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Aza-bodipy derivatives with photothermal effect and their synthesis and application

A technology of photothermal effect and derivatives, which is applied in the field of biochemistry, can solve the problems of high price, and achieve the effect of low cost, obvious effect and high photothermal conversion rate

Active Publication Date: 2022-02-01
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, research literature has found that most of the initial photothermal materials are noble metal nanoparticles represented by expensive Au, Ag, and Pt, or graphene and carbon nanorods that have no near-infrared absorption or weak absorption in the near-infrared region. Therefore, it is challenging and practical to construct a low-cost organic functional small molecule photothermal material with near-infrared absorption.

Method used

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  • Aza-bodipy derivatives with photothermal effect and their synthesis and application
  • Aza-bodipy derivatives with photothermal effect and their synthesis and application
  • Aza-bodipy derivatives with photothermal effect and their synthesis and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Synthesis of compounds of formula Ⅰ-1

[0038]

[0039] Synthesis of Compound A

[0040] N 2 Under gas protection, weigh compound 1 (1.0g, 4.46mmol) and compound 2 (1.5g, 6.23mmol), add it to a 200mL round bottom flask, dissolve it with an appropriate amount of ethanol, add 15mL of 10% sodium hydroxide solution, and Stir overnight. Half-time observation, until the reaction is complete, dichloromethane extraction, combined organic phase, anhydrous Na 2 SO 4 Dry, evaporate the organic phase to dryness, and separate by column chromatography. The ratio of developer is DCM:EA=20:1. The product A is a yellow oily liquid with a yield of 72%. 1 H NMR (400MHz, CDCl 3 )δ=8.02(d, J=8Hz, 2H), 7.77(d, J=16Hz, 1H), 7.59(d, J=8Hz, 2H), 7.43(d, J=16Hz, 1H), 6.97(dd ,J=8Hz,4H),4.23(t,J=4Hz,2H),4.19(t,J=4Hz,2H),3.89(q,J=4Hz,4H),3.75-3.72(m,4H), 3.60-3.58(m,4H),3.40(s,6H).

[0041] Synthesis of Compound B

[0042] N 2 Under gas protection, weigh compound A (1.0g, 2.25mmol) an...

Embodiment 2

[0048] Synthesis of compounds of formula Ⅰ-2

[0049]

[0050] Synthesis of Compound D

[0051] N 2 Under gas protection, compound 1 (1.0 g, 4.46 mmol) and compound 3 (2.5 g, 10.63 mmol) were weighed, dissolved in an appropriate amount of ethanol, 15 mL of 10% sodium hydroxide was added, and stirred overnight at room temperature. After the reaction was completed, DCM was extracted, the organic phases were combined, dried over anhydrous Na2SO4, evaporated to dryness, and separated by column chromatography. The developer ratio was PE:EA=8:1, and the product was a bright yellow colloidal solid with a yield of 76.2 %. 1 H NMR (400MHz, CDCl3) δ=8.01(d, J=8Hz, 2H), 7.78(d, J=8Hz, 1H), 7.59(d, J=8Hz, 2H), 7.49(d, J=8Hz, 2H), 7.42(d, J=8Hz, 1H), 4.19(t, J=4Hz, 2H), 3.88(q, J=4Hz, 4H), 3.74-3.72(m, 4H), 3.60-3.58(m ,4H),3.40(s,3H),1.54(s,9H).

[0052] Synthesis of Compound E

[0053] N 2 Under gas protection, compound D (1.55g, 3.51mmol) and nitromethane (2.8mL, 52.3mmol) wer...

Embodiment 3

[0059] All in vivo experiments in the present invention abide by the rules and regulations for the feeding and use of experimental animals. The tumor-bearing mice used in the experiments were purchased from Jiangsu Jicui Yaokang Biotechnology Co., Ltd., and were raised in a sterile mouse cage in a laminar flow fume hood in a sterile room. Autoclaved steam treated water and food were fed.

[0060] Inject aza-BODIPY of formula Ⅰ-2 subcutaneously in the tumor site of tumor-bearing mice, with a dose of 100 nmol at a time, and use laser irradiation after injection (remarks: laser wavelength: 785nm, power density: 1.57Wcm -2 ), while using thermal imaging to monitor the temperature in real time, the body temperature of the tumor site can rise above 70°C after 10 minutes of irradiation (such as Figure 6 Shown), the size of the mouse tumor was recorded every day, and it was found that the administered probe was cured after 10 days without recurrence, while the tumor volume of the mou...

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Abstract

The invention belongs to the field of biochemistry, and relates to a class of aza-BODIPY derivatives with photothermal effect and their synthesis and application. The aza-BODIPY compounds have the general structural formula shown in formula I (see the description for details). The aza-BODIPY compound provided in the present invention has a very good photothermal effect, can convert light energy into heat energy in a very short time, and has excellent stability, can be recycled many times, and is widely used in biochemistry and medicine. It has a considerable application prospect in the field of photothermal therapy.

Description

technical field [0001] The invention belongs to the field of biochemistry, relates to a class of aza-BODIPY derivatives and their synthesis and application, which can realize the photothermal therapy of tumors, specifically, to the synthesis method and biological Thermotherapy application. Background technique [0002] Photothermal therapy (PTT) is one of the tumor treatment methods that have emerged in recent years. Compared with general drug chemotherapy, PTT has inherent advantages such as less invasiveness, simple operation, short treatment time and quick recovery, making PTT an unlimited potential. promising anti-tumor therapy. For a long time, researchers have devoted themselves to the development of new photothermal materials and formulations to meet the increasing demand for photothermal diagnosis and treatment in clinical applications. However, research literature has found that most of the initial photothermal materials are noble metal nanoparticles represented b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06A61K41/00A61K49/00A61P35/00
CPCC07F5/022C09K11/06A61K41/0052A61K49/0021A61P35/00C09K2211/1007C09K2211/1029C09K2211/1051C09K2211/107
Inventor 赵春常徐格王晓
Owner EAST CHINA UNIV OF SCI & TECH
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