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Carboline ruthenium complex as well as preparation method and application thereof

A technology of carboline ruthenium complexes and complexes is applied in the field of carboline ruthenium complexes and their preparation, and can solve the problems that the biological activity needs to be improved and the like

Active Publication Date: 2020-09-29
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition to platinum-based antitumor drugs, ruthenium-based metal complexes have been extensively studied in the past few decades due to their unique biochemical characteristics, and some ruthenium metal complexes have been shown to inhibit tumor growth and anti-tumor metastasis. However, it has no inhibitory effect on primary tumors, and its biological activity still needs to be improved

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  • Carboline ruthenium complex as well as preparation method and application thereof
  • Carboline ruthenium complex as well as preparation method and application thereof
  • Carboline ruthenium complex as well as preparation method and application thereof

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preparation example Construction

[0051] In the present invention, when the carboline ruthenium complex has the structure shown in formula I, the preparation method comprises the following steps:

[0052] Will R 1 The corresponding ligand compound, cis-dichlorobis(2,2'-bipyridine) ruthenium dihydrate, ethanol and water are mixed for the first complexation reaction, and the carboline ruthenium with the structure shown in formula I is obtained complexes.

[0053] In the present invention, the R 1 The corresponding ligand compound is the ligand compound 3, the ligand compound 5 or the ligand compound 6 in table 1; the R 1 The corresponding ligand compound and cis-dichlorobis(2,2'-bipyridyl)ruthenium dihydrate ((bpy) 2 RuCl 2 (2H 2 O)) The molar ratio is preferably 1:1, the (bpy) 2 RuCl 2 (2H 2 O), the usage ratio of ethanol and water is preferably 0.2mmol: (9-11) mL: (9-11) mL, more preferably 0.2 mmol: 10 mL: 10 mL. The present invention preferably R 1 Corresponding ligand compound, (bpy) 2 RuCl 2 (2H ...

Embodiment 1

[0067] Preparation of 3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (4H-KLSS, ligand compound 1)

[0068] Measure 40mL of distilled water into a 250mL eggplant bottle, add 0.1mL of concentrated sulfuric acid (98wt%) and stir for 5 minutes; add 2.50g of tryptophan for ultrasonic dissolution, put the rotor on the stirrer and stir; add 5mL of formaldehyde, room temperature (25 ℃ ) under stirring conditions for 4 hours (monitor the reaction by TLC, the developer is ethyl acetate: water: glacial acetic acid = 3: 1: 1, and the product is light yellow after ninhydrin staining); after the reaction Add ammonia water to adjust the pH value of the resulting system to 6, let it stand for 30min, a large amount of off-white solid precipitates out, then use the Buchner funnel to suction filter, collect the filter cake and place it in a watch glass to dry to obtain 2.568g of the target compound, namely 3S- 1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acid as a white solid. ESI-MS:217[M+...

Embodiment 2

[0070] preparation (bpy) 2 Ru(II)(4H-KLSS)(complex 1a)

[0071] Weigh 44mg (0.2mmol) Ligand Compound 1 in a 50mL eggplant bottle, then add 104mg (0.2mmol) (bpy) 2 RuCl 2 (2H 2 O) and 20mL N,N-dimethylformamide (DMF), after ultrasonic dissolution, react at 80°C for 6h; after the reaction is completed, filter while hot, and dry the filter cake to obtain 88mg of the target compound, namely (bpy) 2 Ru(II)(4H-KLSS), is purple-red solid powder. ESI / MS(m / z):629.3[M-Cl] + .

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Abstract

The invention provides a carboline ruthenium complex as well as a preparation method and application thereof, and belongs to the technical field of biological medicines. The series of carboline ruthenium complexes provided by the invention not only can inhibit tumor metastasis, but also have an inhibition effect on primary tumors, and are high in biological activity. The complex provided by the invention has a selective killing effect on tumor cells, can form relatively stable spherical nano-molecules in vitro, and can interact with DNA and transferrin; in vivo experiments, an S180 mouse sarcoma model evaluates the inhibition effect of the complex on primary tumors, and the LLC anti-metastasis model evaluates the anti-metastasis effect of the complex on lung cancer; in addition, ICP-MS isutilized to determine the distribution of the complex 2b in a living body, immunohistochemistry and immunofluorescence analysis are carried out on tumor tissues at the same time, and results show thatthe complex 2b can inhibit the growth of primary tumors in the living body and can inhibit the metastasis of tumors on lungs.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to a carboline ruthenium complex and a preparation method and application thereof. Background technique [0002] With the increasing incidence of tumors year by year, the research and development of anticancer drugs has received more and more attention. Cisplatin is a metal complex antineoplastic drug widely used clinically. In addition to platinum-based antitumor drugs, ruthenium-based metal complexes have been extensively studied in the past few decades due to their unique biochemical characteristics, and some ruthenium metal complexes have been shown to inhibit tumor growth and anti-tumor metastasis. However, it has no inhibitory effect on primary tumors, and its biological activity still needs to be improved. Contents of the invention [0003] The purpose of the present invention is to provide carboline ruthenium complexes and their preparation methods and applications. ...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61P35/00
CPCC07F15/0053A61P35/00
Inventor 王玉记刘家望桂琳卢玉朱迪阿依江
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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