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Preparation of mitochondria targeting near-infrared fluorescent probe with aggregation-induced emission effect

A technology of aggregation-induced luminescence and fluorescent probes, applied in the field of preparation of mitochondria-targeted near-infrared fluorescent probes, can solve problems such as poor photostability, unfavorable long-distance tracking, and strong photobleaching, and achieve low background interference and good Photostability and photobleaching resistance, the effect of great application value

Active Publication Date: 2020-07-14
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Due to the ACQ effect, traditional small molecule dyes have poor photostability and strong photobleaching, which is not conducive to long-range tracking

Method used

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  • Preparation of mitochondria targeting near-infrared fluorescent probe with aggregation-induced emission effect
  • Preparation of mitochondria targeting near-infrared fluorescent probe with aggregation-induced emission effect
  • Preparation of mitochondria targeting near-infrared fluorescent probe with aggregation-induced emission effect

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of intermediate mCy-Br

[0026] The synthesis method is attached figure 1 shown.

[0027] Specific steps: Take a dry 10 mL two-necked bottle equipped with a magnet, add IR-780 (50 mg, 0.0775 mmol) and 5-bromocatechol (27.0 mg, 0.143 mmol), replace with vacuum-nitrogen three times, Under the condition of nitrogen protection, 2ml of anhydrous DMF and 0.1ml of anhydrous triethylamine were added to the reaction flask, heated to 80°C for 4h, and vacuum-dried to obtain a crude product. The crude product was separated and purified by flash chromatography (dichloromethane:methanol = 20 / 1, v / v) to obtain a blue solid compound (yield about 62.9%). Characterized by NMR and mass spectrometry. 1H NMR (400 MHz, 298 K, CDCl3): δ 8.53 (d, 1H),7.46−7.25 (m, 6H), 7.15(s, 1H), 6.26 (d, 1H), 4.22 (t, 2H), 2.73 (t, 2H),2.67 (t, 2H), 1.96−1.91 (m, 4H), 1.25 (s, 6H), 1.09 (t, 3H). 13C NMR (400MHz, 298 K, CD3OD): δ 177.3 , 162.6, 154.5, 141.6, 144.0, 133.4, 128.9, 127.1,126.6, 1...

Embodiment 2

[0029] Probe Synthesis

[0030] The synthesis method is attached figure 1 shown.

[0031] Specific steps: Add intermediate 1 (30 mg, 0.048 mmol), 4-(1,2,2-tristyryl)-phenylboronic acid pinacol ester (40 mg, 0.087 mmol), K2CO3 (0.338 g, 2.45 mmol), vacuum-nitrogen replacement 3 times, added under nitrogen protection, added 4ml THF, Pd(PPh3)4 (5 mg, 0.004 mmol), 1ml H2O, heated to reflux, added dichloromethane to extract after 24 hours 4 times, the organic phases were combined and concentrated to obtain the crude product. The crude product was separated and purified by flash chromatography (dichloromethane:methanol = 20 / 1, v / v) to obtain a blue solid compound (yield about 24%). Characterized by NMR and mass spectrometry. 1H NMR (400 MHz, 298 K, CDCl3): δ8.58 (d, 1H), 7.52 (s, 1H), 7.37(d, 2H), 7.26 (s, 1H), 7.16−7.06 (m,22H) , 6.96(s, 1H), 6.08 (d, 1H), 4.06 (t, 2H), 2.60-2.63 (t, 2H), 1.89−1.91 (m, 4H), 1.29 (s, 6H), 1.07 (t , 3H). 13C NMR (400 MHz, 298 K, CDCL3): Δ 175.7...

Embodiment 3

[0033] Prepare probe 10μM 70% PBS / THF solutions with different pH values, measure on a visible-ultraviolet spectrophotometer, the results are as attached figure 2 .

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Abstract

The invention discloses preparation of a mitochondria targeting near-infrared fluorescent probe with an aggregation-induced emission effect. The fluorescent probe is composed of a hemicyanine part with near-infrared excitation and emission and a TPE part with aggregation-induced emission molecules. The probe has weak near-infrared fluorescence in a benign solvent, the fluorescence is gradually enhanced along with the addition of poor solvent water, and an obvious AIE effect is displayed; and along with the increase of the pH value, the fluorescence is also gradually enhanced, and the strong pHdependence is shown. The probe is simple to prepare, has good light stability and biocompatibility, is excited and emitted in a near-infrared region, has small biological light damage and small background interference, and opens up a new thought for development and application of near-infrared fluorescent probes with aggregation-induced emission.

Description

technical field [0001] The invention belongs to the technical field of fluorescent biosensors, and in particular relates to the preparation of a type of mitochondria-targeted near-infrared fluorescent probe with an aggregation-induced luminescence effect. Background technique [0002] Mitochondria is the site of cellular oxidative phosphorylation, has its own genetic material and genetic system, and is a semi-autonomous organelle. In addition to providing energy for cells, it also participates in life processes such as cell differentiation, cell information transmission, and cell apoptosis, and has the ability to regulate cell growth. Changes in mitochondrial morphology and pH are associated with certain diseases, such as Parkinson's disease, Alzheimer's disease and cancer. Therefore, the visualization of mitochondria is crucial to the study of mitochondria and the diagnosis of diseases. [0003] Bio-optical imaging is widely used in medical and biological research due to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06C09K11/06G01N21/64
CPCC09K11/06C07D405/06G01N21/6428G01N21/6456C09K2211/1029C09K2211/1088
Inventor 孟萌赵秀杰郗日沫陈韵王建宁曹彦梅
Owner NANKAI UNIV
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