Fully detachable molecular umbrellas as peptide delivery agents.
A persulfated molecular umbrella, derived from cholic acid and spermidine, has been covalently attached to H-Tyr-D-Ala-Gly-Phe-D-Leu-OH (DADLE) by use of an o-dithiobenzyl carbamate linkage. Treatment of the resulting conjugate (1) with glutathione in solution resulted in the liberation of the free form of the peptide. Addition of 1 to glutathione-entrapped liposomes, prepared from 1-palmitoyl-2-oleyol-sn-glycero-3-phosphocholine (POPC), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidylglycerol (POPG), and cholesterol [POPC/POPG/cholesterol, 72/4/24 (mol/mol/mol)], resulted in the delivery of DADLE into their aqueous interior.
Jing
Bingwen
B
Department of Chemistry, Lehigh University, Bethlehem, Pennsylvania 18015, USA.
Janout
Vaclav
V
Regen
Steven L
SL
D000596:Amino Acids / Q000737:chemistry*; D002240:Carbohydrate Sequence; D019826:Cholic Acid / Q000737:chemistry; D016503:Drug Delivery Systems; D005978:Glutathione / Q000737:chemistry; D008051:Lipid Bilayers / Q000378:metabolism; D008081:Liposomes / Q000378:metabolism; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D010743:Phospholipids / Q000378:metabolism; D013095:Spermidine / Q000737:chemistry; D013431:Sulfates / Q000737:chemistry*
D000596:Amino Acids; D008051:Lipid Bilayers; D008081:Liposomes; D010455:Peptides; D010743:Phospholipids; D013431:Sulfates; D019826:Cholic Acid; D005978:Glutathione; D013095:Spermidine