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Double saturated aliphatic chain alcohol His-Gly-Lys-Asp tetrapeptide esters and preparation method and application thereof

A technology of his-gly-lys-asp and fatty chain alcohol, applied in the application field of double saturated fatty chain alcohol His-Gly-Lys-Asp tetrapeptide ester, artificially synthesized compound, and preparation of immunosuppressive drugs, can solve the problem of Low bioavailability, difficult to penetrate biomembrane, poor fat solubility, etc.

Inactive Publication Date: 2014-01-29
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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 shortcomings

Method used

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  • Double saturated aliphatic chain alcohol His-Gly-Lys-Asp tetrapeptide esters and preparation method and application thereof
  • Double saturated aliphatic chain alcohol His-Gly-Lys-Asp tetrapeptide esters and preparation method and application thereof
  • Double saturated aliphatic chain alcohol His-Gly-Lys-Asp tetrapeptide esters and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1 prepares Boc-Asp[OCH 2 (CH 2 ) 6 CH 3 ]-OCH 2 (CH 2 ) 6 CH 3 (1a)

[0041] Dissolve 1.1g (4.8mmol) Boc-Asp-OH in 20mL of anhydrous THF, add 1.5g (1.2mmol) N-hydroxybenzotriazole (HOBt) to the resulting solution under ice-cooling, and make it completely dissolve. After 10 minutes 2.3 g (1.2 mmol) of dicyclohexylcarbodiimide (DCC) were added. Obtain reaction liquid (I), stand-by. 1.5g (1.2mmol) CH 3 (CH 2 ) 6 CH 2OH was suspended in 20 mL of anhydrous THF, and then 1 mL of N-methylmorpholine (NMM) was added to adjust the pH to 8-9. Stir for 35 minutes to obtain the reaction solution (II), which is ready for use. The reaction solution (I) was added to the reaction solution (II) under ice bath, stirred for 1 h under ice bath, and then stirred at room temperature for 12 h. TLC (ethyl acetate / petroleum ether=2:1) ​​showed that Boc-Asp disappeared. Dicyclohexylurea (DCU) was filtered off and THF was removed under reduced pressure. The residue was ...

Embodiment 2

[0042] Embodiment 2 prepares Boc-Asp[OCH 2 (CH 2 ) 8 CH 3 ]-OCH 2 (CH 2 ) 8 CH 3 (1b)

[0043] According to the preparation method of Example 1, by 0.6g (2.5mmol) Boc-Asp and 0.1g (6.1mmol) CH 3 (CH 2 ) 8 CH 2 OH yielded 1.2 g (90.2%) of the title compound of this example as a colorless oil. ESI-MS(m / e): 514[M+H] + ;

Embodiment 3

[0044] Embodiment 3 prepares Boc-Asp[OCH 2 (CH 2 ) 10 CH 3 ]-OCH 2 (CH 2 ) 10 CH 3 (1c)

[0045] According to the method of embodiment 1 by 2.3g (10.0mmol) Boc-Asp and 4.1g (24.0mmol) CH 3 (CH 2 ) 10 CH 2 OH yielded 5.0 g (87.7%) of the title compound of this example as a colorless solid. ESI-MS(m / e): 570[M+H] + ;

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Abstract

The invention relates to six saturated aliphatic chain alcohol His-Gly-Lys-Asp tetrapeptide esters which are shown as a general formula I and have immunosuppressive activity, and a preparation method thereof. The general formula I is His-Gly-Lys-Asp[OCH2(CH2)nCH3]-OCH2(CH2)nCH3, wherein n is 6, 8, 10, 12, 14 or 16. By studying inhibition effects of aliphatic chain alcohol on proliferation reaction of a splenic lymphocyte mitogen and the phagocytic activity of a macrophage, and the survival time of a mouse subjected to opisthotic cardiac transplantation, experimental data further shows that the compounds have a good immunosuppressive effect, so the compounds have a wide application prospect in preparation of immunosuppressive medicines.

Description

technical field [0001] The present invention relates to an artificially synthesized compound, in particular to a His-Gly-Lys-Asp tetrapeptide ester of 6 kinds of double-saturated fatty chain alcohols with general formula I having immunosuppressive activity, and also relates to their preparation method, and their The application in the preparation of immunosuppressive drugs 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 immunosuppres...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/117C07K1/06A61K38/07A61K9/107A61K9/127A61P37/06
CPCY02P20/55
Inventor 彭师奇赵明李婕
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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