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A kind of bovine serum albumin self-assembled triphenylamine photosensitizer and preparation method and application

A technology of bovine serum albumin and triphenylamine, applied in carboxylate preparation, photodynamic therapy, carboxylate preparation, etc., can solve problems such as side effects and loss of normal organ function, and achieve good biocompatibility and low dark toxicity , the effect of obvious application value

Active Publication Date: 2022-08-02
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Traditional cancer treatments include surgery, radiotherapy, and chemotherapy, all three of which are prone to loss of normal organ function and serious side effects

Method used

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  • A kind of bovine serum albumin self-assembled triphenylamine photosensitizer and preparation method and application
  • A kind of bovine serum albumin self-assembled triphenylamine photosensitizer and preparation method and application
  • A kind of bovine serum albumin self-assembled triphenylamine photosensitizer and preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] A bovine serum albumin self-assembled triphenylamine-based photosensitizer in this embodiment is formed by self-assembly of an organic small molecule photosensitizer L and BSA; the organic small molecule photosensitizer L is a triphenylamine derivative containing a bipyridine salt, It forms BSA@L nanoparticles by self-assembly with BSA.

[0067] In this embodiment, the triphenylamine derivatives containing bipyridine salts are specifically 4-bis[(N,N-diphenylamine)styryl]-N-[1,2-bis(ethoxy)ethyl yl]-4-dipyridine iodide salt, 4-bis[(N,N-diphenylamine)styryl]-N-[1,2-bis(ethoxy)ethyl]-4-dipyridine Nitrate, 4-bis[(N,N-diphenylamine)styryl]-N-[1,2-bis(ethoxy)ethyl]-4-dipyridine-4-methylbenzenesulfonic acid acid salt, 4-bis[(N,N-diphenylamine)styryl]-N-[1,2-bis(ethoxy)ethyl]-4-dipyridine hexafluorophosphate, 4- Bis[(N,N-diphenylamine)styryl]-N-[1,2-bis(ethoxy)ethyl]-4-dipyridine trifluoroacetate, 4-bis[(N ,N-diphenylamine) styryl]-N-[1,2-bis(ethoxy)ethyl]-4-dipyridine tetr...

Embodiment 2

[0072] A preparation method of the BSA@L1 nanophotosensitizer in the above-mentioned embodiment 1 of the present embodiment comprises the following steps:

[0073] (1) Preparation of intermediate M1

[0074] Weigh 1,2-bis(2'-iodoethoxy)-ethane (1.01 g, 2.7 mmol) and 4-picoline (0.76 g, 8.1 mmol), dissolve in 20.0 mL of absolute ethanol, 60 Reflux at ~80°C, and the reaction was traced by thin layer chromatography (TLC); after 24 hours of reaction, the reaction was completed, and column chromatography was performed to obtain a white solid M1, namely 4-dimethyl-N-[1,2-bis( Ethoxy)ethyl]-4-dipyridinium iodide salt.

[0075] Yield: 64.7%. 1 H NMR (400MHz, DMSO-d 6 ),δ(ppm):8.88-8.86(d,J=8.00Hz,4H),8.02-8.01(d,J=4.00Hz,4H),4.73-4.70(t,J=6.00Hz,4H),3.85 -3.83(t, J=4.00Hz, 4H), 3.49(s, 4H), 2.64(s, 6H);13 C NMR (100MHz, DMSO-d 6 ), δ(ppm): 159.12, 144.06, 128.03, 69.42, 68.62, 59.45, 21.47; MS(ESI): calcd for: C 18 H 26 N 2 O 2 2+ [M / 2], 151.10; found, 151.0982.

[0076] (2...

Embodiment 3

[0083] A preparation method of the BSA@L2 nanophotosensitizer in the above-mentioned embodiment 1 of the present embodiment comprises the following steps:

[0084] (1) Preparation of intermediate M1

[0085] Same as step (1) of Example 2.

[0086] (2) Preparation of L1

[0087] With the step (2) of embodiment 2.

[0088] (3) Preparation of L2

[0089] Silver nitrate (0.064g, 0.38mmol) was dissolved in 20mL of anhydrous acetonitrile solution, then L1 (0.20g, 0.19mmol) was added to the reaction system, refluxed at 60-80°C for 4h; after the reaction was over, the precipitate was removed by filtration, and the filtrate was concentrated , to obtain 0.12g of red product L2, namely 4-bis[(N,N-diphenylamine)styryl]-N-[1,2-bis(ethoxy)ethyl]-4-dipyridine nitric acid Salt.

[0090] Yield: 66.7%. 1 H NMR (400MHz, DMSO-d 6 ),δ(ppm):8.72-8.71(d,J=4.00Hz,4H),8.08-8.07(d,J=4.00Hz,4H),7.87-7.83(d,J=16.00Hz,2H),7.55 -7.53(d,J=8.00Hz,4H),7.34-7.31(t,J=8.00Hz,8H),7.22-7.18(d,J=16.00Hz,2H)...

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Abstract

The invention relates to the field of preparation of photosensitizer composite materials, and provides a bovine serum albumin self-assembled triphenylamine photosensitizer, which is formed by self-assembly of an organic small molecule photosensitizer L and BSA; Bispyridine salt-like triphenylamine derivatives, which self-assemble with BSA to form BSA@L nanoparticles. The present invention also provides a preparation method and application of the above bovine serum albumin self-assembled triphenylamine photosensitizer. The advantages of the present invention are: the organic small molecule photosensitizer used is a triphenylamine derivative containing a bipyridine salt, which forms corresponding nanoparticles by self-assembly with BSA; It is taken up by cervical cancer cells, and it can also quickly kill cancer cells under white light irradiation to achieve the effect of photodynamic therapy.

Description

technical field [0001] The invention relates to the field of preparation of photosensitizer composite materials, in particular to a bovine serum albumin self-assembled triphenylamine photosensitizer and a preparation method and application. Background technique [0002] Cancer has become one of the deadliest diseases in our society, and billions of dollars are spent on research every year around the world to cure or improve cancer treatments. [0003] Traditional cancer treatments include surgery, radiotherapy and chemotherapy, all three of which are prone to loss of normal organ function and serious side effects. Photodynamic therapy, as a new type of cancer treatment, is minimally invasive, targeted, precise and novel. It can selectively kill cancer cells while preserving normal tissues. The principle of photodynamic therapy is: using photodynamic effect to irradiate the tumor site with a specific wavelength, and activate the photosensitizer selectively accumulated in the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/07C07D213/38C07C309/30C07C303/32C07C53/18C07C51/41C07F5/02C09K11/06A61K41/00A61K9/14A61K47/42A61P35/00
CPCC09K11/07C07D213/38C07C309/30C07C303/32C07C53/18C07C51/412C07F5/027C09K11/06A61K41/0057A61K9/146A61P35/00C09K2211/1014C09K2211/1029Y02B20/00
Inventor 王君君刘刚朱小姣余志鹏张杰汪联可周虹屏
Owner ANHUI UNIVERSITY
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