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Cyclometalated iridium (III) complex and preparation method and application thereof in living cell mitochondria dyeing

A technology of cyclometals and complexes, applied in biochemical equipment and methods, indium organic compounds, platinum group organic compounds, etc., can solve the problems of unfavorable mitochondrial dynamic changes, easy generation of singlet oxygen, small Soke shift, etc., and achieve good Effects of mitochondrial targeting function, good photophysical and photochemical properties, and good water solubility

Inactive Publication Date: 2015-09-16
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are only two types of organic small molecular mitochondrial dyes that have been commercialized: one is mitochondrial membrane potential dependent such as Rhodamine dyes (Rhodamine 123, TMRM and TMRE), Carbocyanine dyes (JC-1, JC-9 and DiOC6 and Rosamine dyes (MitoTrackers Orange CMTMRos and MitoTrackers Red CMXRos, etc.); however, mitochondrial membrane potential-dependent fluorescent dyes will be eluted as the membrane potential decreases, which is not conducive to studying the dynamic changes of mitochondria
The other is membrane potential-independent mitochondrial probes (MitoTracker Green FM, MitoTrackers Red FM and MitoTrackers Deep Red), Mito Fluor Green and MitoID Red, etc.; although these mitochondrial dyes do not depend on membrane potential, they are small molecule organic fluorescent Dyes, small Soke shift, poor water solubility, severe photobleaching and other shortcomings also limit their application
In addition, the above-mentioned commercial mitochondrial dyes require high-energy single-photon laser excitation, which is easy to generate singlet oxygen, which is not conducive to long-term observation of dynamic changes in mitochondria

Method used

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  • Cyclometalated iridium (III) complex and preparation method and application thereof in living cell mitochondria dyeing
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  • Cyclometalated iridium (III) complex and preparation method and application thereof in living cell mitochondria dyeing

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Embodiment 1

[0040] Embodiment 1 The preparation method of ligand and complex

[0041] 1. Synthesis method of ligand ttpy:

[0042] The molecular structure of the ligand is attached figure 1 As shown, the synthesis pathway of the ligand ttpy is shown in the attached image 3 shown.

[0043] According to the references ( Synlett 2005, No. 8, 1251–1254) Dissolve 4.84 g (40 mmol) of 2-acetylpyridine and 2. 40 g of benzaldehyde (20 mmol) in 100 mL of ethanol. Afterwards, 3.08 g (85%, 40 mmol) of KOH particles and 58 mL of ammonia water (29.3%, 50 mmol) were added, and stirred for 25 h at room temperature in the dark. The off-white solid was collected by filtration and washed three times with 10 mL of ethanol. Then recrystallized from chloroform-methanol solvent to obtain a white solid. Yield 4.2 g, 61 % yield. 1 H NMR (300 MHz, DMSO) δ = 8.73 (d, J = 4.2 Hz, 2H), 8.66 (s, 2H), 8.64 (d, J = 9.0 Hz, 2H), 7.99 (t, J = 11.4 Hz, 2H), 7.80 (d, J = 6.0 Hz, 2H), 7.54 – 7.46 (m, 2H), 7....

Embodiment 2

[0052] Example 2 Laser Confocal Experiment

[0053] 1. Experimental method

[0054] Hela cells in the logarithmic phase were cultured in DMEM medium containing 10% fetal bovine serum, and the cells were seeded in a special glass-bottom culture dish for confocal microscopy. The diameter of the dish was 35 mm, and the thickness of the cover glass was 0.085-0.13 mm. The diameter of the micropore in the center of the dish is 10 mm, 5% CO 2 and 95% air conditions, cultured at 37°C, and grown adherently for 24 hours. Incubate with 5 μM complex for 1 h, and then co-stain with mitochondrial red fluorescent dye Mitotracker-Red FM (50 nM) for 30 min, aspirate the culture solution, and then wash with PBS buffer for 3 to 4 times, and scan the cells in a Zeiss two-photon laser scanner. For imaging on a focusing microscope, use a 63' oil lens, use 750 nm light as the excitation light source, and collect fluorescence in the range of 500-630 nm.

[0055] 2. Results

[0056] (1) Fluoresc...

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Abstract

The invention discloses a novel cyclometalated iridium (III) complex and a preparation method and an application thereof in living cell mitochondria dyeing. A cationic portion of the novel cyclometalated iridium (III) complex has the structural formula represented by the formula I. The synthesized cyclometalated iridium (III) complex is stable in structure, good in photophysical and photochemical properties and low in cytotoxicity, exhibits a good mitochondrial targeting function, and is a novel living cell mitochondria two-photon fluorescent probe. A study indicates that the complex has the optical stability and the two-photon absorption cross section which are obviously superior to those of commercial mitochondrial dyes, and is a potential excellent two-photon mitochondrial dye.

Description

technical field [0001] The invention belongs to the technical field of mitochondrial fluorescence imaging. More specifically, it relates to a cyclometalated iridium complex, a preparation method thereof and an application in mitochondrial staining of living cells. Background technique [0002] With the development of science and technology, human beings have a deeper understanding of mitochondria. The shape, size, quantity and distribution of mitochondria are very different. Mitochondria in living cells are generally rod-shaped or egg-shaped, and can also become flat disk-shaped, branch-shaped, etc. during cell division. The length of a single mitochondria is generally 1.5-3.0 μm, while the mitochondria of human fibroblasts can be as long as 40 μm. The function of mitochondria in cells is mainly the oxidative phosphorylation of glucose, which provides the energy needed for the life activities of cells, and also plays a role in regulating the ion homeostasis of the intrace...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06C09B57/10C12Q1/02G01N21/64
CPCC07F15/0033C09B57/10C09K11/06C12Q1/025G01N21/6486
Inventor 巢晖黄怀义张平玉计亮年
Owner SUN YAT SEN UNIV
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