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Last Updated: March 28, 2024

Claims for Patent: 10,227,383


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Summary for Patent: 10,227,383
Title:Specific modification of antibody with IgG-binding peptide
Abstract: This invention relates to an IgG-binding peptide, an IgG-binding peptide modified with a cross-linking agent, a conjugate of the IgG-binding peptide modified with a cross-linking agent and IgG, and a method for producing the conjugate, etc.
Inventor(s): Ito; Yuji (Kagoshima, JP)
Assignee: Kagoshima University (Kagoshima, JP)
Application Number:15/575,138
Patent Claims:1. A peptide comprising the amino acid sequence of the following formula (I): (X).sub.1-3-C-(X).sub.2-H-Xaa1-G-Xaa2-L-V-W-C-(X).sub.1-3 (SEQ ID NO: 43) (I), wherein each X is independently any amino acid residue other than cysteine, C is a cysteine residue, H is a histidine residue, Xaa1 is a lysine residue, a cysteine residue, an aspartic acid residue, a glutamic acid residue, 2-aminosuberic acid, or diaminopropionic acid, G is a glycine residue, Xaa2 is a glutamic acid residue or an asparagine residue, L is a leucine residue, V is a valine residue, and W is a tryptophan residue, wherein the peptide is 13 to 17 amino acid residues in length; and wherein the peptide exhibits the activity of binding to human immunoglobulin G (IgG) and/or rabbit IgG, and optionally wherein the cysteine residue that is between two to four amino acids from the N-terminus of formula (I) and the cysteine residue that is between two to four amino acids from the C-terminus of formula (I) are linked via a linker.

2. The peptide according to claim 1, wherein the peptide comprises the amino acid sequence of the following formula (II): (X).sub.1-3-C-Xaa3-Xaa4-H-Xaa1-G-Xaa2-L-V-W-C-(X).sub.1-3 (SEQ ID NO: 44) (II), wherein each X is independently any amino acid residue other than cysteine, C is a cysteine residue, H is a histidine residue, Xaa1 is a lysine residue, a cysteine residue, an aspartic acid residue, a glutamic acid residue, 2-aminosuberic acid, or diaminopropionic acid, G is a glycine residue, Xaa2 is a glutamic acid residue or an asparagine residue, L is a leucine residue, V is a valine residue, W is a tryptophan residue, Xaa3 is an alanine residue, a serine residue or a threonine residue, and Xaa4 is a tyrosine residue or a tryptophan residue.

3. The peptide according to claim 1, wherein the peptide comprises the amino acid sequence of the following formula (III): (X).sub.1-3-C-A-Y-H-Xaa1-G-E-L-V-W-C-(X).sub.1-3 (SEQ ID NO: 45) (III) wherein each X is independently any amino acid residue other than cysteine, C is a cysteine residue, A is an alanine residue, Y is a tyrosine residue, H is a histidine residue, Xaa1 is a lysine residue, a cysteine residue, an aspartic acid residue, a glutamic acid residue, 2-aminosuberic acid, or diaminopropionic acid, G is a glycine residue, E is a glutamic acid residue, L is a leucine residue, V is a valine residue, and W is a tryptophan residue.

4. The peptide according to claim 1, wherein the peptide is 17 amino acid residues in length, and wherein the amino acid residues from the 1st to 3rd and the 15th to 17th positions from the N terminus are each as follows: the 1st amino acid residue is S, G, F or absent, the 2nd amino acid residue is D, G, A, S, P, homocysteine, or absent, the 3rd amino acid residue is S, D, T, N, E or R, the 15th amino acid residue is S, T or D, the 16th amino acid residue is H, G, Y, T, N, D, F, homocysteine, or absent, and the 17th amino acid residue is Y, F, H, M or absent.

