (10mmol, 1.23g), dissolve tetrakistriphenylphosphopalladium (0.5mmol, 577.78mg) and potassium carbonate (10mmol, 1.38g) In a mixed solution of methanol and tetrahydrofuran with a volume ratio of 1:1, the crude product of 4-pyridyl-triphenylamine (TPA-PY) was obtained by reacting at 90° C. under nitrogen protection for 24 h (its NMR results are as follows: Figure 5 shown), purified by column chromatography to obtain a light yellow solid, the solid has blue fluorescence, and the yield is 80%;

[0077] Its reaction equation is as follows:

[0078]

[0079] S2. Dissolve TPA-PY (386mg, 1.2mmol) and 1,6-triphenylphosphine (1mmol...

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Abstract

The invention discloses a triphenylamine triphenylphosphine compound as well as a preparation method and application thereof. The triphenylamine triphenylphosphine compound has a molecular structure as shown in a formula (I), wherein R is one of a hydrogen atom, halogen, methoxyl and diphenyl oxide. The triphenylamine triphenylphosphine compound is of an electron-donating and electron-withdrawingstructure (DA) or has a plurality of heavy atoms, intersystem crossing can be promoted, and oxygen can be converted into superoxide free radicals under low exciting light; in addition, the triphenylamine triphenylphosphine compound disclosed by the invention not only has the double functions of photodynamic therapy and mitochondria-mediated cancer cell apoptosis, but also has the AIE performance,has better fluorescence characteristic, and can be used for preparing a photodynamic therapy drug for cancer cell apoptosis, and the photodynamic therapy and mitochondria-mediated cancer cell apoptosis can be effectively inhibited.

Description

technical field [0001] The present invention relates to the technical field of photodynamic therapy, more specifically, to a triphenylamine-triphenylphosphine compound and its preparation method and application. Background technique [0002] The incidence of cancer has been increasing year by year, and the mortality rate has also remained high. Photodynamic therapy is an emerging cancer treatment method. This method has the advantages of minimal invasiveness, high targeting and low drug resistance. Photodynamic therapy mainly relies on light conditions, and photosensitizers can generate active oxygen to induce cancer. Apoptosis and tissue destruction. [0003] Chinese patent CN107722055B discloses a mitochondria-targeted fluorescent probe photosensitizer driven by low-power white light. The targeting molecule modified on the surface of the fluorescent probe photosensitizer can target mitochondria in cells, and can be used for mitochondrial fluorescence imaging labeling. Lo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/58C09K11/06A61K31/675A61K41/00A61K49/00A61P35/00G01N21/64
CPCC07F9/58C09K11/06A61K41/0061A61K49/0021A61P35/00G01N21/6428C09K2211/1014C09K2211/1007C09K2211/1029Y02E10/549
Inventor 马钰程籍少敏庄泽燕邢龙江徐建兴赵祖金霍延平
Owner GUANGDONG UNIV OF TECH
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