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Efficacy of Glycoconjugated Dinitroanilines against Cryptosporidium parvum

The dinitroaniline compounds are highly active (in vitro) against C. purvum [1,2]. This same class of compounds has been shown to selectively inhibit other protozoa such as Leishmania, Plasmodium, and Toxoplusma [3,4,5]. These compounds act by binding tubulin, thus impeding the function of the microtubules. Microtubules are a potentially useful target of anti-cryptosporidial therapy since protozoan (including C. parvum) tubulin is more closely related to plants than to mammalian tubulin. Two of the properties the dinitroaniline herbicides have are low water solubility and an unusually low vapor pressure, which created problems in their development as anti-parasitic agents. Since glycoconjugate chemistry has in recent years been shown to be an effective strategy for the delivery of molecules with poor transport profiles several analogs were synthesized. These include dinitroanilines with (1) two types of sugars, mannose and glucose, (2) sulfur linkages to prevent hydrolysis of the sugar, and (3) acetylated sugar conjugates to facilitate transport across the membrane.