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Anti-tumor metal iridium (III) complex as well as preparation method and application thereof

An anti-tumor drug, metal iridium technology, applied in the direction of anti-tumor drugs, indium organic compounds, platinum group organic compounds, etc., can solve the problems of interaction, difficulty, short remission period, etc., and achieve inhibition of tumor growth and high yield , the effect of strong tumor growth

Active Publication Date: 2017-11-28
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

From the 1980s to the 1990s, carboplatin, circulating platinum, and oxaliplatin were developed. However, due to the poor water solubility of platinum drugs, short remission period, slow excretion, and severe side effects, long-term use will cause drug resistance
This is mainly because of the chemical inertness of iridium itself, and the ligands of its complexes are difficult to dissociate, which makes it difficult to interact with biomolecules (such as DNA, proteins, etc.) in the body, thus making it difficult to produce biological activity.
Mura et al. synthesized two iridium complexes with a structure similar to the ruthenium complex NAMI-A, and found in experiments that these two compounds have no good inhibitory effect on various tumor cell lines, and do not bind to DNA or proteins.

Method used

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  • Anti-tumor metal iridium (III) complex as well as preparation method and application thereof
  • Anti-tumor metal iridium (III) complex as well as preparation method and application thereof
  • Anti-tumor metal iridium (III) complex as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthetic BDPIP ligand

[0031] 1.5mmol (0.315g) of 1,10-phenanthroline-5,6-dione and 1.5mmol (0.165g) of 2-methyl-3-(3,4-methylenedioxyphenylcyclo)propane Add aldehyde to the reaction vessel, add 30mmol (2.31g) ammonium acetate and 20mL glacial acetic acid solvent, heat to reflux for 2 hours, cool, adjust the pH value to close to 7.0 with ammonia water, filter with suction to obtain a light red solid, wash with 30mL distilled water three times, The BDPIP ligand is obtained, and then the obtained BDPIP ligand is dried in a vacuum oven.

[0032] Yield: 76%.Anal.Calcd for C 23 h 18 N 4 o 2 : C, 72.22; H, 4.75; N, 14.66.Found: C, 72.35; H, 4.91; N, 14.53%.IR(KBr, cm -1 ):3434b, 2972m, 1622s, 1566w, 1542w, 1502w, 1489w, 1442m, 1410w, 1355m, 1281m, 1248s, 1190m, 1125m, 1099m, 1064m, 1038s, 929s, 808s, 739s.ESI=-MS:m / z 383[M+1].

[0033] The main synthesis route of the above-mentioned process is as follows:

[0034]

Embodiment 2

[0036] In this experiment, the iridium metal complex [Ir(ppy) 2 (BDPIP)]PF 6

[0037] Complexes [Ir(ppy) 2 (BDPIP)]PF 6 Synthesis of: [Ir(ppy) 2 Cl] 2 Mix with BDPIP ligand at a molar ratio of 1:2, in a mixed solvent of 42mL dichloromethane and methanol (2:1 by volume), reflux under argon protection for 6 hours, cool to room temperature, add NH 4 PF 6 The solution was then stirred at room temperature for 2 hours to obtain a red precipitate, which was filtered under reduced pressure to obtain a large amount of solid. The obtained solid mixture was dissolved in dichloromethane, suction-filtered, and the insoluble matter was filtered off to obtain a yellow liquid, which was then rotary evaporated under reduced pressure to obtain an orange-yellow solid.

[0038] Yield: 72%. Anal. Calc for C 45 h 34 N 6 o 2 IrPF 6 : C, 52.52; H, 3.33; N, 8.17%.Found: C, 52.68; H, 3.51; N, 8.23%.IR(KBr, cm -1 ):3399w, 3137s, 1625m, 1608m, 1584w, 1502w, 1479s, 1402s, 1316w, 1282w, 1268w...

Embodiment 3

[0042] The present embodiment detects the iridium metal complex [Ir(ppy) by experiment 2 (BDPIP)]PF 6 Inhibitory effect on proliferation of tumor cell A549

[0043] Cytotoxicity test: In this example, the in vitro cytotoxicity of the compounds was studied by the MTT method. First, trypsinize the target cells cultured into a single layer, count them with a cell counter, and add appropriate RPMI-1640 to make the number of cells reach 10 5 For each milliliter, take 0.1mL of cell-containing culture solution in a 96-well cell culture plate, and then place the inoculated cell plate at 37°C, 5% CO 2 cultured in an incubator for 24 h. Add different concentrations of compounds to the discarded liquid of the monolayer cell culture plate, and the concentration of the test compound reaches 10 -6 to 10 -4 M, and set up a control group (0.1mL medium was added to the cell culture plate), placed in 37°C, 5% CO 2 After culturing in the incubator for 48 hours, the culture medium was aspir...

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Abstract

The invention provides an anti-tumor metal iridium (III) complex, belonging to the technical field of biological medicine. The chemical formula of the anti-tumor metal iridium (III) complex is [Ir(ppy)2(BDPIP)]PF6. Furthermore, the invention also provides a preparation method of the anti-tumor metal iridium (III) complex and application of the anti-tumor metal iridium (III) complex in anti-tumor drugs. The anti-tumor metal iridium (III) complex has a very strong inhibiting effect for the growth of tumor cells, especially for the growth of cells A549, can induce the apoptosis of the tumor cells, has an IC50 value of 3.6mu M, and can be used as a medicine for treating tumor A549; in vivo tests prove that the tumor inhibiting rate of the anti-tumor metal iridium (III) complex reaches up to 63.84%. The preparation method of the metal iridium (III) complex is high in yield.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and in particular relates to an anti-tumor metal iridium (III) complex and its preparation method and application. Background technique [0002] In 1969, Rosenberg et al. found that cisplatin (cis-dichlorodiammine platinum (II)) had antitumor activity. From the 1980s to the 1990s, carboplatin, circulating platinum, and oxaliplatin were developed. However, due to the poor water solubility of platinum drugs, short remission period, slow excretion, and severe side effects, long-term use will cause develop drug resistance. In addition to platinum complexes, the antitumor effect of non-diamond metal complexes has also been widely concerned. [0003] Compared with ruthenium(II) and gallium complexes, its congener iridium(III) has received less attention for its potential antitumor potential. This is mainly because of the chemical inertness of iridium itself, and the ligands of its complexes are ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61P35/00
CPCC07F15/0033
Inventor 刘云军万丹黄宏靓汤兵衣巧艳
Owner GUANGDONG PHARMA UNIV
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