Synthesis of N-succinimidyl 4-guanidinomethyl-3-[*I]iodobenzoate: a radio-iodination agent for labeling internalizing proteins and peptides.

Journal Article

This protocol describes a detailed procedure for the synthesis of N-succinimidyl 4-guanidinomethyl-3-[*I]iodobenzoate ([*I]SGMIB), an agent useful in the radio-iodination of proteins, including monoclonal Abs, and peptides that undergo internalization after receptor or antigen binding. In this procedure, the tin precursor N-succinimidyl 4-[N1,N2-bis(tert-butyloxycarbonyl)guanidinomethyl]-3-(trimethylstannyl)benzoate (Boc-SGMTB, 3) was first radio-iodinated to [*I]Boc-SGMIB, a derivative of [*I]SGMIB with the guanidine function protected with Boc groups. Treatment of [*I]Boc-SGMIB with trifluoroacetic acid delivered the final product. The total time for the synthesis and purification of [*I]Boc-SGMIB and its subsequent de-protection is approximately 140 min.

Full Text

Duke Authors

Cited Authors

  • Vaidyanathan, G; Zalutsky, MR

Published Date

  • 2007

Published In

Volume / Issue

  • 2 / 2

Start / End Page

  • 282 - 286

PubMed ID

  • 17406587

Electronic International Standard Serial Number (EISSN)

  • 1750-2799

Digital Object Identifier (DOI)

  • 10.1038/nprot.2007.20

Language

  • eng

Conference Location

  • England