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Saturated fat chain acid His-Gly-AA tripeptide amide, and synthesis method and use thereof

A his-gly-aa, n-co-his-gly-aai technology, applied in the field of biomedicine, can solve the problems of cyclosporin A, such as poor water solubility, unsatisfactory dosage form or unsatisfactory curative effect, strong nephrotoxicity, etc., to achieve Excellent immunosuppressive effect

Inactive Publication Date: 2010-12-01
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the extremely poor water solubility and strong nephrotoxicity of cyclosporin A, neither the dosage form nor the curative effect is satisfactory

Method used

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  • Saturated fat chain acid His-Gly-AA tripeptide amide, and synthesis method and use thereof
  • Saturated fat chain acid His-Gly-AA tripeptide amide, and synthesis method and use thereof
  • Saturated fat chain acid His-Gly-AA tripeptide amide, and synthesis method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 Preparation of Boc-Gly-Glu(OBzl)-OBzl

[0040]3.50 g (20.00 mmol) of Boc-Gly was dissolved in 200 ml of anhydrous THF, and 2.72 g (20.00 mmol) of N-hydroxybenzotriazole (HOBt) was added to the resulting solution under ice cooling to completely dissolve it. After 10 minutes 4.96 g (24.00 mmol) of dicyclohexylcarbodiimide (DCC) were added. Obtain reaction liquid (I), stand-by. Suspend 10.38g (20.00mmol) TosH·Glu(OBzl)-OBzl in 20ml anhydrous THF under ice-cooling, then add 1ml N-methylmorpholine (NMM) 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 (chloroform / methanol, 10:1) showed that Boc-Gly-OH disappeared. Dicyclohexylurea (DCU) was filtered off and THF was removed under reduced pressure. The residue was dissolved with 50 ml of ethyl ...

Embodiment 2

[0041] Example 2 Preparation of HCl Gly-Glu(OBzl)-OBzl

[0042] Dissolve 8.91g (18.38mmol) Boc-Gly-Glu(OBzl)-OBzl in 200ml 4mol / l hydrogen chloride-ethyl acetate solution, stir at room temperature for 2 hours, TLC (chloroform:methanol, 5:1) shows that the raw material point disappears , concentrated under reduced pressure to remove ethyl acetate, and the residue was repeatedly added with a small amount of ether for concentration under reduced pressure to remove hydrogen chloride gas. Finally, a small amount of diethyl ether was added to triturate the residue to obtain 6.94 g (90%) of the title compound as a colorless solid powder, which was directly used in the next reaction. ESI-MS(m / z): 385[M+H] + .

Embodiment 3

[0043] Example 3 Preparation of Boc-His(Boc)-Gly-Glu(OBzl)-OBzl

[0044] According to the method of Example 1, a beige oil was obtained from 5.42g (7.63mmol) Boc-His (Boc) and 6.94g (15.26mmol) HCl·Gly-Glu(OBzl)-OBzl. The obtained compound was purified by silica gel column chromatography to obtain 8.24 g of a colorless oily substance. Purification conditions: chloroform:methanol=100:1, the yield was 75%. ESI-MS(m / z): 722[M+H] + , [α] 20 D =-25.2 (c=1.0, CH 3 OH).

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Abstract

The invention relates to 12 saturated fat chain acid His-Gly-AA tripeptide amide conjugates having immunosuppressive activity in a general formula I: CH3(CH2)n-CO-His-Gly-AA, wherein AA is Glu or Lys; and n in the saturated fat chain acid is equal to 6, 8, 10, 12, 14 or 16. The invention relates to a preparation method for the tripeptide amide conjugates and use of the tripeptide amide conjugates as immunosuppressive agents. Experimental results that the saturated fat chain acid His-Gly-AA tripeptide amide has the effects of inhibiting splenic lymphocyte cell mitogen breeder reaction and inhibiting macrophage phagocytosis activities show that the compounds have good immunodepression effect and can be clinically used as the immunosuppressive agents.

Description

technical field [0001] The present invention relates to saturated fatty chain acid tripeptide amides, in particular to a series of saturated fatty chain acid His-Gly-AA tripeptide amides with immunosuppressive activity, also to the preparation method of these saturated fatty chain acid tripeptide amides and their use as immune The application of the inhibitor belongs to the field of biomedicine. Background technique [0002] According to statistics, by the end of 2002, a total of 935,792 cases of various organ transplants had been performed in the world, including 585,877 cases of kidney transplants, 112,153 cases of liver transplants, and 66,559 cases of heart transplants. In addition, pancreas, lung, small intestine and other organ transplants, as well as multi-organ transplants such as heart-lung, pancreas-kidney, liver-kidney, and liver-intestine, have also been successfully applied in clinical practice. Currently, the 1-year human / kidney survival rate of kidney transpl...

Claims

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Application Information

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IPC IPC(8): C07K5/097C07K1/06C07K1/02A61K38/06A61P37/06A61K47/42A61K9/107A61K9/127A61K47/18
Inventor 赵明彭师奇赵淑锐
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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