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Enzymatic hydrolysis of stampidine and other stavudine phosphoramidates in the presence of mammalian proteases.
Venkatachalam, T K; Samuel, P; Uckun, F M.
Afiliación
  • Venkatachalam TK; Department of Chemistry, Pharmaceutical Sciences and Virology, Parker Hughes Institute, 2699, Patton Road, Roseville, MN 55113, USA.
Bioorg Med Chem ; 13(7): 2651-5, 2005 Apr 01.
Article en En | MEDLINE | ID: mdl-15755664
Mammalian proteases have not been implicated in the metabolism of any nucleoside phosphoramidate prodrug. The results presented herein provide unprecedented and conclusive experimental evidence that mammalian proteases are capable of hydrolyzing stavudine phosphoramidates. Specifically, cathepsin B and Proteinase K are able to metabolize stampidine and other phosphoramidate derivatives of stavudine. Additionally, cathepsin B exhibits chiral selectivity at the phosphorus center. The elucidation of the metabolic pathways leading to activation of stampidine may provide the basis for pharmacologic interventions aimed at modulating the metabolism and thereby improving the therapeutic window of stampidine as an anti-HIV agent.
Asunto(s)
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Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Péptido Hidrolasas / Ácidos Fosfóricos / Timidina Monofosfato / Estavudina / Amidas Límite: Animals Idioma: En Revista: Bioorg Med Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2005 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Reino Unido
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Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Péptido Hidrolasas / Ácidos Fosfóricos / Timidina Monofosfato / Estavudina / Amidas Límite: Animals Idioma: En Revista: Bioorg Med Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2005 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Reino Unido