Polymer-supported organotin reagent for prosthetic group labeling of biological macromolecules with radioiodine

Andrew N. Gifford, Sonja Kuschel, Colleen Shea, Joanna S. Fowler

Research output: Contribution to journalArticlepeer-review

18 Scopus citations


In this study, we investigated the use of poly-mer-bound precursor for generating a radiolabeled prosthetic group to be used for conjugate labeling of biological macromolecules. For the approach, a trialkyltin chloride in which the tin was bound to a hydrophilic PEG-based resin support via one of the alkyl groups was synthesized. This resin was then used to prepare a resin-bound trialkyltin benzoic acid, which in some cases was further derivatized on-resin by converting it to a succinimidyl ester. Exposure of the resin-bound compounds to electrophilic radioiodine (125I) in either an aqueous or methanol solvent liberated either free radiolabeled [125I]iodobenzoic acid or its succinimidyl ester without co-release of the resin-bound precursors. Radiochemical yield was between 35% and 75%, depending on the solvent system and precursor. As example applications for the released compounds, the amine-reactive N-succinimidyl-[125I]iodobenzoate prosthetic group was used for conjugate radiolabeling of a peptide, tomato plant systemin, and two proteins, albumin and IgG antibody. These results demonstrate that resin-bound organotin precursors in which the compound to be labeled is tethered to the support via the tin group to be substituted can be used to produce radioiodine-labeled aromatic prosthetic groups in good specific activity without the need for HPLC purification. This solid-phase approach is potentially adaptable to kit-formulation for performing conjugate radiolabeling of biological macromolecules.

Original languageEnglish
Pages (from-to)406-412
Number of pages7
JournalBioconjugate Chemistry
Issue number3
StatePublished - 16 Mar 2011
Externally publishedYes


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