A kind of near-infrared metal iridium complex and its preparation method and application

A metal complex and near-infrared technology, which is applied in the fields of pharmaceutical formulations, indium organic compounds, chemical instruments and methods, etc., can solve the problems of unfavorable biological diagnosis and treatment application, single treatment effect, damage, etc., and achieve convenient and easy operation and reaction in the purification process. Effects in simple steps

Active Publication Date: 2019-03-22
SHANGHAI NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the vast majority of metal iridium complexes are still in the ultraviolet light region, and have not reached the 600-900nm bioluminescent region for biological treatment.
Moreover, the emission center is single, and the therapeutic effect is also single. It is well known that ultraviolet light has a certain harmful effect on the human body, which is not conducive to the application of biological diagnosis and treatment.

Method used

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  • A kind of near-infrared metal iridium complex and its preparation method and application
  • A kind of near-infrared metal iridium complex and its preparation method and application
  • A kind of near-infrared metal iridium complex and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Preparation of 1,10-phenanthroline-5,6-dione:

[0036] In the three-necked flask, add a mixture of 1,10-phenanthroline (5g) and potassium bromide (25g) to mix uniformly, add 100mL of concentrated sulfuric acid and 50mL of concentrated nitric acid dropwise at 0°C, and slowly Raise the temperature to 80°C and react at 80°C for 2h. After the reaction is complete, pour into 2L crushed ice and neutralize to neutral with sodium hydroxide, extract the product from water with dichloromethane, and collect the dichloromethane layer. Spin dry to obtain a yellow solid. Recrystallized with methanol to obtain 1,10-o-phenanthroline-5,6-dione.

[0037] 1 H NMR (400MHz, DMSO-d6) δ9.03 (dd, J = 4.6, 1.8Hz, 2H), 8.43 (dd, J = 7.8, 1.8Hz, 2H), 7.71 (dd, J = 7.8, 4.7Hz, 2H).

Embodiment 2

[0039] Preparation of 4-(1-phenyl-1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol:

[0040] 1,10-phenanthroline-5,6-dione (3mmol,), ammonium acetate (36mmol,) and p-hydroxybenzaldehyde (3mmol,) were dissolved in 25mL of glacial acetic acid, and aniline (3.6mmol,) was added , reflux overnight. Cool to room temperature, pour into 50mL of water, adjust the pH to be neutral with 25% aqueous ammonia solution, filter out the solid with suction, extract the filtrate with dichloromethane, spin dry, finally combine with the solid, and recrystallize from methanol to obtain 4-( 1-phenyl-1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol.

[0041] 1 H NMR (400MHz, DMSO-d6) δ9.92(s, 1H), 9.12(dd, J=4.3, 1.8Hz, 1H), 9.05(dd, J=8.1, 1.8Hz, 1H), 8.98(dd, J=4.3, 1.6Hz, 1H), 7.91(dd, J=8.1, 4.3Hz, 1H), 7.81–7.72(m, 5H), 7.52(dd, J=8.5, 4.3Hz, 1H), 7.45(d ,J=8.7Hz,2H),7.37(dd,J=8.5,1.6Hz,1H),6.76(d,J=8.7Hz,2H).

Embodiment 3

[0043] Add 4-(1-phenyl-1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol (1.6mmol) and NaH (1.6mmol) in the flask, and 25mL anhydrous DMF, stirred at room temperature for 1 h, added ethyl cyanine dye (0.8 mmol), stirred at room temperature for 24 h, extracted with DCM and water, freeze-dried, and column chromatography with a mixed solvent of dichloromethane and methanol , to obtain the imidazole ligand of the cyanine dye.

[0044] 1 H NMR (400MHz, CDCl 3)δ9.30(s,2H),9.09(s,1H),8.03(d,J=8.5Hz,2H),7.97–7.90(m,6H),7.86(dd,J=8.0,4.7Hz,1H ),7.76(d,J=8.5Hz,2H),7.68(t,J=7.4Hz,1H),7.61(s,4H),7.51–7.39(m,6H),7.32(d,J=2.9Hz ,2H),7.14(d,J=8.7Hz,2H),6.24(s,2H),4.36(d,J=7.2Hz,4H),2.83(s,4H),2.10(s,2H),1.65 (s,12H),1.49(t,J=7.2Hz,6H).

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Abstract

The invention relates to fluorescent probe design technology in biological fields, in particular to a near-infrared iridium metal complex, a preparation method thereof and an application. According to the preparation method, imidazole ligand and NaH are dissolved in anhydrous dimethyl formamide and mixed at the indoor temperature in the atmosphere of nitrogen or inert gas, cyanine dye with ethyl is added into the mixture, the mixture is mixed at the indoor temperature ranging from 18 DEG C to 26 DEG C and extracted by methylene dichloride and water, and extract is freeze-dried, cyanine dye imidazole ligand is obtained by column chromatography. The cyanine dye imidazole ligand and an iridium dichloro-bridged complex with C-N ligand are dissolved in mixed liquor of the methylene dichloride and methyl alcohol, heating is performed at the temperature ranging from 50 DEG C to 65 DEG C, and backflow is performed under the light-proof condition for 1-12 hours. Saturated KPF6 methyl alcohol solution is added into the mixed liquor, and the near-infrared iridium metal complex is obtained by extraction filtration, rotary evaporation and column chromatography separation and purification. The emission center of the complex ranges from 580 nanometers to 825 nanometers under excitation of 400 nanometers, and the complex can simultaneously serve as a photo-thermal conversion reagent and a photodynamic reagent and can be applied to photo-thermal and photodynamic collaborative treatment.

Description

technical field [0001] The invention relates to a fluorescent probe design technology in the biological field, in particular to a near-infrared metal iridium complex and a preparation method and application thereof. Background technique [0002] As fluorescent probes, metal iridium complexes play an important role in bioimaging, due to their metal-ligand charge transfer triplet state exhibiting excellent photophysical properties, such as: large Stokes shift, absorption The spectrum and emission spectrum are tunable, the fluorescence quantum yield is high, and the phosphorescence lifetime is long. In particular, iridium atoms in metallic iridium complexes can induce strong spin-inductive coupling to enhance the interstitial crossing efficiency between excited singlet states and excited triplet states, reaching the energy side of excited triplet state iridium metal complexes Released in the form of phosphorescence, while generating active oxygen or singlet oxygen through ener...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06A61K41/00
CPCA61K41/0052A61K41/0057C07F15/0033C09K11/06C09K2211/185A61K2300/00
Inventor 杨红靳红玉王杰杨琪邓晶晶崔丽丽杨仕平
Owner SHANGHAI NORMAL UNIVERSITY
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