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Intermedin analogue prepared by bonding ring core sequence with biotin or cell-penetrating peptides

A technology of melanocyte-stimulating hormone and analogs, which is applied in the direction of melanocyte-stimulating hormone, cyclic peptide components, peptide preparation methods, etc., which can solve the problems of difficult treatment of diseases and the inability of macromolecules such as polypeptides to directly enter cells.

Inactive Publication Date: 2012-10-03
张嘎
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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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  • Intermedin analogue prepared by bonding ring core sequence with biotin or cell-penetrating peptides
  • Intermedin analogue prepared by bonding ring core sequence with biotin or cell-penetrating peptides
  • Intermedin analogue prepared by bonding ring core sequence with biotin or cell-penetrating peptides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0094] In the amino group (NH 2 ) type solid phase resin to prepare functional unit amino acid sequence

[0095] Step 1. Accurately weigh 10 g (0.36 mmol / g) of Fmoc-Lys(Mmt)-Linker Amide AM Resin into a 200 ml reaction bottle, add 100 ml of DMF to swell the resin for 30 minutes, drain, and then Shake and wash the resin three times with DMF, 50 ml each time, once every 2 minutes, drain and add 50 ml of deprotection reagent (20% piperidine / DMF, that is, the piperidine / DMF mixture contains 20% by volume of piperidine) Shake the reaction for 30 minutes, take out the deprotection solution, wash the resin three times with DMF, drain it, take a little ninhydrin and test it, it is positive.

[0096] 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 Negat...

Embodiment 2

[0104] Synthesis of Peptide 1

[0105] The functional unit amino acid sequence polypeptide resin prepared in Example 1 was connected with biotin according to the operation of step 2 in Example 1, the connection time was 2 hours, and there was no deprotection step to obtain the polypeptide resin, the structure of which was:

[0106] Biotin-Arg(Pbf)-c(Asp-Dab(Boc)-D-Phe-Arg(Pbf)-Trp-Lys)-Linker Amide AM Resin.

[0107] The resin in the previous step was cleaved with trifluoroacetic acid to obtain crude peptides, which were purified by high performance liquid chromatography (C-18 column, acetonitrile / water / 1%TFA, reverse phase elution), and freeze-dried Polypeptide 1 was obtained with the structure:

[0108] Biotin-Arg-c(Asp-Dab-D-Phe-Arg-Trp-Lys)-NH 2 .

Embodiment 3

[0110] Synthesis of Peptide 3

[0111] The functional unit amino acid sequence polypeptide resin prepared in Example 1 was sequentially protected from amino acids Fmoc-Arg(Pbf)-OH, Fmoc-Arg(Pbf)-OH, Fmoc-Arg(Pbf) according to the operation of step 2 in Example 1 -OH is connected with it to obtain a polypeptide resin with the structure: Arg(Pbf)-Arg(Pbf)-Arg(Pbf)-Arg(Pbf)-c(Asp-Dab(Boc)-D-Phe-Arg(Pbf)- Trp-Lys)-Linker Amide AM Resin.

[0112] The resin in the previous step was cleaved with trifluoroacetic acid to obtain crude peptides, which were purified by high performance liquid chromatography (C-18 column, acetonitrile / water / 1%TFA, reverse phase elution), and freeze-dried Polypeptide 3 was obtained with the structure:

[0113] Arg-Arg-Arg-Arg-c(Asp-Dab-D-Phe-Arg-Trp-Lys)-NH 2 .

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Abstract

The invention relates to an intermedin analogue prepared by bonding a ring core sequence with biotin or cell-penetrating peptides and a preparation method and application of the intermedin analogue. The intermedin analogue is prepared by bonding a functional unit with the biotin or a load unit; the functional unit is a seven-peptide structure formed by connecting the ring core sequence c (Asp-Dab-D-Phe-Arg-Trp-Lys) with a connection unit Arg, the structure is Arg-c (Asp-Dab-D-Phe-Arg-Trp-Lys); the load unit is the 48th-57th peptide segments Gly-Arg-Lys-Lys-Arg-Arg-Gln-Arg-Arg-Arg or the 55th-57th peptide segments Arg-Arg-Arg in the 47th-60th segments of HIV (human immunodeficiency virus)-1TAT protein. The intermedin analogue disclosed by the invention can penetrate through mucosa or skin to be absorbed, and can be applied to treatment of diseases such as male and female sexual dysfunction, obesity, pigmentation deficiency and the like.

Description

technical field [0001] The invention relates to a melanotropin analogue formed by linking a circular core sequence with biotin or a membrane-penetrating peptide, a preparation method and application thereof. 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 ...

Claims

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Application Information

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IPC IPC(8): C07K7/64C07K1/06C07K1/04A61K38/12A61P15/10A61P15/00A61P3/04A61P5/00
CPCC07K1/04A61K38/34A61K38/12A61K47/02C07K1/06C07K14/68C07K7/64A61P3/04A61P5/00A61P15/00A61P15/10
Inventor 张嘎
Owner 张嘎
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