title: Synthesis of radioiodinated N-succinimidyl iodobenzoate: optimization for use in antibody labelling.
abstract: N-succinimidyl-3-(tri-n-butylstannyl)benzoate (m-BuATE), N-succinimidyl-3-(tri-methylstannyl)benzoate (m-MeATE) and N-succinimidyl-4-(tri-n-butylstannyl)benzoate (p-BuATE) were synthesized and radioiodinated using either N-chlorosuccinimide (NCS) or t-butylhydroperoxide (TBHP) as the oxidant. Radiohalogenation of m-MeATE proceeded more rapidly than m-BuATE. NCS was the more efficient oxidant at reaction times less than 15 min; use of both TBHP and NCS resulted in nearly quantitative yields after 15 min when m-MeATE was used. Using NCS, achieving optimal antibody coupling and specific binding required purification of the active ester by HPLC; in contrast, with TBHP, only Sep-Pak purification was needed.
authors.affiliation: Department of Radiology, Duke University Medical Center, Durham, NC 27710.
authors.forename: P K
authors.initials: PK
authors.lastname: Garg
authors.forename: G E
authors.initials: GE
authors.lastname: Archer
authors.forename: D D
authors.initials: DD
authors.lastname: Bigner
authors.forename: M R
authors.initials: MR
authors.lastname: Zalutsky
mesh_terms: D000912:Antibodies, Neoplasm; D001565:Benzoates / Q000138:chemical synthesis; D001932:Brain Neoplasms / Q000276:immunology; D007457:Iodine Radioisotopes; D007553:Isotope Labeling / Q000379:methods*; D014220:Trialkyltin Compounds / Q000138:chemical synthesis; D014298:Trimethyltin Compounds / Q000138:chemical synthesis
chemical_list: D000912:Antibodies, Neoplasm; D001565:Benzoates; D007457:Iodine Radioisotopes; D014220:Trialkyltin Compounds; D014298:Trimethyltin Compounds; C061344:N-succinimidyl 4-(tri-n-butylstannyl)benzoate; C055156:N-succinimidyl-3-(tri-n-butylstannyl)benzoate; C061345:N-succinimidyl 3-(trimethylstannyl)benzoate