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Self-assembling ultrashort aliphatic depsipeptides for biomedical applications

A technology for self-assembling, aliphatic amino acids with applications in cell and tissue engineering and nanomedicine

Inactive Publication Date: 2017-11-28
AGENCY FOR SCI TECH & RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although self-assembly was observed, the authors attributed it to π-π stacking of the Fmoc group and thus only explored the Fmoc-protected desipeptide

Method used

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  • Self-assembling ultrashort aliphatic depsipeptides for biomedical applications
  • Self-assembling ultrashort aliphatic depsipeptides for biomedical applications
  • Self-assembling ultrashort aliphatic depsipeptides for biomedical applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0246] 1. Materials and Methods

[0247] 1.1 Materials

[0248] Fmoc-lys-rink resin (0.42 mg / mol resin), Fmoc-protected amino acids, namely glycine, alanine, valine, leucine and isoleucine, 2-(7-aza-1H-phenyl Triazole)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) was purchased from GL Biochem (Shanghai) Co., Ltd. Dimethylformamide (DMF) (analytical grade) was purchased from Fisher Scientific UK. Acetic anhydride (Ac 2 O) and dimethylsulfoxide (DMSO) were purchased from Sigma Aldrich. N,N-Diisopropylethylamine (DIPEA), dichloromethane (DCM), trifluoroacetic acid (TFA) and TIS (triisopropylsilane) were purchased from Alfa Aesar, a Johnson Matthey Company. Piperidine was purchased from Merck Schuchardt OHG. Diethyl ether (Et 2 O) was purchased from Tedia Company Inc. and lactic acid was purchased from Sigma-Aldrich. All chemicals were used as received.

[0249] All peptide-based compounds were purified on an Agilent 1260 Infinity preparative HPLC system equipped ...

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Abstract

The present invention relates to ultrashort depsipeptides which are capable of self-assembling into hydrogels. One preferred embodiment is of Ac-ILVaGK-NH2, where a represents lactic acid. The invention also relates to the use of these depsipeptides in formulating hydrogels, co-gels or co-hydrogels, and pharmaceutical compositions or biomedical device or surgical implants or kits comprising these depsipeptides for various therapeutic applications such as regenerative medicine, tissue regeneration and tissue replacement.

Description

technical field [0001] The present invention is in the fields of cell and tissue engineering and nanomedicine. The present invention generally relates to depsipeptides and their use in hydrogels and in co-gels or co-hydrogels. Background technique [0002] The following discussion of the background of the invention is intended to facilitate an understanding of the invention. It should be understood, however, that the discussion is not an acknowledgment or admission that any of the material referred to was published, known or part of the common general knowledge in any jurisdiction as at the priority date of the invention. [0003] The development of readily biodegradable hydrogel-forming peptides is a long-standing desire. Early studies by Zhang et al. (1993) have reported that β-sheet forming peptides such as (AEAEAKAK) 2 Contains amino acid sequences that are expected to be enzymatically digested but instead remain undigested upon exposure to alpha-chymotrypsin, trypsin...

Claims

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Application Information

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IPC IPC(8): C07K11/00A61K47/34A61P17/02A61P19/00
CPCA61L27/227A61L27/52A61L27/54A61L2400/06A61L2430/34A61P17/02A61P19/00C07K11/00G01N2800/7095A61K47/34
Inventor C·A·E·霍瑟M·R·赖特霍费尔卢意华
Owner AGENCY FOR SCI TECH & RES
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