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Saxitoxin
Author(s) -
Thottumkara Arun P.,
Parsons William H.,
Du Bois J.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201308235
Subject(s) - saxitoxin , chemistry , natural product , sodium channel , tetrodotoxin , derivative (finance) , heteroatom , biophysics , stereochemistry , sodium , biochemistry , toxin , biology , organic chemistry , ring (chemistry) , financial economics , economics
The paralytic agent (+)‐saxitoxin (STX), most commonly associated with oceanic red tides and shellfish poisoning, is a potent inhibitor of electrical conduction in cells. Its nefarious effects result from inhibition of voltage‐gated sodium channels (Na V s), the obligatory proteins responsible for the initiation and propagation of action potentials. In the annals of ion channel research, the identification and characterization of Na V s trace to the availability of STX and an allied guanidinium derivative, tetrodotoxin. The mystique of STX is expressed in both its function and form, as this uniquely compact dication boasts more heteroatoms than carbon centers. This Review highlights both the chemistry and chemical biology of this fascinating natural product, and offers a perspective as to how molecular design and synthesis may be used to explore Na V structure and function.