A kind of cyclometalated iridium-azo complex and its preparation method and application

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

Inactive Publication Date: 2015-12-02
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are some shortcomings in this class of organic fluorescence analysis reagents (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 cause 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 in the air or in the medium State oxygen, etc.), after the dye is irradiated at 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.PascalandS.Bernhard. J.Am.Chem.Soc. 2004, 126 ,14129-14135); Excitation and emission spectra have serious crossover (stokeshif is small), generally around tens of nanometers, which is not conducive to distinguishing endogenous fluorescence and reducing the self-quenching of the dye itself

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  • A kind of cyclometalated iridium-azo complex and its preparation method and application
  • A kind of cyclometalated iridium-azo complex and its preparation method and application
  • A kind of cyclometalated iridium-azo complex and its preparation method and application

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Experimental program
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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 7.8g of 2,2'-bipyridine in 40mL of trifluoroacetic acid, add 8.5mL of 30% hydrogen peroxide, stir at room temperature for 4h, neutralize with 6N sodium hydroxide solution, and then use 4'50cm 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 in vacuo overnight to obtain a white needle-like solid.

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

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

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 5mM complex solution with acetonitrile / HEPES (10mM, pH7.5) buffer solution with a volume ratio of 1:1, add different concentrations of cysteine, homocysteine ​​or glutathione dropwise, and stir well After standing at room temperature for 5 min, the fluorescence intensity was measured. The excitation wavelength and maximum emission wavelength of the complex are 430nm and 560nm 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 special glass bottom culture dish for confocal microscopy, 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, 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 medium was aspirated, and then washed with PBS buffer for 3 to 4 times, imaged on a Leica TCSSP5 laser scanning confocal microscope, using a 63′ / 1.4 oil lens , use 405nm...

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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 ​​r...

Claims

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Application Information

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Patent Type & Authority Patents(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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