N-[2-(maleimido)ethyl]-3-(trimethylstannyl)benzamide, a molecule for radiohalogenation of proteins and peptides

Emma Aneheim; Mark R StJ Foreman; Holger Jensen; Sture Lindegren

doi:10.1016/j.apradiso.2014.11.007

N-[2-(maleimido)ethyl]-3-(trimethylstannyl)benzamide, a molecule for radiohalogenation of proteins and peptides

Appl Radiat Isot. 2015 Feb:96:1-5. doi: 10.1016/j.apradiso.2014.11.007. Epub 2014 Nov 11.

Authors

Emma Aneheim¹, Mark R StJ Foreman², Holger Jensen³, Sture Lindegren⁴

Affiliations

¹ Targeted Alpha Therapy, Department of Radiation Physics, Sahlgrenska Academy at Gothenburg University, Gothenburg 41345, Sweden. Electronic address: emma.aneheim@radfys.gu.se.
² Nuclear Chemistry, Department of Chemical and Biological Engineering, Chalmers University of Technology, Gothenburg 41296, Sweden.
³ PET and Cyclotron Unit, KF3982, Copenhagen University Hospital, Copenhagen, Denmark.
⁴ Targeted Alpha Therapy, Department of Radiation Physics, Sahlgrenska Academy at Gothenburg University, Gothenburg 41345, Sweden.

PMID: 25474765
DOI: 10.1016/j.apradiso.2014.11.007

Abstract

In this work a new coupling reagent, N-[2-(maleimido)ethyl]-3-(trimethylstannyl)benzamide, for radiohalogenation has been synthesized and characterized. The reagent is intended to either be attached to reduced disulfide bridges of proteins (making the halogenation site-specific) or to free terminal cysteine groups on peptides. The new reagent was also shown to be easily halogenated with inactive bromine and iodine as well as (125)I and (211)At, indicating potential use within targeted radiotherapy.

Keywords: Astatine-211; Electrophilic aromatic substitution; Halogenation; Peptide labelling; Site specific antibody labelling; Targeted radiotherapy.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Astatine / chemistry
Astatine / therapeutic use
Benzamides / chemical synthesis
Benzamides / chemistry*
Bromine / chemistry
Chromatography, High Pressure Liquid
Halogenation*
Humans
Indicators and Reagents
Iodine Radioisotopes / chemistry
Iodine Radioisotopes / therapeutic use
Molecular Structure
Organotin Compounds* / chemistry
Peptides / chemistry
Peptides / therapeutic use
Proteins / chemistry
Proteins / therapeutic use
Radiopharmaceuticals / chemical synthesis*
Radiopharmaceuticals / chemistry
Radiopharmaceuticals / therapeutic use

Substances

Benzamides
Indicators and Reagents
Iodine Radioisotopes
N-(2-(maleimido)ethyl)-3-(trimethylstannyl)benzamide
Organotin Compounds
Peptides
Proteins
Radiopharmaceuticals
Bromine
Astatine