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Iridium-selenium polypyridine complex as well as preparation method and application thereof

A technology of polypyridine and complexes, applied in the field of living cell staining, to achieve the effect of simple and stable structure, high dyeing sensitivity, and low resistance to photobleaching

Inactive Publication Date: 2013-02-13
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 as well as preparation method and application thereof
  • Iridium-selenium polypyridine complex as well as preparation method and application thereof
  • Iridium-selenium polypyridine complex as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 Preparation of Ligand Selenium-5,6-Diamine-1,10-phenanthroline (phen-Se)

[0030] The synthesis of ligand phen-Se can refer to the existing literature (Qian Li, Dongdong Sun, Yanhui Zhou, Du Liu, Qianling Zhang and Jie Liu, Inorg. Chem. Commun. , 2012, 20 , 142), the synthetic route was partially optimized and adjusted, and the synthetic steps were reduced to make 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] Reference can be made to the literature (M. Yamada, Y. Tanaka, Y. Yoshimato, S. Kuroda and I. Shimao, Bull. Chem. Soc. Jpn. , 1992, 65, 1006) method to prepare. Under cooling in an ice bath, add dropwise a 40 cm 3 concentrated sulfuric acid and 20 cm 3 Mixed solution of concentrated nitric acid while magnetically stirring. After the dropwise addition was completed, th...

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 refer to existing literature (T. Peng, Y. Yang, Y. Liu, D. Ma, Z. Hou and Y. Wang, Chem. Commun. , 2011, 47, 3150) prepared. Weigh IrCl 3 0.33 g (about 1.1 mmol), 2-(2,4-difluorophenyl) pyridine (dfppy) 0.501 g (2.62 mmol), in 40 mL ethylene glycol ether and water (V1:V2=3:1) The mixture was refluxed 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 Sy...

Embodiment 3

[0058] Example 3 Laser Confocal Experiment of Iridium Complexes

[0059] Cell culture: Hela cells were cultured in DMEM medium containing 10% fetal bovine serum, cells (5′ l0 8 / L) inoculated in a confocal microscope special glass-bottom culture dish, the diameter of the culture dish is 35 mm, the thickness of the cover glass is 0.085~0.13 mm, the diameter of the micropore in the center of the dish is 10 mm, and 5% CO 2 and 95% air conditions, cultured at 37°C, and grown adherently for 24 hours.

[0060] 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 30 min, and then incubate with mitochondrial green fluorescent dye Mitotracker-Green (50 nM) for a certain period of time, aspirate the culture medium, and then wash with PBS buffer for 3 to 4 times, and...

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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 are also becoming 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, easy to pro...

Claims

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Application Information

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Patent Type & Authority Applications(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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