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Near-infrared fluorescent dye THX-Np capable of achieving mitochondrial localization and preparation method and application of near-infrared fluorescent dye THX-Np

A fluorescent dye and near-infrared technology, which is applied in the field of dye molecular fluorescent probes, can solve the problems of small anti-interference ability and small Stokes shift, and achieve large Stokes shift, simple preparation method, and good cell membrane communication. The effect of permeability

Inactive Publication Date: 2018-12-14
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 type of dye is small (<50nm), and the anti-interference ability is small

Method used

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  • Near-infrared fluorescent dye THX-Np capable of achieving mitochondrial localization and preparation method and application of near-infrared fluorescent dye THX-Np
  • Near-infrared fluorescent dye THX-Np capable of achieving mitochondrial localization and preparation method and application of near-infrared fluorescent dye THX-Np
  • Near-infrared fluorescent dye THX-Np capable of achieving mitochondrial localization and preparation method and application of near-infrared fluorescent dye THX-Np

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Preparation of Compound 1

[0049]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.

[0050] The synthetic route is as follows:

[0051]

Embodiment 2

[0053] Preparation of fluorescent dye THX-Np

[0054] Compound 1 (3.76g, 10mmol) prepared in Example 1 and 6-hydroxy-2-naphthaldehyde (1.72g, 10mmol) were dissolved in 50ml of glacial acetic acid, stirred and reacted at 95°C, TLC followed the reaction to the end point, about 1h , glacial acetic acid was removed by rotary distillation, and the solid was separated and purified by dichloromethane / methanol (v / v 20:1) column chromatography to obtain the target product as a blue solid (1.34 g, yield: 25%). 1 H NMR(400MHz,DMSO)δ9.84(s,1H),7.96(d,J=7.6Hz,1H),7.86(s,1H),7.80(dd,J=7.8,6.0Hz,2H),7.69 (dd, J=14.5,7.7Hz,2H),7.50(d,J=9.0Hz,2H),7.34(d,J=7.7Hz,1H),7.16-7.06(m,2H),6.58(s, 1H), 6.44(dd, J=23.8, 8.8Hz, 2H), 3.41-3.35(m, 4H), 2.87(d, J=15.5Hz, 1H), 2.70(s, 1H), 1.91(s, 1H ), 1.59(d, J=12.9Hz, 2H), 1.23(s, 1H), 1.10(t, J=6.9Hz, 6H). 13 C NMR(125MHz,DMSO)δ169.44,156.32,135.68,134.14,131.28,130.50,130.40,130.26,129.55,128.92,128.72,128.27,127.99,127.29,126.38,125.24,124.24,119.48...

Embodiment 3

[0058] Preparation of hydrogen sulfide probe

[0059] The near-infrared fluorescent dye (1.06g, 2.0mmol) prepared in Example 1, 2,4-dinitrofluorobenzene (1.12g, 6.0mmol), anhydrous potassium carbonate (0.83g, 6mmol) were dissolved in 60mL dichloro Methane, stirring reaction at room temperature, TLC tracking reaction to the end point, about 2h, the solution color from dark blue to brown, rotary evaporation to remove dichloromethane, solid with dichloromethane / methanol (v / v 20:1) column Chromatographic separation and purification gave the target product as a brown solid (0.53 g, yield: 37%). 1 H NMR (400MHz, DMSO) δ8.95(d, J=2.8Hz, 1H), 8.45(dd, J=9.3, 2.8Hz, 1H), 8.14(d, J=9.0Hz, 1H), 8.08(s ,1H),7.99-7.92(m,2H),7.85-7.76(m,2H),7.69(dd,J=7.9,5.2Hz,2H),7.57(s,1H),7.47(dd,J=8.9 ,2.4Hz,1H),7.35(d,J=7.7Hz,1H),7.29(d,J=9.3Hz,1H),6.57(d,J=2.1Hz,1H),6.44(dt,J=19.1 ,5.6Hz,2H),3.38(d,J=6.7Hz,4H),2.88(d,J=14.2Hz,1H),2.73(d,J=15.6Hz,1H),1.91(d,J=11.9 Hz,1H),1.61(t,J=14.3Hz,3H),1.11(t,...

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Abstract

The invention discloses near-infrared fluorescent dye THX-Np capable of achieving mitochondrial localization and a preparation method and application of the near-infrared fluorescent dye THX-Np. The structural formula of the dye is shown in (I). The dye has a stable pH fluorescence opening effect in an aqueous phase under the conditions of different pH values, and 2,4-dinitrophenyl ether derivatives prepared by using the dye can be applied to detection of hydrogen sulfide. The invention has the following advantages that the fluorescent dye has pH stability, large Stokes shift, good water solubility, good cell membrane permeability and excellent mitochondrial localization performance, and hydroxyl groups and carboxyl groups of the dye can be easily modified so as to produce tracers relatedto organisms, the 2,4-dinitrophenyl ether derivatives prepared through etherification of hydroxyl groups of the dye have excellent selective recognition of hydrogen sulfide, and an excellent selectivefluorescent probe of hydrogen sulfide 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-Np and its preparation method and application. Background technique [0002] 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 have stronger tissue penetration and greatly reduce background interference, thus increasing the sensitivity of fluorescence techniques. The characteristics of fluorescent dyes will directly affect the accuracy and sensitivity of detection results, so the development of new near-infrared fluorescent dyes suitable for fluorescent labeling will be of great sig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/04C09K11/06G01N21/64
CPCC09B23/04C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1088G01N21/6428
Inventor 蒋玉仁赵雄杰李雨婷杨冰清
Owner CENT SOUTH UNIV
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