Melanocortin analogue as well as preparation method and application thereof

A technology of melanocortin and analogues, which is applied in the field of melanocortin analogues and their preparation and application, and can solve the problems of difficult treatment of diseases and the inability of macromolecules such as polypeptides to directly enter cells.

Active Publication Date: 2010-06-09
上海瀚鸿科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Due to the barrier of biological cell membranes, macromolecules such as polypeptides cannot directly enter cells, which brings difficulties to the treatment of many diseases

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] Synthesis of Functional Amino Acid Sequence Polypeptide Resin

[0094]Step 1. Accurately weigh 10 grams (0.73 mmol / g) of Fmoc-Lys(Mmt)-Wang Resin into a 200 ml reaction bottle, add 100 ml of DMF to swell the resin for 30 minutes, drain, and then use DMF Shake and wash the resin three times, 50 ml each time, once every 2 minutes, drain, add 50 ml of deprotection reagent (20% piperidine / DMF, that is, the piperidine / DMF mixture contains 20% by volume of piperidine) shake reaction After 30 minutes, the deprotection solution was taken out, the resin was washed three times with DMF, drained, and a little ninhydrin was taken for detection, which was positive.

[0095] Step 2. Add 50 milliliters of DMF, three times the molar amount of Fmoc-Trp-OH, three times the molar amount of HBTU, and three times the molar amount of NMM to the reaction bottle in turn, shake and react for 30 minutes, take a little resin for ninhydrin detection, and it is Negative, take out the reaction solu...

Embodiment 2

[0103] Synthesis of Peptide 1

[0104] With all the functional amino acid sequence polypeptide resins prepared in Example 1, the protected amino acids Fmoc-Arg(Pbf)-OH, Fmoc-Arg(Pbf)-OH, Fmoc-Arg( Pbf)-OH is connected with it to obtain a polypeptide resin. The structure is:

[0105] Arg(Pbf)-Arg(Pbf)-Arg(Pbf)-Nle-c(Asp-His(Trt)-DPhe-Arg(Pbf)-Trp-Lys)-Wang Resin

[0106] Add 50% acetic anhydride / DMF (that is, the acetic anhydride / DMF mixed solution contains 50% acetic anhydride by volume) to 50 ml of the polypeptide resin in the previous step, shake the reaction solution for 30 minutes, drain the reaction solution, and wash with DMF, DCM, and methanol respectively. N-terminal acetylated polypeptide resin was prepared after washing three times. The structure is:

[0107] Ac-Arg(Pbf)-Arg(Pbf)-Arg(Pbf)-Nle-c(Asp-His(Trt)-DPhe-Arg(Pbf)-Trp-Lys)-Wang Resin

[0108] Polypeptide 1 was obtained by lyophilizing the resin in the previous step after cleavage with trifluoroacetic acid...

Embodiment 3

[0111] Synthesis of Peptide 2

[0112] With all the functional amino acid sequence polypeptide resins prepared in Example 1, the protected amino acids Fmoc-Arg(Pbf)-OH, Fmoc-Arg(Pbf)-OH, Fmoc-Arg( Pbf)-OH, Fmoc-Gln(Trt)-OH, Fmoc-Arg(Pbf)-OH, Fmoc-Arg(Pbf)-OH, Fmoc-Lys(Boc)-OH, Fmoc-Lys(Boc)-OH, Fmoc-Arg(Pbf)-OH and Fmoc-Gly-OH are connected with it to obtain a polypeptide resin. The structure is:

[0113] Gly-Arg(Pbf)-Lys(Boc)-Lys(Boc)-Arg(Pbf)-Arg(Pbf)-Gln(Trt)-Arg(Pbf)-Arg(Pbf)-Arg(Pbf)-Nle-c (Asp-His(Trt)-DPhe-Arg(Pbf)-Trp-Lys)-Wang Resin

[0114] Add 50% acetic anhydride / DMF (that is, the acetic anhydride / DMF mixed solution contains 50% acetic anhydride by volume) to 50 ml of the polypeptide resin in the previous step, shake the reaction solution for 30 minutes, drain the reaction solution, and wash with DMF, DCM, and methanol respectively. N-terminal acetylated polypeptide resin was prepared after washing three times. The structure is:

[0115] Ac-Gly-Arg(Pbf)-Lys(B...

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PUM

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Abstract

The invention discloses melanocortin analogue as well as preparation method and application thereof. A polypeptide structure of the melanocortin analogue consists of a functional amino acid sequence and a load amino acid sequence, wherein the functional amino acid sequence is an annular melanocortin analogue consisting of heptamers, and the load amino acid sequence consists of a plurality of polypeptide segments in 47th-60th segments of HIV-1 (human immunodeficiency virus type 1)TAT (trans-activator of transcription) protein. The melanocortin analogue can be absorbed through mucous membranes or skin and used for treating male and female sexual dysfunctions, obesities and pigmentation deficiencies.

Description

technical field [0001] The invention relates to a melanocortin analogue and its preparation method and application. Background technique [0002] With the acceleration of the pace of life, the increase of work pressure, the influence of genetic factors, male and female sexual dysfunction, obesity, and hypopigmentation are increasingly prominent, seriously affecting people's quality of life. Among them, obesity is well-known as one of the factors that lead to common diseases such as arteriosclerosis, high blood pressure, heart disease, and diabetes, and diseases such as sexual disharmony and skin cancer caused by male and female sexual dysfunction and hypopigmentation also seriously affect to the physical and mental health of patients and the well-being of families. [0003] At present, the first-line drugs for the treatment of male sexual dysfunction are phosphodiesterase inhibitors such as sildenafil, but these drugs are ineffective for female patients, and some patients r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/64C07K1/06C07K1/04A61K38/12A61P15/00A61P15/10A61P3/04A61P17/00
CPCC07K14/685A61K38/12A61P3/04A61P15/00A61P15/10A61P17/00
Inventor 张嘎张贲
Owner 上海瀚鸿科技股份有限公司
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