Phosphorescent polymer probe capable of detecting peroxynitrite by using ratio method and preparation method and application thereof

A technology of peroxynitrite and polymer, which is applied in the direction of fluorescence/phosphorescence, material analysis by optical means, measuring device, etc. It can solve the problems of short life of peroxynitrite and difficulty in mediating the process, and achieve good results. Water solubility and biocompatibility, low biological toxicity, and small damage effect

Active Publication Date: 2019-01-25
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Understanding the processes mediated by peroxy

Method used

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  • Phosphorescent polymer probe capable of detecting peroxynitrite by using ratio method and preparation method and application thereof
  • Phosphorescent polymer probe capable of detecting peroxynitrite by using ratio method and preparation method and application thereof
  • Phosphorescent polymer probe capable of detecting peroxynitrite by using ratio method and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1: Preparation of phosphorescent iridium complex Ir2 capable of detecting peroxynitrite

[0047]

[0048] The specific operation steps are:

[0049] Preparation of compound 2: 1 (3.0 mmol) was added to a round-bottomed flask, and the nitrogen was evacuated three times to remove water in the air; then, dry dichloromethane, triethylamine (0.5 mL) and tert-Butyldiphenylchlorosilane (4.5mmol) was stirred at room temperature for 6 hours; after the reaction, the white precipitate was filtered off, the filtrate was spun to remove the organic solvent, and column chromatography gave a pale yellow oily liquid 2 with a yield of 80% .

[0050] 1 H NMR (400MHz, CDCl 3 ): 7.78(dd, J=8.0Hz, 2.4Hz, 4H), 7.72(d, J=2.8 Hz, 1H), 7.66(dd, J=8.8Hz, 2.8Hz, 1H), 7.47-7.40(m, 6H), 6.80(d, J=8.8Hz, 1H), 3.68(s, 3H), 1.22(s, 9H).δ(ppm): 13 C NMR (100MHz, CDCl 3)δ(ppm): 151.3, 150.6, 142.1, 135.3, 132.4, 130.2, 127.9, 119.5, 117.3, 107.3, 55.6, 26.6, 19.9.

[0051] Preparation o...

Embodiment 2

[0059] Example 2: Preparation of Peroxynitrite-Sensitive Complex Water-soluble Polymer Probe P-ONOO

[0060]

[0061] Among them, a, b, c are natural numbers;

[0062] The specific operation steps are: add Ir1 (0.03 mmol), Ir2 (0.3 mmol), AIBN (0.3 mmol), pyrrolidone (10.0 mmol) and a small amount of tetrahydrofuran (5 mL) into the schlenk reaction tube; freeze-exhaust-thaw, and so on for three times , heated to 70°C, stirred and refluxed for 6 hours; after the reaction was stopped, sedimentation with ether was used for three times, and P was obtained by suction filtration with a yield of 32%.

Embodiment 3

[0063] Example 3: Emission Spectrum Test of Complexes Ir1 and Ir2 to Peroxynitrite Responsiveness

[0064] The spectral test concentration of the iridium complexes Ir1 and Ir2 used in the present invention is 10 μM, the test solvent is a PBS solution mixed with 1% DMSO, and the excitation wavelength is 605 nm when measuring the emission spectrum.

[0065] The emission spectrum results of the iridium complex Ir1 in the presence and absence of peroxynitrite are as follows figure 1 It can be seen from the figure that the emission wavelength of the complex Ir1 in the presence and absence of peroxynitrite is 605 nm, and the luminescence intensity is almost unchanged with the change of the peroxynitrite concentration. The result It is shown that the iridium complex Ir1 can be used as a reference in the detection of peroxynitrite, and the ratio method constructed with Ir2 can reduce unnecessary interference in the environment and increase the detection accuracy.

[0066] The emissio...

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Abstract

The invention discloses a phosphorescent polymer probe capable of detecting peroxynitrite by using a ratio method and a preparation method and application thereof. Two types of phosphorescent iridiumcomplexes (Ir1 and Ir2) and a water-soluble polymer are copolymerized to form the phosphorescent polymer probe, wherein the phosphorescent iridium complex (Ir1) is an inert phosphorescent reference unit, which does not respond to peroxynitrite; as a phosphorescent response unit, the phosphorescent iridium complex (Ir2) can chemically react with peroxynitrite, thereby realizing specific response toperoxynitrite; and as a main chain formation unit for the polymer, the water-soluble polymer endows the polymer with good water solubility and biocompatibility. The phosphorescent polymer probe P-ONOO can be used in the detection and imaging of peroxynitrite in aqueous solutions, living cells and living bodies by the ratio method, and has an important application prospect in terms of biological imaging and sensing.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric functional materials, and in particular relates to a water-soluble phosphorescent polymer probe capable of detecting peroxynitrite by a ratio method, and preparation and application thereof. Background technique [0002] Peroxynitrite is a short-lived reactive nitrogen species, and intracellular peroxynitrite is formed by the rapid reaction of nitric oxide and superoxide radicals, which is stronger than that of nitric oxide or superoxide radicals alone. more cytotoxic. Normal levels of peroxynitrite are essential to control cellular integrity. However, a growing number of findings suggest that abnormal concentrations of peroxynitrite may contribute to many human diseases, including ischemia-reperfusion injury, rheumatoid arthritis, septic shock, multiple sclerosis, stroke, Inflammatory bowel disease and cancer, etc. Due to the short lifetime of peroxynitrite, it is difficult to un...

Claims

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Application Information

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IPC IPC(8): C08F230/04C08F226/06G01N21/64
CPCC08F226/06C08F230/04G01N21/6428G01N21/6456G01N2021/6432
Inventor 刘淑娟赵强刘超陈泽晶孟祥春黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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