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5-Fu-ruthenium (II) complex with anti-tumor and antibacterial activity and preparation method and application thereof

A 5-fu-, complex technology, applied in the field of medicine, can solve problems such as hindering DNA synthesis, therapeutic effect and long-term application limitations, and significant first-pass metabolism

Active Publication Date: 2020-12-11
GUANGDONG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 5-Fluorouracil (5-Fu) is an antimetabolite drug that inhibits thymidylate synthase. Its structure is similar to the metabolite uracil in tumor cells. It competes with each other in the same system enzymes, blocks the metabolic link, and hinders DNA synthesis. , thereby inhibiting the proliferation of tumor cells, but due to its low selectivity, significant first-pass metabolism, low lipophilicity and narrow therapeutic window, its therapeutic effect and long-term application are limited

Method used

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  • 5-Fu-ruthenium (II) complex with anti-tumor and antibacterial activity and preparation method and application thereof
  • 5-Fu-ruthenium (II) complex with anti-tumor and antibacterial activity and preparation method and application thereof
  • 5-Fu-ruthenium (II) complex with anti-tumor and antibacterial activity and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0065] Example 1 Preparation Example

[0066] (1) Preparation of Ligand L:

[0067] Dissolve 0.128g [1,10]-phenanthroline-5-amino (0.66mmol) in an appropriate amount of N,N-dimethylformamide, heat and stir for 30min, and then take an equivalent amount of 1-(5 -Bromopentyl)-5-fluorouracil (0.194g, 0.66mmol), catalyst tris(dibenzylideneacetone)dipalladium (0.006g, 0.007mmol), tris(o-methylphenyl)phosphorus (abbreviation: P( o-tolyl) 3 , 0.008g, 0.026mmol), sodium tert-butoxide (abbreviation: NaOt-Bu, 0.041g, 0.43mmol) and 1,1'-binaphthyl-2,2'-bisdiphenylphosphine (0.016g, 0.026mmol) , add 10mL N,N-dimethylformamide, under the protection of Ar, reflux at 100°C for 12h, after the reaction solution is cooled, dilute with an appropriate amount of ether, filter with diatomaceous earth, wash the diatomaceous earth with ether, and combine the organic phase and concentrate as much as possible. Yield: 32.5%.

[0068] Elemental Analysis C 21 h 20 FN 5 o 2 (Molecular weight is 393...

Embodiment 2

[0082] Embodiment 2 in vitro antitumor activity test

[0083] (1) Anti-tumor activity test (MTT method): The anti-tumor ability of 5-Fu-ruthenium (Ⅱ) complexes is mainly determined by MTT method: MTT method is a classic method for determining drug toxicity, and the operation steps are roughly as follows. Add 4,000 Hela cells to well culture plate, CO 2 After culturing in the incubator for 24 hours, add different concentrations of drugs diluted with the medium, and then incubate in the incubator for 44 hours, then add MTT, absorb the medium after 4 hours, add DMSO, shake well and measure the OD at 595nm value.

[0084] The test results are shown in Table 1 below:

[0085] Table 1 Results of in vitro antitumor activity of 5-Fu-ruthenium(Ⅱ) complexes

[0086]

[0087] a IC 50 is the concentration of the complex corresponding to the inhibition of tumor Hela by 50%. The experimental data is the average value obtained after three parallel experiments. b SI is the selectivi...

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Abstract

The invention provides a 5-Fu-ruthenium (II) complex with anti-tumor and antibacterial activity and a preparation method and application thereof. The 5-Fu-ruthenium (II) complex has a structure as shown in a formula I which is described in the specification. Compared with traditional small organic molecules, the complex has the advantages that in-vivo permeation and retention effects are enhanceddue to the fact that the complex contains metal ions and is charged, and the metal complex has a multi-coordination structure and can be used for modifying different ligands so that excellent biological activity of the complex is achieved. Experimental results show that the 5-Fu-ruthenium (II) complex provided by the invention not only has excellent anti-tumor activity, but also has certain antibacterial activity. The complex mainly enters cells in an energy-dependent mode and is positioned in lysosome, the intracellular active oxygen level is increased, the cell cycle is retarded in the G0 / G1phase in a concentration-dependent mode, and finally apoptosis and autophagy of cancer cells are induced. The complex has a certain inhibition effect on staphylococcus aureus and pseudomonas aeruginosa.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a 5-Fu-ruthenium (II) complex with antitumor and antibacterial activities, a preparation method and application thereof. Background technique [0002] 5-Fluorouracil (5-Fu) is an antimetabolite drug that inhibits thymidylate synthase. Its structure is similar to the metabolite uracil in tumor cells. It competes with each other in the same system enzymes, blocks the metabolic link, and hinders DNA synthesis. , thereby inhibiting the proliferation of tumor cells, but due to its low selectivity, significant first-pass metabolism, low lipophilicity and narrow therapeutic window, its therapeutic effect and long-term application are limited. Transition metal ruthenium compounds not only have good physical and chemical properties such as large Stokes shift, photobleaching resistance, long phosphorescent lifetime and high quantum yield, but also the ligands are easy to modify, and funct...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61P35/00A61P31/04
CPCC07F15/0053A61P35/00A61P31/04
Inventor 孙静潘南莲陈嘉曦廖嘉欣黄敏莹陈冰冰李琳
Owner GUANGDONG MEDICAL UNIV