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Anti-tumor bipyridine methyl substituted manganese amino acid complex, and preparation and application thereof

A manganese complex and picolinyl amine group technology are applied in the field of targeted anti-tumor dipyridylmethyl substituted amino acid manganese complexes and their preparation, achieving the effect of strong recognition ability

Inactive Publication Date: 2009-04-22
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these manganese complexes are insoluble in water and have varying degrees of inhibition on the growth of normal cells.

Method used

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  • Anti-tumor bipyridine methyl substituted manganese amino acid complex, and preparation and application thereof
  • Anti-tumor bipyridine methyl substituted manganese amino acid complex, and preparation and application thereof
  • Anti-tumor bipyridine methyl substituted manganese amino acid complex, and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1 (best reaction condition example):

[0038] The ligand bis(2-pyridylamino)acetic acid (L 1 ) and MnCl 2 Dissolve in aqueous solution at a molar ratio of 1:1, control the reaction temperature at 50°C, and the reaction time for 3 hours, remove the solution to obtain a yellow manganese complex: [L 1 MnCl] or . Yield: 80%. Molecular formula: C 14 h 14 ClN 3 o 2 Mn. Elemental analysis: found C, 48.78%; H, 4.03%; N, 12.09; Mn, 15.92%; calculated C, 48.50; H, 4.07; N, 12.12; Infrared spectral data (IR, cm-1): 2936, 1624, 1572, 1493, 1035, 841, 776, 506.

[0039] Ligand L-bis(2-pyridylmethylamino) ethyl propionate) (L 2 ) and MnCl 2 Soluble in aqueous solution at a molar ratio of 1:1, the optimal reaction temperature is 50°C, and the optimal reaction time is 3 hours. Go to the solution to obtain a yellow manganese complex: [L 2 MnCl 2 ]or. Yield: 82%. Molecular formula: C 17 h 21 Cl 2 N 3 o 2 Mn. Elemental analysis: found C, 48.18%; H, 4.93%; N, ...

Embodiment 2

[0043] The ligand bis(2-pyridylamino)acetic acid (L 1 ) and MnCl 2 Dissolve in aqueous solution at a molar ratio of 1:1.3, control the reaction temperature to 80°C, and the reaction time to 6 hours, remove the solution to obtain a yellow manganese complex: [L 1 MnCl] or . Yield: 74%. Molecular formula: C 14 h 14 ClN 3 o 2 Mn.

[0044] The ligand bis(2-pyridylamino)propionic acid (L 2 ) and MnCl 2 Dissolve in methanol solution at a molar ratio of 1:1.2, add 0.45 g of NaOH, control the reaction temperature to 78°C, and the reaction time is 8 hours, evaporate the methanol to obtain the yellow manganese complex: [L 2 MnCl]. Yield: 65%. Molecular formula: C 17 h 21 Cl 2 N 3 o 2 Mn.

[0045] The ligand L-bis(2-pyridylaminopropionic acid) (L 3 ) and MnCl 2 Dissolve in methanol solution at a molar ratio of 1:1.2, add 0.45 g of NaOH, control the reaction temperature to 68°C, and the reaction time is 6 hours, evaporate the methanol to obtain the yellow manganese complex...

Embodiment 3

[0048] The ligand bis(2-pyridylamino)acetic acid (L 1 ) and MnCl 2 Dissolve in aqueous solution at a molar ratio of 1:1.1, control the reaction temperature to 30°C, and the reaction time to 2 hours, remove the solution to obtain a yellow manganese complex: [L 1 MnCl] or . Yield: 44%. Molecular formula: C 14 h 14 ClN 3 o 2 Mn.

[0049] The ligand bis(2-pyridylamino)propionic acid (L 2 ) and MnCl 2 Dissolve in methanol solution at a molar ratio of 1:1.2, add 0.15 g of NaOH, control the reaction temperature to 30°C, and the reaction time is 8 hours, evaporate the methanol to obtain a light yellow manganese complex: [L 2 MnCl]. Yield: 45%. Molecular formula: C 17 h 21 Cl 2 N 3 o 2 Mn.

[0050] The ligand L-bis(2-pyridylaminopropionic acid) (L 3 ) and MnCl 2 Dissolve in methanol solution at a molar ratio of 1:1.1, add 0.25 g of NaOH, control the reaction temperature to 38°C, and the reaction time is 3 hours, evaporate the methanol to obtain a light yellow manganese...

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Abstract

The invention relates to a novel targeted antitumor small molecular compound and the technical field of preparation thereof, in particular to a targeted antitumor bipyridine methyl substituted aminophenol manganese composition, a preparation method and application thereof. Two new chiral bipyridine methyl substituted aminophenol compounds (L-model) and four new bipyridine methyl substituted aminophenol ligand manganese compositions are synthesized through a chemical method; and a structure of the composition is determined by a physical means. An in-vitro antitumor activity test researches the influence of the composition on tumor cells and finds out that the manganese composition with small lipin distribution coefficient has strong inhibiting function on the growth of the tumor cells of A549, Hela, HepG-2 and Eca109; and the manganese composition synthesized by the L-model compositions has stronger capacity for identifying the tumor cells. Data of an animal test of the manganese composition show that the composition has good tumor inhibiting function. The manganese composition and mitochondria have direct action; and the new manganese composition can be used as a new antitumor activity medical composition with the mitochondria as a target spot.

Description

technical field [0001] The invention relates to the technical field of targeted anti-tumor novel small molecule compounds and their preparation, in particular to targeted anti-tumor bipyridylmethyl-substituted amino acid manganese complexes and their preparation methods and applications. Background technique [0002] Traditional chemotherapeutic drugs kill tumor cells by destroying the structure of DNA, inhibiting the expression of related proteins, and interfering with the metabolism of tumor tissues. However, the selectivity of chemotherapeutic drugs is poor. While killing tumor cells, it can also cause damage and death of normal cells in the body. Therefore, the research and development of novel, potent, and low-toxic antitumor drugs is an important topic in the field of life sciences. [0003] Most of the early inorganic anti-tumor drugs revolved around the classic platinum anti-tumor drugs, that is, divalent platinum complexes modeled on cisplatin. Scientists have done...

Claims

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Application Information

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IPC IPC(8): C07F13/00C07D213/38A61K31/555A61P35/00
Inventor 陈秋云刘颖奇
Owner JIANGSU UNIV
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