(+)-Saxitoxin (STX) is the archetype of a large family of tricyclic bis-guanidinium toxins commonly associated with red tides and infamous as the primary causative agent of toxicity in paralytic shellfish poisoning. STX targets voltage-gated sodium channels (NaVs), transmembrane protein complexes responsible for the generation and propagation of action potentials, and binds to the extracelluar pore to inhibit the passage of sodium ions into cells. The malfunction and mis-regulation of NaVs is associated with several human pathologies including congenital insensitivity to pain and epilepsy. Thus, chemical tools for investigating NaV structure and function are highly desired to better understand these and other NaV-related diseases. We have developed an efficient, step-economical synthesis of STX that enables access to natural and modified toxins, including ester derivatives that have not been previously prepared. Details of our improved route to these compounds will be presented along with results from electrophysiology studies. The latter reveal interesting structure-activity trends for toxin binding to different NaV subtypes.

Synthesis and evaluation of novel ester derivatives of (+)-saxitoxin

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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