Preparation method and antineoplastic activity of novel ruthenium complex containing 4,4'-dibromo-2,2'-dipyridyl

A technology of complexes and anti-cancer activity, applied in containing 4, can solve the problems of low water solubility, large toxic and side effects, drug resistance of cancer cells, etc., and achieve the effect of enhancing binding ability and high affinity

Active Publication Date: 2016-08-24
JIANGNAN UNIV
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Problems solved by technology

Drugs such as cisplatin have problems such as high toxicity and side effec

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  • Preparation method and antineoplastic activity of novel ruthenium complex containing 4,4'-dibromo-2,2'-dipyridyl
  • Preparation method and antineoplastic activity of novel ruthenium complex containing 4,4'-dibromo-2,2'-dipyridyl
  • Preparation method and antineoplastic activity of novel ruthenium complex containing 4,4'-dibromo-2,2'-dipyridyl

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Embodiment 1

[0020] A compound containing 2,3-bis(4-nitrophenyl)pyrazine[2,3-f][1,10]phenanthroline and 4,4'-dibromo-2,2'-bipyridine The synthesis of novel Ru (II) complex comprises the following process steps:

[0021] (1) Synthesis of 4-nitrobenzoin

[0022] Put 20mL of 4-nitrobenzaldehyde and 30mL of absolute ethanol into a 250mL three-necked flask, stir, add 7mL of an aqueous solution containing 3.5g of vitamin B1 (8.75mmol), and adjust the pH of the reaction system to 8-9 with 3mol / L NaOH solution , After stirring for 1 h, let it stand at room temperature for more than 24 h. When a large amount of white solids are precipitated, filter with suction, and rinse the filter cake with deionized water three times (20 mL×3). After the solid was dried, it was recrystallized with absolute ethanol to obtain 15.4 g of white needle-like crystals with a yield of 76.9%. The reaction formula was:

[0023]

[0024] (2) Synthesis of 4-nitrobenzil

[0025] Add 2.10 g of 4-nitrobenzoin (10 mmol), ...

Embodiment example 2

[0036] Implementation Case 2: Anti-tumor activity experiment of Ru(II) complexes

[0037]The invention adopts the MTT method to measure the toxicity of Ru(II) complexes to tumor cells in vitro, and takes liver cancer cell line Hep G2 and human melanoma cell line F10-B16 as detection objects. The cultured cancer cell suspension was inoculated into a clean 96-well culture plate, 200 μL / well, and the obtained Ru(II) complex was added to the cell culture plate in a concentration gradient (6.25 μM-100 μM), and each Well 100 μL, the concentration of each Ru(II) complex is 2 parallel plates, the blank control group does not add Ru(II) complex, only culture solution is added. Place in a 37°C incubator at a constant temperature for 48 hours, add 20 μL of 5 g / L MTT to each well, continue to incubate for 5 hours, then add 100 μL of SDS to each well, and measure the absorbance value of each well at a wavelength of 570 nm on a microplate reader after 10 hours. The inhibition rate was calc...

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Abstract

The invention provides a preparation method and antineoplastic activity of a novel ruthenium complex containing 4,4'-dibromo-2,2'-dipyridyl. The preparation method is characterized by comprising the following steps that 1, 4-nitrobenzaldehyde and vitamin B1 with the mole ratio of 22.4:1 are synthesized into an intermediate product 1; 2, the intermediate product 1 and NBS with the mole ratio of 1:1.5 are synthesized into an intermediate product 2; 3, the intermediate product 2 and 5,6-diamine-1,10-o-phenanthroline with the mole ratio of 1:1 are synthesized into an intermediate product 3; 4, ruthenium trichloride and 4,4'-dibromo-2,2'-dipyridyl with the mole ratio of 1:2 are synthesized into an intermediate product 4; 5, the intermediate product 3 and the intermediate product 4 are synthesized into the Ru(II) complex. The Ru(II) complex has planar aromatic heterocyclic ring and has quite high DNA affinity. In addition, both nitryl and bromine have the strong electrophilic effect, and the combining capacity of the complex and DNA is enhanced.

Description

technical field [0001] The present invention relates to a compound containing 2,3-bis(4-nitrophenyl)pyrazine[2,3-f][1,10]phenanthroline and 4,4'-dibromo-2,2'- A preparation method of a novel Ru(II) complex of bipyridyl, and the antitumor activity of the Ru(II) complex. Background technique [0002] Metal complexes interact with DNA through electrostatic binding, channel binding, and insertion binding. Among them, the insertion combination method is the best, because the insertion into the base pair of DNA can directly damage the base pair and affect the DNA replication of cancer cells. If the metal complex can recognize the gene mutation site of cancer cells, insert into the mismatched base pair, and prevent its replication, it can be used as a good anticancer drug to treat genetic diseases fundamentally. [0003] In 1969, cisplatin was first reported to have anti-tumor activity, and was subsequently used in clinical trials. Drugs such as cisplatin have problems such as h...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61K31/555A61P35/00
Inventor 郑昌戈谢晨李明月
Owner JIANGNAN UNIV
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