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Perylene diimide derivative, hollow nanocapsule PDI-R-4b@SNC as well as preparation method and application of hollow nanocapsule PDI-R-4b@SNC

A perylene diimide and PDI-R technology, applied in the field of photodiagnosis and treatment, can solve the problems of few types and low photothermal conversion efficiency

Inactive Publication Date: 2021-09-14
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the inventors found that there are fewer types of peryleneimide (PDI) derivatives as photothermal therapy (PTT) and the photothermal conversion efficiency is not high.

Method used

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  • Perylene diimide derivative, hollow nanocapsule PDI-R-4b@SNC as well as preparation method and application of hollow nanocapsule PDI-R-4b@SNC
  • Perylene diimide derivative, hollow nanocapsule PDI-R-4b@SNC as well as preparation method and application of hollow nanocapsule PDI-R-4b@SNC
  • Perylene diimide derivative, hollow nanocapsule PDI-R-4b@SNC as well as preparation method and application of hollow nanocapsule PDI-R-4b@SNC

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Preparation of perylene diimide derivative PDI-R-4b:

[0049] Synthesis of N,N′-bis((R)-(+)-1-phenethylamino)-1,7-dibromo-3,4,9,10-perylenediimide (PDI-R):

[0050] Dissolve 1,7-dibromo-3,4,9,10-perylenediimide (1 g, 1.82 mmol) and (R)-(+)-1-phenylethylamine (2.2 g, 18.2 mmol) in 50mL of isopropanol was reacted at 82°C for 18h under nitrogen protection. After cooling, the isopropanol was distilled off under reduced pressure. The obtained solid was purified by silica gel column chromatography (dichloromethane:n-hexane=2:1) ​​to obtain pure dark red solid PDI-R with a yield of 46.03%. The specific data of the NMR spectrum of the prepared PDI-R are: 1 H NMR (300MHz, CDCl 3 ,δ):9.45(d,2H),8.89(s,2H),8.65(d,2H),7.50(d,4H),7.36-7.23(m,6H),6.50(m,2H),2.00( d,6H).

[0051] Synthesis of N,N′-bis((R)-(+)-1-phenethylamino)-1,7-dicyclohexylamino-3,4,9,10-perylenediimide (PDI- R-4b):

[0052] PDI-R (300 mg, 0.4 mmol) was dissolved in 15 mL of cyclohexylamine, and the mixture ...

Embodiment 2

[0057] Preparation of perylene diimide derivative PDI-R-4b:

[0058] Synthesis of N,N′-bis((R)-(+)-1-phenethylamino)-1,7-dibromo-3,4,9,10-perylenediimide (PDI-R):

[0059] 1,7-dibromo-3,4,9,10-perylenediimide (0.6g, 1.09mmol) and (R)-(+)-1-phenylethylamine (1.32g, 10.92mmol) were dissolved React in 50 mL of isopropanol at 82°C for 18 h under nitrogen protection, and distill off isopropanol under reduced pressure after cooling. The obtained solid was purified by silica gel column chromatography (dichloromethane:n-hexane=2:1) ​​to obtain pure dark red solid PDI-R with a yield of 52.26%.

[0060] Synthesis of N,N′-bis((R)-(+)-1-phenethylamino)-1,7-dicyclohexylamino-3,4,9,10-perylenediimide (PDI- R-4b):

[0061] PDI-R (150 mg, 0.2 mmol) was dissolved in 15 mL of cyclohexylamine, and the mixture was reacted at 110° C. for 12 h under nitrogen protection. After cooling to room temperature, cyclohexylamine was distilled off under reduced pressure. The obtained solid was purified ...

Embodiment 3

[0063] Preparation of PDI-R-4b@SNC

[0064] Preparation of hollow nanocapsules PDI-R-4b@SNC of polymer and silica-wrapped PDI-R-4b:

[0065] Prepare four small vials, weigh F127 (75mg), then add THF (1mL), ultrasonically dissolve for 5 minutes to obtain a clear and transparent solution, then weigh 5mg of PDI-R-4b and add them to each vial, ultrasonically dissolve, and cap tightly Cover to ensure that the solvent does not evaporate, and stir at 200rpm for 3h; then add TMOS (52μL) and TMVS (13μL) to THF, sonicate, and let stand for use. Then prepare a 20mL vial, weigh 10g of deionized water, and slowly inject 1mL of the organic phase into the deionized water with a syringe under high-speed stirring at 1100rpm, leave it open to allow the organic solvent to volatilize naturally, and stir at 990rpm for 4 days; after the reaction The solution was dialyzed with a dialysis membrane to remove unreacted F127, washed with water for 1 day, and changed water 2-3 times; finally, the obtain...

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Abstract

The invention relates to the technical field of light diagnosis and treatment, in particular to a perylene diimide derivative and a preparation method and application thereof. The structure of the perylene diimide derivative is shown as a formula I. The novel perylene diimide derivative PDI-R-4b successfully prolongs the absorption wavelength of perylene diimide to 697 nm, and an aggregate of the perylene diimide derivative PDI-R-4b has strong absorption and excellent photo-thermal performance in a first near-infrared biological window (650-950 nm), has high photo-thermal conversion efficiency as high as 59.4%, shows extremely strong anti-tumor capability in an in-vitro tumor experiment; the anti-tumor activity of the PDI-R-4b@SNC on breast tumor cells and the biotoxicity of the PDI-R-4b@SNC are low, and the PDI-R-4b@SNC is basically harmless to the cells under a dark condition; compared with an existing photo-thermal preparation, under the same anti-tumor effect, the dosage of the PDI-R-4b@SNC is greatly reduced; and the PDI-R-4b@SNC with low dosage and low toxicity provides a novel photo-thermal preparation for developing an effective cancer treatment method with high curative effect and low side effect.

Description

technical field [0001] The invention relates to the technical field of photodiagnosis and treatment, in particular to a perylene diimide derivative, a hollow nanocapsule PDI-R-4b@SNC and a preparation method and application thereof. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Photothermal therapy (PTT) is considered to be a major breakthrough in tumor treatment due to its non-invasiveness, high efficiency and precise controlled release of encapsulated drugs. Photodiagnosis and therapy techniques including PTT can not only effectively destroy tumor cells, but also trigger an immune response by disrupting tumor-associated antigens of cancer cells, thereby effectively in...

Claims

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Application Information

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IPC IPC(8): C07D471/06A61K41/00A61K9/50A61K47/10A61K47/04A61P35/00
CPCC07D471/06A61K41/0052A61K9/5031A61K9/501A61P35/00
Inventor 孙绚赵悦安富豪
Owner SHANDONG UNIV
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