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Bifunctional peptide based on opioid peptide and cannabis sativa peptide as well as preparation method and application thereof

A bifunctional peptide and cannabinoid technology, applied in the field of biochemistry, can solve the problems of limited application scope, large differences in absorption and metabolism properties, complex pharmacokinetic properties, etc., to achieve enhanced analgesic activity and effective analgesic effect. Effect

Active Publication Date: 2021-06-15
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the absorption and metabolism properties of different drug molecules in the body are quite different, so when patients use multiple drugs in combination, they often need to follow complex drug regimens to achieve the best curative effect of the drug
Moreover, due to the complex pharmacokinetic properties of various drug molecules, potential interactions in vivo will significantly increase the incidence of adverse reactions, thereby limiting the scope of application of this program in clinical treatment (Lancet2000, 356: 1255 )

Method used

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  • Bifunctional peptide based on opioid peptide and cannabis sativa peptide as well as preparation method and application thereof
  • Bifunctional peptide based on opioid peptide and cannabis sativa peptide as well as preparation method and application thereof
  • Bifunctional peptide based on opioid peptide and cannabis sativa peptide as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] The synthesis of embodiment 1OCP 001

[0063] (1) Resin pretreatment: Weigh 600 mg of Rink-Amide-MBHA resin, stir and swell in 6 mL of dichloromethane at 80 rpm, the reaction time is 30 min, and drain for 30 min after the reaction. Then add DMF to wash 3 times, each 3min.

[0064] (2) Removal of Fmoc group protection: Add a mixed solution of piperidine with a volume fraction ratio of 1:1:98: DBU:DMF to the swollen resin, and the volume-to-mass ratio of the mixed solution to the swollen resin is 10 mL / g; according to 80rpm stirring 5min, repeat 2 times. After draining, the above mixed solution was added again, and stirred at 80 rpm for 10 min. After that, it was washed 4 times with DMF, each time for 3 min, to remove residual piperidine. Resin from which Fmoc protecting group has been removed is obtained.

[0065] (3) Indene detection: pick a small amount of resin into a colorless transparent glass tube, add indene detection reagent, and place it in boiling water fo...

Embodiment 2

[0070] The synthesis of embodiment 2OCP 002

[0071] (1) Resin pretreatment: Weigh 600 mg of Rink-Amide-MBHA resin, stir and swell in 6 mL of dichloromethane at 80 rpm, the reaction time is 30 min, and drain for 30 min after the reaction. Then add DMF to wash 3 times, each 3min.

[0072] (2) Removal of Fmoc group protection: Add a mixed solution of piperidine with a volume fraction ratio of 1:1:98: DBU:DMF to the swollen resin, and the volume-to-mass ratio of the mixed solution to the swollen resin is 10 mL / g; according to 80rpm stirring 5min, repeat 2 times. After draining, the above mixed solution was added again, and stirred at 80 rpm for 10 min. After that, it was washed 4 times with DMF, each time for 3 min, to remove residual piperidine. Resin from which Fmoc protecting group has been removed is obtained.

[0073] (3) Indene detection: pick a small amount of resin into a colorless transparent glass tube, add indene detection reagent, and place it in boiling water fo...

Embodiment 3

[0082] Example 3: Based on opiate peptide DALDA and cannabinoid peptide (m)VD-Hpα-NH 2 Analgesic experiments of bifunctional peptides

[0083] The present invention is based on the opioid peptide DALDA and the cannabinoid peptide (m) VD-Hpα-NH 2 A bifunctional peptide based on the opioid peptide DALDA and the cannabinoid peptide (m)VD-Hpα-NH 2 The newly constructed bifunctional peptide effectively reduces the side effects of analgesic tolerance while exerting high-efficiency analgesic effects. The analgesic and tolerance effects of the bifunctional peptides OCP 001 and OCP002 of the present invention will be described below through pharmacological experiments.

[0084] 1. Analgesic experiment

[0085] The compounds OCP 001 and OCP 002 prepared in Example 1 and Example 2 were injected into the ventricle of the brain and subcutaneously, respectively, to regulate pain in vivo in the models of acute pain induced by light and heat and inflammatory pain induced by carrageenan Ac...

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Abstract

The invention discloses a bifunctional peptide based on opioid peptide and cannabis sativa peptide as well as a preparation method and application thereof. The bifunctional peptide is a brand-new bifunctional peptide constructed based on an N-terminal sequence of opioid peptide DALDA and a C-terminal sequence of cannabis sativa peptide (m) VD-Hpalpha-NH2. Compared with the prior art, the analgesic activity of OCP 001 and OCP 002 in vivo is enhanced, an analgesic effect which is more effective than that of parent molecules is generated, the problem of analgesic tolerance existing in opioid and hemp agonists and the parent molecules is solved, an analgesic effect in a non-tolerance form is generated, and the bifunctional peptide can be used for treating acute pain and pathological pain.

Description

technical field [0001] The invention belongs to the technical field of biochemistry, and in particular relates to a class based on opioid peptide DALDA and cannabinoid peptide (m) VD-Hpα-NH 2 The bifunctional peptide and its preparation method and application. Background technique [0002] Pain is one of the most common complaints of clinical patients, and more than 1 billion people worldwide suffer from chronic pain for a long time. Currently, opioids are the drug of choice for the treatment of acute and chronic moderate to severe pain. However, the side effects associated with their use seriously affect patients' medication compliance and quality of life. In recent years, peptide analgesic molecules have become one of the hot spots in the research and development of new drugs because of their high biological activity and low immunogenicity. DALDA is a tetrapeptide derivative of dermorphin, which behaves as a selective agonist of MOR (J Pharmacol Exp Ther 2001, 298:57). ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K19/00C07K1/08C07K1/06C07K1/04A61K38/42A61K38/33A61P25/04
CPCC07K14/665C07K5/1016C07K14/805A61P25/04C07K2319/00A61K38/00Y02P20/55
Inventor 方泉许彪张梦娜张润李宁
Owner LANZHOU UNIVERSITY
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