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Octapeptide modified dexamethasone, preparation, nano-structure and application thereof

A technology of dexamethasone and -his-gly-lys, 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: 2016-05-18
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, nano-structure and application thereof
  • Octapeptide modified dexamethasone, preparation, nano-structure and application thereof
  • Octapeptide modified dexamethasone, preparation, nano-structure and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Preparation of HCl Gly-Lys(Z)-OBzl

[0027] Weigh 1.154g (6.6mmol) Boc-Gly, 0.938g (6.9mmol) HOBt, dissolve in dry tetrahydrofuran (THF), stir under ice bath, add dropwise 1.614g (7.8mmol) DCC dissolved in THF, stir and activate for 30 Minutes later, add 3.000g (7.4mmol) HCl Lys(Z)-OBzl, adjust pH=8 with NMM, react at room temperature for 12 hours, TLC (CH 2 Cl 2 / MeOH=20 / 1), showing that the raw material point disappeared. DCU was removed by filtration, the filtrate was concentrated under reduced pressure, the residue was dissolved in 100 mL of ethyl acetate, and the obtained ethyl acetate solution was successively washed with 20 mL of saturated aqueous sodium bicarbonate, 20 mL of saturated aqueous sodium chloride, 20 mL of saturated aqueous potassium hydrogensulfate, and 20 mL of saturated aqueous chlorine Sodium chloride aqueous solution, 20mL saturated sodium bicarbonate aqueous solution, 20mL saturated sodium chloride aqueous solution were washed 3 tim...

Embodiment 2

[0028] Example 2 Preparation of Boc-His(Boc)-Gly-Lys(Z)-OBzl

[0029] Weigh 4.894g (13.8mmol) Boc-His (Boc), 1.960g (14.7mmol) HOBt, dissolve in dry tetrahydrofuran (THF), stir under ice bath, add dropwise 3.408g (16.5mmol) DCC dissolved in THF, After stirring and activating for 30 minutes, add 8.200 g (16.4 mmol) of HCl Gly-Lys(Z)-OBzl, adjust the pH to 8 with NMM, react at room temperature for 12 hours, TLC (CH 2 Cl 2 / MeOH=20 / 1), showing that the raw material point disappeared. DCU was removed by filtration, the filtrate was concentrated under reduced pressure, the residue was dissolved in 200 mL of ethyl acetate, and the obtained ethyl acetate solution was sequentially washed with 50 mL of saturated aqueous sodium bicarbonate, 50 mL of saturated aqueous sodium chloride, 50 mL of saturated aqueous potassium hydrogensulfate, and 50 mL of saturated aqueous chlorine Aqueous sodium chloride solution, 50 mL saturated aqueous sodium bicarbonate solution, and 50 mL saturated aqu...

Embodiment 3

[0030] Example 3 Preparation of HCl His-Gly-Lys(Z)-OBzl

[0031]To 10.0g (12.5mmol) Boc-His(Boc)-Gly-Lys(Z)-OBzl, add 100mL of 4M ethyl acetate solution of hydrogen chloride under ice bath, after reacting for 2 hours, TLC (CH 2 Cl 2 / MeOH=20 / 1) showed disappearance of starting point. 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 in anhydrous ether and concentrated under reduced pressure. This operation was also repeated 3 times. Yield 7.5 g (94.9%) of the title compound.

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Abstract

The invention discloses dexamethasone modified by octapeptide Lys(AA-Asp-Gly-Arg)-His-Gly-Lys, and the AA in the octapeptide is L-Val or L-Phe. Also, the invention 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. Results show that the compound provided by the invention not only has excellent immunosuppressive effect and anti-inflammatory activity, but also improves the osteoporosis and thrombus side effects of dexamethasone. Therefore, the octapeptide modified dexamethasone disclosed by the invention has definite application prospect in preparation of immunosuppressive and anti-inflammatory drugs.

Description

technical field [0001] The invention relates to dexamethasone modified by octapeptide Lys(AA-Asp-Gly-Arg)-His-Gly-Lys, wherein AA in the octapeptide is L-Val or L-Phe residue. It relates to their preparation method, to their nanostructure, to their inhibitory effect on immune rejection of mouse myocardium transplantation behind the ear, to their inhibitory effect on xylene-induced inflammatory response, and to their further involvement that they do not Produce osteoporosis and thrombosis side effects. Therefore, the present invention relates to the application prospect of the octapeptide modified dexamethasone of the following formula in the preparation of immunosuppressive and anti-inflammatory drugs. The invention belongs to the field of biomedicine. Background technique [0002] Replacing obsolete organs through organ transplantation has become a routine treatment in clinical surgery. Immune rejection in organ transplantation is the most important factor for organ tran...

Claims

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Application Information

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IPC IPC(8): C07K7/06C07K1/06C07K1/02B82Y30/00A61K38/08A61P37/06A61P29/00
CPCA61K38/08B82Y30/00C07K1/02C07K1/06C07K7/06
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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