Glucosyl phosphotriesters of nucleosides: exchange mechanism of transmembrane transport and application to 5-fluoro-deoxyuridine.
The structure and membrane interactions of lipophilic glucosyl phosphotriester derivatives of thymidine and 5-fluoro-deoxy thymidine are investigated by NMR spectroscopy. The self-association of these molecules, found in different solvents, presents a diastereoisomeric effect which is also observed in the transmembrane transport inside large unilamellar vesicles. The influence of the hydrophobic chain and the nature of the nucleoside in the water-membrane exchange process is discussed.
Debouzy
J C
JC
CEN Saclay, Service de Biophysique, Gif/Yvette, France.
Hervé
M
M
Neumann
J M
JM
Gouyette
C
C
Dupraz
B
B
Huynh-Dinh
T
T
D001692:Biological Transport; D055598:Chemical Phenomena; D002621:Chemistry; D005467:Floxuridine / Q000031:analogs & derivatives* / Q000378:metabolism; D005958:Glucosephosphates / Q000378:metabolism; D008051:Lipid Bilayers; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010755:Organophosphates / Q000378:metabolism; D009943:Organophosphorus Compounds / Q000378:metabolism; D012997:Solvents; D013237:Stereoisomerism; D013696:Temperature
D005958:Glucosephosphates; D008051:Lipid Bilayers; D010755:Organophosphates; D009943:Organophosphorus Compounds; D012997:Solvents; D005467:Floxuridine