Electrochemical reduction products of azido nucleosides, including Zidovudine [AZT]: mechanisms and relevance to their intracellular metabolism

• Autorzy: Kawczynski W. , Czochralska B. , Schugar D.
• Języki publikacji: EN

Abstrakty

Previous studies on electrochemical reduction of the HTV reverse transcriptase inhibitor, 3'-azido-3'-deoxy thymidine (Zidovudine, AZT) and several of its analogues, have been extended to 2'-AZdT and two of the intracellular metabolites of AZT, the 5'-0-glucuronide (GAZT) and the 5'-phosphate (AZTMP). Also investigated were azido nucleosides with aglycons susceptible to electrochemical reduction, cytosine and adenine. The surface activities of these compounds at the mercury electrode were examined. In all instances, reduction of the azido group was a two-electron process, with conversion to an amino group. For an azido adenine nucleoside, it proved possible to reduce the azido group without affecting the aglycon. Electrochemical reduction is shown to provide a simple one-step synthesis of amino nucleosides from the available azido nucleosides. The reduced compounds, several hitherto unknown, are useful reference standards for following intracellular metabolism of azido nucleosides, and may also prove of interest as new potential antimetabolites.

Słowa kluczowe

EN

metabolism; intracellular metabolism; azido nucleoside; electrochemical reduction

• Wydawca: -
• Czasopismo: Acta Biochimica Polonica
• Rocznik: 1993
• Tom: 40
• Numer: 2
• Opis fizyczny: p.213-223,fig.

Twórcy

autor

Kawczynski W.

• Warsaw University, Zwirki i Wigury 93, 02-089 Warsaw, Poland

autor

Czochralska B.

autor

Schugar D.

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