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Semiconductor polymer for treating hypoxic tumors, preparation method and application

A semiconductor and polymer technology, applied in the field of nanomedicine, can solve the problems that there are no organic/polymer photosensitizers in NIR-III type PDT/PTT, and achieve the effects of improving photothermal conversion efficiency, promoting production, and strong absorption

Pending Publication Date: 2022-01-21
UNIVERSITY OF CHINESE ACADEMY OF SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, although a few NIR-II type II PDT / PTT photosensitizers have been reported, there are still no NIR-II type I PDT / PTT organic / polymeric photosensitizers reported

Method used

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  • Semiconductor polymer for treating hypoxic tumors, preparation method and application
  • Semiconductor polymer for treating hypoxic tumors, preparation method and application
  • Semiconductor polymer for treating hypoxic tumors, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The synthesis steps of semiconducting polymers for the treatment of hypoxic tumors are as follows:

[0039] Step 1: According to the procedure described in the literature (Adv. Funct. Mater. 2013, 23, 5317), synthesize the bilateral iodide of thiophene isoindigo.

[0040] Step 2: According to the procedure described in the literature (Angew.Chem.Int.Ed.2014, 53, 10691), a double-sided tin compound of tellurophene was synthesized.

[0041] Step 3: Under the protection of nitrogen, the bilateral iodide ((E)-2,2'-diiodo-4,4'-bis(2-octyldodecyl)-[6,6'-bithieno[3, 2-b]pyrrolylidene]-5,5'(4H,4'H)-dione) (0.05 mmol) and bistannide of tellurphene (0.05 mmol) were added to a Schlenk reaction flask. After the reaction flask was degassed and refilled with nitrogen for 3 times, dry toluene (2.0 mL) was added, and nitrogen was bubbled for 15 minutes. Then, add Pd under the protection of nitrogen 2 (dba) 3 (0.0025mmol) and tris(o-methylphenyl)phosphorus (0.010mmol). The solution...

Embodiment 2

[0045] The synthesis of semiconducting polymers for the treatment of hypoxic tumors is as follows:

[0046] Step 1: According to the procedure described in the literature (Polym.Chem.2016, 7, 1181), synthesize the double-sided tin compound of thiophene isoindigo.

[0047] Step 2: According to the procedure described in the literature (Organometallics 2016, 35, 2140), the bilateral bromide of tellurocyclohexane was synthesized.

[0048] Step 3: Under the protection of nitrogen, the double-sided tin compound of thiophene isoindigo ((E)-4,4'-bis(2-hexyldecyl)-2,2'-bis(trimethylstannyl)-[6,6'-bithieno [3,2-b]pyrrolylidene]-5,5'(4H,4'H)-dion) (0.05 mmol) and tellurocyclohexane bis bromide (0.05 mmol) were added to a Schlenk reaction vial. After the reaction flask was degassed and refilled with nitrogen for 3 times, dry toluene (2.0 mL) was added, and nitrogen was bubbled for 15 minutes. Then, add Pd under the protection of nitrogen 2 (dba) 3 (0.0025mmol) and tris(o-methylphenyl...

Embodiment 3

[0052] Step 1: According to the procedure described in the literature (Polym.Chem.2016, 7, 1181), synthesize the double-sided tin compound of thiophene isoindigo.

[0053] Step 2: According to the procedure described in the literature (Angew.Chem.Int.Ed.2010, 49, 10140), synthesize the double-sided iodide of bitellurphene.

[0054] Step 3: Under the protection of nitrogen, the double-sided tin compound of thiophene isoindigo ((E)-4,4'-bis(2-hexyldecyl)-2,2'-bis(trimethylstannyl)-[6,6'-bithieno [3,2-b]pyrrolylidene]-5,5'(4H,4'H)-dion) (0.05 mmol) and ditellurene bi-iodide (0.05 mmol) were added to a Schlenk reaction vial. After the reaction flask was degassed and refilled with nitrogen for 3 times, dry toluene (2.0 mL) was added, and nitrogen was bubbled for 15 minutes. Then, Pd2(dba)3 (0.0025 mmol) and tris(o-methylphenyl)phosphorus (0.010 mmol) were added under nitrogen protection. The solution was then bubbled again with nitrogen for 15 minutes. The above mixture was heat...

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Abstract

The invention provides a semiconductor polymer for near-infrared two-region photothermal and photodynamic synergistic treatment of hypoxic tumors, a preparation method and application. According to the preparation method disclosed by the invention, thiophene isoindigo is taken as an electron acceptor, a telluracyclopentadiene derivative is taken as an electron donor, and the near-infrared two-region semiconductor polymer is synthesized through Stille reaction. Semiconductor polymer nanoparticles are prepared by a nanoprecipitation method. The semiconductor polymer synthesized by the method shows wide and strong absorption in a near-infrared second region, the photo-thermal conversion efficiency of the material is improved, and the semiconductor polymer shows the photo-thermal conversion efficiency of 47.5% under the irradiation of laser in the near-infrared second region. The introduction of heavy atoms promotes the generation of active oxygen species. Due to insufficient triplet excited state energy of the semiconductor polymer nanoparticles, oxygen cannot be sensitized to generate singlet oxygen, but superoxide anion free radicals can be generated, and the semiconductor polymer nanoparticles are used for photodynamic therapy of hypoxic tumors in a near-infrared second region.

Description

technical field [0001] The invention relates to the technical field of nanomedicine, in particular to a semiconductor polymer for treating hypoxic tumors, a preparation method and an application. Background technique [0002] In clinical treatment, some malignant tumors (MTs) with deep invasion, large volume, complex location, and low possibility of surgery / radiotherapy are difficult to cure. Therefore, photodynamic / photothermal therapy (PDT / PTT) has been used to treat such tumors due to its advantages of non-invasiveness, remarkable tumor penetration depth, and negligible side effects. To realize the excellent efficacy of MTs, there are several requirements for PDT / PTT photosensitizers. First, the photosensitizer should be responsive to near-infrared II region (NIRⅡ) laser (1000-1700nm) irradiation, which exhibits deeper penetration (>1cm for 1064nm laser) and higher maximum permissible exposure (MPE, MPE for skin , 1064nm laser is 1.0W cm -2 , 808nm laser is 0.33W cm...

Claims

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Application Information

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IPC IPC(8): C08G61/12A61K9/51A61K41/00A61P35/00
CPCC08G61/126C08G61/123A61K41/0057A61K9/5146A61P35/00C08G2261/124C08G2261/3226C08G2261/3244C08G2261/3243C08G2261/414Y02E10/549
Inventor 黄辉温凯凯彭谦陈皓彭爱东史钦钦
Owner UNIVERSITY OF CHINESE ACADEMY OF SCIENCES
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