5. The peptide according to claim 1, wherein the peptide consists of any one of the following amino acid sequences 1) to 15): TABLE-US-00007 1) (SEQ ID NO: 1) DCAYHXaa1GELVWCT, 2) (SEQ ID NO: 2) GPDCAYHXaa1GELVWCTFH, 3) (SEQ ID NO: 3) RCAYHXaa1GELVWCS, 4) (SEQ ID NO: 4) GPRCAYHXaa1GELVWCSFH, 5) (SEQ ID NO: 5) SPDCAYHXaa1GELVWCTFH, 6) (SEQ ID NO: 6) GDDCAYHXaa1GELVWCTFH, 7) (SEQ ID NO: 7) GPSCAYHXaa1GELVWCTFH, 8) (SEQ ID NO: 8) GPDCAYHXaa1GELVWCSFH, 9) (SEQ ID NO: 9) GPDCAYHXaa1GELVWCTHH, 10) (SEQ ID NO: 10) GPDCAYHXaa1GELVWCTFY, 11) (SEQ ID NO: 11) SPDCAYHXaa1GELVWCTFY, 12) (SEQ ID NO: 12) SDDCAYHXaa1GELVWCTFY, 13) (SEQ ID NO: 13) RGNCAYHXaa1GQLVWCTYH, 14) (SEQ ID NO: 36) GXaa2DCAYHXaa1GELVWCTXaa2H, and 15) (SEQ ID NO: 37) RRGPDCAYHXaa1GELVWCTFH,

wherein Xaa1 is a lysine residue, a cysteine residue, an aspartic acid residue, a glutamic acid residue, 2-aminosuberic acid, or diaminopropionic acid, and Xaa2 is homocysteine.

6. The peptide according to claim 1, wherein the peptide comprises the amino acid sequence of the following formula (IV): D-C-Xaa3-Xaa4-H-Xaa1-G-Xaa2-L-V-W-C-T (SEQ ID NO: 46) (IV), wherein D is an aspartic acid residue, C is a cysteine residue, H is a histidine residue, Xaa1 is a lysine residue, a cysteine residue, an aspartic acid residue, a glutamic acid residue, 2-aminosuberic acid, or diaminopropionic acid, G is a glycine residue, Xaa2 is a glutamic acid residue or an asparagine residue, L is a leucine residue, V is a valine residue, W is a tryptophan residue, T is a threonine residue, Xaa3 is an alanine residue or a threonine residue, and Xaa4 is a tyrosine residue or a tryptophan residue.

7. The peptide according to claim 6, wherein the peptide consists of any one of the following amino acid sequences 1) to 4): TABLE-US-00008 1) (SEQ ID NO: 14) DCTYHXaa1GNLVWCT, 2) (SEQ ID NO: 15) DCAYHXaa1GNLVWCT, 3) (SEQ ID NO: 16) DCTYHXaa1GELVWCT, and 4) (SEQ ID NO: 17) DCAWHXaa1GELVWCT,

wherein Xaa1 is a lysine residue, a cysteine residue, an aspartic acid residue, a glutamic acid residue, 2-aminosuberic acid, or diaminopropionic acid.

8. The peptide according to claim 1, wherein the peptide has a disulfide bond formed between the two cysteine residue that is between two to four amino acids from the N-terminus of formula (I) and the cysteine residue that is between two to four amino acids from the C-terminus of formula (I), or the sulfide groups in the cysteine residue that is between two to four amino acids from the N-terminus of formula (I) and the cysteine residue that is between two to four amino acids from the C-terminus of formula (I) are linked via a linker represented by the following formula: ##STR00008##

9. The peptide according to claim 1, wherein the peptide is labeled with a labeling agent.

10. The peptide according to claim 1, wherein the peptide is bound with a drug.

11. The peptide according to claim 1, wherein Xaa1 is a lysine residue.

12. The peptide according to claim 1, wherein Xaa1 is modified with a cross-linking agent.

13. The peptide according to claim 12, wherein the cross-linking agent is selected from the group consisting of DSG (disuccinimidyl glutarate), DSS (disuccinimidyl suberate), DMA (dimethyl adipimidate dihydrochloride), DMP (dimethyl pimelimidate dihydrochloride), DMS (dimethyl suberimidate dihydrochloride), DTBP (dimethyl 3,3'-dithiobispropionimidate dihydrochloride), and DSP (dithiobis(succinimidyl propionate)).

