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

A dexamethasone, -glu-asp-gly technology, applied in the field of biomedicine, can solve the problem of no obvious improvement in curative effect

Active Publication Date: 2016-04-20
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, and preparation, nanometer structure and application thereof
  • Octapeptide-modified dexamethasone, and preparation, nanometer structure and application thereof
  • Octapeptide-modified dexamethasone, and preparation, nanometer structure and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1 Preparation of Boc-Asp(OBzl)-Gly-OBzl

[0029] Weigh 17.6g (54.2mmol) Boc-Asp (OBzl), 7.3g (53.9mmol) HOBt, dissolve in dry tetrahydrofuran (THF), stir under ice bath, add dropwise 13.4g (65.0mmol) DCC dissolved in THF, After stirring and activating for 30 minutes, add 12.0g (59.6mmol) HCl Gly-OBzl, adjust pH=8 with NMM, react at room temperature for 12 hours, TLC (CH 2 Cl 2 / MeOH=20 / 1) showed disappearance of starting point. 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 aqueous sodium chloride solution were wash...

Embodiment 2

[0030] Example 2 Preparation of HCl Asp(OBzl)-Gly-OBzl

[0031] To 24.0g (50.8mmol) Boc-Asp(OBzl)Gly-OBzl, add 200mL concentration 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 19.6 g (93.3%) of the title compound.

Embodiment 3

[0032] Example 3 Preparation of Boc-Glu(OBzl)-Asp(OBzl)-Gly-OBzl

[0033]Weigh 3.9g (11.6mmol) Boc-Glu (OBzl), 1.65g (12.2mmol) HOBt, dissolve in dry tetrahydrofuran (THF), stir under ice bath, add dropwise 2.86g (13.9mmol) DCC dissolved in THF, After stirring and activating for 30 minutes, add 5.7g (13.9mmol) HCl Asp(OBzl)Gly-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. The DCU was removed by filtration, the filtrate was concentrated under reduced pressure, the residue was dissolved in 200mL ethyl acetate, and the obtained ethyl acetate solution was sequentially washed with 50mL saturated aqueous sodium bicarbonate solution, saturated 50mL aqueous sodium chloride solution, 50mL saturated aqueous potassium hydrogensulfate solution, and 50mL saturated aqueous chloride solution. Sodium chloride aqueous solution, 50mL saturated sodium bicarbonate aqueous solution, 50mL saturated ...

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Abstract

The invention discloses dexamethasone modified by an octapeptide Lys(AA-Asp-Gly-Arg)-Glu-Asp-Gly, and AA in the octapeptide is L-Va or L-Phe. The invention discloses a preparation method and the nanometer structure of the octapeptide-modified dexamethasone, discloses inhibition effect of the octapeptide-modified dexamethasone on mice opisthotic myocardial transplantation immunological rejection, discloses inhibition effect of the octapeptide-modified dexamethasone on xylene-caused inflammatory response, and further discloses that the octapeptide-modified dexamethasone does not generate osteoporosis and thrombus side-effect like dexamethasone.

Description

technical field [0001] The invention relates to dexamethasone modified by octapeptide Lys(AA-Asp-Gly-Arg)-Glu-Asp-Gly, 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 octapeptide-modified dexamethasone 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 transplantation failure. For pat...

Claims

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Application Information

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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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