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High-efficiency and low-toxicity anticancer compound synthesized by autocatalysis in cells and living bodies and its synthesis method

A synthesis method and compound technology, applied in the direction of steroidal compounds, osmium organic compounds, ruthenium organic compounds, etc., can solve the problems of cell damage, toxic side effects of cancer patients, limited application, etc., and achieve good tumor growth, good anti-tumor effect, Effect with little side effects

Active Publication Date: 2021-11-12
NANJING NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the "indiscriminate attack" of cisplatin drugs on cells makes it kill tumor cells and also cause serious damage to normal cells, causing great toxic and side effects to cancer patients, such as nephrotoxicity, ear Toxicity and neurotoxicity, etc., make patients suffer a lot
In addition, cisplatin drugs have low activity on certain tumor cells (breast cancer, colon cancer, etc.) and primary and acquired drug resistance, etc., this series of defects seriously limits its application in clinical treatment

Method used

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  • High-efficiency and low-toxicity anticancer compound synthesized by autocatalysis in cells and living bodies and its synthesis method
  • High-efficiency and low-toxicity anticancer compound synthesized by autocatalysis in cells and living bodies and its synthesis method
  • High-efficiency and low-toxicity anticancer compound synthesized by autocatalysis in cells and living bodies and its synthesis method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042]

[0043] Under argon protection, 0.5 mmol rhein, 0.5 mmol 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride, 0.5 mmol triethylamine and 0.5 mmol 4-dimethylaminopyridine Dissolve in DMF (N,N-dimethylformamide) and stir overnight (reaction temperature is room temperature, stirring time is 10-24h), after the reaction is completed, DMF is removed by rotary evaporation, washed with water, extracted with chloroform, Dry, separate and purify by column chromatography to obtain a yellow powdery product with a yield of 56%. 1 H NMR (400MHz, DMSO, 25°C, TMS) δ11.91(s, 1H), 9.41(t, J=5.5Hz, 1H), 8.15(d, J=1.7Hz, 1H), 7.89-7.80(m , 1H), 7.79-7.72(m, 1H), 7.42(dd, J=8.4, 1.2Hz, 1H), 4.10(dd, J=5.5, 2.5Hz, 1H), 3.35(s, 5H); 13 C NMR (100MHz, DMSO, 25°C, TMS) δ191.85, 181.46, 164.18, 161.83, 161.57, 141.26, 138.04, 134.05, 133.67, 125.01, 122.97, 119.92, 118.18, 118.01, 116.37, 83 40.31, 40.11, 39.90, 39.69, 39.48, 39.27, 29.27. ESI-MS [Rhein-alkyne] + : Theoretical valu...

Embodiment 2

[0047]

[0048] Under argon protection, 0.03mmol of dichloro(p-methylisopropylphenyl)ruthenium (II) dimer and 0.06mmol of 4-methyl-2,2-bipyridine-azide (prepared by reference: Xun , Z.Q.et al.J.Mater.Chem.A, 2015, 3, 12965-12971) was dissolved in methanol solution and reacted at 65°C for 24h; Stir at room temperature for 0.5-24 hours, and finally add diethyl ether to precipitate to obtain a relatively pure yellow powder product with a yield of 43%, named Ru-N 3 . 1 H NMR (400 MHz, CD 3 OD, 25°C, TMS) δ9.43(d, J=5.9Hz, 1H), 9.29(d, J=5.8Hz, 1H), 8.45(d, J=19.1Hz, 2H), 7.68(ddd, J =44.9, 5.9, 1.4Hz, 2H), 6.15-6.05(m, 2H), 5.88-5.76(m, 2H), 4.83(s, 2H), 2.65(m, 4H), 2.28(s, 3H), 1.06 (dd, J = 6.9, 1.0 Hz, 6H). ESI-MS (+): theoretical value: [Ru-N 3 -PF 6 ] + : Theoretical value: m / z: 496.08, experimental value: m / z 496.25.

[0049] 0.05mmol Rhein-alkyne prepared in Example 1, 0.05mmol Ru-N 3 and 0.01 mmol of copper sulfate and 0.01 mmol of sodium ascorbate were dissolv...

Embodiment 3

[0053]

[0054] Under the protection of argon, 0.05 mmol of dichloro(p-methylisopropylphenyl) osmium (II) dimer and 0.1 mmol of 4-methyl-2,2-bipyridine-azide were dissolved in methanol, 70 React at ℃ for 48 hours, add 20 times the equivalent of ammonium hexafluorophosphate to it after the reaction, stir at room temperature for 0.5-24 hours, and finally add ether to precipitate to obtain a relatively pure yellow powder product with a yield of 32%, named Os -N 3 . 1 H NMR (400MHz, CD 3 OD, 25°C, TMS) δ9.21(d, J=5.9Hz, 1H), 9.02(d, J=5.8Hz, 1H), 8.33(d, J=19.1Hz, 2H), 7.52(ddd, J =44.9, 5.9, 1.4Hz, 2H), 6.31-6.15(m, 2H), 5.74-5.59(m, 2H), 4.81(s, 2H), 2.58(m, 4H), 2.23(s, 3H), 1.11 (dd, J = 6.9, 1.0 Hz, 6H). ESI-MS (+): theoretical value: [Os-N 3 -PF 6 ] + : Theoretical value: m / z: 586.14, experimental value: m / z 586.35.

[0055] 0.06mmol Rhein-alkyne prepared in Example 1, 0.06mmol Os-N 3 and 0.012 mmol of cuprous iodide were dissolved in DMF and stirred for 12 h. Aft...

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Abstract

The invention discloses a high-efficiency and low-toxicity anti-cancer compound synthesized by autocatalysis in cells and living bodies. Orthogonal reaction synthesis; among them, metal complexes are platinum, ruthenium, iridium or osmium metal complexes, organic active molecules refer to small organic molecules with certain biological activities, such as anti-inflammatory, antibacterial, anti-angiogenesis and Anti-cancer and other biologically active small organic molecules. The precursor of the organic active molecule is a chemically modified organic active molecule, and the organic active molecule is rhein, oleanolic acid, ursolic acid, naphthalimide, coumaric acid, nonanthrenecarboxylic acid or indomethacin kind of. The invention also discloses a synthesis method of the above-mentioned anticancer compound. The anticancer compound of the present invention has good antitumor effect no matter it is synthesized by extracellular reaction or intracellular reaction.

Description

technical field [0001] The present invention relates to a class of metal complexes based on organic active molecules, and also relates to the self-catalyzed synthesis method of the above-mentioned metal complexes in cells and living bodies and the application in the preparation of anti-tumor drugs or anti-cancer drug components, belonging to biomedical technology field. [0002] technical background [0003] Metal anti-tumor drugs represented by cisplatin have been widely used in the clinical treatment of various types of cancer, and have shown good therapeutic effects on various cancers such as ovarian cancer, testicular cancer, bladder cancer and colorectal cancer, among which The cure rate for testicular cancer patients is as high as 90%. However, the "indiscriminate attack" of cisplatin drugs on cells makes it kill tumor cells and also cause serious damage to normal cells, causing great toxic and side effects to cancer patients, such as nephrotoxicity, ear Toxicity and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C07F17/02C07J63/00A61P35/00C12P17/16C12P33/20
CPCA61P35/00C07F15/002C07F15/0033C07F15/0046C07F15/0053C07F15/0093C07F17/02C07J63/008C12P17/165C12P33/20
Inventor 刘红科薛旭玲陶钦吕梦迪陈俊钱晓婷
Owner NANJING NORMAL UNIVERSITY
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