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US-12624067-B2 - Cyclic peptide, cell scaffold material, cell separating material, and medium

US12624067B2US 12624067 B2US12624067 B2US 12624067B2US-12624067-B2

Abstract

There is provided a cyclic peptide having an amino acid sequence represented Formula (1). In the formula, X a and X b , and X c and X d each independently represent amino acid residues crosslinked through a thioether bond; X 1 to X 5 each independently represent an amino acid residue; R represents an arginine residue; G represents a glycine residue; D represents an aspartic acid residue; and m1 to m5 each independently represent an integer of 0 or more. However, the total number of amino acid residues represented by X a , X b , X c , and X d and represented by X 1 , X 3 , and X 4 is 7 to 16.

Inventors

  • Koichi Minami

Assignees

  • FUJIFILM CORPORATION

Dates

Publication Date
20260512
Application Date
20211209
Priority Date
20190611

Claims (7)

  1. 1 . A cyclic peptide comprising an amino acid sequence selected from the group consisting of SEQ ID NOs: 1-47.
  2. 2 . A cell scaffold material comprising: the cyclic peptide according to claim 1 ; and a base material.
  3. 3 . A cell separating material comprising: the cyclic peptide according to claim 1 ; and a holding material.
  4. 4 . A medium comprising: the cyclic peptide according to claim 1 ; and a culture component.
  5. 5 . The cyclic peptide according to claim 1 , comprising an amino acid sequence selected from the group consisting of SEQ ID NOs: 3, 8, 11, 12, 14-18, 20, 22-30, 35, 38-40, and 42-47.
  6. 6 . The cyclic peptide according to claim 1 , comprising an amino acid sequence selected from the group consisting of SEQ ID NOs: 1-5, 7, 9, 11, and 13-47.
  7. 7 . The cyclic peptide according to claim 1 , comprising an amino acid sequence selected from the group consisting of SEQ ID NOs: 3, 11, 14-18, 20, 22-30, 35, 38-40, and 42-47.

Description

CROSS-REFERENCE TO RELATED APPLICATION This application is a Continuation of International Application No. PCT/JP2020/022559, filed Jun. 8, 2020, which claims priority to Japanese Patent Application No. 2019-108953 filed Jun. 11, 2019. Each of the above applications is hereby expressly incorporated by reference, in its entirety, into the present application. INCORPORATION BY REFERENCE OF SEQUENCE LISTING The content of the electronically submitted sequence listing, file name: Q268729SubstituteSequenceListing.txt; size: 35,120 bytes; and date of creation: Jan. 14, 2026, is hereby incorporated by reference in their entirety. BACKGROUND OF THE INVENTION 1. Field of the Invention The present disclosure relates to a cyclic peptide, a cell scaffold material, a cell separating material, and a medium. 2. Description of the Related Art Integrin is a cell adhesion molecule and is a heterodimeric protein consisting of two subunits, an α chain and a β chain. Integrin plays an important role not only in cell adhesion but also in cel extension, cell migration, cell proliferation, tissue formation, cancer metastasis, tissue repair, blood coagulation, and the like. In the related art, cyclic peptides such as those described in JP2005-507376A, JP1994-509551A (JP-H6-509551A), and Bioconjugate Chem., 1995, 6, p. 269-277, are known. JP2005-507376A discloses a cyclic peptide that is cyclized by a disulfide bond and that binds to integrin. Other cyclic peptides having an affinity to integrin are also known. For example, JP1994-509551A (JP-H6-509551A) discloses a cyclic peptide obtained by cyclizing Tyr-Arg-Gly-Asp, as a platelet aggregation inhibitor having high specificity to GP IIb IIIa. In addition, Bioconjugate Chem., 1995, 6, p. 269-277 describes a technique for subjecting a peptide to cyclization and/or binding to a carrier protein or glass coverslip using (bromoacetyl) diaminopropionic acid. SUMMARY OF THE INVENTION An object to be achieved by an aspect of the present disclosure is to provide a cyclic peptide excellent in the integrin binding property and excellent in the molecule stability, for example, excellent in the alkali resistance, and a cell scaffold material, a cell separating material, and a medium, which contain the cyclic peptide. The technique for achieving the above object includes the following aspects. <1> A cyclic peptide comprising an amino acid sequence represented Formula (1). In Formula (1), Xa and Xb, and Xc and Xd each independently represent amino acid residues crosslinked through a thioether bond, X1 to X5 independently represent an amino acid residue,R represents an arginine residue; G represents a glycine residue; D represents an aspartic acid residue, and m1 to m5 each independently represent an integer of 0 or more, provided that a total number of amino acid residues represented by Xa, Xb, Xc, and Xd, amino acid residues represented by X1, X3, and X4, and amino acid residues of RGD is 7 to 16. <2> The cyclic peptide according to <1>, in which X2 and X5 in Formula (1) comprise an amino acid residue derived from an amino acid having an immobilizing functional group in a side chain. <3> The cyclic peptide according to <2>, in which the immobilizing functional group is an amino group or a thiol group. <4> The cyclic peptide according to <2> or <3>, in which the amino acid having the immobilizing functional group in the side chain is at least one amino acid selected from the group consisting of L-lysine, D-lysine, L-cysteine, D-cysteine, L-homocysteine, and D-homocysteine. <5> The cyclic peptide according to any one of <1> to <4>, in which any one of Xc or Xd in Formula (1) is an amino acid residue, which is derived from an amino acid selected from the group consisting of (2S)-2-amino-3-[(2-acetyl)amino]propanoic acid, (2R)-2-amino-3-[(2-acetyl)amino]propanoic acid, (2S)-2-amino-4-[(2-acetyl)amino]butanoic acid, (2R)-2-amino-4-[(2-acetyl)amino]butanoic acid, N-δ-acetyl-L-ornithine, N-δ-acetyl-D-ornithine, N-ε-acetyl-L-lysine, and N-ε-acetyl-D-lysine, and the other is an amino acid residue derived from L-homocysteine, D-homocysteine, L-penicillamine, or D-penicillamine. <6> The cyclic peptide according to any one of <1> to <5>, in which Xb in Formula (1) is an amino acid residue derived from L-homocysteine, D-homocysteine, L-penicillamine, or D-penicillamine. <7> The cyclic peptide according to any one of <1> to <6>, in which the amino acid sequence represented by Formula (1) is an amino acid sequence represented Formula (2). In Formula (2), Xa and Xb, and Xc and Xd each independently represent amino acid residues crosslinked through a thioether bond; X1 and X2 each independently represent an amino acid residue; R represents an arginine residue; G represents a glycine residue; D represents an aspartic acid residue; and m1 and m2 each independently represent an integer of 1 or more. However, a total number of amino acid residues represented by Xa, Xb, Xc, and Xd, amino acid residues represented by X