Preparation of N-succinimidyl 3-[*I]iodobenzoate: an agent for the indirect radioiodination of proteins

Abstract

A procedure for the synthesis of N-succinimidyl 3-iodobenzoate labeled with any iodine isotope ([*I]SIB), which is an agent used in the radioiodination of proteins and peptides, from its tin precursor N-succinimidyl 3-(tri-n-butylstannyl)benzoate (STB) is described. Also included are protocols for the synthesis of an unlabeled standard of SIB and the tin precursor. Radioiododestannylation of STB using tert-butylhydroperoxide as the oxidant gives [*I]SIB in 80% radiochemical yields. The total time for the synthesis of [*I]SIB from STB is ∼95 min. Use of [*I]SIB yields radioiodinated proteins that are considerably more stable in vivo than those radioiodinated by the direct electrophilic method.