14. The peptide according to claim 13, wherein the cross-linking agent is DSG (disuccinimidyl glutarate) or DSS (disuccinimidyl suberate).

15. A peptide comprising the amino acid sequence of the following formula (V): D-C-Xaa2-Xaa3-Xaa4-Xaa1-G-Xaa5-L-Xaa6-W-C-T (SEQ ID NO: 47) (V), wherein D is an aspartic acid residue, C is a cysteine residue, G is a glycine residue, L is a leucine residue, W is a tryptophan residue, T is a threonine residue, Xaa1 is a lysine residue, a cysteine residue, an aspartic acid residue, a glutamic acid residue, 2-aminosuberic acid, or diaminopropionic acid, Xaa2 is an alanine residue, a serine residue or a threonine residue, Xaa3 is a tryptophan residue or a tyrosine residue, Xaa4 is a histidine residue, an arginine residue, a serine residue or a threonine residue, Xaa5 is a glutamic acid residue, an asparagine residue, an arginine residue, or an aspartic acid residue, and Xaa6 is an isoleucine residue or a valine residue, wherein the peptide is 13 amino acid residues in length; and wherein the peptide exhibits the activity of binding to human IgG and/or rabbit IgG.

16. A conjugate comprising the peptide according to claim 12 and IgG, wherein the conjugate is formed through a cross-linking reaction of the modified peptide and the IgG.

17. A pharmaceutical composition comprising the peptide according to claim 1 or a conjugate comprising the peptide according to claim 1 and IgG, wherein Xaa1 in the peptide of the conjugate is modified with a cross-linking agent, and wherein the conjugate is formed through a cross-linking reaction of the modified peptide and the IgG.

18. A method for producing the conjugate according to claim 16, wherein the method comprises: (a) modifying Xaa1 in the peptide with a cross-linking agent, and (b) mixing the modified peptide with IgG to cross-link the modified peptide and the IgG.

19. A method for producing a peptide having two or more cysteine residues linked via a linker, wherein the method comprises mixing the peptide according to claim 1 with a compound represented by the following formula: ##STR00009## wherein R.sub.1 and R.sub.2 are each independently any halogen atom, to obtain a peptide in which sulfide groups in the two or more cysteine residues are linked via a linker represented by the following formula: ##STR00010##

20. The method according to claim 19, wherein R.sub.1 and R.sub.2 in the compound are the same and are Cl, Br, or I.

Details for Patent 10,227,383

Applicant Tradename Biologic Ingredient Dosage Form BLA Approval Date Patent No. Expiredate
Csl Behring Ag CARIMUNE, CARIMUNE NF, PANGLOBULIN, SANDOGLOBULIN immune globulin intravenous (human) For Injection 102367 07/27/2000 ⤷  Try a Trial 2035-05-20
Csl Behring Ag PRIVIGEN immune globulin intravenous (human), 10% liquid Injection 125201 07/26/2007 ⤷  Try a Trial 2035-05-20
Csl Behring Ag PRIVIGEN immune globulin intravenous (human), 10% liquid Injection 125201 10/02/2009 ⤷  Try a Trial 2035-05-20
Csl Behring Ag PRIVIGEN immune globulin intravenous (human), 10% liquid Injection 125201 02/07/2013 ⤷  Try a Trial 2035-05-20
Bio Products Laboratory GAMMAPLEX immune globulin intravenous (human) Injection 125329 09/17/2009 ⤷  Try a Trial 2035-05-20
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Approval Date >Patent No. >Expiredate

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