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RGD modified 5-fluorouracil and preparation method, nanostructure, activity and application thereof

A technology of fluorouracil and f-obzl, applied in the field of biomedicine, can solve the problems of compounds with anti-tumor, anti-inflammation, anti-thrombotic and anti-tumor metastasis effects

Inactive Publication Date: 2015-12-30
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the inventor has spent a lot of research effort and screened hundreds of compounds, no compound with anti-tumor, anti-inflammation, anti-thrombotic and anti-tumor metastasis effects has been obtained

Method used

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  • RGD modified 5-fluorouracil and preparation method, nanostructure, activity and application thereof
  • RGD modified 5-fluorouracil and preparation method, nanostructure, activity and application thereof
  • RGD modified 5-fluorouracil and preparation method, nanostructure, activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1 prepares 5-fluorouracil-1-base acetic acid

[0020] 1.30g (10mmol) of 5-fluorouracil was placed in a 100mL eggplant bottle, and 10mL of NaOH (30%) aqueous solution was added to dissolve it, and the reaction was heated up to 60°C. °C for 12 h, TLC (ethyl acetate: glacial acetic acid: water = 5:2:0.5) showed that the reaction was complete. Cool the reaction solution to room temperature, slowly add concentrated hydrochloric acid dropwise in an ice bath, adjust the pH to 2, stir for 0.5 h, a colorless solid precipitates, filter, wash the filter cake three times with ice water and diethyl ether, and dry in the shade. Yield 0.56 g (30%) of the title compound as a colorless powder. ESI-MS(m / e): 189[M+H] + . 1 HNMR (500MHz, DMSO-d 6 ): δ / ppm=13.21(s, 1H), 11.89(d, J=4.5Hz1H), 8.07(d, J=6.5Hz1H), 4.37(s, 2H).

Embodiment 2

[0021] Embodiment 2 prepares HCl Arg (NO 2 )-Gly-Asp(OBzl)-Val-OBzl

[0022] 1) Boc-Arg (NO 2 Preparation of )-Gly-OBzl

[0023] 19.94g (62.5mmol) Boc-Arg (NO 2 ) was dissolved in a 500mL reaction flask with 100mL of anhydrous THF, and 9.65g (68.75mmol) of N-hydroxybenzotriazole (HOBt) and 15.45g (75.0mmol) of dicyclohexylcarbodiimide (DCC ), stirred for 30min to obtain reactant A. Another 30.36g (85.53mmol) of Tos·Gly-OBzl was dissolved in 150mL of anhydrous THF in a 250mL reaction flask, and N-methylmorpholine (NMM) was slowly added dropwise in an ice bath to adjust the pH to 9 to obtain reactant B. Under ice bath, reactant B was added to reactant A, slowly added dropwise N-methylmorpholine (NMM) to adjust the pH to 9, stirred at room temperature for 12 h, thin layer chromatography TLC (dichloromethane: methanol: ice Acetic acid=20:1:0.1) showed that the reaction was complete. The reaction solution was filtered, the solvent was removed under reduced pressure, and the r...

Embodiment 3

[0034] Embodiment 3 prepares HCl Arg (NO 2 )-Gly-Asp(OBzl)-Phe-OBzl

[0035] 1) Boc-Arg (NO 2 Preparation of )-Gly-OBzl

[0036] Method is with embodiment 2 in 1).

[0037] 2) Boc-Arg (NO 2 )-Gly Preparation

[0038] Method is the same as 2) in embodiment 2.

[0039] 3) Preparation of Boc-Asp(OBzl)-Phe-OBzl

[0040] According to the operation of 1) in Example 2, by 22.10g (68.30mmol) Boc-Asp (OBzl), 10.10g (75.13mmol) N-hydroxybenzotriazole (HOBt), 16.90g (81.90mmol) bicyclic Hexylcarbodiimide (DCC) and 30.39 g (68.30 mmol) Tos·Phe-OBzl yielded 18.28 g (52.3%) Boc-Asp(OBzl)-Phe-OBzl as a colorless solid. ESI-MS(m / e): 561[M+H] + .

[0041] 4) Preparation of HCl Asp(OBzl)-Phe-OBzl

[0042] According to the operation of 4) in Example 2, 16.77g (91.2%) HCl·Asp(OBzl)-Phe-OBzl was prepared from 20.01g (35.74mmol) Boc-Asp(OBzl)-Phe-OBzl. ESI-MS(m / e): 459[M-H] - .

[0043] 5) Boc-Arg (NO 2 Preparation of )-Gly-Asp(OBzl)-Phe-OBzl

[0044] According to the operation of 1)...

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Abstract

The invention discloses a compound being 5-fluorouracil-1-acetyl-Arg-Gly-Asp tetrapeptide, a preparation method, nanostructure, anti-tumor effect and tumor cell adhesion, invasion and migration resisting effect thereof, and application thereof in medical science.

Description

technical field [0001] The present invention relates to 5-fluorouracil-1-ylacetyl-RGDV / F / S. It relates to its preparation method, its nanostructure, its in vivo and in vitro anti-tumor effects, and its anti-tumor cell adhesion, invasion, and migration effects. Therefore, the present invention relates to its application in the preparation of anti-tumor drugs and anti-tumor cell migration, adhesion and invasion drugs. The invention belongs to the field of biomedicine. Background technique [0002] 5-Fluorouracil is a commonly used clinical anti-tumor drug, which can be used for the treatment of various cancers, such as gastric cancer, liver cancer, colon and so on. Although 5-fluorouracil has a good curative effect on the treatment of tumors, it also has some problems that cannot be ignored. For example, the half-life in the body is short, the oral bioavailability is low, the dosage is similar to the toxic dose, and the toxic and side effects are large. In order to better ...

Claims

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Application Information

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IPC IPC(8): C07K7/06C07K1/107C07K1/06A61K38/08A61P35/00B82Y30/00
Inventor 赵明彭师奇王玉记吴建辉王松伟
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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