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A-D-A type condensed ring conjugated organic small molecule photosensitizer and application thereof

A photosensitizer and small molecule technology, applied in the field of biomedicine, can solve the problems of high toxicity of cyano groups, etc., and achieve the effects of high-efficiency photothermal therapy, good biological safety and biocompatibility

Pending Publication Date: 2022-04-29
NANTONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The molecular structure of this type of photosensitizer is composed of an electron-donating group in the middle and an electron-pull group at both ends. Through pushing and pulling electrons, a stronger light absorption ability can be obtained. At present, most of the electron-pull end groups are cyanoindanone molecules ( Lu, B.; Zhang, Z.; Wang, J.; Cai, G.; Wang, J.; Yuan, X.; Ding, Y.; Wang Y.; Yao, Y. Mater. 2021,5,5549), in which the dicyano group plays the main role in pulling electrons, but the cyano group is more toxic, so the structure of the traditional terminal molecule containing the dicyano group is optimized, and a A new type of A-D-A fused ring conjugated organic small molecule photosensitizer with better biological safety is very meaningful

Method used

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  • A-D-A type condensed ring conjugated organic small molecule photosensitizer and application thereof
  • A-D-A type condensed ring conjugated organic small molecule photosensitizer and application thereof
  • A-D-A type condensed ring conjugated organic small molecule photosensitizer and application thereof

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Experimental program
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Effect test

Embodiment 1

[0022] Novel A-D-A type fused ring conjugated organic small molecule photosensitizer F8CA among the present invention, its structural formula is as shown in the following formula:

[0023]

[0024] Its synthetic route, as shown in the following formula:

[0025]

[0026] Under the protection of nitrogen, F8-CHO (114mg, 0.10mmol), CA (145mg, 0.60mmol) were dissolved in an appropriate amount of chloroform, and pyridine (0.5mL) was added, and the mixture was reacted at 65°C for 20 hours. After the reaction, the solution was After adding a large amount of methanol, the crude product was obtained by filtration, and the crude product was further purified by column chromatography to obtain the compound F8CA.

[0027] Dissolve the product in CD 2 Cl 2 Medium (about 0.4mL), seal the tube, measure and characterize on Unity Inova-400 NMR instrument: 8.78(m,2H),8.17-8.03(m,4H),7.90-7.82(m,2H),7.77- 7.63(m,4H),7.24-7.12(m,16H),4.47-4.37(m,4H),2.60-2.54(m,8H),1.58(m,12H),1.40(m,6H)...

Embodiment 2

[0029] Preparation and Characterization of Nanomedicines

[0030] DSPE-PEG2000 (6 mg) and photosensitizer F8CA (1.2 mg) were dissolved in 1 mL of THF, and the THF solution was dropped into rapidly stirring 10 mL of deionized water at a rate of 4 mL / h using a syringe pump, and stirred for 2 hours. The mixed solution was dialyzed using a 10,000 molecular weight dialysis bag to obtain a blue clear nanomedicine aqueous solution.

[0031] Characterization of nanomedicine self-assembly morphology by SEM ( figure 1 shown).

[0032] (1) Photothermal heating curve:

[0033] Using 660nm, 1.0W / cm 2 The laser was irradiated, and the heating curves of five different concentrations of F8CA NPs of 0 μg / mL, 50 μg / mL, 100 μg / mL, 200 μg / mL and 300 μg / mL were drawn.

[0034] Such as figure 2 As shown, the heating rate of the F8CA NPs aqueous solution increased with the increase of the concentration, and the temperature increased by more than 40°C at the maximum concentration, which was suf...

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Abstract

The invention discloses an ADA type condensed ring conjugated organic small molecule photosensitizer and application thereof, and belongs to the technical field of biological medicine. The novel ADA type condensed ring conjugated organic small molecule photosensitizer F8CA designed and synthesized by the invention has better biological safety and biocompatibility, a nano-drug prepared based on the photosensitizer is low in toxicity and efficient, and efficient photothermal therapy and photodynamic therapy of two mechanisms of tumors can be realized.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and specifically relates to an A-D-A type fused ring conjugated organic small molecule photosensitizer and application thereof. Background technique [0002] In recent years, A-D-A type fused ring conjugated organic small molecule photosensitizers have received extensive attention due to their advantages of easy synthesis, variable structure, and strong photoresponsiveness. Since 2019, Han et al. Since photothermal therapy of tumors (Cai, Y.; Wei, Z.; Song, C.; Tang, C.; Huang, X.; Hu, Q.; Dong, X.; Han, W. Chem. Commun.2019 ,55,8967), this type of molecule has gradually received more and more attention in the field of tumor phototherapy. This type of molecule not only has a high photothermal conversion efficiency, but also can produce 1 o 2 and OH two highly active oxygen species (He, Z.; Zhao, L.; Zhang, Q.; Chang, M.; Li, C.; Zhang, H.; Lu, Y.; Chen, Y. Adv. .Funct.Mater.2020,30.1910301...

Claims

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Application Information

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IPC IPC(8): A61K41/00A61K9/51A61K47/24A61P35/00
CPCA61K41/0057A61K9/5146A61K41/0052A61P35/00A61K2300/00
Inventor 卢冰张哲成
Owner NANTONG UNIVERSITY
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