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Iridium coordination aza-pyrrolidone optical diagnosis and treatment reagent as well as preparation method and application thereof

A technology of pyrrolidone and diagnostic reagent, which is applied in the field of iridium-coated azapyrrolidone photodiagnostic reagent and preparation thereof, can solve the problems of unfavorable in vivo application, short absorption wavelength, low penetration depth, etc., and achieves good photothermal and photodynamic effects, The effect of reducing damage and simple process

Active Publication Date: 2020-08-18
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, traditional iridium complexes face short absorption wavelengths, mostly located in the ultraviolet-visible region, resulting in low penetration depth during application, which is not conducive to the application at the living body level

Method used

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  • Iridium coordination aza-pyrrolidone optical diagnosis and treatment reagent as well as preparation method and application thereof
  • Iridium coordination aza-pyrrolidone optical diagnosis and treatment reagent as well as preparation method and application thereof
  • Iridium coordination aza-pyrrolidone optical diagnosis and treatment reagent as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: Preparation of azapyrrolidone auxiliary ligand

[0041]

[0042] Preparation of Compound 2: Compound 1 (26mmol) and benzaldehyde (26mmol) were dissolved in methanol solution, then 50% NaOH aqueous solution was added, and after stirring and reacting at room temperature for 22 hours, the pH was adjusted to neutrality, and the methanol solvent was removed by filtration to obtain Pale yellow solid powder, then washed three times with water to remove the salt to give the white product 2. Yield: 91%.

[0043] 1 H NMR (400MHz, CDCl 3 )δ (ppm): 8.01 (d, J = 8.4Hz, 2H), 7.78 (d, J = 16.4Hz, 1H), 7.53 (d, J = 8.4Hz, 2H), 7.35 (d, J = 16.4Hz ,2H),6.98(d,J=8.4Hz,2H),6.69(d,J=8.4Hz,2H),3.77-3.65(s,6H). 13 C NMR (100MHz, CDCl 3 )δ (ppm): 188.85, 169.10, 162.20, 151.91, 144.95, 131.97, 130.49, 130.27, 122.82, 116.63, 114.27.

[0044] The preparation of compound 3: in the methanol solution of compound 2 (5mmol), add 10mL diethylamine and 15mL nitromethane, after ...

Embodiment 2

[0049] Embodiment 2: Preparation of iridium coordination azapyrrolidone complex

[0050]

[0051] The preparation of compound 7: compound 6 (0.14mmol) and iridium trichloride trihydrate are dissolved in the mixed solution of ethylene glycol ether and water, under N 2 Stir overnight at 110°C under atmosphere, then add water to the reaction solution, at this time, a large amount of yellow solid precipitates, the solution is removed by suction filtration, and then washed repeatedly with ethanol to obtain a yellow solid 7.

[0052] Preparation of Compound 8: Compound 7 (0.10 mmol) and silver trifluoromethanesulfonate were dissolved in an aqueous ethanol solution, and refluxed at 100° C. for 24 h. Subsequently, the reaction solution was removed, the obtained solid was dissolved in dichloromethane, the filter residue was removed by filtration, and the filtrate was spin-dried to obtain a yellow solid 8.

[0053] Preparation of compound IrDipy-7: Compound 5 was dissolved in tetrah...

Embodiment 3

[0055] Embodiment 3: Absorption and emission spectrum test of iridium complex IrDipy-7

[0056] The spectrum test concentration used is 10μM, and the test solvent is CH 2 Cl 2 solution, when measuring the emission spectrum, the excitation wavelength is 690nm.

[0057] The absorption and emission spectra of IrDipy-7 as image 3 and Figure 4 shown. The complex shows strong absorption at 400-500nm in the ultraviolet region and 600-800nm ​​in the near-infrared region. In particular, the complex can be excited by near-infrared light, which greatly reduces the impact of the excitation light source on the cells when doing cell imaging experiments. damage.

[0058] Its emission is wide, and the emission peak is located at 730nm. Red light emission increases the penetration depth of biological tissue, making it more suitable for biological imaging.

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Abstract

The invention discloses an iridium coordination aza-pyrrolidone optical diagnosis and treatment reagent as well as a preparation method and application thereof. The complex is composed of a cyclo-metal ligand, a metal center and an aza-pyrrolidone auxiliary ligand, the overall preparation process is simple, and the prepared complex has a long absorption wavelength, so that the complex has a deep tissue penetration depth in the field of living body application and is more suitable for biological imaging. The complex has strong absorption in an ultraviolet region and a near-infrared region, andcan be excited by near-infrared light, so that the damage of an excitation light source to a biological sample can be weakened; and the complex can be used in the field of photodynamic photo-thermal combined therapy guided by biological imaging, and has important application prospects.

Description

technical field [0001] The invention belongs to the technical fields of organic photoelectricity and biomaterials. In particular, it relates to an iridium-coordinated azapyrrolidone photodiagnosis and therapy reagent with near-infrared absorption, a preparation method thereof, and applications thereof in the fields of fluorescence imaging, photothermal imaging, photoacoustic imaging, photodynamic and photothermal combined therapy, and the like. Background technique [0002] As a disease with high mortality rate, tumor seriously threatens human health. Although traditional tumor treatment methods, such as surgery, chemotherapy, and radiotherapy, have achieved certain results in the treatment of tumors, their further application is limited due to problems such as high toxicity and side effects and drug resistance. In contrast, photodynamic and photothermal combined therapy is increasingly popular as a non-invasive, non-toxic, targeted and efficient tumor treatment method. Thi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K49/00A61K49/22A61K41/00
CPCC07F15/0033A61K49/0002A61K49/0021A61K49/22A61K41/0052A61K41/0057
Inventor 赵强冯伟赵梦龙刘淑娟黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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