1. Academic Validation
  2. Lipophilic glycosyl phosphotriester derivatives of AZT: synthesis, NMR transmembrane transport study, and antiviral activity

Lipophilic glycosyl phosphotriester derivatives of AZT: synthesis, NMR transmembrane transport study, and antiviral activity

  • J Med Chem. 1991 Jun;34(6):1830-7. doi: 10.1021/jm00110a011.
Y Henin 1 C Gouyette O Schwartz J C Debouzy J M Neumann T Huynh-Dinh
Affiliations

Affiliation

  • 1 Unité d'Oncologie Virale, URA CNRS 1157, Institut Pasteur, Paris, France.
Abstract

Phosphate derivatives of AZT esterified with a carbohydrate (D-glucose, D-mannose, and ethyl D-mannopyranoside) and a hexadecyl chain were prepared from glucose 6-phosphate and D-mannose precursors. The 31P NMR study of the mannosyl phosphotriester series in the presence of large unilamellar vesicles demonstrated either an interaction with the external lipid layer or a transmembrane transport into the intravesicular interface. The Antiviral activity, measured by the inhibition of cytopathogenicity on different infected cells and of Reverse Transcriptase activity in the supernatant of cultures, appeared to be comparable to that of AZT, in the micromolar range.

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