Iridium-selenium polypyridine complex and its preparation method and application

A technology of polypyridine and complexes, applied in the field of living cell staining, to achieve the effect of enhancing cell transmembrane ability, strong cell penetration ability, and short incubation time

Inactive Publication Date: 2015-10-07
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In general, most of the various iridium metal complexes that have been reported for cell staining and imaging are localized in the cytoplasm, and the iridium metal complexes for mitochondrial staining in living cells have not been reported so far.

Method used

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  • Iridium-selenium polypyridine complex and its preparation method and application
  • Iridium-selenium polypyridine complex and its preparation method and application
  • Iridium-selenium polypyridine complex and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0029] Embodiment 1 Preparation of ligand selenium-5,6-diamine-1,10-phenanthroline (phen-Se)

[0030] The synthesis of ligand phen-Se can be prepared by referring to existing literature (Qian Li, Dongdong Sun, Yanhui Zhou, Du Liu, Qianling Zhang and Jie Liu, Inorg.Chem.Commun., 2012, 20, 142), and its synthetic route was carried out Partial optimization and adjustment reduces the synthesis steps, making the synthesis simpler and faster with high yield. Only two steps are required, and the first step is a common and mature reaction for synthesizing polypyridine ligands.

[0031] (1) 1,10-phenanthroline-5,6-dione

[0032] It can be prepared by referring to the literature (M.Yamada, Y.Tanaka, Y.Yoshimato, S.Kuroda and I.Shimao, Bull.Chem.Soc.Jpn., 1992, 65, 1006). Under cooling in an ice bath, drop 40 cm 3 Concentrated sulfuric acid and 20cm 3 Mixed solution of concentrated nitric acid while magnetically stirring. After the dropwise addition was completed, the ice bath was r...

Embodiment 2

[0035] Example 2 Complex [Ir(ppy) 2 (phenSe)] + (PF 6 ) - , [Ir(dfppy) 2 (phenSe)] + (PF 6 ) - , [Ir(btp) 2 (phenSe)] + (PF 6 ) - , [Ir(2-pq) 2 (phenSe)] + (PF 6 ) - ,[Ir(dbq) 2 (phenSe)] + (PF 6 ) - Synthetic method:

[0036] (1)[(dfppy) 2 Ir(μ-Cl)] 2 Synthesis

[0037] The synthesis of this compound can be prepared by referring to existing literature (T.Peng, Y.Yang, Y.Liu, D.Ma, Z.Hou and Y.Wang, Chem.Commun., 2011, 47, 3150). Weigh IrCl 3 0.33g (about 1.1mmol), 2-(2,4-difluorophenyl)pyridine (dfppy) 0.501g (2.62mmol), mixed in 40mL ethylene glycol ether and water (V1:V2=3:1) liquid, reflux at 120°C for about 24 hours under the protection of argon. After cooling to room temperature, an appropriate amount of water was added, and the solid precipitate was collected by suction filtration, washed with n-hexane and ether several times, and dried to obtain a yellow-green powder with a yield of 53.5%.

[0038] (2)[(ppy) 2 Ir(μ-Cl)] 2 Synthesis

[0039] ...

Embodiment 3

[0059] The laser confocal experiment of embodiment 3 iridium complexes

[0060] Cell culture: Hela cells were cultured in DMEM medium containing 10% fetal bovine serum, cells (5'10 8 / L) inoculated in a special glass bottom culture dish for confocal microscope, the diameter of the culture dish is 35mm, the thickness of the cover glass is 0.085~0.13mm, the diameter of the micropore in the center of the dish is 10mm, 5% CO 2 and 95% air condition, cultured at 37°C, and grown adherently for 24 hours.

[0061] Confocal Microscopy-Cell Imaging: Hela cells with complexes {5 μM, [Ir(ppy)2(phenSe)] + (PF 6 - )(A), [Ir(dfppy)2(phenSe)] + (PF 6 - )(B), [Ir(btp)2(phenSe)] + (PF 6 - )(C), [Ir(2-pq)2(phenSe)] + (PF 6 - )(D), [Ir(dbq)2(phenSe)] + (PF 6 - )(E)} incubate for 30min, and then incubate with mitochondrial green fluorescent dye Mitotracker-Green (50nM) for a certain period of time, suck out the culture medium, and then wash with PBS buffer for 3 to 4 times. For ima...

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Abstract

The invention discloses an iridium-selenium polypyridine complex as well as a preparation method and an application of the iridium-selenium polypyridine complex. The iridium-selenium polypyridine complex disclosed by the invention has the chemical formula of [Ir (N-C)2(phenSe)]+(N-C=ppy, dfppy, btp, 2-pq or dbq), is derived from selenium-5, 6-diamine-1, 10-ortho phenanthroline, has a good living cell mitochondria coloring characteristic, a strong cell membrane penetration capacity and low cytotoxicity and has a great application potential in the aspects of biolabeling and cell imaging.

Description

technical field [0001] The invention relates to the technical field of living cell staining, in particular to a series of novel iridium-selenium polypyridine complexes, a preparation method and application thereof. Background technique [0002] With the deepening of people's research on cells, biomedical optical imaging technologies such as magnetic resonance imaging (MRI), positron emission tomography (PET), single photon emission tomography (SPECT) and laser confocal fluorescence microscopy have also become more and more important. The development of suitable bioimaging reagents is a current research hotspot. At present, most of the commercial fluorescent dyes used in the field of cell imaging are small organic molecules, such as PI, DAPI, EB, Hoechst, MitoTracker, JC-1, etc. However, these small organic molecules have some disadvantages (V.Fernandez-Moreira, F.L.Thorp-Greenwood and M.P.Coogan.Chem.Commun.2010,46,186-202): poor water solubility, in water environment (such...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C12Q1/02
Inventor 巢晖陈禹乔丽萍计亮年
Owner SUN YAT SEN UNIV
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