Granted Patent
B2
US 12,454,552 · App. 17/832,107 · Granted Oct 28, 2025
Cyclic cell penetrating peptides comprising beta-hairpin motifs and methods of making and using thereof
Assignee:
Ohio State Innovation Foundation
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Abstract
Disclosed herein are peptides having activity as cell penetrating peptides. In some embodiments, the peptides can comprise a cell penetrating peptide moiety and beta-haripin turn creating moiety. In other embodiments, the peptides also comprise a cargo moiety.
Claims (16)
1. A compound comprising a cyclic peptide, which comprises:
(i) at least three arginine residues;
(ii) two or more arginines adjacent to each other;
(iii)-D-Pro-L-Pro-or-L-Pro-D-Pro-located between two arginine residues;
(iv) two or more consecutive amino acids having hydrophobic side chains; and
(v) the amino acids having hydrophobic side chains are each independently phenylalanine and naphthylalanine;
wherein the compound has any one of the following structures:
wherein:
AA 1 , AA 2 , AA 3 , AA 4 , AA 5 , AA 6 , AA 7 , AA 8 , AA 9 , AA 10 , AA 11 , AA 12 , AA 13 , AA 14 , AA 15 , AA 16 , AA 17 , and AA 18 , when present, are each, independently, an amino acid residue, each of which is optionally substituted.
2. The compound of claim 1 , wherein the cyclic peptide comprises a sequence selected from any one of SEQ ID NOs: 140 and 143-151.
3. The compound of claim 1 , further comprising a cargo moiety.
4. The compound of claim 1 , wherein the cyclic peptide comprises an amino acid sequence of any one of SEQ ID NOs: 144-151.
5. A pharmaceutical composition comprising the compound of claim 1 .
6. The compound of claim 1 , comprising-D-Pro-L-Pro-.
7. The compound of claim 2 , wherein the compound comprises:
F-Φ-R-D-Pro-L-Pro-R-R; f-F-r-ϕ-D-Pro-L-Pro-R-r; f-Φ-f-r-D-Pro-L-Pro-R-r; F-ϕ-r-D-Pro-L-Pro-R-r-R; F-ϕ-r-R-D-Pro-L-Pro-r-R; f-Φ-R-D-Pro-L-Pro-r-R-r; F-Φ-R-L-Pro-D-Pro-R-R; f-F-ϕ-r-L-Pro-D-Pro-Rr; f-Φ-f-L-Pro-D-Pro-r-R-r; F-ϕ-r-L-Pro-D-Pro-R-r-R; F-ϕ-r-L-Pro-D-Pro-R-r-R; and f-Φ-R-L-Pro-D-Pro-r-R-r.
Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Oct 26, 2022
From: PEI, DEHUA; QIAN, ZIQING
To: OHIO STATE INNOVATION FOUNDATION
Reel/Frame 061544/0357 →
Continuity (3)
Continuation
16462920
Provisional Application
62425438
· Nov 22, 2016
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