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Water-soluble perylene bisimide compound and application of water-soluble perylene bisimide compound serving as DNA intercalator in anticancer cells and tumors

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 water solubility and high fluorescence quantum yield

Active Publication Date: 2014-07-23
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 bisimide compound and application of water-soluble perylene bisimide compound serving as DNA intercalator in anticancer cells and tumors
  • Water-soluble perylene bisimide compound and application of water-soluble perylene bisimide compound serving as DNA intercalator in anticancer cells and tumors
  • Water-soluble perylene bisimide compound and application of water-soluble perylene bisimide compound serving as DNA intercalator in anticancer cells and tumors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] 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%;

[0071] 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): Calcd for C 32 h 28 N 4 o 4 ,532.6;Found,533.6(M+H + ).

[0072] 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%.

[0073] 1 H-NMR (400MHz, CF 3 COOD), δppm:8.76(s,8H),7.77(s,13 C-NMR (100M...

Embodiment 2

[0082] 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%.

[0083] 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):calcd forC 36 h 40 N 8 o 4 :648.75.Found:648.3.

[0084] 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 nitrog...

Embodiment 3

[0092] (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%;

[0093] (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%;

[0094] 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 a water-soluble perylene bisimide compound and an application of a water-soluble perylene bisimide compound for preparing DNA intercalators, inhibiting cancer cell growth and resisting tumors, belonging to the technical field of biological drug chemical synthesis. A cationic amino functional group is introduced into perylene derivatives and single perylene systems, so that the water solubility is greatly improved, the amino functional group is bound to light stability of perylene derivatives, and a series of novel water-soluble perylene bisimide compounds are obtained. The synthetic compound can be effectively embedded into DNA double helix base pairs of the cell nucleus and can serve as a DNA intercalator. The synthetic compound has a planar rigid structure, can be specifically enriched on a fixed tissue cell nucleus, is high in fluorescence intensity and easy in fluorescence imaging and can be compared favorably with commercial cell nucleus dyes DAPI. The synthetic compound can effectively inhibit growth of cancer cells such as U2OS, HCT116, HeLa and AGS, has an obvious antitumor effect and can be applied to preparing antitumor drugs.

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 in anti-cancer cells and tumors. 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 leads to the heli...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06C07D221/18C12Q1/68A61K31/4745A61K31/473A61P35/00
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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