US 11,878,046 B2
Di-sulfide containing cell penetrating peptides and methods of making and using thereof
Dehua Pei, Columbus, OH (US); and Ziqing Qian, Columbus, OH (US)
Assigned to Ohio State Innovation Foundation, Columbus, OH (US)
Filed by Ohio State Innovation Foundation, Columbus, OH (US)
Filed on Nov. 30, 2021, as Appl. No. 17/538,330.
Application 17/538,330 is a continuation of application No. 16/348,706, granted, now 11,351,222, previously published as PCT/US2017/060881, filed on Nov. 9, 2017.
Claims priority of provisional application 62/438,141, filed on Dec. 22, 2016.
Claims priority of provisional application 62/425,550, filed on Nov. 22, 2016.
Claims priority of provisional application 62/419,781, filed on Nov. 9, 2016.
Prior Publication US 2022/0160819 A1, May 26, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 38/12 (2006.01); C07K 7/06 (2006.01); C07K 7/08 (2006.01); C07K 7/50 (2006.01); A61K 38/00 (2006.01); C07K 5/10 (2006.01); C07K 14/00 (2006.01)
CPC A61K 38/12 (2013.01) [C07K 5/10 (2013.01); C07K 7/06 (2013.01); C07K 7/08 (2013.01); C07K 7/50 (2013.01); C07K 14/001 (2013.01); A61K 38/00 (2013.01)] 18 Claims
 
1. A bicyclic peptide comprising a first cyclic peptide and a second cyclic peptide, the bicyclic peptide having one of the following structures:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof,
wherein:
the first cyclic peptide comprises AA1, AA2, AA3, AA4, AA5, AA6, AA7, AA8, and AA9, each independently an amino acid, wherein at least two amino acids are arginine and at least two amino acids independently comprise a hydrophobic side chain;
each m, n, p, and q is independently selected from 0 and 1;
each d is independently 1 or 2;
the second cyclic peptide comprises a peptidyl ligand (Xn);
R1 is OH, OR2, NHR2; and
R2 is alkyl, aryl, heteroaryl, amino acid, peptide sequence of 2 to 20 amino acids, detectable moiety, or solid support.