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Water-soluble perylene imide compounds, usage as DNA intercalator, and applications thereof in growth inhibition of cancer cells

An amine compound, perylene imide technology, applied in the field of biopharmaceutical chemical synthesis, can solve problems such as research on anti-tumor properties, and achieve the effects of good practical application value, good water solubility, and high fluorescence quantum yield

Inactive Publication Date: 2014-01-08
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, perylene derivatives with good planar rigid structures have not been used as DNA intercalators to study their antitumor properties.

Method used

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  • Water-soluble perylene imide compounds, usage as DNA intercalator, and applications thereof in growth inhibition of cancer cells
  • Water-soluble perylene imide compounds, usage as DNA intercalator, and applications thereof in growth inhibition of cancer cells
  • Water-soluble perylene imide compounds, usage as DNA intercalator, and applications thereof in growth inhibition of cancer cells

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] 1) Suspend 0.7846g perylene anhydride (2.0mmol) and 0.34mL N,N-dimethylethylenediamine (6.0mmol) in 4mL water and stir evenly, then heat up to 100°C and reflux for 12h. After the temperature drops to room temperature, use Wash with 1wt% KOH aqueous solution and water, obtain red solid product P1 after vacuum drying, yield rate is 75%;

[0066] 1 H-NMR (400MHz, CF 3 COOD), δppm: 8.77(d, J=12.3Hz, 8H), 4.77(s, 4H), 3.75(s, 4H), 3.19(s, 12H). 13 C-NMR (100MHz, CF 3 COOD), δppm: 168.67, 138.82, 135.64, 131.77, 128.84, 126.85, 123.97, 60.73, 46.42, 38.74. MS (MALDI-TOF, m / z): CalcdforC 32 h 28 N 4 o 4 ,532.6;Found,533.6(M+H + ).

[0067] 2) 0.32g P1 (0.6mmol) and 1.02g p-toluenesulfonic acid (5.4mmol) were reacted in 3.5mL deionized aqueous solution at 50°C for 4h and then filtered. The precipitate was washed, centrifuged and dried to obtain the red solid product P2 with a yield of 85%.

[0068] 1 H-NMR (400MHz, CF 3 COOD), δppm:8.76(s,8H),7.77(s,13 C-NMR (100MHz...

Embodiment 2

[0077] 1) Add 0.81g perylene anhydride (2.1mmol) and 15mL tris(2-aminoethyl)amine (100.5mmol) into the reflux reaction flask, in which tris(2-aminoethyl)amine is also the reaction solvent; Heat to 100°C for 28 hours under atmosphere, then raise the temperature to 170°C and continue to react for 4 hours. After the temperature drops to room temperature, add a mixed solvent of ethanol and ether with a volume ratio of 1:3, filter, and then wash with toluene and ether The solid product was dried to obtain the red solid product P4 with a yield of 90%.

[0078] 1 H-NMR (400MHz, CF 3 COOD), δppm: 8.82-8.98(m,8H), 4.93(m,4H), 4.40(m,4H), 4.04-4.21(m,16H).UV-Vis(H 2 O,c=10 -5 M):λ max =498nm;Emission(H 2 O,λ ex =498nm):λ max =545nm.MS(MALDI-TOF,m / z):calcdforC 36 h 40 N 8 o 4 :648.75.Found:648.3.

[0079] 2) Add 138mg of P4 to a mixed solution consisting of 0.64mL85wt% formic acid solution and 0.44mL30wt% formaldehyde solution, stir and react at room temperature under nitroge...

Embodiment 3

[0087] (1) Add 0.644g of perylene monoanhydride (2.0mmol) and 0.34mL of N,N-dimethylethylenediamine (6.0mmol) into 3mL of water and stir evenly, then heat up to 110°C, reflux for 15h, after cooling down to room temperature, use Washed with 1wt% KOH aqueous solution and water, and dried in vacuo to obtain dark red solid product M1 with a yield of 79%;

[0088] (2) React 0.196g M1 (0.5mmol) with 0.51g p-toluenesulfonic acid (2.7mmol) in 2mL deionized aqueous solution at 55°C for 5h, then filter, remove the solvent by rotary evaporation, wash with ether precipitation, centrifuge, After drying, red solid product M2 was obtained with a yield of 88%;

[0089] M1 (0.196g, 0.5mmol) was reacted with 1.25mL methyl p-toluenesulfonate (2.7mmol) at 53°C for 19h, and after the temperature dropped to room temperature, filtered, the filtrate was concentrated by rotary evaporation, and then carried out with diethyl ether. The precipitate was washed, centrifuged and dried to obtain the red sol...

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Abstract

The invention discloses water-soluble perylene imide compounds, a usage as a DNA intercalator, and applications thereof in the growth inhibition of cancer cells, and belongs to the technical field of chemical synthesis of biological drugs. Through inducing cation amino functional groups into perylene anhydride derivatives and a perylene mono-anhydride system, the water solubility of the perylene anhydride derivatives and the perylene mono-anhydride system is greatly improved; furthermore, the cation amino functional groups are in a photo-stability combination with perylene derivatives, and thus a series of novel water-soluble perylene imide compounds are obtained. The synthesized water-soluble perylene imide compounds can effectively be embedded between the base pairs of DNA double helix of nucleus and be used as a DNA intercalator. The synthesized water-soluble perylene imide compounds have a planar rigid structure, so that the compounds can be specifically enriched around fixed tissue cell nucleus, the compounds have the advantages of strong fluorescence and easiness in fluorescent imaging, and have a similar effect as the DAPI effect of commercial cell nucleus dye. The synthesized water-soluble perylene imide compounds can effectively inhibit the growth of cancer cells such as U2OS, HTC116, Hela, AGS, etc., and have a very prominent anti-tumor effect.

Description

technical field [0001] The invention belongs to the technical field of biopharmaceutical chemical synthesis, and particularly relates to a water-soluble perylene imide compound and its application as a DNA intercalation agent and in inhibiting the growth of cancer cells. Background technique [0002] Perylene and its derivatives have good light, thermal and chemical stability, almost 100% fluorescence quantum yield, narrow fluorescence emission peak, can be separated from cell background fluorescence (395-479nm) and excellent dyeing performance. It has been widely used in the fields of organic optoelectronic devices, laser dyes and bioluminescent probes. [0003] Intercalator refers to the reversible interaction between polycyclic aromatic hydrocarbon small molecule substances and DNA. This type of molecule is small in size, in an electron-deficient state, and has a certain planar rigidity. It can be inserted between two stacked base pairs of DNA. The insertion process lead...

Claims

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Application Information

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IPC IPC(8): C07D221/18C07D471/06C12Q1/68G01N1/30C09K11/06A61P35/00
CPCC07D221/18C07D471/06C09K11/06C09K2211/1029
Inventor 尹梅贞许泽军刘柯兰郭坤茹沈杰
Owner BEIJING UNIV OF CHEM TECH
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