A fine line between molecular umbrella transport and ionophoric activity.
A persulfated molecular umbrella derived from one spermine, four lysine, and eight deoxycholic acid molecules was found to exhibit ionophoric activity, as shown by pH discharge and Na(+) and Cl(-) transport experiments. In sharp contrast, a moderately more hydrophilic analogue derived from cholic acid showed no such ionophoric activity. Both molecular umbrellas crossed liposomal membranes by passive transport with experimental rates that were similar. These findings show how the interactions between such amphomorphic molecules and phospholipid bilayers are a sensitive function of the umbrella's hydrophilic/lipophilic balance (HLB). They also raise the possibility of exploiting molecular umbrellas in fundamentally new ways.
Chen
Wen-Hua
WH
Department of Chemistry, Lehigh University, Bethlehem, Pennsylvania 18015, USA.
Janout
Vaclav
V
Kondo
Masaharu
M
Mosoian
Arevik
A
Mosoyan
Goar
G
Petrov
Ravil R
RR
Klotman
Mary E
ME
Regen
Steven L
SL
D001692:Biological Transport; D002712:Chlorides / Q000378:metabolism; D003840:Deoxycholic Acid / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D057927:Hydrophobic and Hydrophilic Interactions; D007476:Ionophores / Q000138:chemical synthesis*; D007700:Kinetics; D008081:Liposomes; D008239:Lysine / Q000737:chemistry*; D012964:Sodium / Q000378:metabolism; D013096:Spermine / Q000737:chemistry*
D002712:Chlorides; D007476:Ionophores; D008081:Liposomes; D003840:Deoxycholic Acid; D013096:Spermine; D012964:Sodium; D008239:Lysine
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