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Cyclo-metalated iridium-azo complex as well as preparation method and application thereof

A technology of cyclometalation and complexes, which is applied in the field of preparation of cyclometalated iridium complexes, can solve the problems of self-quenching of endogenous fluorescent dyes, unfavorable imaging stability, and influence of cell observation, etc., and achieve background fluorescence intensity Weak, simple and stable results, high dyeing sensitivity

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

This class of organic fluorescent assay reagents has some disadvantages (V. Fernandez-Moreira, F. L. Thorp-Greenwood and M. P. Coogan. Chem. Commun. 2010, 46, 186-202) : It has relatively high cytotoxicity. After the dye interacts with the cells, it will lead to cell death and affect the observation of the normal state of the cells; the photostability is low, due to the influence of active agent groups (singlet oxygen, etc.) in the air or in the medium After the dye is irradiated with the excitation wavelength, the fluorescence is continuously weakened, and the photodrifting phenomenon is serious, which is not conducive to the stability of the imaging (M. S. Lowry, W. R. Hudson, R. A. Pascal and S. Bernhard. J. Am. Chem. Soc. 2004, 126, 14129-14135); Excitation and emission spectra have serious intersection (stoke shift is small), generally around tens of nanometers, which is not conducive to distinguishing endogenous fluorescence and reducing the self-sufficiency of the dye itself Quenched

Method used

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  • Cyclo-metalated iridium-azo complex as well as preparation method and application thereof
  • Cyclo-metalated iridium-azo complex as well as preparation method and application thereof
  • Cyclo-metalated iridium-azo complex as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1 Preparation of Ligand Selenium-5,6-dione-1,10-phenanthroline (phendione-Se)

[0024] (1) 2,2'-bipyridine-N-oxide

[0025] You can refer to the literature ( Chem. Comm. 2011, 47 , 11011-11013) method to prepare. Dissolve 7.8 g of 2,2’-bipyridine in 40 mL of trifluoroacetic acid, add 8.5 mL of 30% hydrogen peroxide, stir at room temperature for 4 h, neutralize with 6 N sodium hydroxide solution, and then use 4′ 50 cm 3 After extraction with chloroform, the organic phases were combined and washed with saturated sodium chloride solution, then dried over anhydrous sodium sulfate, filtered and evaporated to remove chloroform to obtain a colorless oil, which was dried overnight in vacuum to obtain a white needle-like solid.

[0026] (2) 4-Nitro-2,2'-bipyridine-N-oxide

[0027] Dissolve 3 g of 2,2'-bipyridine-N-oxide in 19 mL of concentrated sulfuric acid with stirring in an ice bath, then add dropwise to fuming nitric acid / concentrated sulfuric acid (30 mL / 14...

Embodiment 2

[0036] Example 2 [Ir(pq) 2 (azobpy)Ir(pq) 2 ] 2+ In Vitro Response Experiments to Physiological Thiols

[0037] The complexes used below are the compounds prepared in Example 1.

[0038] Prepare a 5 mM complex solution with acetonitrile / HEPES (10 mM, pH 7.5) buffer solution with a volume ratio of 1:1, add different concentrations of cysteine, homocysteine ​​or glutathione dropwise, fully After stirring, let it stand at room temperature for 5 min, and then measure its fluorescence intensity. The excitation wavelength and maximum emission wavelength of the complex are 430, 560 nm, respectively. See the experimental results image 3 . It can be seen from the figure that the original fluorescence of the complex is relatively weak, but after adding a small amount of physiological thiols, such as cysteine, homocysteine ​​or glutathione, the fluorescence of the complex is greatly enhanced. Has a very sensitive fluorescence response.

Embodiment 3

[0039] Example 3 [Ir(pq) 2 (azobpy)Ir(pq) 2 ] 2+ Intracellular Response Experiments to Physiological Thiols

[0040] The complexes used below are the compounds prepared in Example 1.

[0041] 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 Incubate at 37°C under 95% air conditions, and after 24 hours of adherent growth, replace with serum-free medium and continue to incubate for 4 hours.

[0042] Confocal microscope-cell imaging: Hela cells were incubated with the complex (5 μM) for 30 minutes, the culture solution was aspirated, and then washed with PBS buffer for 3 to 4 times, imaged on a Leica TCS SP5 laser scanning confocal microscope, using a 63′ / 1.4 Oil objective, ...

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Abstract

The invention discloses the preparation of a cyclo-metalated iridium-azo complex and an application of the cyclo-metalated iridium-azo complex to the detection of physiological thiol. The complex provided by the invention can react with the physiological thiol specifically to produce the fluorescent response, has strong cell membrane penetration capacity and low cytotoxicity, can be used for identifying the thiol in the cells and has a great application potential in the aspect of real-time and quick detection of the physiological thiol.

Description

technical field [0001] The invention relates to the field of thiol detection, in particular to a preparation method and application of a novel cyclometalated iridium complex. Background technique [0002] Physiological thiols refer to amino acids, oligopeptides or proteins containing sulfhydryl residues, mainly including cysteine, homocysteine ​​and glutathione. Due to their strong reducing ability, physiological thiols act as very effective antioxidants in the body, which can efficiently and quickly scavenge free radicals and protect organisms from oxidative damage. Studies have shown that cysteine ​​deficiency can appear in many diseases, such as slow growth in children, lethargy, skin relaxation, liver damage, etc., and the concentration of homocysteine ​​is also a risk factor for Alzheimer's disease and cardiovascular diseases. incentive. Glutathione, as the most abundant non-protein thiol in cells, is the main factor for maintaining the thioether group of cysteine ​​...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06G01N21/64
Inventor 巢晖李观营陈禹许文超刘疆平计亮年
Owner SUN YAT SEN UNIV
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