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Preparation and Application of Phosphorescent Iridium Complexes with Mitochondrial Targeting Function

A phosphorescent iridium complex, iridium complex technology, applied in indium organic compounds, platinum group organic compounds, compounds containing periodic table Group 8/9/10/18 elements, etc., can solve unfavorable synthesis and preparation, exploration. Needle structure is complex and other problems, to achieve the effect of good biocompatibility, improved signal-to-noise ratio, and deep tissue penetration depth

Active Publication Date: 2018-04-20
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the structures of these probes are relatively complex, which is not conducive to synthesis and preparation.

Method used

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  • Preparation and Application of Phosphorescent Iridium Complexes with Mitochondrial Targeting Function
  • Preparation and Application of Phosphorescent Iridium Complexes with Mitochondrial Targeting Function
  • Preparation and Application of Phosphorescent Iridium Complexes with Mitochondrial Targeting Function

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Preparation of auxiliary ligand containing triphenylphosphine

[0026]

[0027] Preparation of Compound 2: Compound 1 (26mmol) and sodium methoxide solution were stirred and reacted at room temperature for 22 hours, then ammonium chloride (28mmol) was added to continue the reaction for 6 hours, unreacted ammonium chloride was removed by filtration, and the filtrate was spin-dried to remove methanol solvent , to obtain a light yellow solid powder, and then washed three times with ether to remove unreacted compound 1, and then recrystallized using a mixed solvent of ethanol-ether to obtain compound 2 as a white product. 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 = 162.67, 150.33, 144.37, 138.76, 129.01, 124.00.

[0028] serial number

[0029] Preparation of Compound 3: Compound 2 (5 mmol) and ethyl acetoacetate (5 mmol)...

Embodiment 2

[0036] Embodiment 2: Contain triphenylphosphorus iridium complex Ir-P(Ph) 3 (7) Preparation

[0037]

[0038] Compound Ir-P(Ph)3 Preparation of (7): Mix compound 5 (0.14mmol) and iridium dichloro bridge (0.06mmol) in a mixed solvent of dichloromethane (3mL) and methanol (1mL), stir and reflux overnight at 55°C under a nitrogen atmosphere, and then The reaction solution was cooled to room temperature, and KPF was added thereto 6 (1.4mmol) continued to stir for 4 hours, and after the reaction was completed, the organic solvent was removed by rotary evaporation, and the obtained solid was purified through a column to obtain a red powdery solid Ir-P(Ph) 3 (7). Yield 36%. 1 H NMR (400MHz, DMSO) δ8.43 (d, J = 8.1Hz, 1H), 8.11 (dt, J = 10.7, 5.4Hz, 3H), 8.03–7.95 (m, 2H), 7.93–7.70 (m, 22H),7.36–7.28(m,2H),7.23–6.97(m,14H),6.96–6.88(m,3H),6.86–6.70(m,9H),6.52(dd,J=6.9,4.4Hz, 2H), 4.37 (s, 2H), 3.56 (s, 2H), 1.99 (s, 3H), 1.50 (dd, J = 60.1, 31.4 Hz, 8H).

[0039] se...

Embodiment 3

[0040] Embodiment 3: Iridium complex Ir-P(Ph) 3 (7) Absorption and emission spectrum test

[0041] The spectrum test concentration adopted in the present invention is 10 μM, the test solvent is PBS solution mixed with 1% DMSO, and when the emission spectrum is measured, the excitation wavelength is 405 nm.

[0042] Ir-P(ph) 3 The absorption and emission spectra of the figure 1 with figure 2 shown. The complex exhibits strong absorption at 250-380nm in the ultraviolet region and 400-500nm in the visible blue light region. In particular, the complex can be excited by visible light, which greatly reduces the damage to cells caused by the excitation light source in cell imaging experiments. Its emission is wide, and the emission peak is located at 602nm. Red light emission increases the penetration depth of biological tissue, making it more suitable for biological imaging.

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Abstract

The invention discloses phosphorescence iridium complexes with a mitochondrial targeting function, and a preparation method thereof, and an application thereof in biological imaging and oxygen detection. The complexes are composed of a cyclic metal ligand, a metal center and an auxiliary ligand containing a mitochondrial targeting function group, and the structure of the complexes is represented by a general formula shown in the description; the luminous intensity and the emission life of the complexes reduce with the increase of the oxygen concentration; mitochondria of living cells are marked; the change of the concentration of oxygen in the mitochondria of living cells is detected through a confocal imaging and life imaging technology; and the phosphorescence iridium complexes have important application prospect in biological imaging and sensing fields.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials. It specifically relates to a preparation method of a phosphorescent iridium complex with mitochondrial targeting function and its application in the fields of cell imaging, mitochondrial labeling and oxygen sensing. Background technique [0002] Mitochondria are the main sites of aerobic respiration in cells, and changes in the oxygen content in mitochondria can have a major impact on respiration. Studies have shown that many diseases, such as Alzheimer's disease and multiple sclerosis, are associated with abnormal functioning of mitochondria. Therefore, it is of great significance to study the changes of oxygen concentration in mitochondria in living cells to study related diseases. Commercial fluorescent mitochondria-targeting dyes, such as Mito-Track Green, have good mitochondria-targeting functions, but because they are not sensitive to oxygen, changes in oxygen conc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06G01N21/39G01N21/31
CPCC07F15/0033C09K11/06C09K2211/185G01N21/31G01N21/39
Inventor 赵强黄维吕雯许文娟刘淑娟张璋
Owner NANJING UNIV OF POSTS & TELECOMM
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