Preparation method of iridium complex and application in biphoton mitochondrial dyes

An iridium complex, mitochondrial technology, applied in the field of fluorescent dye research and development, can solve problems such as unfavorable mitochondrial morphology and changes, small Stokes displacement, unfavorable mitochondrial dynamic changes, etc., to achieve good water solubility and stability, less damage to cells, The effect of excellent fluorescence intensity

Inactive Publication Date: 2019-02-01
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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  • Preparation method of iridium complex and application in biphoton mitochondrial dyes
  • Preparation method of iridium complex and application in biphoton mitochondrial dyes
  • Preparation method of iridium complex and application in biphoton mitochondrial dyes

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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 MitoTracker GreenFM, 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 MitoTracker Green FM was added first and t...

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Abstract

Belonging to the field of research and development fluorescent dyes for cell imaging, the invention discloses a preparation method of an iridium complex and application of the complex in cell mitochondrial fluorescent dyes with biphoton absorption properties. The iridium complex synthesized by the method has good water solubility and stable chemical structure. The complex not only has excellent biphoton absorption properties and excellent fluorescence intensity, but also can specifically combine cell mitochondria, is a potential novel cell mitochondrial biphoton fluorescent probe and cell mitochondrial imaging dye. Experiments prove that the fluorescence intensity of one iridium complex reaches 6 times or more that of the commercial mitochondrial fluorescent dye MitoTracker Green FM. The iridium complex synthesized by the method provided by the invention also can achieve 3D stereoimaging of cell mitochondria, and has important application value in the study aspects of cells and mitochondrial structures of different depths in cells and even animal organs and 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 state. Important functions of mitochondria are understood to include: energy production mediated by oxidative pho...

Claims

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Application Information

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Patent Type & Authority Applications(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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