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Application of ruthenium pyridine (II) complexes as antitumor drugs

A technology of ruthenium pyridine complexes, which is applied in the application field of ruthenium pyridine complexes as anti-tumor drugs, and can solve problems such as unreported and lack of research work

Inactive Publication Date: 2014-06-18
TENTH PEOPLES HOSPITAL OF TONGJI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the research work on the design of antitumor drugs based on the structural advantages of polypyridine ruthenium(II) complexes is relatively lacking
[0004] The Chinese journal "Journal of Higher School Chemistry", No. 04, 1999, published a paper "Δ-and Λ-[Ru(bpy)_2(HPIP)] 2+ CD Spectra Proof of Different Bonding Rates of Two Isomers to Calf Thymus DNA", showing the interaction of the above-mentioned polypyridine ruthenium(II) complex with calf thymus DNA, but At present, there is no report about the polypyridine ruthenium (II) complex of the following structural formula in the preparation of anti-tumor applications

Method used

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  • Application of ruthenium pyridine (II) complexes as antitumor drugs
  • Application of ruthenium pyridine (II) complexes as antitumor drugs
  • Application of ruthenium pyridine (II) complexes as antitumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1 The microwave-assisted synthesis of compound I

[0030] To a 30 mL microwave Pyrex reaction tube add: cis -[Ru(bpy) 2 Cl 2 ]·2H 2 O (105 mg, 0.2 mmol), p -BrPIP (compound name is 2-(4-bromophenol)-1H-imidazol[4, 5f ][1,10]phenanthroline) (113 mg, 0.3 mmol), 15 mL ethanol. Stir for 10 min under nitrogen protection, and react at 130 °C for 20 min with microwave assistance. After the reaction was completed, spin-dried under reduced pressure to obtain a red solid, which was dried in a vacuum desiccator to obtain an orange-yellow solid. The crude product was dissolved in acetonitrile, passed through a 200-300 mesh neutral alumina column, and the main red component was washed with acetonitrile, and the solvent was spin-dried under reduced pressure to obtain a brown-red solid with a yield of 85.7%. ESI-MS (in CH 3 CN, m / z ): 789.2 ([M-H] + , calculated value: 788.1); 1 H NMR (in DMSO-d 6 , δ / ppm) 9.06 (d, J =8.3 Hz, H c , 2H), 8.86 (d, J =8.1 Hz...

Embodiment 2

[0031] Example 2 The microwave-assisted synthesis of compound II

[0032] by cis -[Ru(phen) 2 Cl 2 ]·2H 2 O alternative cis -[Ru(bpy) 2 Cl 2 ]·2H 2 O, synthetic method is basically the same as embodiment 1 [Ru (bpy) 2 ( p -BrPIP)] (ClO 4 ) 2 The synthesis of brown-red solid was obtained, and the yield was 87.9%. ESI-MS (in CH 3 CN, m / z ): 837.3 ([M+H] + , calculated value: 836.2); 1 H NMR (in DMSO-d 6 , δ / ppm) 9.03 (d, J =8.3, H c , 2H), 8.76 (d, J =8.3, H 4, 7 , 4H), 8.38 (s, H 5,6 , 4H), 8.29–8.20 (d, J =8.4, H j , 2H), 8.12 (d, J =5.3, 1.2 Hz, H 2’ , 2H), 8.07 (d, J =5.2, 1.2 Hz, H 2 , 2H), 7.99 (d, J =5.3, 1.2 Hz, H a , 2H), 7.85 (d, J =8.6 Hz, H i , 2H), 7.79 (t, J =6.6 Hz, H b , 2H), 7.76 (t, J =6.6 Hz, H 3 , 4H); 13 C NMR (101 MHz, DMSO-d 6 ) δ 152.65 (d, J =12.9 Hz), 150.13 (s), 147.17 (d, J =9.0 Hz), 145.38 (s), 136.87 (s), 136.65 (s), 132.16 (s), 130.41 (s), 128.40 (s), 128.09 (s), 126.29 (s), 126.07 (s), 123.42(s).

Embodiment 3

[0033] Example 3 Compound I was tested for growth inhibition of highly metastatic human breast cancer cell line (MDA-MB-231)

[0034] Will MDA-MB-231 Cells were inoculated at a certain density in 96-well plates in RPMI1640 medium (containing 0.1% penicillin, 0.1% streptomycin, and 1% glutamine) containing 10% calf serum, 5% CO 2 After culturing at 37°C for 24 h, replace with fresh medium with different concentrations of Compound I (1 μg / mL working solution prepared with PBS, diluted with medium when used) and continue culturing for 48 h; then each well Add 50 μL of pre-cooled 50% trichloroacetic acid (TCA, the final concentration is 10%), let stand for 5 min, wash with distilled water 5 times, air dry, add 100 μL of MTT staining solution, dye for 10 min, 1% acetic acid solution The cells were washed 4 times to remove unbound dye, air-dried, and finally 150 μL of 10 mmol / L Tris solution was added, and after thorough mixing, the OD value was measured with a microplate reader...

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Abstract

The invention relates to an application of ruthenium pyridine (II) complexes as antitumor drugs. In particular, the inhibition effect of two ruthenium pyridine (II) complexes on growth of a highly invasive human breast cancer cell line (MDA-MB-231), a hepatoma carcinoma cell (HepG2), a human esophageal carcinoma cell (EC-1), a human breast cancer cell (MCF-7) and a normal breast epithelial cell (HAcat) is tested. The result shows that the complexes have inhibiting effects on four cancer cells to different extents, and in particular, the complex I has strong inhibiting effect on the MDA-MB-231 and the complex II has a very remarkable inhibiting effect on MDA-MB-231 and HepG2. The two complexes have weak toxicity to the HAcat and show good selectivity.

Description

technical field [0001] The invention relates to the fields of chemistry and pharmacy, in particular to the application of a pyridine ruthenium (II) complex as an antitumor drug. Background technique [0002] Cancer has gradually replaced cardiovascular and other diseases as the number one killer threatening human life and health. In the drug development strategies of governments around the world, the development of new anti-tumor drugs with high efficiency, low toxicity and high selectivity has also become an important strategic goal. The great success of cisplatin in anti-tumor and the marketing of various modified platinum compounds in the later stage have attracted a large number of researchers to study the anti-tumor mechanism of transition metal complexes. Because cisplatin compounds have relatively large toxic and side effects on the human body, including nephrotoxicity, ototoxicity, neurotoxicity and gastrointestinal toxicity, it is easy to cause nephrotoxicity, nause...

Claims

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Application Information

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IPC IPC(8): A61K31/555A61P35/00
Inventor 孙奋勇梅文杰温传俊潘秋辉
Owner TENTH PEOPLES HOSPITAL OF TONGJI UNIV
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