Development of saxitoxin-conjugated affinity gels

Bioconjugate Chemistry
Ryuichi WatanabeY Oshima

Abstract

Saxitoxin (STX) and its analogues accumulated in bivalves cause food poisoning through the blockade of sodium channels in the nervous system. In the current studies, STX-conjugated agarose gels as affinity chromatography reagents were prepared for investigation of the fate of the toxins in natural environments and in the human body. A carboxyl moiety was introduced through positions C11 and C13 to leave the most characteristic part of the molecule intact. Two types of synthesized derivatives, 11-(2-carboxyethylthio)saxitoxin and 13-O-hemisuccinyldecarbamoylsaxitoxin, were successfully conjugated to Sepharose 4B in high yield. Affinity gels containing 500 nmol of STX or decarbamoylsaxitoxin per milliliter of gel were accomplished by masking the residual amino groups by acetylation. Finally, the STX-conjugated affinity gel was effective for concentrating STX-binding proteins from pufferfish and bullfrog plasma.

Citations

Jun 12, 2010·Toxicon : Official Journal of the International Society on Toxinology·Ryuichi WatanabeYasukatsu Oshima
Jan 17, 2014·Natural Product Reports·Ryuichi Sakai, Geoffrey T Swanson
Apr 29, 2014·Angewandte Chemie·Arun P ThottumkaraJ Du Bois
Oct 27, 2020·Organic Letters·Yuya OkuyamaNoritaka Chida
Jul 31, 2007·Journal of the American Chemical Society·James J FlemingJ Du Bois

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