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Hypochlorous acid trigger activation type near-infrared fluorescent probe as well as preparation method and application thereof

A fluorescent probe, near-infrared technology, applied in the field of fluorescent materials

Pending Publication Date: 2022-07-05
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although near-infrared (NIR; 700–1700 nm) fluorescence imaging has been widely used for high-contrast imaging in complex tissue environments, HOCl-responsive NIR fluorescent probes with high activation magnifications are rarely reported.

Method used

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  • Hypochlorous acid trigger activation type near-infrared fluorescent probe as well as preparation method and application thereof
  • Hypochlorous acid trigger activation type near-infrared fluorescent probe as well as preparation method and application thereof
  • Hypochlorous acid trigger activation type near-infrared fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Fc 2 -The synthetic route of CBDP is as follows:

[0062]

[0063] The specific process is as follows:

[0064] (1) Synthesis of compound A1: N-ethylcarbazole-3-carbaldehyde (3.55 g, 15.0 mmol), 3-acetyl-9-ethylcarbazole (3.30 g, 15.0 mmol), potassium hydroxide ( 2.52 g, 45 mmol) was dissolved in 100 mL of ethanol by ultrasonic, reacted at 60° C. overnight, then filtered with suction and washed twice with cold ethanol to obtain a yellow solid product A1 with a yield of 62%. 1 H NMR (400MHz, DMSO-d 6 ,δ,ppm)δ=9.18(s,1H),8.78(s,1H),8.40(d,J=7.8,1H),8.32(d,J=8.7,1H),8.28–8.19(m,2H ),8.07(d,J=8.6,1H),8.00(d,J=15.4,1H),7.76(d,J=8.7,1H),7.71(dd,J=8.2,6.2,2H),7.66( d, J=8.4, 1H), 7.57–7.46 (m, 2H), 7.30 (dt, J=14.9, 7.5, 2H), 4.50 (m, J=15.1, 7.5, 4H), 1.35 (m, J= 12.6, 6.9, 6H). 13 C NMR (101MHz, DMF-d 6 ,δ,ppm)δ=188.42,145.12,142.87,141.62,141.00,140.80, 130.14,127.65,127.17,127.14,126.98,126.71,125.11,123.40,122.97,122.92,122.76, 122.50,121.62,121.36,120.47,120.17...

Embodiment 2

[0068] Example 2: Fc 2 The synthetic route of -OBDP is as follows:

[0069]

[0070] The specific process is as follows:

[0071] (1) Synthesis of compound B1: N-ethylcarbazole-3-carbaldehyde (2.2 g, 10.0 mmol), p-methoxyacetophenone (1.5 g, 10.0 mmol), potassium hydroxide (1.68 g, 30 mmol) ) was dissolved in 100 mL of ethanol by ultrasound, reacted overnight at 60° C., then suction filtered and washed twice with cold ethanol to obtain a yellow solid product B1 with a yield of 73%. 1 H NMR (400MHz, DMSO-d 6 ,δ,ppm)δ=8.73(s,1H),8.21(m,J=8.9,3H),7.97(dd,J=22.7,9.6,4H),7.68(d,J=8.6,1H),7.64 (d, J=8.2, 1H), 7.49 (t, J=8.1, 1H), 7.26 (t, J=7.4, 1H), 7.10 (d, J=8.9, 2H), 4.47 (q, J=7.0 , 2H), 3.87(s, 3H), 1.32(t, J=7.1, 3H). 13 C NMR (101MHz, DMSO-d 6 ,δ,ppm)δ=187.87,163.68,145.56,141.66,140.78,131.61, 131.42,127.63,126.97,126.49,123.37,122.96,122.57,121.31,120.17,119.35,114.64, 110.25,110.21,56.22,37.87,14.44 .MALDI-TOF-MS(m / z):calc.for[C 24 H 21 NO 2 Na] + , 378.4188...

Embodiment 3

[0076] First verify Fc 2 - Photostability of CBDP probes. like Figure 15 shown at 730nm laser (180mW / cm 2 ) irradiated for 3000s and found that the fluorescence intensity did not change significantly, while the fluorescence of ICG decreased significantly, indicating that Fc 2 -CBDP probe has good photostability.

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Abstract

The invention belongs to the technical field of fluorescent materials, and particularly relates to a hypochlorous acid activated near-infrared fluorescent probe as well as a preparation method and application thereof. The invention adopts a new strategy to construct a high-proportion fluorescence-enhanced near-infrared organic small molecule fluorescent probe with hypochlorous acid response. The fluorescent probe comprises a luminous core based on a boron dipyrromethene near-infrared fluorescent dye with excellent light stability and chemical stability; ferrocene is introduced into the fluorescent dye as a quenching element to obtain a series of probes. The fluorescence change condition of the series of probes under the action of hypochlorous acid is studied, and the near-infrared fluorescent dye with high activation rate and long emission wavelength is obtained. The Fc2-BDP series fluorescent probe obtained by the invention has good fluorescent response performance, relatively low detection limit and excellent stability, and can be used for high-sensitivity imaging of inflammations such as lymphatis and enteritis.

Description

technical field [0001] The invention belongs to the technical field of fluorescent materials, and in particular relates to a near-infrared fluorescent probe and a preparation method and application thereof. Background technique [0002] Reactive oxygen species / reactive nitrogen species (ROS / RNS, such as O 2 - , H 2 O 2 , OH, HOCl, ONOO - ) substances are highly active molecules produced during biological oxygen metabolism. Among them, hypochlorous acid (HOCl) is an important bactericidal oxidant, which is produced by the peroxidation of chloride ions in the phagosome catalyzed by myeloperoxidase (MPO). Causes mitochondrial permeability, lysosomal rupture and cell death, and is closely related to a variety of diseases such as atherosclerosis, cancer, inflammation and neurodegenerative diseases. Therefore, specific and highly sensitive detection of HOCl, especially in vivo, is of great significance for HOCl-related disease diagnosis and mechanism research. [0003] Alth...

Claims

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Application Information

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IPC IPC(8): C07F17/02C09K11/06G01N21/64
CPCC07F17/02C09K11/06G01N21/6402G01N21/6428G01N21/6456C09K2211/187G01N2021/6432G01N2021/6439
Inventor 张凡姚陈志殷东瑞
Owner FUDAN UNIV
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