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A cyclometalated iridium complex with tumor hypoxia sensing and photoactivity and its application

A technology of iridium complexes and ring metals, which is applied in the direction of indium organic compounds, platinum group organic compounds, and medical preparations containing active ingredients, etc., can solve the problems of affecting the therapeutic effect and the decrease of photodynamic efficiency, and achieve good stability, Good mitochondrial targeting performance and enhanced photodynamic therapy activity

Active Publication Date: 2021-05-28
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, the process of PDT treatment itself will consume oxygen in the process of generating singlet oxygen, causing hypoxia and affecting its own therapeutic effect
[0003] The development of photosensitizers with type I photosensitization mechanism is a solution to the decrease in photodynamic efficiency caused by tumor hypoxia

Method used

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  • A cyclometalated iridium complex with tumor hypoxia sensing and photoactivity and its application
  • A cyclometalated iridium complex with tumor hypoxia sensing and photoactivity and its application
  • A cyclometalated iridium complex with tumor hypoxia sensing and photoactivity and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The synthesis of embodiment 1 complex Mito-IrL3

[0036]

[0037] Take the synthesized iridium complex chlorine bridge dimer Ir 2 (iqbt) 4 Cl 2 (154mg, 0.1mmol), L3 (157mg, 0.2mmol) and a mixed solvent of dichloromethane and methanol (12mL, 2:1, volume ratio) were placed in a reaction vessel, and heated to reflux for 6h under an argon atmosphere. After the reaction, the reaction mixture was cooled to room temperature, and ten times the equivalent of ammonium hexafluorophosphate was added. The suspension was stirred for 15 min and filtered to remove insoluble inorganic salts. The solvent was evaporated under reduced pressure, and column chromatography gave dark red Mito-IrL3 solid (56%). 1 H NMR (400MHz, CD 3 CN-d 3)δ9.21(dd, J=8.3, 1.4Hz, 1H), 9.07(dd, J=13.3, 8.8Hz, 2H), 8.30(dd, J=5.1, 1.4Hz, 1H), 8.15(dd, J =5.1, 1.2Hz, 1H), 7.97–7.80(m, 12H), 7.75–7.65(m, 18H), 7.55(d, J=8.8Hz, 2H), 7.45–7.34(m, 3H), 7.24– 7.13(m, 4H), 6.84-6.81(m, 2H), 6.70(q, J=7.6, 7.1...

Embodiment 2

[0038] The synthesis of embodiment 2 complex IrL4

[0039]

[0040] Take the synthesized iridium complex chlorine bridge dimer Ir 2 (iqbt) 4 Cl 2 (154mg, 0.1mmol), L4 (89mg, 0.2mmol) and a mixed solvent of dichloromethane and methanol (12mL, 2:1, volume ratio) were placed in a reaction vessel, and heated to reflux for 6h under an argon atmosphere. After the reaction, the reaction mixture was cooled to room temperature, and ten times the equivalent of ammonium hexafluorophosphate was added. The suspension was stirred for 15 min and filtered to remove insoluble inorganic salts. The solvent was evaporated under reduced pressure, and column chromatography gave dark red IrL4 solid (61%). 1 H NMR (400MHz, CD 3 CN-d 3 )δ9.13(d, J=8.3Hz, 1H), 9.04(dd, J=14.7, 8.5Hz, 2H), 8.25(d, J=4.4Hz, 1H), 8.12(d, J=4.4Hz, 1H), 7.96–7.72(m, 9H), 7.71–7.51(m, 6H), 7.48(d, J=8.7Hz, 2H), 7.42–7.32(m, 3H), 7.18-7.11(m, 4H) , 6.78(d, J=8.7Hz, 2H), 6.69-6.64(m, 2H), 6.19(t, J=7.1Hz, 2H), 3.91(...

Embodiment 3

[0043] Example 3 Study on the Response of Complexes Mito-IrL3 and IrL4 to Oxygen Concentration

[0044] The phosphorescence response of 10μM complexes Mito-IrL3 and IrL4 to oxygen concentration was studied in toluene.

[0045] Experimental results such as figure 1 as shown, figure 1 a is the phosphorescence emission spectrum of the complex Mito-IrL3 at different oxygen concentrations, figure 1 c is the attenuation curve of the intensity of the phosphorescent emission peak at 685 nm of Mito-IrL3 toluene solution (10 μM) with the increase of oxygen concentration. figure 1 b is the phosphorescence emission spectrum of the complex IrL4 at different oxygen concentrations, figure 1 d is the attenuation curve of the intensity of the phosphorescent emission peak at 685 nm of IrL4 toluene solution (10 μM) with the increase of oxygen concentration.

[0046] pass figure 1 a It can be seen that the phosphorescence intensity response experiment of the complex Mito-IrL3 to oxygen conce...

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Abstract

The present invention designs a new ring metal iridium complex based on Ir(III), which has the following structure: or the present invention can realize direct and reversible detection of oxygen concentration by utilizing its oxygen-dependent phosphorescent quenching characteristics. At the same time, the cyclometal iridium complex showed high anti-tumor activity in both normoxia and hypoxia modes of photodynamic therapy of tumors.

Description

technical field [0001] The invention belongs to the field of metal complexes, in particular to a cyclometal iridium complex with tumor hypoxia sensing and photoactivity and application thereof. Background technique [0002] The concentration of oxygen in normal tissue cells is about 5-20%, while the concentration of oxygen in solid tumors is lower than 4%, and the concentration of oxygen in areas far from tumor blood vessels even reaches 0%. Hypoxic tumor tissue is resistant to conventional radiation therapy. Similar to radiation therapy, the mechanism of photodynamic therapy also depends on the generation of singlet oxygen to kill tumor cells, and most of the photosensitizers reported so far are oxygen-dependent. Under hypoxic conditions, the PDT effect of the classic photosensitizer-hematoporphyrin derivatives is significantly inhibited, and the oxygen concentration critical value of its PDT activity is about 15-35mm Hg. Similarly, the photodynamic efficiency of the photo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00A61K41/00A61P35/00C09K11/06G01N21/64
CPCA61K41/0052A61K41/0057A61P35/00C07F15/0033C09K11/06C09K2211/185G01N21/6486
Inventor 何卫江郭子建韩重齐芬
Owner NANJING UNIV
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