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A preparation method of iridium complex and its application in two-photon mitochondrial dye

A technology of iridium complexes and mitochondria, which is applied in the research and development of fluorescent dyes, can solve the problems of unfavorable mitochondrial morphology and changes, unfavorable mitochondrial dynamic changes, small Stokes shift, etc., and achieve good water solubility and stability, excellent fluorescence intensity, cell The effect of small damage

Inactive Publication Date: 2021-04-20
YUNNAN UNIV
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Problems solved by technology

Dyes dependent on mitochondrial membrane potential, such as rhodamines, carbocyanines, etc., are easy to be eluted with the decrease of membrane potential, which is not conducive to the study of dynamic changes in mitochondria
Dyes that are not dependent on mitochondrial membrane potential, such as MitoTracker FM series dyes, have significantly improved anti-elution ability, but have disadvantages such as small Stokes shift, low water solubility, and severe photobleaching, which also limit their application.
More importantly, high-energy (short-wavelength) single-photon lasers are required to excite such single-photon-absorbing dyes, which tend to generate singlet oxygen in cells, which is not only not conducive to long-term observation of mitochondrial morphology and changes, but also easily causes cell damage

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  • A preparation method of iridium complex and its application in two-photon mitochondrial dye
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  • A preparation method of iridium complex and its application in two-photon mitochondrial dye

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Embodiment 1

[0032] The preparation of embodiment 1 iridium complex

[0033] 1. Preparation of iridium complexes:

[0034] The synthetic route of the iridium complex synthesized by the present invention is as follows figure 1 shown. On preparation method, as the productive rate of similar compound is basically in 50% (with IrCl 3 According to the traditional synthetic route (that is, the imidazophenanthroline ligand L is first synthesized, and then combined with [Ir 2 (L') 4 Cl 2 ] generates [Ir(L') 2 L] + ) optimization, the present invention has designed a new synthetic route (that is, first synthesize the precursor iridium complex Y0 of o-phenanthroline-5,6-dione, and then generate the target compound with cinnamaldehyde), and the yield (with IrCl 3 Total) reaches 80%, and the product is single, and it is easy to separate and purify, which significantly reduces the loss of precious metal iridium and the complexity of synthesis.

[0035] (1) The synthesis method of the precursor ...

Embodiment 2

[0045] Example 2 The study of iridium complexes as two-photon dyes in cell mitochondria

[0046] Human lung cancer cells A549 with logarithmic growth cycle were co-stained with nuclear dye DAPI, mitochondrial dye MitoTrackerGreen FM, and iridium complex, washed 5 times with phosphate buffer solution, and imaged on a Nikon A1plus two-photon confocal microscope with a 25x objective lens (Apo LWD / 1.10 DIC N2), NDD mirror, excitation light 800nm, record fluorescence images under 420nm (blue), 515nm (green), 590nm (red) filters respectively ( figure 2 ). From figure 2 It can be seen that the distribution of the four iridium complexes synthesized by the present invention completely overlaps with the mitochondrial dyes, but does not overlap with the cell nucleus dyes, which proves that they are all cell mitochondria-specific dyes. Judging from the fluorescence intensity ratio ( F red / F Green ), when the commercial mitochondrial dye MitoTrackerGreen FM was first added and th...

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Abstract

The invention belongs to the field of research and development of fluorescent dyes for cell imaging, and discloses a preparation method of an iridium complex and its application in cell mitochondrial fluorescent dyes with two-photon absorption properties. The iridium complex synthesized by the invention has good water solubility and stable chemical structure. The complex not only has excellent two-photon absorption properties and excellent fluorescence intensity, but also can specifically bind to cell mitochondria, and is a potential new two-photon fluorescent probe for cell mitochondria and a cell mitochondrial imaging dye. Experiments have shown that the fluorescence intensity of one of the iridium complexes is more than 6 times that of the commercial mitochondrial fluorescent dye MitoTracker Green FM. The iridium complex synthesized by the invention can also perform 3D stereoscopic imaging of cell mitochondria, and has important application value in the study of cell and mitochondria structures at different depths in cells and even animal organ tissues.

Description

technical field [0001] The invention belongs to the field of research and development of fluorescent dyes for cell imaging, and in particular relates to a preparation method of an iridium complex and its application in cell mitochondrial fluorescent dyes with two-photon absorption properties. Background technique [0002] Cell fluorescence imaging is an important tool that can understand the basic process of life activities at the subcellular level, and is widely used in various fields of life sciences. Excellent fluorescent dyes are one of the important conditions for obtaining high-quality cell fluorescence images. Mitochondria are two-membrane organelles present in most eukaryotic cells, accounting for about 10% of the cell volume. As a polymorphic organelle, its structure is constantly changing due to cell type, cell cycle status and intracellular metabolic status. Important functions of mitochondria are understood to include: energy production mediated by oxidative ph...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09B57/00C09K11/06G01N21/64
CPCC07F15/0033C09B57/00C09K11/06C09K2211/185G01N21/6428G01N2021/6439
Inventor 高峰马国兰毕徐丹
Owner YUNNAN UNIV
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