methyl-4-(adenin-9-yl)-2-hydroxybutanoate and aristeromycin

Trypanosoma brucei and Trichomonas vaginalis are both parasitic protozoans that are known to share many similar biochemical pathways. Aristeromycin, as well as 5'-iodovinyl and 5'-oxime analogues of adenosine, are potent inhibitors of AdoHcy hydrolase in T. brucei, an enzyme that catalyses the hydrolysis of AdoHcy to adenosine and L-homocysteine. To help determine the role of this enzyme in T. vaginalis, we have tested a library of 5'-modified adenosine derivatives, including 5'-deoxy-5'-(iodomethylene)-adenosine and related 6-N-cyclopropyl analogues. Our results indicate that these inhibitors are effective at inhibiting the growth of T. vaginalis, by as much as 95%.

Topics: Adenosine; Adenosylhomocysteinase; Amino Acid Sequence; Antiprotozoal Agents; Cyclopropanes; Molecular Sequence Data; Sequence Alignment; Structure-Activity Relationship; Trichomonas vaginalis