Selective transport of ATP across a phospholipid bilayer by a molecular umbrella.
Acylation of each primary group of spermidine with cholic acid, followed by acylation of the secondary amino group using an activated form of Nalpha,Ndelta,Nomega-tri-CBZ-l-arginine, and subsequent hydrogenolysis, afforded a conjugate (i.e., 1) which readily transports adenosine 5-triphosphate, but not glutathione, across phospholipid bilayers made from 1-palmitoyl-2-oleyol-sn-glycero-3-phosphocholine and 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidylglycerol.
Janout
Vaclav
V
Department of Chemistry, Lehigh University, Bethlehem, PA 18015, USA.
Jing
Bingwen
B
Staina
Irina V
IV
Regen
Steven L
SL
D000255:Adenosine Triphosphate / Q000737:chemistry / Q000378:metabolism*; D001120:Arginine / Q000031:analogs & derivatives* / Q000737:chemistry; D001692:Biological Transport; D002793:Cholic Acids / Q000737:chemistry*; D004337:Drug Carriers; D005978:Glutathione / Q000737:chemistry / Q000378:metabolism; D008051:Lipid Bilayers / Q000737:chemistry / Q000378:metabolism*; D010713:Phosphatidylcholines / Q000737:chemistry; D010715:Phosphatidylglycerols / Q000737:chemistry; D010743:Phospholipids / Q000737:chemistry / Q000378:metabolism*; D013095:Spermidine / Q000031:analogs & derivatives* / Q000737:chemistry
D002793:Cholic Acids; D004337:Drug Carriers; D008051:Lipid Bilayers; D010713:Phosphatidylcholines; D010715:Phosphatidylglycerols; D010743:Phospholipids; C060037:1-palmitoyl-2-oleoylglycero-3-phosphoglycerol; D000255:Adenosine Triphosphate; D001120:Arginine; D005978:Glutathione; C028694:1-palmitoyl-2-oleoylphosphatidylcholine; D013095:Spermidine