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Near infrared fluorescent dye THX-Ba for mitochondrial localization and preparation method and application thereof

A technology of fluorescent dyes and mitochondria, which is applied in the field of dye molecular fluorescent probes, can solve the problems of small Stokes shift and low anti-interference ability, and achieve simple preparation methods, good photostability, and good cell membrane permeability Effect

Inactive Publication Date: 2018-11-16
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the Stokes shift of this kind of dye is small (<50nm), and the anti-interference ability is small

Method used

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  • Near infrared fluorescent dye THX-Ba for mitochondrial localization and preparation method and application thereof
  • Near infrared fluorescent dye THX-Ba for mitochondrial localization and preparation method and application thereof
  • Near infrared fluorescent dye THX-Ba for mitochondrial localization and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Preparation of Compound 1

[0050] Add 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid (5.0g, 16mmol) to 35mL of 98wt% concentrated sulfuric acid containing 3.3mL (31.8mmol) cyclohexanone at 0°C, The reaction was stirred, TLC followed the reaction to the end point, about 1.5h, the reaction solution was cooled to room temperature and poured into 150mL of ice water, 3.5mL of 70wt% perchloric acid was added dropwise, filtered and washed with 100mL of ice water, and the solid was dried to obtain compound 1.

[0051] The synthetic route is as follows:

[0052]

Embodiment 2

[0054] Preparation of fluorescent dye THX-Ba

[0055] Compound 1 (3.76g, 10mmol) prepared in Example 1 and terephthalaldehyde (1.72g, 10mmol) were dissolved in 50ml of glacial acetic acid, stirred at 95°C for reaction, followed by TLC to the end of the reaction, about 1h, and removed by rotary distillation Glacial acetic acid, the solid was separated and purified by dichloromethane / methanol (v / v 20:1) column chromatography to obtain the target product as a purple solid (2.23 g, yield: 45%). 1 HNMR(400MHz,DMSO)δ10.02(s,1H),7.95(d,J=8.1Hz,3H),7.80(t,J=7.8Hz,1H),7.68(t,J=7.5Hz,3H) ,7.47(s,1H),7.33(d,J=7.7Hz,1H),6.55(d,J=2.2Hz,1H),6.43(dt,J=21.1,5.6Hz,2H),3.39–3.33( m,4H),2.79(d,J=15.5Hz,1H),2.65(d,J=14.5Hz,1H),1.93–1.83(m,1H),1.58(d,J=11.1Hz,3H), 1.10(t,J=6.9Hz,6H). 13 C NMR(125MHz,DMSO)δ193.03,169.48,152.02,149.52,146.33,143.19,135.81,135.05,133.07,130.46,129.92,128.66,127.08,125.09,124.45,124.06,109.70,109.48,104.48,97.31,85.98,44.16 ,27.21,23.05,22.36,12.86.MS(ESI):m / z:[M]...

Embodiment 3

[0059] Preparation of hypochlorous acid fluorescent probe

[0060] The near-infrared fluorescent dye (0.98g, 2.0mmol) prepared in Example 1 and diaminomaleonitrile (0.22g, 2.0mmol) were dissolved in 50mL of methanol, then a drop of 98wt% concentrated sulfuric acid (about 0.04mmol) was added, and the The reaction was stirred, TLC tracked the reaction to the end point, about 2h, the color of the solution changed from black purple to light brown, and the methanol was removed by rotary evaporation, and the solid was separated and purified by dichloromethane / methanol (v / v 20:1) column chromatography to obtain the target product As a brown solid (0.79 g, yield: 68%). 1 H NMR (400MHz, DMSO) δ8.29 (s, 1H), 8.08 (d, J = 7.8Hz, 2H), 8.04–7.90 (m, 3H), 7.80 (t, J = 7.2Hz, 1H), 7.68 (t,J=7.3Hz,1H),7.55(d,J=7.8Hz,2H),7.45(s,1H),7.33(d,J=7.4Hz,1H),6.56(s,1H),6.43 (dd,J=22.9,8.4Hz,2H),3.35(s,4H),2.81(d,J=14.5Hz,1H),2.68(s,1H),1.89(d,J=12.5Hz,1H) ,1.58(d,J=11.6Hz,3H),1.10(t,J=6.5Hz,6H). 1...

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Abstract

The invention relates to a near infrared fluorescent dye THX-Ba for mitochondrial localization and a preparation method and an application thereof. The dye has the structural formula (I) and has stable pH fluorescence opening effect in water phases under different pH conditions, and prepared diaminomaleonitrile condensation derivatives can be used for hypochloric acid detection. The fluorescent dye has the following advantages: the fluorescent dye has the properties of stability to pH, large Stokes displacement (116 nm), good light stability, good water solubility, good cell membrane permeability and excellent mitochondrial localization performance, aldehyde and carboxyl groups of the fluorescent dye can be easily modified to generate biologically related tracers, and derivatives obtainedafter the aldehyde groups are condensated with diaminomaleonitrile have remarkable selective recognition performance for hypochloric acid and are excellent mitochondrial localization near infrared fluorescence probes for selective hypochloric acid detection.

Description

technical field [0001] The invention relates to the technical field of dye molecular fluorescent probes, in particular to a mitochondria-localized near-infrared fluorescent dye THX-Ba and its preparation method and application. Background technique [0002] Organic small molecule fluorescent probes are widely used in the fields of environmental science, life science and material science, and have increasingly become an indispensable research method in the fields of modern life science and disease diagnosis. Therefore, the development of functional fluorescent dye molecules with practical value much attention. Molecular fluorescent probes based on organic fluorophores have many advantages such as high sensitivity, easy operation, good reproducibility, good membrane permeability, and in-situ detection. It has important applications in the fields of engineering and medical testing. Compared with fluorescent probes in the visible light region, near-infrared fluorescent probes ...

Claims

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Application Information

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IPC IPC(8): C09B57/00C09K11/06G01N21/64
CPCC09B57/00C09K11/06C09K2211/1007C09K2211/1088G01N21/643G01N21/6486
Inventor 蒋玉仁赵雄杰李雨婷杨冰清
Owner CENT SOUTH UNIV
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