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Ultrabright nir-ii aiegen for bioimaging

A technology of aggregation-induced luminescence and compounds, applied in the field of fluorophores

Pending Publication Date: 2021-12-28
THE HONG KONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, it is still challenging to obtain high QY of NIR-II fluorophores using AIE molecular design principles

Method used

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  • Ultrabright nir-ii aiegen for bioimaging
  • Ultrabright nir-ii aiegen for bioimaging
  • Ultrabright nir-ii aiegen for bioimaging

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0134] synthesis

[0135] Compound 2TT-oC6B :

[0136] To synthesize compound 2TT-oC6B, organotin (0.7 g, 1 mmol), dibromo-BBT (87 mg, 0.25 mmol), Pd 2 (dba) 3 (22mg, 0.025mmol), P(o-tol) 3 (66 mg, 0.21 mmol) and degassed dry toluene (1.5 mL) and seal with a Teflon cap. in N 2 Under atmosphere, the reaction mixture was heated to 130 °C and stirred for 48 h. After cooling, the crude product was quenched with KF solution and extracted with DCM. use Na 2 SO 4 The combined organic phases are dried. After removing the solvent, the product was purified with a silica gel column to obtain a dark green solid (yield: 35%). 1 H NMR (400MHz, CDCl 3 ),δ(ppm)=7.59-7.56(4H,m),7.37(2H,s),7.31-7.26(8H,m), 7.16-7.12(8H,m),7.11-7.03(8H,m), 2.61-2.57(4H,t,J=8Hz),1.63,(4H,m),1.15-1.10(12H,m),0.73(6H,m). 13 C NMR (100MHz, CDCl 3 ), δ (ppm): 152.6, 146.9, 146.8, 146.3, 145.0, 128.7, 127.5, 126.1, 124.1, 124.0, 122.7, 122.5, 115.4, 99.3, 30.8, 29.8, 29.6, 28.4, 21.8, 13.3. / z: [M]+C...

Embodiment 2

[0138] Determination of the fluorescence quantum yield (QY) of the dye.

[0139] The QY of the dye was determined (QY = 0.5%) using the NIR-II fluorescent IR-26 dye as a reference. For reference calibration, IR-26 dissolved in 1,2-dichloroethane (DCE) was diluted to form a DCE solution to prepare absorbance values ​​at 808 nm of ~0.1, ~0.08, ~0.06, ~0.04, and ~0.02 for five samples, as these highly diluted samples minimize secondary optical processes such as reabsorption and reluminescence effects. Then, a total of five concentrations of linearly spaced DCE solutions of IR-26 were transferred at once into fluorescent tubes with a path of 10 mm. The excitation source is a diode laser of 808nm. Luminescence was collected in transmission geometry with a 900nm longpass filter to block excitation light, and emission spectra were taken in the 900nm to 1500nm region. DCE and H for ACQ and AIE dyes 2 O solution for the same operation. Then, the entire emission spectrum of both ...

Embodiment 3

[0143] Production of AIE points

[0144] A mixture of 2TT-oC6B (1 mg), DSPE-PEG2000-maleimide (1.5 mg) and THF (1 mL) was sonicated (output 12W, XL2000, Misonix Incorporated, NY) to obtain a clear solution. The mixture was quickly injected into 9 mL of water, and vigorously sonicated in water for 2 min. The mixture was stirred for 12 h in smoked food to remove THF. The AIE point suspension was subjected to ultrafiltration at 3000 g for 30 min (molecular weight cut-off 100 kDa). The amount of 2TT-oC6B aggregates successfully encapsulated into the DSPE-PEG2000-maleimide matrix was estimated by absorbance spectra using the calibration curve of 2TT-oC6B in THF solution as reference.

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Abstract

The present subject matter contemplates small molecule, fluorescent compounds having aggregation-induced emission (AIE) characteristics. The compounds can exhibit emission in the second near-infrared window (NIR-II) (1000 nm-1700 nm). The compounds can provide imaging for deeply located diseases with ultrahigh signal background ratio. For example, neutrophils carrying the present compounds can penetrate the brain and visualize inflammation deeply located within the brain tissue through intact scalp and skull.

Description

technical field [0001] This subject relates to fluorophores for imaging in the second near-infrared window (1000nm to 1700nm), and in particular for imaging deep lesions with ultrahigh signal-to-background ratios. Background technique [0002] Fluorescence imaging with high spatiotemporal resolution and sensitivity provides a powerful tool for direct visualization of dynamic biological processes. Fluorophores emitting in the second near-infrared window (NIR-II, 1000nm to 1700nm) clearly show the significant advantages of deeper tissue penetration, higher spatial resolution and better signal-to-noise ratio (SNR) , which is due to the reduction of light scattering and autofluorescence in tissues at longer wavelengths. Therefore, NIR-II fluorescence imaging offers broad prospects for accurate diagnosis of deep lesions. [0003] While deep lesions such as brain tumors can be visualized using fluorophores emitting in the second near-infrared window (referred to herein as "NIR-I...

Claims

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Application Information

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IPC IPC(8): C07D519/00
CPCA61P35/00C07D513/04C09K11/06C09K11/02C07D487/04G01N21/6458A61K49/0034A61K49/0097A61K49/0021
Inventor 唐本忠刘顺杰丁丹
Owner THE HONG KONG UNIV OF SCI & TECH
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