Inactivation of S-adenosyl-L-homocysteine hydrolase with novel 5′-thioadenosine derivatives. Antiviral effects

Article abstract of DOI:10.1016/S0960-894X(03)00279-8

Synthesis of 5′-S-vinyl-5′-thioadenosine 5, 5′-S-ethynyl-5′-thioadenosine 7 and 5′-S-cyano-5′-thioadenosine 9 is described. Incubation of AdoHcy hydrolase with 5, 7 and 9 resulted in time- and concentration-dependent inactivation of the enzyme and partial depletion of its NAD⁺ content. From these results and characterisation of metabolites released during the inactivation process, hypothetical mechanisms are suggested. The antiviral activity of 5, 7 and 9 was examined. Significant activities were noted with 5 against Vaccinia, Junin and Taccaribe viruses.