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Ruthenium (II) complex with curcumin derivative as ligand, and preparation method and application thereof

A technology of curcumin derivatives and complexes, applied in ruthenium organic compounds, compounds containing group 8/9/10/18 elements of the periodic table, drug combinations, etc., can solve low cell uptake and tissue distribution, and clinical application Obstacles, instability and other problems, to achieve the effect of improving hydrolysis stability, simple and convenient preparation method, and good inhibition of activity

Active Publication Date: 2019-10-08
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its clinical application has been hampered by its poor water solubility and instability under physiological conditions resulting in extremely low cellular uptake and tissue distribution.

Method used

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  • Ruthenium (II) complex with curcumin derivative as ligand, and preparation method and application thereof
  • Ruthenium (II) complex with curcumin derivative as ligand, and preparation method and application thereof
  • Ruthenium (II) complex with curcumin derivative as ligand, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Synthesis of complex 1:

[0054] Cis-(bpy) 2 RuCl 2 (48.40mg, 0.10mmol), curcumin (368.4mg, 1.0mmol), LiCl (42.0mg, 1.0mmol) in EtOH / H 2 O (30 / 10ml) was mixed, stirred and refluxed for 12h to obtain a black solution, the solvent was removed, and column chromatography DCM:MeOH=10:1 gave a dark brown powder.

[0055] Yield: 52.0%. Black-brown powder. Anal. Calcd (%) for C 41 h 35 ClN 4 o 6 Ru: C 60.33, H 4.32, N 6.86. Found: C 60.18, H 4.37, N 6.97; ESI-MS: m / z [M-Cl] + =781.16; 1 HNMR (600MHz, DMSO-d 6 )δ3.75(s,6H),5.96(s,1H),6.58-6.61(d,2H,J=15.8Hz),6.79-6.81(d,2H,J=8.2Hz),6.88-6.90(m ,2H),6.95-6.97(d,2H,J=15.7Hz),7.11-7.12(m,2H),7.29-7.32(t,2H,J=6.6Hz),7.76-7.80(m,4H), 7.91-7.93(t, 2H, J=7.6Hz), 8.16-8.19(t, 2H, J=7.6Hz), 8.64-8.65(d, 2H, J=5.3Hz), 8.74-8.76(d, 2H, J=8.0Hz), 8.85-8.86(d, 2H, J=8.1Hz); 13 C NMR (150MHz, DMSO-d 6 )δ56.02,101.87,110.68,116.08,122.42,123.97,124.02,126.26,126.39,126.93,127.31,135.44,136.47,137.04,148.39,148.77,149.81,153.23,15...

Embodiment 2

[0057] Synthesis of complex 2:

[0058] Cis-(phen) 2 RuCl 2 (53.2mg, 0.10mmol), curcumin (368.4mg, 1.0mmol), LiCl (42.0mg, 1.0mmol) in EtOH / H 2 O (30 / 10ml) was mixed, stirred and refluxed for 12h to obtain a black solution, the solvent was removed, and column chromatography DCM:MeOH=15:1 gave a dark brown powder.

[0059] Yield: 48.6%. Black-brown powder. Anal. Calcd (%) for C 45 h 35 ClN 4 o 6 Ru: C 62.53, H 4.08, N 6.48. Found: C 62.38, H 4.27, N 6.69; ESI-MS: m / z [M-Cl] + =829.16; 1 HNMR (600MHz, DMSO-d 6 )δ3.73(s,6H),6.05(s,1H),6.58-6.61(d,2H,J=15.9Hz),6.77-6.79(d,2H,J=8.2Hz),6.85-6.86(m ,2H),6.93-6.95(d,2H,J=15.8Hz),7.07(m,2H),7.53-7.55(m,2H),8.01-8.02(d,2H,J=5.1Hz),8.20- 8.22(m,2H),8.28-8.30(d,2H,J=8.8Hz),8.37-8.38(d,2H,J=8.9Hz),8.49-8.50(d,2H,J=8.0Hz),8.84 -8.85(d, 2H, J=8.1Hz), 9.12-9.13(d, 2H, J=5.0Hz), 9.66(m, 2H); 13 CNMR (150MHz, DMSO-d 6 )δ56.03,100.00,101.76,110.81,116.08,122.33,125.34,126.02,126.34,127.31,128.07,128.15,130.30,130.45,134.38,136.06,13...

