Prodigiosin belongs to a family of tripyrrole natural products, the prodiginines, with anti-bacterial, anti-malarial, anti-cancer and immunosuppressive properties. Prodigiosin can also act as an ionophore, facilitating the transport of charged ions across cellular membranes. However, prodigiosin is toxic and consequently there is an interest in finding less toxic analogs that maintain anti-cancer activity. In this study, the influence of C-ring substitution on transmembrane anion transport, protonation and conformation distribution of prodigiosin and its analogs was investigated. Transport experiments using EYPC liposomes showed that changes in substitution on ring C affected the transport activity of analogs. A series of 1H NMR experiments were used to study the inter conversion between protonated and deprotonated forms of the prodiginine analogs. Furthermore, the NMR experiments also revealed the change in conformations for prodigiosin and its analogs, in the presence of a counter-anion. 

Transmembrane anion transport studies of prodigiosin and its analogs

244th National Meeting (2012)

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