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Dexamethasone-RGD polypeptide conjugate, preparation method thereof and application

A technology of dexamethasone and conjugates, applied in the field of dexamethasone-RGD polypeptide conjugates, can solve problems such as osteoporosis, and achieve the advantages of reduced side effects of osteoporosis, excellent immunosuppressive effect, and excellent anti-inflammatory effect. Effect

Active Publication Date: 2013-04-17
SHANDONG HUBBLE KISEN BIOLOGICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Dexamethasone has been widely used clinically as an immunosuppressant, but it has a series of side effects such as osteoporosis

Method used

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  • Dexamethasone-RGD polypeptide conjugate, preparation method thereof and application
  • Dexamethasone-RGD polypeptide conjugate, preparation method thereof and application
  • Dexamethasone-RGD polypeptide conjugate, preparation method thereof and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1 prepares BocArg (NO 2 )-Gly-OBzl

[0036] 800mg (2.5mmol) Boc-Arg (NO 2 )-OH was dissolved in an appropriate amount of anhydrous THF, and anhydrous THF solution of 338 mg (2.5 mmol) HOBt and 619 mg (3.0 mmol) DCC was added under ice cooling. After 20 minutes of reaction, the corresponding active ester was obtained, which was directly used in the following reaction.

[0037] 775mg (2.3mmol) Tos·Gly-OBzl and 230mg (2.3mmol) N-methylmorpholine were miscible with an appropriate amount of anhydrous THF, added to the above reaction solution, and reacted at room temperature for 24 hours. TLC (CH 2 Cl 2 :MeOH=20:1) shows that the raw material point disappears. Spin to dry the solvent, add 150ml ethyl acetate, wash with saturated NaHCO 3 30ml×3, saturated sodium chloride aqueous solution 30ml×3, saturated KHSO 4 30ml×3, after washing with saturated aqueous sodium chloride solution 30ml×3, the ethyl acetate layer was washed with anhydrous NaCl2 SO 4 Dry and ...

Embodiment 2

[0038] Embodiment 2 prepares Boc-Arg (NO 2 )-Gly

[0039] 1.167g (2.5mmol) Boc-Arg (NO 2 )-Gly-OBzl dissolved in an appropriate amount of anhydrous CH 3 OH, add 2.5ml (5mmol) 2N NaOH aqueous solution under ice-cooling. Reacted for 30 minutes, TLC (CH 2 Cl 2 :MeOH=20:1) shows that the raw material point disappears, add saturated KHSO 4 Adjust pH-7, spin dry methanol, add saturated KHSO 4 Adjust pH-2, extract with ethyl acetate, wash the ethyl acetate layer with anhydrous Na 2 SO 4 Dried, filtered and spin-dried to obtain 1.075g, the yield (90%) was directly used in the following reaction.

Embodiment 3

[0040] Embodiment 3 prepares Boc-Ser(Bzl)-OBzl

[0041] 739mg (2.5mmol) Boc-Ser(Bzl)-OH was dissolved in 10ml absolute ethanol, and 405mg (1.25mmol) Cs was added 2 CO 3 The aqueous solution was reacted at room temperature for 15 minutes, and TLC (ethyl acetate:petroleum ether=1:1) showed that the starting point disappeared. Concentrate under reduced pressure to remove the solvent to obtain the corresponding cesium salt Boc-Ser(Bzl)OCs. The obtained cesium salt was first dissolved in 2 ml of anhydrous DMF, and then 0.3 ml (2.5 mmol) of benzyl bromide was added thereto. The reaction mixture was stirred at 55-60 ° C for 4 h, TLC (CHCl 3 :MeOH=30:1) shows that the cesium salt of Boc-Ser(Bzl) disappears. The reaction mixture was concentrated to dryness under reduced pressure, the residue was dissolved in ethyl acetate, and the insoluble matter was filtered off. The filtrate was successively washed with saturated NaHCO 3 30ml×3 and 30ml×3 saturated aqueous sodium chloride solu...

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Abstract

The invention relates to a dexamethasone-RGD polypeptide conjugate shown as general formula i, a preparation method thereof and application. In the formula i, RGDX is tetrapeptide Arg-Gly-Asp-X, wherein X is any amino acid of Val, Phe and Ser. Proved by experiments, the compound of the present invention has excellent immunosuppressive effect and anti-inflammatory effect, and the side effects of osteoporosis is reduced. The conjugate can be used as an immunosuppressant and anti-inflammatory agent for the side effect of low osteoporosis clinically. At the same time, the dexamethasone-RGD polypeptide conjugate of the present invention can self-assemble into stable nanoparticles with particle size of 200-500 nm, therefore the conjugate can be prepared into a target drug of immunosuppressive pharmacosome, microemulsion or liposome.

Description

technical field [0001] The invention relates to a dexamethasone-RGD polypeptide conjugate, its preparation method and application, and belongs to the field of biomedicine. Background technique [0002] Thousands of years ago, people had imagined replacing diseased organ tissue with normal organ tissue, but most of the transplants before the 20th century failed except for corneal transplantation. Until the 1940s, British surgeon Mdewaar used the experimental model of rabbit skin transplantation to demonstrate for the first time that rejection in organ tissue transplantation is essentially an immune response, thus laying the foundation for transplantation immunology. After the 1980s, the discovery and application of effective immunosuppressants such as cyclosporin A and FK506 further prolong the survival time of transplanted organs. However, there are some shortcomings such as biofilm, so it is urgent to study pharmaceutical nano-packaging materials to improve these shortcomi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/11C07K1/107A61K31/573A61K47/48A61P37/06A61P29/00A61K47/64
CPCY02P20/55
Inventor 王彦明闫庆连彭师奇赵明梅升辉
Owner SHANDONG HUBBLE KISEN BIOLOGICAL TECH CO LTD
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