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D-A-D structure-based metal complexes with near-infrared light absorption function, and application thereof

A technology of metal complexes and complexes, applied in the direction of ruthenium organic compounds, indium organic compounds, platinum group organic compounds, etc., can solve the problems of short absorption wavelength, hindering the clinical application of metal photosensitizers, and weak skin penetration

Active Publication Date: 2020-10-23
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, most metal photosensitizers absorb wavelengths below 600nm, and there is a common problem of short absorption wavelengths, so the skin penetration is weak, which seriously hinders the clinical application of metal photosensitizers.

Method used

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  • D-A-D structure-based metal complexes with near-infrared light absorption function, and application thereof
  • D-A-D structure-based metal complexes with near-infrared light absorption function, and application thereof
  • D-A-D structure-based metal complexes with near-infrared light absorption function, and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Synthesis of complex 1:

[0053]

[0054] Cis-(bpy) 2 RuCl 2 (48.40mg, 0.10mmol), ligand L (82.6mg, 0.1mmol) in EtOH / H 2 Mix in O (30 / 10ml), stir and reflux at 80°C for 12h to obtain a dark green solution, remove the solvent, and perform column chromatography with DCM:MeOH=10:1 to obtain a green powder. Yield: 45.5%. Anal. Calcd(%) for C 74 h 50 Cl 2 N 12 RuS: C 67.78, H 3.84, N 12.82. Found: C 67.63, H 3.82, N 12.85; 1 HNMR (600MHz, DMSO-d 6 )δ7.13-7.16(t, 4H, J=7.4Hz), 7.22-7.24(m, 12H), 7.40-7.45(m, 10H), 7.61-7.63(t, 2H, J=6.6Hz), 7.82 -7.85(m,4H),7.97-8.00(m,6H),8.15-8.18(m,4H),8.24-8.26(t,2H,J=7.8Hz),8.93-8.97(m,4H),9.08 -9.09 (m, 2H, J = 7.8 Hz) ppm. NMR spectrum such as figure 2 shown.

Embodiment 2

[0056] Synthesis of complex 2:

[0057]

[0058] Dimer of iridium (1.0mmol), ligand L (2.0mmol) in CH 2 Cl 2 / MeOH (20 / 20ml), stirred and refluxed at 40°C for 24h, the solvent was removed, column chromatography DCM:MeOH=10:1 gave a bright green powder. Yield: 45.7%. Bright-green powder. Anal. Calcd (%) for C 82 h 62 ikB 10 o 4 S: C65.17, H 4.14, N 9.27. Found: C65.04, H 4.16, N 9.21; 1 H NMR (600MHz, DMSO-d 6 )δ1.57(m,4H),3.28(m,4H),3.82(m,2H),3.91(m,2H),4.52(m,2H),6.27-6.28(d,2H,J=7.3Hz ), 6.94-6.96(t, 2H, J=7.3Hz), 7.05-7.07(t, 2H, J=7.5Hz), 7.12-7.14(t, 4H, J=7.2Hz), 7.19-7.20(m, 14H), 7.38-7.40(m, 8H), 7.68-7.69(d, 2H, J=7.9Hz), 7.88-7.92(m, 6H), 8.12(m, 2H), 8.24-8.27(m, 4H) ,9.14(m,2H)ppm. NMR spectrum such as image 3 shown.

Embodiment 3

[0060] Synthesis of complex 3:

[0061]

[0062] dimer of aromatic ruthenium (1.0mmol), ligand L (2.0mmol) in CH 2 Cl 2 / MeOH (40 / 20ml), stirred and refluxed at 40°C for 24h, the solvent was removed, and column chromatography DCM:MeOH=15:1 gave a green powder with a yield of 43.7%. 1 H NMR (600MHz, DMSO-d 6 )δ0.98-0.99(d,6H,J=6.2Hz),2.25(m,3H),2.69(m,1H),6.24(m,2H),6.47(m,2H),7.15-7.20(m ,8H),7.22-7.23(d,8H,J=7.6Hz),7.42-7.45(m,8H),7.79(m,4H),8.15(m,2H),8.98(m,2H),10.04( m,2H)ppm. NMR spectrum such as Figure 4 shown.

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Abstract

The invention discloses D-A-D structure-based metal complexes with a near-infrared light absorption function, and application thereof. The metal complexes or pharmaceutically acceptable salts or solvates thereof are shown as a formula I, a formula II or a formula III, and singlet oxygen tests show that the compounds have relatively strong singlet oxygen generation capability under the excitation of near-infrared light; photo-thermal research shows that the compounds have high photo-thermal conversion efficiency, so that the compounds are expected to become a potential photosensitizer for clinical photodynamic therapy and are effectively applied to preparation of optical therapeutic drugs. In addition, a preparation method of the metal complexes with the near-infrared absorption function issimple and is very beneficial to industrial production.

Description

technical field [0001] The invention belongs to anti-tumor iridium and ruthenium complexes, and relates to a kind of metal iridium or ruthenium complexes with near-infrared light absorption based on D-A-D structure and applications thereof. Such complexes can generate singlet oxygen under near-infrared light excitation, At the same time, it has strong photothermal conversion efficiency, so it is expected to become a potential photosensitizer for clinical photodynamic therapy. Background technique [0002] Photodynamic therapy (PDT) is another therapy after the traditional treatment. It has shown great application prospects in the treatment of cancer and other malignant diseases, as well as skin diseases (psoriasis, acne), eye diseases (age-related macular degeneration) . PDT activates the photosensitizer in the tumor tissue by irradiating the tumor site with light of a specific wavelength, and the photosensitizer molecules in the excited state can undergo energy transfer or...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06A61K41/00A61P35/00
CPCC07F15/0053C07F15/0033C07F15/0046C09K11/06A61K41/0057A61K41/0052A61P35/00C09K2211/185
Inventor 赵健许正杨博超张廉臣
Owner SOUTHEAST UNIV
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