A phosphorescent iridium complex with lysosome targeting function and its preparation method and application

A phosphorescent iridium complex, iridium complex technology, applied in biochemical equipment and methods, indium organic compounds, platinum group organic compounds, etc., can solve the problems of non-destructive imaging of unfavorable living cells, easy inactivation, high price, etc., Achieve excellent anti-photobleaching performance, improve image signal-to-noise ratio, and good biocompatibility

Active Publication Date: 2018-11-30
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

General dyes will have photobleaching and phototoxicity, and will lose their fluorescence activity in a short period of time under the irradiation of ultraviolet and visible light, or produce singlet oxygen and other substances that are easily toxic to living cells, which is not conducive to the non-destructive imaging of living cells
Although antibodies are low in toxicity, they are expensive and easily inactivated, which limits their application
The patent application with application publication number CN101962536A describes a lysosome-targeted fluorescent substance, but its chemical structure is complex and its biocompatibility is not very good

Method used

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  • A phosphorescent iridium complex with lysosome targeting function and its preparation method and application
  • A phosphorescent iridium complex with lysosome targeting function and its preparation method and application
  • A phosphorescent iridium complex with lysosome targeting function and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0027] Embodiment 1: Preparation of auxiliary ligands containing alkyl chains

[0028]

[0029] Preparation of Compound 2: Take 20ml of methanol and add it to a 50ml single-necked bottle, add 50mg of metal Na, stir at room temperature until Na is completely reacted and dissolved, stir and react Compound 1 (24mmol) with sodium methoxide solution for 22 hours at room temperature, and then add to the reaction solution Ammonium chloride (26mmol) was added to react for 6 hours. After the reaction, the unreacted ammonium chloride was filtered off, and the filtrate was spun dry to remove methanol solvent to obtain a light yellow powder, which was then washed three times with ether to remove unreacted compound 1, and then Recrystallized from a mixed solvent of ethanol-ether to obtain compound 2 as a white solid. Yield: 83%. 1 H NMR (400MHz, DMSO) δ = 9.69 (s, 4H), 8.85–8.73 (m, 1H), 8.45 (d, J = 8.0Hz, 1H), 8.14 (td, J = 7.8, 1.7Hz, 1H) ,7.85–7.71(m,1H). 13C NMR (101 MHz, DMSO) δ...

Embodiment 2

[0038] Embodiment 2: the preparation that contains alkyl chain iridium complex Ir-alkyl (7)

[0039]

[0040] Preparation of compound Ir-alkyl (7): compound 4 (0.22mmol) and iridium dichloro bridge (0.1mmol) in a mixed solvent of dichloromethane (3mL) and methanol (1mL), reflux at 55°C under nitrogen atmosphere Stir overnight, after the reaction is completed, the temperature of the reaction solution is down to room temperature, and then KPF is added thereto 6 (2.2 mmol) was stirred for 2 hours, and then the organic solvent was removed by rotary evaporation, and the obtained solid was purified by column chromatography to obtain Ir-alkyl (7) as a red powdery solid. Yield 23%. 1 H NMR (400MHz, DMSO-d 6 )δ (ppm): 8.45 (d, J = 7.6Hz, 1H), 8.12-8.08 (m, 3H), 8.01-7.68 (m, 9H), 7.36-7.31 (m, 2H), 7.15-7.14 (m ,1H),7.08-6.98(m,10H),6.94-6.85(m,4H),6.82-6.79(m,4H),6.76-6.70(m,5H),6.50(ddd,J=2.0,4.0, 8.4Hz, 2H), 5.84(d, J=2.0Hz, 1H), 5.53(d, J=2.4Hz, 1H), 4.46-4.34(m, 2H), 1.97(s...

Embodiment 3

[0044] Embodiment 3: Absorption and emission spectrum test of iridium complex Ir-alkyl (7)

[0045] The spectrum test concentration adopted in the present invention is 10 μM, the test solvent is toluene solution, and when measuring the emission spectrum, the excitation wavelength is 405 nm.

[0046] The absorption and emission spectra of Ir-alkyl(7) are as follows figure 1 with figure 2 shown. analyze figure 1 with figure 2 It can be concluded that the complex exhibits strong absorption at 250-380nm in the ultraviolet region and 400-500nm in the visible blue light region, especially the complex can be excited by visible light, so it can greatly reduce the excitation light source when doing cell imaging experiments damage to cells. When measuring its emission spectrum, the airflow with different volume ratios of oxygen and nitrogen is used to blow gas into the solution for 10 minutes, and then the test is carried out. It can be seen from the results that its emission is...

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Abstract

The invention relates to a phosphorescent iridium complex with a lysosome targeting function and its preparation method and use and belongs to the technical field of organic photoelectric materials. The phosphorescent iridium complex comprises a C^N ligand, a metal core and an alkyl chain-containing auxiliary ligand and has a structural formula shown in the description. The phosphorescent iridium complex can be excited by visible light, produce emission light in a near infrared area and reduce an excitation light source-caused damage to a biological sample and has deep tissue penetrating depth. The phosphorescent iridium complex has good photobleaching resistance and realizes long-term effective observation of cell tissue. The phosphorescent iridium complex can be used in the field of lysosome labeling and bioimaging, has a simple chemical structure and good biocompatibility and is a good lysosome targeting phosphorescent probe.

Description

technical field [0001] The invention relates to a phosphorescent iridium complex with lysosome targeting function and its preparation method and application, belonging to the technical field of organic photoelectric materials. Background technique [0002] At present, electrophosphorescent materials that have been studied mainly include organometallic complexes such as iridium, ruthenium, platinum, and osmium. Among them, phosphorescent ring metal iridium complexes have excellent phosphorescent properties, such as high quantum yield, large Stokes shift, long Phosphorescent lifetime, easy adjustment of luminescent color and good photobleaching resistance are currently the most studied phosphorescent materials. Moreover, the emission lifetime of phosphorescent transition metal complexes (hundreds of nanoseconds to tens of microseconds) is much longer than that of fluorescence (several nanoseconds), which not only endows them with oxygen-sensitive properties, but also enables t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06C12N5/00G01N21/33
CPCC07F15/0033C09K11/06C09K2211/185C12N5/00G01N21/33
Inventor 赵强黄维张璋刘淑娟许文娟吕雯
Owner NANJING UNIV OF POSTS & TELECOMM
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