Granted Patent B2

US 12,559,733 · App. 17/409,306 · Granted Feb 24, 2026

Inventors: Campbell McInnes (Irmo, SC); Chad Beneker (Columbia, SC)

Assignee: UNIVERSITY OF SOUTH CAROLINA

C12N9/12A61K38/45A61P35/00C07K7/64C12Y207/11001A61K38/00

Abstract

Claims (28)

1 . A peptide comprising no more than 19 amino acid residues, the peptide comprising a macrocycle including 5 or more amino acid residues in the ring structure of the macrocycle, the peptide comprising one of SEQ ID NO: 50 (VKRKTRHVNILLFMEY) or SEQ ID NO: 53 (VLRKKRHVNELLFMG).

2 . The peptide of claim 1 , the peptide comprising SEQ ID NO: 50, the macrocycle ring structure consisting of the amino acid residues from the first lysine to the glutamic acid of SEQ ID NO: 50.

3 . The peptide of claim 1 consisting of SEQ ID NO: 50.

4 . The peptide of claim 1 , the peptide comprising SEQ ID NO: 53, the macrocycle ring structure consisting of the amino acid residues from the second lysine to the glutamic acid of SEQ ID NO: 53.

5 . The peptide of claim 4 consisting of SEQ ID NO: 53.

6 . The peptide of claim 1 , the peptide comprising an N-terminal capping group and/or a C-terminal capping group.

7 . The peptide of claim 1 , wherein the peptide further comprises an N-methylation of a residue.

8 . The peptide of claim 1 , the peptide further comprising an N-terminal capping group and/or a C-terminal capping group.

9 . The peptide of claim 8 , wherein the N-terminal capping group and/or the C-terminal capping group are independently selected from Structure I:

in which R 2 -R 6 are independently selected from hydrogen, carboxyl, alkyl, alkyl ester, hydroxyl, methoxy, halogen, amino, alkylamino, thiol, thioalkylether, sulfonamide, phosphate, nitro, methylamine, or boronic acid, and R 10 is C or N, and R 3 is relevant only when R 10 is C;

Structure II:

in which R1, R2, and R3 are selected from a hydrogen (H) or an alkyl group having a chain length of 1-3 carbons and n=0-3;

Structure III:

in which R1-R5 can be independently selected from a hydrogen (H) a linear or branched alkyl group having a chain length of 1-5 carbons, an amine, aminoalkyl, thiol, thioalkylether, an amide, a carboxylate, a sulfate, a sulfamide, a cyano, or a halogen, and n=0-4;

Structure IV:

in which R1-R3 can be independently selected from a hydrogen (H) a linear or branched alkyl group having a chain length of 1-5 carbons, an amine, an amide, a carboxylate, a sulfate, a sulfamide, a cyano, or a halogen; and the alkyl chain having a chain length, n=0-3, may be positioned on the phenyl ring at any position including ortho, meta, or para, relative to the alkoxy group having a chain length, m=1-5; and

Structure V:

10 . The peptide of claim 8 , wherein the N-terminal capping group is selected from the group consisting of:

11 . The peptide of claim 8 , wherein the C-terminal capping group is selected from the group consisting of:

12 . A peptide comprising no more than 19 amino acid residues, the peptide comprising a sequence of Lysine-N-methylated arginine-octyl-Glutamic Acid (K-MeR-octyl-E).

13 . The peptide of claim 12 , the amino acid residues of the peptide consisting of SEQ ID NO: 65.

14 . A peptide comprising no more than 19 amino acid residues, the peptide comprising:

a macrocycle consisting of six amino acid residues in the ring structure of the macrocycle, the peptide comprising SEQ ID NO: 61 (KRHPAELLFMG) or a sequence comprising Lysine-N-methylated arginine-D-alanine-Proline-Alanine-Glutamic Acid (K-MeR-a-PAE).

15 . The peptide of claim 14 , the amino acid residues of the peptide comprises SEQ ID NO: 61.

16 . The peptide of claim 14 , the amino acid residues of the peptide comprises K-MeR-a-PAE.

17 . The peptide of claim 14 , the peptide further comprising a linear peptide portion.

18 . The peptide of claim 17 , wherein the linear peptide portion comprises one or more of the modifications of SEQ ID NO: 1.

19 . The peptide of claim 18 , wherein the modifications comprise N-methylation of a residue of SEQ ID NO: 1.

Assignments (2)

Continuity (2)

References Cited (138)