Near-infrared IIb fluorescent probe, nano particle and preparation method and application thereof

A technology of fluorescent probes and nanoparticles, applied in the field of bio-optical diagnosis and treatment, can solve the problems of long-term biological toxicity limiting clinical practical application, and achieve the effects of low toxicity, good repeatability, and high fluorescence brightness

Pending Publication Date: 2022-06-07
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Despite their high fluorescence brightness, their potential long-term biotoxicity issues greatly limit their practical clinical applications

Method used

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  • Near-infrared IIb fluorescent probe, nano particle and preparation method and application thereof
  • Near-infrared IIb fluorescent probe, nano particle and preparation method and application thereof
  • Near-infrared IIb fluorescent probe, nano particle and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A NIR-IIb fluorescent probe based on diketopyrrolopyrrole (DPP) conjugated polymer, wherein the conjugated polymer DT-H has the following structure:

[0033]

[0034] The synthesis steps of the above-mentioned conjugated polymer DT-H include: 2,5-bis(2-octyldodecyl)-3,6-bis(5-(trimethyltin)thiophene-2-yl) -2,5-Dihydropyrrolo[3,4-c]pyrrole-1,4-dione (0.05 g, 0.042 mmol), 4,7-bis(5-bromothiophen-2-yl)benzo[ c][1,2,5]thiadiazole (0.0193 g, 0.042 mmol), Pd (PPh 3 ) 4 (5 mg, 0.0042 mmol) and 10 mL of toluene in N 2 It was added to a 50 mL preset reaction tube under the atmosphere, and the mixture was refluxed for 7 h. After cooling to room temperature, the reaction solution was added dropwise to 200 mL methanol solution, and the mixture was collected by filtration under reduced pressure to obtain the final product DT-H (the yield was 58%). ), and its H NMR spectrum is shown in figure 1 As shown, the peak between 6.5-8.0 in the figure is the hydrogen on the aromatic ri...

Embodiment 2

[0041] A NIR-IIb fluorescent probe based on diketopyrrolopyrrole (DPP) conjugated polymer, wherein the conjugated polymer DT-NO 2 Has the following structure:

[0042]

[0043] The above conjugated polymer DT-NO 2 The synthesis steps include: 2,5-bis(2-octyldodecyl)-3,6-bis(5-(trimethyltin)thiophen-2-yl)-2,5-dihydropyrrole Do[3,4-c]pyrrole-1,4-dione (0.1 g, 0.084 mmol), 4,7-bis(5-bromothiophen-2-yl)-5,6-dinitrobenzo[ c][1,2,5]thiadiazole (0.04 g, 0.084 mmol), Pd (PPh 3 ) 4 (10 mg, 0.0084 mmol) and 10 mL of toluene in N 2 It was added to a 50 mL preset reaction tube under the atmosphere, and the mixture was refluxed for 7 hours. After cooling to room temperature, the reaction solution was added dropwise to 200 mL methanol solution, and the mixture was collected by filtration under reduced pressure to obtain the final product DT-NO. 2 (the yield is 60%), and its hydrogen nuclear magnetic resonance spectrum is as follows Figure 5 As shown, the peak between 6.5-8.0 in the ...

Embodiment 3

[0051] A NIR-IIb fluorescent probe based on diketopyrrolopyrrole (DPP) conjugated polymer, wherein the conjugated polymer DT-F has the following structure:

[0052]

[0053] The synthesis steps of the above-mentioned conjugated polymer DT-F include: 2,5-bis(2-octyldodecyl)-3,6-bis(5-(trimethyltin)thiophene-2-yl) -2,5-Dihydropyrrolo[3,4-c]pyrrole-1,4-dione (0.1 g, 0.084 mmol), 4,7-bis(5-bromothienyl-2-)-5, 6-Difluoro-2,1,3-benzothiadiazole (0.04 g, 0.084 mmol), Pd (PPh 3 ) 4 (10 mg, 0.0084 mmol) and 10 mL of toluene in N 2 It was added into a 50 mL preset reaction tube under the atmosphere, and the mixture was refluxed for 7 h. After cooling to room temperature, the reaction solution was added dropwise to 200 mL methanol solution, and the mixture was collected by filtration under reduced pressure to obtain the final product DT-F (the yield was 52%). ), its synthetic route is as follows:

[0054]

[0055] This embodiment provides a nanoparticle of the above-mentioned n...

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Abstract

The invention discloses a near-infrared IIb fluorescent probe which is based on a DPP (diketopyrrolopyrrole) conjugated polymer DT-R. The invention further discloses a preparation method of the fluorescent probe and nanoparticles of the fluorescent probe. The maximum emission peak of the prepared nanoparticles is located in the range of a near-infrared second region (NIR-II), and the longest emission wavelength of the prepared nanoparticles can extend to a near-infrared IIb region (NIR-IIb). The nanoparticle provided by the invention can realize NIR-IIb mouse blood vessel imaging under 808nm laser excitation, has high imaging resolution and signal-to-noise ratio, and has wide application prospects in the aspects of blood vessel monitoring, repairing and the like.

Description

technical field [0001] The invention belongs to the field of bio-optical diagnosis and treatment, and more particularly relates to a near-infrared IIb fluorescent probe, a nanoparticle and a preparation method and application thereof. Background technique [0002] Fluorescence imaging (FLI) has unique advantages over various conventional imaging modalities, such as positron emission tomography (PET), X-ray computed tomography (CT), and magnetic resonance imaging (NMRI), including high spatial and temporal resolution High-speed and real-time rapid detection is becoming one of the mainstream imaging modalities in recent years. To date, FLI has mature or preliminary applications in high-resolution vascular imaging, gastrointestinal imaging, and imaging-guided clinical tumor resection. In recent years, the emission wavelength located at 900-1700 nm, that is, the second near-infrared (NIR-II), has attracted extensive and in-depth research by researchers at home and abroad. Comp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C08G61/12A61K49/00
CPCC09K11/06C08G61/126A61K49/0019C09K2211/1458C09K2211/1466C09K2211/1483C08G2261/124C08G2261/1412C08G2261/3223C08G2261/3246C08G2261/522Y02E10/549
Inventor 王其刘加伟范曲立陆峰
Owner NANJING UNIV OF POSTS & TELECOMM
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