Open AccessSynthesis of New, Highly Radioactive Tetrodotoxin Derivatives and Their Binding Properties to the Sodium Channel
Author(s) -
CHICHEPORTICHE Robert,
BALERNA Marco,
LOMBET Alain,
ROMEY Georges,
LAZDUNSKI Michel
Publication year - 1980
Publication title -
european journal of biochemistry
Language(s) - English
Resource type - Journals
eISSN - 1432-1033
pISSN - 0014-2956
DOI - 10.1111/j.1432-1033.1980.tb04466.x
Subject(s) - tetrodotoxin , chemistry , glycine , saxitoxin , sodium , ethylenediamine , sodium channel , biophysics , chromatography , biochemistry , toxin , amino acid , organic chemistry , biology
The Pfitzner‐Moffatt oxidation procedure has been used to prepare five derivatives of tetrodotoxin by covalent attachment of the oxidized toxin to lysine, glycine, β‐alanine or ethylenediamine. These derivatives reach specific radioactivities between 5 and 45 Ci/mmol. The equilibrium properties of binding of these tetrodotoxin derivatives to membrane‐embedded or solubilized sodium channels from crustacean nerves have been analysed and compared to the binding properties of tritiated tetrodotoxin and saxitoxin to the same biological systems. All these highly radiolabelled derivatives associate to the tetrodotoxin binding component with properties similar to those of tetrodotoxin itself. The synthetic route described in this paper may be used to prepare other types of tetrodotoxin derivatives such as fluorescent derivatives for example.