Preparation method and application of phosphorescence iridium complexes with mitochondrial targeting function

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

Active Publication Date: 2016-03-16
NANJING UNIV OF POSTS & TELECOMM
View PDF4 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method and application of phosphorescence iridium complexes with mitochondrial targeting function
  • Preparation method and application of phosphorescence iridium complexes with mitochondrial targeting function
  • Preparation method and application of phosphorescence iridium complexes with mitochondrial targeting function

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0026]

[0027] Preparation of compound 2: compound 1 (26mmol) and sodium methoxide solution were stirred and reacted at room temperature for 22 hours, ammonium chloride (28mmol) was added and the reaction continued for 6 hours, filtered to remove unreacted ammonium chloride, and the filtrate was spin-dried to remove the methanol solvent , A light yellow solid powder was obtained, and then washed three times with ether to remove the unreacted compound 1, and then recrystallized using a mixed solvent of ethanol and ether to obtain a white product compound 2. Yield: 83%. 1 HNMR(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). 13CNMR (101MHz, DMSO) δ=162.67, 150.33, 144.37, 138.76, 129.01, 124.00.

[0028] Serial number

[0029] Preparation of compound 3: under the catalysis of sodium ethoxide, compound 2 (5mmol) and ethyl acetoacetate (5mmol) ...

Embodiment 2

[0036] Example 2: Ir-P(Ph) containing triphenylphosphoric iridium complex 3 (7) Preparation

[0037]

[0038] Compound Ir-P(Ph) 3 (7) Preparation: Compound 5 (0.14mmol) and iridium dichloride bridge (0.06mmol) were stirred and refluxed overnight at 55°C in a mixed solvent of dichloromethane (3mL) and methanol (1mL) under nitrogen atmosphere. Cool the reaction solution to room temperature and add KPF to it 6 (1.4mmol) continue to stir for 4 hours. After the reaction, the organic solvent is removed by rotary evaporation, and the obtained solid is purified by column to obtain a red powdery solid Ir-P(Ph) 3 (7). The yield was 36%. 1 HNMR(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] Serial number

Embodiment 3

[0040] Example 3: Ir-P(Ph) complex of iridium 3 (7) Absorption and emission spectrum test

[0041] The spectrum test concentration adopted in the present invention is 10 μM, the test solvent is a 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 such as figure 1 with figure 2 Shown. The complex exhibits strong absorption in the ultraviolet region of 250-380nm and the visible blue region of 400-500nm. In particular, the complex can be excited by visible light, which greatly reduces the damage of the excitation light source to cells when doing cell imaging experiments. Its emission is relatively wide, and the emission peak is at 602nm. The red light emission increases the penetration depth of biological tissues, making it more suitable for biological imaging.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

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. Specifically, it 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 place for aerobic respiration in cells, and changes in oxygen content in mitochondria will have a significant impact on respiration. Studies have shown that many diseases are related to the abnormal functioning of mitochondria, such as Alzheimer's disease and multiple sclerosis. Therefore, studying the changes of oxygen concentration in mitochondria in living cells is of great significance to the study of related diseases. Commercially available fluorescent mitochondrial targeting dyes, such as Mito-TrackGreen, have a good mitochondrial targeting function, but because they are not sensitive to oxygen, change...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap