Radiobromination of anti-HER2/neu/ErbB-2 monoclonal antibody using the p-isothiocyanatobenzene derivative of the [<sup>76</sup>Br]undecahydro-bromo-7, 8-dicarba-nido-undecaborate(1-) ion

Abstract

The monoclonal humanized anti-HER2 antibody trastuzumab was radiolabeled with the positron emitter ⁷⁶Br (T₁₂ =16.2 h). Indirect labeling was performed using the p-isothiocyanatobenzene derivative of the [⁷⁶Br]undecahydro-bromo-7,8-dicarba-nido-undecaborate(1-) ( ⁷⁶Br-NBI) as a precursor molecule. ⁷⁶Br-NBI was prepared by bromination of the 7-(p-isothiocyanato-phenyl)dodecahydro-7,8-dicarba-nido- undecaborate(1-) ion (NBI) with a yield of 93-95% using Chloramine-T (CAT) as an oxidant. Coupling of radiobrominated NBI to antibody was performed without intermediate purification, in an "one pot" reaction. An overall labeling yield of 55.7 ± 4.8% (mean ± maximum error) was achieved when 300 μg of antibody was labeled. The label was stable in vitro in physiological and denaturing conditions. In a cell binding test, trastuzumab remained immunoreactive after labeling.

Original language	English
Pages (from-to)	425-433
Number of pages	9
Journal	Nuclear Medicine and Biology
Volume	31
Issue number	4
DOIs	https://doi.org/10.1016/j.nucmedbio.2003.11.007
Publication status	Published - May 2004
Externally published	Yes

Keywords

Bromine-76
Monoclonal antibodies
nido-Carborate derivatives
Prosthetic group
Radiobromination
Trautzumab

ASJC Scopus subject areas

Molecular Medicine
Radiology Nuclear Medicine and imaging
Cancer Research

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Radiobromination of anti-HER2/neu/ErbB-2 monoclonal antibody using the p-isothiocyanatobenzene derivative of the [⁷⁶Br]undecahydro-bromo-7, 8-dicarba-nido-undecaborate(1-) ion. / Winberg, Karl Johan; Persson, Mikael; Malmström, Per Uno; Sjöberg, Stefan; Tolmachev, Vladimir.

In: Nuclear Medicine and Biology, Vol. 31, No. 4, 05.2004, p. 425-433.

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@article{50d3706189054f44ac1ca3e46d812f7d,

title = "Radiobromination of anti-HER2/neu/ErbB-2 monoclonal antibody using the p-isothiocyanatobenzene derivative of the [76Br]undecahydro-bromo-7, 8-dicarba-nido-undecaborate(1-) ion",

abstract = "The monoclonal humanized anti-HER2 antibody trastuzumab was radiolabeled with the positron emitter 76Br (T12 =16.2 h). Indirect labeling was performed using the p-isothiocyanatobenzene derivative of the [76Br]undecahydro-bromo-7,8-dicarba-nido-undecaborate(1-) ( 76Br-NBI) as a precursor molecule. 76Br-NBI was prepared by bromination of the 7-(p-isothiocyanato-phenyl)dodecahydro-7,8-dicarba-nido- undecaborate(1-) ion (NBI) with a yield of 93-95% using Chloramine-T (CAT) as an oxidant. Coupling of radiobrominated NBI to antibody was performed without intermediate purification, in an {"}one pot{"} reaction. An overall labeling yield of 55.7 ± 4.8% (mean ± maximum error) was achieved when 300 μg of antibody was labeled. The label was stable in vitro in physiological and denaturing conditions. In a cell binding test, trastuzumab remained immunoreactive after labeling.",

keywords = "Bromine-76, Monoclonal antibodies, nido-Carborate derivatives, Prosthetic group, Radiobromination, Trautzumab",

author = "Winberg, {Karl Johan} and Mikael Persson and Malmstr{\"o}m, {Per Uno} and Stefan Sj{\"o}berg and Vladimir Tolmachev",

