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Novel pentapeptide analogue and application thereof

A technology of analogues and drugs, applied in the field of new pentapeptide analogues, can solve the problems of unsatisfactory in vivo effects, unsatisfactory in vivo activity, high synthesis cost, etc., achieve good development and application prospects, and inhibit the in vitro activity of juvenile hormone synthesis , the effect of simple structure

Inactive Publication Date: 2009-09-02
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still the following disadvantages: 1) the structure is complex, some structures are even more complex than natural peptides, and the synthesis cost is high
2) The in vivo effect of the compound is not ideal
Among them, only Nachman's literature involves an AST core pentapeptide analog modified with phenylpropionic acid, which partially retains the in vitro activity of natural AST, but its in vivo activity is not ideal

Method used

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  • Novel pentapeptide analogue and application thereof
  • Novel pentapeptide analogue and application thereof
  • Novel pentapeptide analogue and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0024] The present invention can be further described in detail by the following examples, but the present invention is not limited to these examples. Synthesis of Preparation Example 1, C1 compound

[0025] (1) Resin activation: Weigh 200mg Rink Amide-AM resin, wash 4 times with DCM, add 15ml DCM to swell and activate for 3 hours, wash 4 times with DMF, add 20% piperidine DMF solution to cut for 20min, wash 4 times with 5ml DMF, 5ml DCM washed 4 times, Kaiser's reagent detection.

[0026] (2) Connect with Leu: DMF wash 3 times, add 106mg Fmoc-Leu-OH (3 times the amount), 114mg HBTU (3 times the amount), 41mg HOBt (3 times the amount), 105ul DIEA (6 times the amount), dissolve in 15ml DMF, stirred at room temperature for 2h, washed 4 times with 5ml DMF, cut by adding 20% ​​piperidine DMF solution for 20min, washed 4 times with 5ml DMF, washed 4 times with 5ml DCM, detected by Kaiser's reagent.

[0027] (3) Connect to Gly: wash 3 times with DMF, add 90mg Fmoc-Gly-OH, 114mg HB...

preparation Embodiment 2、C14

[0034] Synthesis of Preparation Example 2, C14 Compound

[0035] (1) Resin activation: Weigh 200mg Rink Amide-AM resin, wash 4 times with DCM, add 15ml DCM to swell and activate for 3 hours, wash 4 times with DMF, add 20% piperidine DMF solution to cut for 20min, wash 4 times with 5ml DMF, 5ml DCM washed 4 times, Kaiser's reagent detection.

[0036] (2) Connect with Leu: DMF wash 3 times, add 106mg Fmoc-Leu-OH (3 times the amount), 114mg HBTU (3 times the amount), 41mg HOBt (3 times the amount), 105ul DIEA (6 times the amount), dissolve in 15ml DMF, stirred at room temperature for 2h, washed 4 times with 5ml DMF, cut by adding 20% ​​piperidine DMF solution for 20min, washed 4 times with 5ml DMF, washed 4 times with 5ml DCM, detected by Kaiser's reagent.

[0037] (3) Connect to Gly: wash 3 times with DMF, add 90mg Fmoc-Gly-OH, 114mg HBTU, 41mg HOBt, 105ul DIEA, dissolve in 15ml DMF, stir at room temperature for 2h, wash 4 times with 5ml DMF, add 20% piperidine DMF solution Cu...

preparation Embodiment 3、C15

[0044] Synthesis of Preparation Example 3, C15 Compound

[0045] (1) Resin activation: Weigh 200mg Rink Amide-AM resin, wash 4 times with DCM, add 15ml DCM to swell and activate for 3 hours, wash 4 times with DMF, add 20% piperidine DMF solution to cut for 20min, wash 4 times with 5ml DMF, 5ml DCM washed 4 times, Kaiser's reagent detection.

[0046] (2) Connect with Leu: DMF wash 3 times, add 106mg Fmoc-Leu-OH (3 times the amount), 114mg HBTU (3 times the amount), 4lmg HOBt (3 times the amount), 105ul DIEA (6 times the amount), dissolve in 15ml DMF, stirred at room temperature for 2h, washed 4 times with 5ml DMF, cut with 20% piperidine DMF solution for 20min, washed 4 times with 5ml DMF, 4 times with 5ml DCM, detected by Kaiser's reagent.

[0047] (3) Connect to Gly: wash 3 times with DMF, add 90mg Fmoc-Gly-OH, 114mg HBTU, 41mg HOBt, 105ul DIEA, dissolve in 15ml DMF, stir at room temperature for 2h, wash 4 times with 5ml DMF, add 20% piperidine DMF solution Cut for 20min, w...

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Abstract

The invention discloses a novel pentapeptide analogue and application thereof. The structure general formula of the compound provided by the invention is C: CR-Xaa-Phe-Gly-Leu-NH2, wherein the Xaa stands for the Gly, Asp, Asn, Ser or Ala; and the R stands for (substituted) benzoyl, (substituted) benzene acetyl, (substituted) hydrocinnamoyl, (substituted) butylbenzene, (substituted) benzene valeryl, (substituted) benzene hexanoyl, (substituted) benzenesulfonyl, 9-dimethoxycarbonyl, or benzyloxycarbonyl. Various organic acids with aromatic rings are introduced to replace Y / F in AST core pentapeptide (Y / FXFGLa) to prepare the pentapeptide analogue with simple structure and good inhibited juvenile hormone synthesis in-vitro activity, and the activity of partial compound with the formula C is superior to that of natural core pentapeptide. The further research indicates that partial compound with the formula C has better in-vivo activity, and the compound with the formula C conforms to the characteristic of an insect growth regulator and has better development and application prospects.

Description

technical field [0001] The invention relates to a novel pentapeptide analogue and its application in cockroach control. Background technique [0002] Pharyngeal-suppressant hormone (AST) is a kind of insect neuropeptide isolated from cockroach for the first time and has the function of inhibiting the synthesis of juvenile hormone in pharyngeal body. Subsequent studies have found that these molecules also exhibit other biological functions, such as regulating intestinal tissue and spinal duct muscle activity, inhibiting fat body vitellogenin synthesis, and stimulating midgut carbohydrase activity. [0003] More than 230 ASTs have been isolated, and these peptides can be divided into three different families: the cockroach-type AST isolated from the Pacific cockroach Diplotera puncata, the cricket-type AST isolated from crickets, and the N. Moth-type AST isolated from Manduca Sexta and Drosophila melanogaster. The cockroach-type ASTs have a common C-terminal sequence Y / FXFGL...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/103C07K5/113A01N37/46A01P23/00
Inventor 杨新玲开振鹏凌云谢勇黄娟斯蒂芬.斯.陶博张莉张金蕊陈馥衡
Owner CHINA AGRI UNIV
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