Embodiment 3

[0061] Synthesis of complex 3:

[0062] [Ru(bpy)(dppn)Cl 2 ] (66.1mg, 0.1mmol), curcumin (368.4mg, 1.0mmol), LiCl (42.0mg, 1.0mmol) in EtOH / H 2 O (30 / 10ml) was mixed, stirred and refluxed for 12h to obtain a black solution, the solvent was removed, and column chromatography DCM:MeOH=15:1 gave a dark brown powder. Yield: 40.5%. Black-brown powder. Anal. Calcd (%) for C 53 h 39 ClN 6 o 6 Ru: C 64.14, H 3.96, N 8.47. Found: C 63.98, H 4.13, N 8.69; ESI-MS: m / z [M-Cl] + =957.21; 1 H NMR (600MHz, DMSO-d 6 )δ3.54(s,3H),3.79(s,3H),6.09(s,1H),6.60-6.61(d,1H,J=8.3Hz),6.69-6.71(d,2H,J=15.9Hz ),6.78-6.82(m,2H),6.94-6.95(m,1H),6.99(m,1H),7.06-7.09(d,1H,J=15.8Hz),7.15-7.17(m,2H), 7.21-7.23(t,1H,J=6.6Hz),7.63(m,2H),7.71-7.72(m,1H),7.83-7.84(d,1H,J=5.6Hz),7.88-7.93(m, 2H),8.09-8.10(m,1H),8.23-8.29(m,4H),8.75-8.77(d,1H,J=8.2Hz),8.84-8.90(m,3H),8.96(m,1H) ,9.03-9.04(d,2H,J=5.2Hz),9.26(m,1H),9.43(s,1H),9.57(s,1H); 13 C NMR(150MHz,DMSO-d6)δ55.70,56.10,102.66,110.86,116.06,116.19,122....

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Abstract

The invention discloses a ruthenium (II) complex with a curcumin derivative as a ligand, and a preparation method and application thereof. The structures of pharmaceutically acceptable salts and solvates of the ruthenium (II) complex with the curcumin derivative as the ligand are represented by formula I. By the method, the curcumin derivative with a diketone structure is used as the ligand for the first time, and a series of ruthenium (II) complexes are synthesized. The curcumin derivative is coordinately bonded with ruthenium (II), the hydrolytic stability of curcumin of the obtained ruthenium (II) complex is remarkably improved, and the ruthenium (II) complex has remarkable toxicity on several tumor cells; activity tests show that the ruthenium (II) complex has high anti-tumor activityand a potential anti-tumor application prospect; the ruthenium (II) complex has higher anti-tumor activity than the curcumin, cisplatin and the like.

Description

technical field [0001] The invention belongs to the field of anti-tumor ruthenium complexes, in particular to a ruthenium (II) complex with curcumin derivatives as a ligand, a preparation method thereof and a ruthenium (II) complex with curcumin derivatives as a ligand It is used for the preparation of antitumor drugs. Background technique [0002] Curcumin, a diketone polyphenol derived from the rhizome of the herb Curcuma longa, is known for its wide range of medicinal properties, curcumin has antibacterial, anti-inflammatory, antioxidant, antitumor and other biological activity. In terms of anti-tumor, curcumin can be used as an anti-proliferation, anti-metastasis and anti-angiogenesis drug to inhibit canceration and limit tumor growth, and exhibits extremely low toxicity to normal cells. However, their clinical applications are hampered by their poor water solubility and instability under physiological conditions resulting in extremely low cellular uptake and tissue di...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61P35/00A61K31/555
CPCC07F15/0053A61P35/00
Inventor 赵健
Owner SOUTHEAST UNIV
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