note = "Funding Information: This work was supported by grants from the Swedish Cancer Society (Cancerfonden) and INTAS (grant No. 99-00806). The authors thank Genentech for their generous gift of Herceptin. The authors give special thanks to Assoc. Prof. Adolf Gogol for valuable help in recording the NMR spectra. The authors also thank Mr. Lars Einarsson of the Svedberg Laboratory, Uppsala, Sweden, and personnel of the Uppsala University PET centre for providing technical support. Copyright: Copyright 2008 Elsevier B.V., All rights reserved.",

year = "2004",

month = may,

doi = "10.1016/j.nucmedbio.2003.11.007",

language = "English",

volume = "31",

pages = "425--433",

journal = "Nuclear Medicine and Biology",

issn = "0969-8051",

publisher = "Elsevier Inc.",

number = "4",

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TY - JOUR

T1 - Radiobromination of anti-HER2/neu/ErbB-2 monoclonal antibody using the p-isothiocyanatobenzene derivative of the [76Br]undecahydro-bromo-7, 8-dicarba-nido-undecaborate(1-) ion

AU - Winberg, Karl Johan

AU - Persson, Mikael

AU - Malmström, Per Uno

AU - Sjöberg, Stefan

AU - Tolmachev, Vladimir

N1 - Funding Information: This work was supported by grants from the Swedish Cancer Society (Cancerfonden) and INTAS (grant No. 99-00806). The authors thank Genentech for their generous gift of Herceptin. The authors give special thanks to Assoc. Prof. Adolf Gogol for valuable help in recording the NMR spectra. The authors also thank Mr. Lars Einarsson of the Svedberg Laboratory, Uppsala, Sweden, and personnel of the Uppsala University PET centre for providing technical support. Copyright: Copyright 2008 Elsevier B.V., All rights reserved.

PY - 2004/5

Y1 - 2004/5

N2 - The monoclonal humanized anti-HER2 antibody trastuzumab was radiolabeled with the positron emitter 76Br (T12 =16.2 h). Indirect labeling was performed using the p-isothiocyanatobenzene derivative of the [76Br]undecahydro-bromo-7,8-dicarba-nido-undecaborate(1-) ( 76Br-NBI) as a precursor molecule. 76Br-NBI was prepared by bromination of the 7-(p-isothiocyanato-phenyl)dodecahydro-7,8-dicarba-nido- undecaborate(1-) ion (NBI) with a yield of 93-95% using Chloramine-T (CAT) as an oxidant. Coupling of radiobrominated NBI to antibody was performed without intermediate purification, in an "one pot" reaction. An overall labeling yield of 55.7 ± 4.8% (mean ± maximum error) was achieved when 300 μg of antibody was labeled. The label was stable in vitro in physiological and denaturing conditions. In a cell binding test, trastuzumab remained immunoreactive after labeling.

AB - The monoclonal humanized anti-HER2 antibody trastuzumab was radiolabeled with the positron emitter 76Br (T12 =16.2 h). Indirect labeling was performed using the p-isothiocyanatobenzene derivative of the [76Br]undecahydro-bromo-7,8-dicarba-nido-undecaborate(1-) ( 76Br-NBI) as a precursor molecule. 76Br-NBI was prepared by bromination of the 7-(p-isothiocyanato-phenyl)dodecahydro-7,8-dicarba-nido- undecaborate(1-) ion (NBI) with a yield of 93-95% using Chloramine-T (CAT) as an oxidant. Coupling of radiobrominated NBI to antibody was performed without intermediate purification, in an "one pot" reaction. An overall labeling yield of 55.7 ± 4.8% (mean ± maximum error) was achieved when 300 μg of antibody was labeled. The label was stable in vitro in physiological and denaturing conditions. In a cell binding test, trastuzumab remained immunoreactive after labeling.

KW - Bromine-76

KW - Monoclonal antibodies

KW - nido-Carborate derivatives

KW - Prosthetic group

KW - Radiobromination

KW - Trautzumab

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U2 - 10.1016/j.nucmedbio.2003.11.007

DO - 10.1016/j.nucmedbio.2003.11.007

M3 - Article

C2 - 15093812

AN - SCOPUS:1942424994

VL - 31

SP - 425

EP - 433

JO - Nuclear Medicine and Biology

JF - