Mixed mode affinity chromatography carrier

Patent metadata

Field	Value
Publication number	US-11565240-B2
Application number	US-201916402447-A
Country	US
Kind code	B2
Filing date	May 3, 2019
Priority date	Dec 9, 2016
Publication date	Jan 31, 2023
Grant date	Jan 31, 2023

Abstract

A mixed mode affinity chromatography carrier includes a substrate, a hydrophilic polymer, an antibody-binding cyclic peptide, and a cation exchange group.

First claim

What is claimed is:

1. A mixed mode affinity chromatography carrier, comprising:
a substrate that is at least one selected from the group consisting of a polysaccharide, an acrylate-based polymer, a methacrylate-based polymer, and a styrene-based polymer;
a hydrophilic polymer coated on the substrate, the hydrophilic polymer being a hydrophilic polysaccharide;
an antibody-binding cyclic peptide that includes a cyclic portion cyclized by intramolecular crosslinking between side chains; and
a cation exchange group that is a carboxy group or a sulfoxy group.

2. The mixed mode affinity chromatography carrier according to claim 1 ,
wherein the intramolecular crosslinking includes at least one selected from the group consisting of a disulfide bond, a thioether bond, a triazole bond, and an amide bond.

3. The mixed mode affinity chromatography carrier according to claim 1 ,
wherein the intramolecular crosslinking includes at least one selected from the group consisting of a disulfide bond, a thioether bond, and a triazole bond.

4. The mixed mode affinity chromatography carrier according to claim 3 ,
wherein the disulfide bond is a disulfide bond formed between a side chain thiol group of a first amino acid residue derived from an amino acid having a thiol group in a side chain other than L-cysteine and D-cysteine and a side chain thiol group of a second amino acid residue derived from an amino acid having a thiol group in a side chain other than L-cysteine and D-cysteine, and
wherein the thioether bond is a thioether bond formed between a side chain thiol group of a first amino acid residue derived from an amino acid having a thiol group in a side chain other than L-cysteine and D-cysteine and a side chain haloacetyl group of a second amino acid residue derived from an amino acid having a haloacetyl group in a side chain.

5. The mixed mode affinity chromatography carrier according to claim 3 ,
wherein the disulfide bond is a disulfide bond formed between a side chain thiol group of a first amino acid residue derived from an amino acid having a thiol group in a side chain selected from the group consisting of cysteine, homocysteine, and penicillamine and a side chain thiol group of a second amino acid residue derived from an amino acid having a thiol group in a side chain selected from the group consisting of cysteine, homocysteine, and penicillamine, and
wherein the thioether bond is a thioether bond formed between a side chain thiol group of a first amino acid residue derived from an amino acid having a thiol group in a side chain selected from the group consisting of cysteine, homocysteine, and penicillamine and a side chain haloacetyl group of a second amino acid residue derived from an amino acid having a haloacetyl group in a side chain.

6. The mixed mode affinity chromatography carrier according to claim 3 ,
wherein the disulfide bond is a disulfide bond formed between a side chain thiol group of a first amino acid residue derived from an amino acid having a thiol group in a side chain selected from the group consisting of homocysteine and penicillamine and a side chain thiol group of a second amino acid residue derived from an amino acid having a thiol group in a side chain selected from the group consisting of homocysteine and penicillamine, and
wherein the thioether bond is a thioether bond formed between a side chain thiol group of a first amino acid residue derived from an amino acid having a thiol group in a side chain selected from the group consisting of homocysteine and penicillamine and a side chain haloacetyl group of a second amino acid residue derived from an amino acid having a haloacetyl group in a side chain.

7. The mixed mode affinity chromatography carrier according to claim 1 ,
wherein the intramolecular crosslinking is a disulfide bond formed between a side chain thiol group of a first amino acid residue derived from an amino acid having a thiol group in a side chain selected from the group consisting of homocysteine and penicillamine and a side chain thiol group of a second amino acid residue derived from an amino acid having a thiol group in a side chain selected from the group consisting of homocysteine and penicillamine, or a thioether bond formed between a side chain thiol group of a first amino acid residue derived from an amino acid having a thiol group in a side chain selected from the group consisting of homocysteine and penicillamine and a side chain haloacetyl group of a second amino acid residue derived from an amino acid having a haloacetyl group in a side chain.

8. The mixed mode affinity chromatography carrier according to claim 7 ,
wherein the disulfide bond is a disulfide bond formed between a side chain thiol group of a first amino acid residue derived from homocysteine and a side chain thiol group of a second amino acid residue derived from homocysteine, and
wherein the thioether bond is a thioether bond formed between a side chain thiol group of a first amino acid residue derived from homocysteine and a side chain haloacetyl group of a second amino acid residue derived from an amino acid having a haloacetyl group in a side chain.

9. The mixed mode affinity chromatography carrier according to claim 1 ,
wherein the number of the amino acid residues of the cyclic portion is 8 to 14.

10. The mixed mode affinity chromatography carrier according to claim 1 ,
wherein the antibody-binding cyclic peptide includes a straight chain portion.

11. The mixed mode affinity chromatography carrier according to claim 10 ,
wherein the straight chain portion includes an amino acid residue having at least one selected from the group consisting of a hydroxy group and a carboxy group in a side chain.

12. The mixed mode affinity chromatography carrier according to claim 1 ,
wherein the substrate is at least one selected from the group consisting of a polysaccharide, an acrylate-based polymer, and a methacrylate-based polymer.

13. The mixed mode affinity chromatography carrier according to claim 1 ,
wherein the substrate is at least one selected from the group consisting of agarose and cellulose.

14. The mixed mode affinity chromatography carrier according to claim 1 ,
wherein the hydrophilic polysaccharide is at least one selected from the group consisting of dextran, carboxymethyl dextran, pullulan, hydroxyethyl cellulose, and carboxymethyl cellulose.

15. The mixed mode affinity chromatography carrier according to claim 1 ,
wherein the hydrophilic polysaccharide is at least one selected from the group consisting of dextran, carboxymethyl dextran, and pullulan.

16. The mixed mode affinity chromatography carrier according to claim 1 ,
wherein the cation exchange group is a carboxy group.

17. A mixed mode affinity chromatography carrier, comprising:
a substrate that is at least one selected from the group consisting of a polysaccharide, an acrylate-based polymer, a methacrylate-based polymer, and a styrene-based polymer;
a hydrophilic polymer that is a hydrophilic polysaccharide;
an antibody-binding cyclic peptide that includes a cyclic portion cyclized by intramolecular crosslinking between side chains; and
a cation exchange group that is a carboxy group or a sulfoxy group,
wherein the intramolecular crosslinking includes at least one selected from the group consisting of a disulfide bond, a thioether bond, and a triazole bond,
the disulfide bond is a disulfide bond formed between a side chain thiol group of a first amino acid residue derived from an amino acid having a thiol group in a side chain other than L-cysteine an

Assignees

• Fujifilm Corp

Inventors

• KIHARA Shiori

Classifications

• B01D15/362

  Cation-exchange · CPC title

• C07K1/165

  mixed-mode chromatography · CPC title

• C07K16/00

  Immunoglobulins [IG], e.g. monoclonal or polyclonal antibodies · CPC title

• C07K1/22

  Affinity chromatography or related techniques based upon selective absorption processes · CPC title

• B01D15/3809

  of the antigen-antibody type, e.g. protein A, G or L chromatography · CPC title