US 10,376,592 B2
Stapled acid-sensitive endosome disrupting alginates
Abhinav Acharya, Pittsburgh, PA (US); and Stephen R. Little, Allison Park, PA (US)
Assigned to University of Pittsburgh—Of the Commonwealth System of Higher Education, Pittsburgh, PA (US)
Appl. No. 15/580,646
Filed by University of Pittsburgh—Of the Commonwealth System of Higher Education, Pittsburgh, PA (US)
PCT Filed Jun. 28, 2016, PCT No. PCT/US2016/039873
§ 371(c)(1), (2) Date Dec. 7, 2017,
PCT Pub. No. WO2017/004071, PCT Pub. Date Jan. 5, 2017.
Claims priority of provisional application 62/186,141, filed on Jun. 29, 2015.
Prior Publication US 2018/0161441 A1, Jun. 14, 2018
Int. Cl. A61K 31/734 (2006.01); A61K 47/61 (2017.01); C08L 5/04 (2006.01); C08B 37/00 (2006.01); A61P 25/28 (2006.01); A61P 35/00 (2006.01); A61K 9/06 (2006.01); A61K 9/50 (2006.01); A61K 33/34 (2006.01); A61K 41/00 (2006.01); A61K 45/06 (2006.01); A61K 31/30 (2006.01)
CPC A61K 47/61 (2017.08) [A61K 9/06 (2013.01); A61K 9/5036 (2013.01); A61K 31/30 (2013.01); A61K 31/734 (2013.01); A61K 33/34 (2013.01); A61K 41/0028 (2013.01); A61K 45/06 (2013.01); A61P 25/28 (2018.01); A61P 35/00 (2018.01); C08B 37/0084 (2013.01); C08L 5/04 (2013.01)] 30 Claims
 
1. An agent comprising:
an algin crosslinked with acetal linkages, wherein the acetal linkages have a structure of —X1-A-X2— wherein X1 and X2 are each independently —NH— or —O—, and A includes an acetal group; and
at least one cation coupled to the crosslinked algin; wherein A is:

OG Complex Work Unit Drawing
 wherein R10 and R11 are each independently an alkanediyl, and R12 and R13 are each optionally substituted alkyl.
 
14. A method comprising delivering at least one cation to the cytosol of a cell, comprising contacting the cell with the agent of claim 1.