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Tripeptide wrinkle-reducing compound containing 15N-L-proline residue and preparation method and application thereof

A compound and composition technology, applied in the field of tripeptide anti-wrinkle compound and its preparation, can solve the problems of failure to show wrinkle-reducing effect, failure to show clinical applicability, etc., and achieve good therapeutic effect

Inactive Publication Date: 2015-05-06
张嘎
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chinese patent 200580039359.9 discloses a tripeptide compound with a more simplified structure, in which compounds 4.5 and 4.6 showed better wrinkle-reducing effects than ajirelin at 2 hours and 48 hours in the cell-level test, but their It failed to show satisfactory wrinkle reduction effects in longer wrinkle reduction experiments, and failed to show better clinical applicability in human trial tests

Method used

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  • Tripeptide wrinkle-reducing compound containing 15N-L-proline residue and preparation method and application thereof
  • Tripeptide wrinkle-reducing compound containing 15N-L-proline residue and preparation method and application thereof
  • Tripeptide wrinkle-reducing compound containing 15N-L-proline residue and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Example 1: H—(β-Ala)—( 15 Preparation of N-Pro)-Dab-NH-Bzl and its acetate.

[0062] 1) Preparation of Fmoc-Dab(Boc)-2-Cl-Trt resin

[0063] Weigh 8g (8.8mmol) of 2-Cl-Trt resin and 3.88g (8.8mmol) of Fmoc-Dab(Boc)-OH, and add it into a ground-mouthed round bottom flask, then add DIPEA15.7ml (88mmol) and DCM80ml , Shake well, seal and shake on a shaker for 18 hours. Wash the resin with DMF, then add 85ml of DCM, 10ml of methanol and 5ml of DIPEA to block for 20min. After blocking, the resin was washed four times with DMF (60ml) and twice with DCM (60ml). Aspirate the solution. Shrink the resin three times with 60ml, 30ml and 30ml methanol respectively. Vacuum dry. Weighs 9.1g. Store in dry and low temperature. As determined by FMOC absorption method, the amino acid substitution amount is 0.65mmol / gram of resin.

[0064] 2) Preparation of H—Dab(Boc)—2-Cl-Trt resin

[0065] Weigh 9.1 g of dry Fmoc-Dab(Boc)-2-Cl-Trt resin into a solid-phase reaction synthesi...

Embodiment 2

[0086] Example 2 In vitro model testing.

[0087] 1) Material

[0088] Normal human muscle cells (myoblasts) at the third passage

[0089] Spinal cord explants of 13-day-old rat embryos with "dorsal root ganglia"

[0090] Medium: 2 / 3MEM and 1 / 3M199, 2mML-glutamine, 50UI / ml penicillin, 50μg / ml streptomycin, 5% fetal bovine serum

[0091] Culture conditions: 37°C, 5% CO 2 .

[0092] 2) Test method

[0093] To test the efficacy of the compounds of the present invention, a co-culture model of human myocytes and neurons from the spinal cord of rat embryos was established.

[0094]Normal human muscle cells (myoblasts) are cultured in gelatin-coated 24-well plates until a monolayer of myofibrils (from confluent myocytes) forms. Spinal cord explants of 13-day-old rat embryos with dorsal root ganglia were then placed on the myocyte monolayer. After 1 day of co-culture, the first neurite outgrowth from the explant was visible in contact with the myocyte. The first contraction ...

Embodiment 3

[0101] Example 3 Formulation of the composition.

[0102] 1) Preparation of ointment

[0103]

[0104] Preparation steps: Heat raw material A (ie, compounds No. 1 to 5) to 70°C. Starting material B (ie, compounds Nos. 6 and 7) was heated to 75°C. Add raw material B to raw material A under stirring condition, cool to 50°C, homogenize and cool to 30°C. Then, raw material component C (ie, compounds numbered 8 and 9) and raw material D (ie, compound acetate of Example 1 of the present invention) were added in sequence, and stirred evenly.

[0105] 2) Preparation of gel

[0106]

[0107] Preparation steps: Dissolve the raw materials numbered 2 to 6 in deionized water in sequence. Then adjust the pH to 6.0 with NaOH, and finally add the compound hydrochloride of Example 1, and stir evenly.

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Abstract

The invention provides a tripeptide wrinkle-reducing compound containing 15N-L-proline residue and / or salt formed by the compound and acid. The tripeptide compound has a structural formula shown in the specification, the abbreviate of the compound is H-(beta-Ala)-(15N-Pro)-Dab-NH-Bzl, wherein beta-Ala refers to beta-alanine residue, 15N-Pro refers to L-proline residue with nitrogen element which is specifically nitrogen 15, Dab refers to L-2,4-diaminobutyric acid residue; Bzl refers to benzyl. The tripeptide wrinkle-reducing compound and / or salt formed by the compound and acid is a polypeptide compound with a nitrogen 15 tracer agent and harmless to a human body. The compound is an acetylcholine receptor inhibitor, is capable of loosening muscle, has an obvious wrinkle-reducing effect, and can be used for medicine research and therapy for lightening and reducing wrinkles.

Description

technical field [0001] The invention belongs to the technical field of medicinal cosmetics, and in particular relates to a 15 The tripeptide wrinkle-reducing compound of N-L-proline residue, its preparation method and application. Background technique [0002] The formation of wrinkles is mainly caused by the strong contraction of muscles or the maintenance of muscles in a strongly contracted position for a long time. [0003] Currently, the main method of treating facial wrinkles is injection of botulinum toxin A, which paralyzes the facial muscles by injecting botulinum toxin A into the facial muscles. In this way, the muscles located in the eyes or forehead can no longer move, making eye or forehead wrinkles less likely to appear. However, the treatment with subcutaneous injection of botulinum toxin A must be implemented by professional doctors, and the high cost and high toxicity associated with it also limit the wide application of botulinum toxin A. In addition, its...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/023C07K1/06C07K1/04A61K38/06A61K8/64A61Q19/08A61P17/00
CPCY02P20/55
Inventor 张嘎张贲丁文锋
Owner 张嘎
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