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Thymopentapeptide active isomer and application thereof in pharmaceutical preparation

An isomer, thymus technology, applied in antitumor drugs and antioxidant drugs, the active isomer of thymopentin, in the field of preparation of immunomodulatory drugs, can solve problems such as short half-life and unfavorable treatment

Inactive Publication Date: 2007-03-14
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For healthy individuals, it is normal for peptide hormones to be cleared quickly after they play a regulatory role in the body, but for patients, when medication is needed, the short half-life is not good for treatment.

Method used

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  • Thymopentapeptide active isomer and application thereof in pharmaceutical preparation
  • Thymopentapeptide active isomer and application thereof in pharmaceutical preparation
  • Thymopentapeptide active isomer and application thereof in pharmaceutical preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] The solid-phase synthesis of embodiment 1 LW501

[0049] Raw materials: Fmoc-Tyr(tBu)-Wang resin, Fmoc-Asp-otBu, Fmoc-Arg(pbf)-OH, Fmoc-Lys(Boc)-OH, Fmoc-Val-OH. The condensing agent for the coupling reaction is benzotriazole-1-oxygen-tris(dimethylamino)phosphorus hexafluorophosphate (BOP), 1-hydroxybenzotriazole (HOBT), N-methylmorpholine (NMM ). The deprotecting agent is 20% piperidine / DMF solution. The cleavage reagent is trifluoroacetic acid.

[0050] Reaction: Fmoc-Tyr(tBu)-Wang resin was swelled in DMF at room temperature for 30 minutes, and washed three times with DMF. Add 20% piperidine / DMF solution and react at room temperature for 1 hour to deprotect. Then wash with DMF three times, add Fmoc-Val-OH, react at room temperature for 3 hours, then wash with DMF three times, add 20% piperidine / DMF solution, react at room temperature for 1 hour to deprotect. Add Fmoc-Asp-otBu, react at room temperature for 3 hours, wash with DMF three times, add 20% piperidine / D...

Embodiment 2

[0054] The solid-phase synthesis of embodiment 2 LW502

[0055] Raw materials: Fmoc-Tyr(tBu)-Wang resin, Fmoc-Glu-otBu, Fmoc-Arg(pbf)-OH, Fmoc-Lys(Boc)-OH, Fmoc-Val-OH. The condensing agent for the coupling reaction is benzotriazole-1-oxygen-tris(dimethylamino)phosphorus hexafluorophosphate (BOP), 1-hydroxybenzotriazole (HOBT), N-methylmorpholine (NMM ). The deprotecting agent is 20% piperidine / DMF solution. The cleavage reagent is trifluoroacetic acid.

[0056] Reaction: Fmoc-Tyr(tBu)-Wang resin was swelled in DMF at room temperature for 30 minutes, and washed three times with DMF. Add 20% piperidine / DMF solution and react at room temperature for 1 hour to deprotect. Then wash with DMF three times, add Fmoc-Val-OH, react at room temperature for 3 hours, then wash with DMF three times, add 20% piperidine / DMF solution, react at room temperature for 1 hour to deprotect. Add Fmoc-Glu-otBu, react at room temperature for 3 hours, wash with DMF three times, add 20% piperidine / D...

Embodiment 3

[0061] The solid-phase synthesis of embodiment 3 LW503, LW504, LW505

[0062] The raw material in Example 1 is replaced with Fmoc-Tyr(tBu)-Wang resin, Fmoc-Val-OHFmoc-Asp-otBu, Fmoc-β-Lys(Boc)-OH, Fmoc-Arg(pbf)-OH, with LW503 can be synthesized by the same method as in Example 1.

[0063] The raw materials in Example 1 were replaced with Fmoc-Tyr(tBu)-Wang resin, Fmoc-Val-OH, Fmoc-Glu-otBu, Fmoc-β-Lys(Boc)-OH, Fmoc-Arg(pbf)-OH , LW504 can be synthesized by the same method as in Example 1.

[0064] The raw materials in Example 1 were replaced with Fmoc-Tyr(tBu)-Wang resin, Fmoc-Val-OH, Fmoc-Glu-otBu, Fmoc-γ-Lys(Boc)-OH, Fmoc-Arg(pbf)-OH , LW505 can be synthesized by the same method as in Example 1.

[0065] Its molecular weight was identified by mass spectrometry in full agreement with LW503, LW504, and LW505.

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PUM

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Abstract

The present invention is active thymic peptide 5 (TP-5) isomer and its pharmaceutical application, and belongs to the fields of organic chemistry and chemical medicine. Structurally, the active TP-5 isomer has TP-5 amino sequence of Arg-Lys-Asp-Val-Tyr with one or two amino acids substituted by corresponding beta-amino acids or gamma-amino acids. It is prepares through a conventional Fmoc solid peptide synthesizing process. Phamacodynamical experiment shows that the active TP-5 isomer possesses obvious immunological enhancement effect, antitumor effect and antioxidant effect. Extracorporeal activity and stability measurement shows that the active TP-5 isomer has activity not lower than that of TP-5, raised stability, longer half life and thus enhanced curative effect. The present invention provides theoretic base for the research on the activity mechanism of thymic peptide and the development of new medicine.

Description

technical field [0001] The invention belongs to the field of organic chemistry and chemical medicine, and particularly relates to the active isomer of thymopentin and its application in the preparation of immune regulation medicine, antitumor medicine and antioxidant medicine. Background technique [0002] The thymus is the primary lymphoid epithelial tissue, the primary central immune organ of the human body, and the central organ of T cell development. In addition to providing a microcirculation required for T cell development, it can also produce a variety of thymosin hormones. Thymus hormones can promote the differentiation and maturation of T cell subsets, thereby regulating the function of the entire immune system. After mammals mature, the thymus gradually shrinks and degenerates with age, and the secretion of thymus hormones also gradually decreases. A large number of research results have shown that senile infectious diseases, tumors and autoimmune diseases are re...

Claims

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Application Information

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IPC IPC(8): C07K7/02A61K38/08A61K9/08A61K9/20A61K9/48A61P37/02A61P35/00
Inventor 李惟王丽凤王丽萍陈晓光单慧洁顾景凯
Owner JILIN UNIV
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