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Corannulene-incorporated AIE nanodots with highly suppressed nonradiative decay for boosted cancer phototheranostics in vivo

A technology of sulfene, a therapeutic agent, applied to AIE nanodots wrapped with sulfene with high non-radiative attenuation inhibition for enhancing the field of in vivo cancer photodiagnosis, which can solve the problems of undisclosed and optimized fluorescence and ROS generation capacity of AIE spots.

Active Publication Date: 2020-10-02
THE HONG KONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, previous studies did not reveal how to control and optimize the fluorescence and ROS generation capabilities of AIE dots

Method used

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  • Corannulene-incorporated AIE nanodots with highly suppressed nonradiative decay for boosted cancer phototheranostics in vivo
  • Corannulene-incorporated AIE nanodots with highly suppressed nonradiative decay for boosted cancer phototheranostics in vivo
  • Corannulene-incorporated AIE nanodots with highly suppressed nonradiative decay for boosted cancer phototheranostics in vivo

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0126] Synthesis of compound 2

[0127] Compound 2: At -78 ℃, TiCl 4 (1mL, 9.0mmol) was slowly added to a suspension of Zn powder (1.17g, 18.0mmol) in anhydrous THF (50mL). After refluxing for 2 h, a mixture of compound 1 (2.325 g, 4.5 mmol) and 4-methoxyphenyl-4-pyridyl ketone (0.640 g, 3 mmol) in anhydrous THF (20 mL) was added to the reaction. The mixture continued to reflux for 5 hours. After removing the solvent under reduced pressure, the residue was extracted with DCM and washed with anhydrous Na 2 SO 4 dry. The crude product was purified by silica gel column chromatography using DCM as eluent. Compound 2 is a yellow solid with a yield of 70%. 1 H NMR (400MHz, CD 2 Cl 2 ,δ): 8.33 (d, 2H, J = 0.011), 7.27-7.22 (m, 8H), 7.05-7.03 (m, 9H), 7.02-7.01 (m, 2H), 7.00-6.99 (m, 1H) , 6.97 (d, 2H, J = 0.013), 6.95 (d, 2H, J = 0.011), 6.93 (d, 2H, J = 0.004), 6.92 (d, 2H, J = 0.007), 6.82 (d, 2H ,0.004), 6.79(d,2H,0.005), 6.71(d,2H,J=0.021), 3.77(s,3H); 13 C NMR(100MHz, CD 2 Cl ...

Embodiment 2

[0129] Synthesis of TPP-TPA

[0130] Compound 2 (0.174g, 0.25mmol) was dissolved in 20mL of toluene, and then 0.1mL of CH was added 3 I (excess) to form a mixture. The reaction mixture was refluxed overnight. After cooling to room temperature, the precipitate was filtered and washed three times with cold toluene. The obtained solid was dissolved in 20 mL of acetone and 100 mg of KPF was added 6 Perform ion exchange for 2h. The solvent was removed and the solid was washed with water. The pure yellow product TPP-TPA was obtained by recrystallization in a DCM / n-hexane mixture (volume ratio 1:5) with a yield of 99%. 1 H NMR (400MHz, CD 2 Cl 2 ,δ): 8.11 (d, 2H, J = 0.016), 7.45 (d, 2H, J = 0.016), 7.33-7.30 (m, 4H), 7.28-7.24 (m, 4H), 7.13-7.08 (m, 7H), 7.07-7.04(m,5H), 6.98-6.93(m,4H), 6.90-6.85(m,4H), 6.80-6.75(m,4H), 4.20(s,3H), 3.79(s, 3H); 13 C NMR(100MHz, CD 2 Cl 2 ,δ): 162.95,159.34,151.19,148.96,148.05,147.03,146.84,142.76,134.81,133.82,133.40,132.92,132.75,132.60,129.64,...

Embodiment 3

[0132] Preparation and characterization of Cor-AIE points and DSPE-AIE points

[0133] Cor-PEG or DSPE-PEG (1 mg) powder and TPP-TPA (0.2 mg) were completely dissolved in THF (1 mL). After that, the THF solution was slowly added to 9 mL Milli-Q water (18.2MU) under continuous ultrasound (125W). The mixed solution was further sonicated for 1 minute, then at room temperature in N 2 While stirring, THF was removed by evaporation.

[0134] Finally, a clear solution is obtained for use.

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Abstract

The present subject matter relates to fluorescent compounds that have aggregation-induced emission (AIE) characteristics and exhibit near infrared absorption. Compositions including the present compounds can include a corannulene-modified polyethylene glycol encapsulation matrix. The compositions can be in nanoparticle form. Encapsulating the AIE compounds within a corannulene matrix provides intraparticle rigidity and restricts intramolecular rotation of the encapsulated AIE compound, which results in enhanced fluorescence and ROS generation capacity of the compositions in vivo. Accordingly,the compositions can be useful in NIR imaging-guided cancer surgery and photodynamic cancer therapy.

Description

[0001] Related application [0002] This application claims the priority of the US provisional patent application No. 62 / 710,470 filed on February 21, 2018, which was filed by the inventor of this patent application, which is hereby incorporated by reference in its entirety. Technical field [0003] The subject of the present invention mainly relates to a series of compounds with aggregation-induced luminescence properties and near-infrared absorption and their applications in bioimaging and photodiagnosis and treatment. Background technique [0004] Optical reagents used for cancer photodiagnosis and treatment can perform real-time molecular diagnosis and synchronized light-triggered therapy. Among various photo-diagnostic agents, fluorescent nanoparticles (NPs) have high sensitivity and time resolution of fluorescence imaging, on-demand and in-situ labeling of photodynamic therapy (PDT), and unique high permeability and retention (EPR). ) Effect. In order to meet the needs of id...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06
CPCC09K11/06G01N33/533G01N33/574G01N33/54346A61K49/0023A61K49/0021A61K41/0057
Inventor 唐本忠顾星桂
Owner THE HONG KONG UNIV OF SCI & TECH
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