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Phosphorescent iridium complex probe having mitochondrial targeting function as well as preparation and application thereof

A technology of iridium complexes and mitochondria, which is applied in the direction of indium organic compounds, platinum group organic compounds, fluorescence/phosphorescence, etc., can solve the problems of harm to organisms, and achieve high selectivity, low biological toxicity, and fast response.

Active Publication Date: 2016-10-26
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the production of ROS is essential for life in the normal cellular environment, they can also be harmful to the organism when they are produced in excess under exogenous stimuli

Method used

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  • Phosphorescent iridium complex probe having mitochondrial targeting function as well as preparation and application thereof
  • Phosphorescent iridium complex probe having mitochondrial targeting function as well as preparation and application thereof
  • Phosphorescent iridium complex probe having mitochondrial targeting function as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: when n=2, for , the preparation of probe Ir1:

[0029] The synthetic route is as follows:

[0030]

[0031] Preparation of compound 2a: 51 mmol of potassium hydroxide and 10.2 mmol of 2-pyridylbenzimidazole were added to a reaction flask, and 20 ml of ionic liquid was added. After the mixture was pre-stirred for 5 minutes, 8ml of 1,6-dibromohexane was added, and the reaction was stirred at room temperature for 5h. After the reaction was completed, it was extracted three times with ether, the oil phases were combined, and the solvent was removed by a rotary evaporator. The obtained crude product was separated by column chromatography, and the eluent was petroleum ether:ethyl acetate=3:1, and finally 2.2 g of a colorless oily liquid was obtained, with a yield of 60%. 1 H NMR (400MHz, CDCl 3 ): δ=8.70(d, J=4.80Hz, 1H), 8.41(d, J=7.97Hz, 1H), 7.88-7.33(m, 2H), 7.46-7.44(m, 1H), 7.37-7.30( m, 3H), 4.84(t, J=7.6Hz, 2H), 3.38(t, J=6.8Hz, 2H), 1.95-1.88...

Embodiment 2

[0045] Embodiment 2: when n=1, for When, the preparation of probe Ir2:

[0046] The synthetic route is as follows:

[0047]

[0048] Preparation of compound 2b: 51 mmol of potassium hydroxide and 10.2 mmol of 2-pyridylbenzimidazole were added to a reaction flask, and 20 ml of ionic liquid was added. After the mixture was pre-stirred for 5 minutes, 8ml of 1,4-dibromobutane was added, and the reaction was stirred at room temperature for 5h. After the reaction was completed, it was extracted three times with ether, the oil phases were combined, and the solvent was removed by a rotary evaporator. The obtained crude product was separated by column chromatography, and the eluent was petroleum ether: ethyl acetate = 3:1, and finally 2.2 g of a colorless oily liquid was obtained, with a yield of 62%. 1 H NMR (400MHz, CDCl 3 ): δ=8.70(d, J=4.80Hz, 1H), 8.41(d, J=7.97Hz, 1H), 7.88-7.33(m, 2H), 7.46-7.44(m, 1H), 7.37-7.30( m, 3H), 4.86(t, J=7.6Hz, 2H), 3.39(t, J=6.8Hz, 2H), 1....

Embodiment 3

[0061] Embodiment 3: when n=2, for When, the preparation of probe Ir3:

[0062] The synthetic route is as follows:

[0063]

[0064] Synthesis of p-formylbenzoquinoline (1c): Add 2-chloroquinoline (818mg, 5.0mmol), p-formylphenylboronic acid (750mg, 5.0mmol) and tetrakis (triphenylphosphine) palladium catalyst in a 250mL two-neck flask (200mg). The system is sealed, deoxygenated and filled with nitrogen for protection. Then, the solvent toluene (30 mL), ethanol (10 mL), and saturated aqueous sodium carbonate solution (10 mL) were added by syringe after deoxygenating with nitrogen for half an hour. During the reaction, the system was protected from light, and the reaction was refluxed at 80° C. for 15 hours. After the reaction was finished, the system was cooled to room temperature. The reaction solution was extracted three times with dichloromethane / water, the organic phase was collected, concentrated, and spotted by TLC to confirm the product point. The crude prod...

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Abstract

The invention relates to a phosphorescent iridium complex probe having a mitochondrial targeting function as well as a preparation method and an application thereof, in particular to a phosphorescent iridium complex probe containing a mitochondrial targeting group and a ClO<-> recognition group as well as an application of the probe, and belongs to the technical field of organic photoelectric functional materials. The complex material comprises an oxime group-containing cyclometalated ligand, a metal center and an N^N ligand of the mitochondrial targeting group containing triphenylphosphine and has the general structural formula shown in the specification. Material synthesis steps are simple, material synthesis conditions are mild, and the probe has very good application prospect in ClO<-> detection, mitochondrial targeting imaging and biological marking.

Description

technical field [0001] The invention relates to a phosphorescent ion-type iridium complex probe with mitochondrial targeting function, in particular to a class of probes containing both mitochondrial targeting groups and hypochlorite (ClO - ) recognition group phosphorescent iridium complex probe and application thereof, belonging to the technical field of organic photoelectric functional materials. Background technique [0002] Molecular oxygen is an essential component for all oxygen-consuming organisms to maintain their life activities. Reactive oxygen species (ROS) is a type of molecular oxygen produced during human metabolism, including peroxide, hydroxyl, peroxyl radicals, peroxidation Hydrogen, singlet oxygen and hypochlorous acid / hypochlorite. The reactive oxygen species ROS in the human body is mainly oxygen produced through the process of mitochondrial respiration. At the same time, it can also be induced by external disturbances, such as exogenous chemicals, infe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06G01N21/64
CPCC07F15/0033C09K11/06C09K2211/185G01N21/6486
Inventor 许文娟赵强杨继光黄维刘淑娟杨靖陈键狄隆康
Owner NANJING UNIV OF POSTS & TELECOMM
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