Nucleoside and nucleotide transport through a model liquid membrane. Periodic-catastrophic transport of a novel amantadine phosphoramidate conjugate of 5'-AMP.
Adenosine 5'-phosphor(adamantyl)amidate (5), an analog derived by linking the antiviral drug amantadine to 5'-AMP is transported through a model membrane system in a discontinuous periodic-catastrophic fashion. The system was composed of a glass cell containing two aqueous buffer phases separated by a chloroform layer. A more lipophilic, but structurally related derivative, adenosine 5'-phosphor(n-decyl)amidate (3) showed linear transport in the same system. Less lipophilic substances, including 5'-AMP and adenosine 5'-phosphor(morpholidyl)amidate (2), did not show transport. It is hypothesized that the periodic-catastrophic transport is a result of the collective activity of amidate 5 at the interface between the first aqueous interface and the chloroform layer. The time between catastrophic events is thought to be a reflection of the time necessary for molecular organization at the interface. The phenomenon is a new example of molecular organization in a system far from equilibrium leading to a repetitive dynamic process.
Bergstrom
D E
DE
Department of Medicinal Chemistry and Pharmacognosy, Purdue University, West Lafayette, IN 47907.
Abrahamson
J K
JK
Chan
M Y
MY
D000249:Adenosine Monophosphate / Q000031:analogs & derivatives* / Q000378:metabolism*; D000547:Amantadine / Q000031:analogs & derivatives* / Q000378:metabolism*; D001692:Biological Transport; D001976:Bromouracil / Q000031:analogs & derivatives; D007700:Kinetics; D008051:Lipid Bilayers / Q000737:chemistry / Q000378:metabolism*; D014529:Uridine / Q000031:analogs & derivatives / Q000378:metabolism
D008051:Lipid Bilayers; C067433:adenosine 5'-phosphor(adamantyl)amidate; D000249:Adenosine Monophosphate; D001976:Bromouracil; D000547:Amantadine; C006824:5-bromouridine; D014529:Uridine