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Octapeptide modified dexamethasone, preparation, nanostructure and application

A technology of dexamethasone and -his-gly-glu, which is applied in the field of biomedicine and can solve the problems of no obvious improvement in curative effect and the like

Active Publication Date: 2020-05-05
北京恒润泰生医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there is no significant improvement in efficacy, the side effects of osteoporosis and thrombosis no longer occur

Method used

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  • Octapeptide modified dexamethasone, preparation, nanostructure and application
  • Octapeptide modified dexamethasone, preparation, nanostructure and application
  • Octapeptide modified dexamethasone, preparation, nanostructure and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Preparation of Boc-Gly-Glu(OBzl)-OBzl

[0027] Weigh (30.0mmol) 5.294g (30.0mmol) of Boc-Gly, 4.353g (32.5mmol) of HOBt, dissolve in dry tetrahydrofuran (THF), stir under an ice bath, add dropwise 7.406g (35.9mmol) of DCC dissolved in THF, and activate 30 After 5 minutes, 15.572g (31.3mmol) TosH·Glu(OBzl)-OBzl was added, NMM adjusted pH=8, reacted at room temperature for 12 hours, TLC(CH 2 Cl 2 / MeOH=20 / 1), indicating that the raw material points disappeared. DCU was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was dissolved in 200 mL of ethyl acetate. The ethyl acetate solution obtained was sequentially used with 50 mL of saturated sodium bicarbonate aqueous solution, 50 mL of saturated sodium chloride aqueous solution, 50 mL of saturated potassium hydrogen sulfate aqueous solution, and 50 mL of saturated chlorine Washed with sodium chloride aqueous solution, 50 mL saturated sodium bicarbonate aqueous solution, 50 ...

Embodiment 2

[0028] Example 2 Preparation of HCl·Gly-Glu(OBzl)-OBzl

[0029] To 13.0g (26.9mmol) Boc-Gly-Glu(OBzl)-OBz under ice bath was added 200mL 4M ethyl acetate solution of hydrogen chloride, after reaction for 2 hours, TLC(CH 2 Cl 2 / MeOH=20 / 1) shows the disappearance of raw material spots. Concentrate under reduced pressure. The residue was dissolved in anhydrous ethyl acetate and concentrated under reduced pressure. This operation was repeated 3 times. The residue was dissolved with anhydrous ether and concentrated under reduced pressure. This operation is also repeated 3 times. 12.5 g (96.1%) of the title compound was obtained.

Embodiment 3

[0030] Example 3 Preparation of Boc-His(Boc)-Gly-Glu(OBzl)-OBzl

[0031] Weigh 1.400g (3.9mmol) Boc-His(Boc), 0.561g (4.0mmol) HOBt, dissolve in dry tetrahydrofuran (THF), stir under ice bath, add dropwise 0.975g (4.7mmol) DCC dissolved in THF, After stirring and activating for 30 minutes, add 2.0g (4.8mmol) HCl·Gly-Glu(OBzl)-OBzl, adjust pH=8 by NMM, react at room temperature for 12 hours, TLC(CH 2 Cl 2 / MeOH=20 / 1), indicating that the raw material points disappeared. DCU was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was dissolved in 100 mL of ethyl acetate. The ethyl acetate solution obtained was successively used with saturated sodium bicarbonate 20 mL saturated sodium bicarbonate aqueous solution, saturated 20 mL sodium chloride aqueous solution, and 20 mL saturated potassium hydrogen sulfate aqueous solution. , 20mL saturated sodium chloride aqueous solution, 20mL saturated sodium bicarbonate aqueous solution, 20mL saturated...

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PUM

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Abstract

The invention discloses octapeptide Lys(AA-Asp-Gly-Arg)-His-Gly-Glu modified dexamethasone shown as the formula, wherein the AA is L-Val or L-Phe. The invention also discloses a preparation method, a nano-structure thereof, and an inhibitory effect of the compound on mouse retroauricular cardiac transplantation immunological rejective reaction and xylene induced inflammation reaction, and further discloses that the compound does not generate osteoporosis and thrombus side effects like dexamethasone. Therefore, the octapeptide modified dexamethasone disclosed by the invention has definite application prospect in preparation of immunosuppressive and anti-inflammatory drugs. (formula of the compound).

Description

Technical field [0001] The present invention relates to dexamethasone modified by Lys(AA-Asp-Gly-Arg)-His-Gly-Glu octapeptide, and AA in the octapeptide is L-Val or L-Phe residue. It involves their preparation methods, their nanostructures, their inhibitory effects on the immune rejection of myocardial transplantation behind the ears of mice, their inhibitory effects on xylene-induced inflammatory responses, and further relates to that they are not as effective as dexamethasone. Produce osteoporosis and thrombosis side effects. Therefore, the present invention relates to the application prospect of the octapeptide modified dexamethasone in the preparation of immunosuppressive and anti-inflammatory drugs. The invention belongs to the field of biomedicine. Background technique [0002] Replacing waste organs through organ transplantation has become a routine treatment in clinical surgery. Immune rejection in organ transplantation is the most important factor for organ transplant...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/06C07K1/06C07K1/02B82Y30/00A61K38/08A61P37/06A61P29/00
CPCY02P20/55
Inventor 彭师奇赵明王玉记吴建辉于化龙
Owner 北京恒润泰生医药科技有限公司
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