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Aspirin-Arg-Gly-Asp-Val conjugate, synthesis, nano structure, and application thereof as drug carrying system

A technology of arg-gly-asp-val and aspirin, applied in the field of biomedicine

Inactive Publication Date: 2014-12-17
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the interaction of integrins with RGD sequence peptides has been widely used to prepare macromolecular drug carriers, no studies have used a single RGD tetrapeptide for direct drug delivery.

Method used

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  • Aspirin-Arg-Gly-Asp-Val conjugate, synthesis, nano structure, and application thereof as drug carrying system
  • Aspirin-Arg-Gly-Asp-Val conjugate, synthesis, nano structure, and application thereof as drug carrying system
  • Aspirin-Arg-Gly-Asp-Val conjugate, synthesis, nano structure, and application thereof as drug carrying system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1 prepares Boc-Arg (NO 2 )-Gly-OBzl

[0033] 10.0g (31.3mmol) Boc-Arg (NO 2 ) was dissolved in 100ml of anhydrous tetrahydrofuran (THF), cooled in an ice bath, and 4.3g (31.3mmol) of N-hydroxybenzotriazole (HOBt) and 6.4g (31.3mmol) of dicyclohexylcarbonyldi imine (DCC), the reaction solution was stirred under ice bath for 10 min. Add 10.6g (31.3mmol) Tos·Gly-OBzl and 3.5g (31.3mmol) N-methylmorpholine (NMM), and stir at room temperature for 24h. The reaction mixture was filtered to remove dicyclohexylurea (DCU). The filtrate was concentrated under reduced pressure, and the residue was dissolved in 150 ml of ethyl acetate. The resulting solution was sequentially washed with 5% NaHCO 3 Washing with aqueous solution, washing with saturated NaCl aqueous solution, 5% KHSO 4 Washing with aqueous solution and saturated NaCl aqueous solution. Anhydrous Na for organic phase 2 SO 4 After drying and filtering, the filtrate was concentrated to dryness under red...

Embodiment 2

[0034] Embodiment 2 prepares Boc-Arg (NO 2 )-Gly

[0035] 11.85g (25.4mmol) Boc-Arg (NO 2 )-Gly-OBzl was dissolved in 50ml of methanol, cooled in an ice bath, 12ml of sodium hydroxide-methanol solution (1M) was added, stirred for 1 hour, the reaction solution was neutralized with 2M hydrochloric acid to pH=7, concentrated under reduced pressure to remove methanol, and the remaining The product was acidified with 2M hydrochloric acid to pH=2, and concentrated under reduced pressure to remove water. The residue was dissolved with 100 ml of ethyl acetate. The resulting solution was washed with saturated NaCl aqueous solution. Anhydrous Na for organic phase 2 SO 4 Dry, filter, and concentrate the filtrate to dryness under reduced pressure. The residue was triturated with a small amount of petroleum ether to obtain 8.9 g (93%) of the title compound, which was directly cast into the next reaction. ESI-MS(m / e): 377[M-H] - .

Embodiment 3

[0036] Example 3 Preparation of Boc-Asp(OBzl)-Val-OBzl

[0037]According to the method of Example 1, 10.7 g (89%) of the title compound was obtained as an oil from 7.7 g (23.7 mmol) of Boc-Asp (OBzl) and 9.0 g (23.7 mmol) of Tos.Val-OBzl. ESI-MS(m / e): 513[M+H] + .

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Abstract

The invention relates to an aspirin-Arg-Gly-Asp-Val conjugate, synthesis, a nano structure, and an application thereof as a drug carrying system. The invention discloses a novel aspirin-Arg-Gly-Asp-Val (A-RGDV) conjugate, and also discloses a preparation method and an application thereof as an antithrombotic agent. The A-RGDV is characterized in that in the blood the A-RGDV can be selectively transferred as nano particles, when the A-RGDV nano particles arrive at the thrombus forming parts, the A-RGDV reacts with the GPIIb / IIIa receptors on the platelet surfaces, and thus aspirin is released during the process. So the A-RGDV can be used as a target drug delivery system for aspirin. A-RGDV has a strong antithrombotic activity, and has a good clinical application prospect. The structural formula of A-RGDV is represented in the description.

Description

technical field [0001] The present invention relates to a novel aspirin-Arg-Gly-Asp-Val (A-RGDV) conjugate, its preparation method and its application as an antithrombotic agent. A-RGDV is characterized in that it can be selectively transported in the form of nanoparticles in the blood, and after reaching the site of thrombus formation, it interacts with the GPIIb / IIIa receptors on the surface of activated platelets to release aspirin. Therefore, A-RGDV is a targeted drug delivery system for aspirin. A-RGDV has strong antithrombotic activity and has good clinical application prospects. The invention belongs to the field of biomedicine. The following is the structural formula of A-RGDV. [0002] Background technique [0003] Aspirin has been widely used clinically for more than a century to treat acute inflammation, pain, cardiovascular disease, stroke, pregnancy complications, cancer, diabetes, and Alzheimer's disease, demonstrating its remarkable efficacy. For differ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/11C07K1/06C07K1/02A61K47/42A61K31/616A61P7/02
Inventor 彭师奇赵明吴建辉王玉记马海萍
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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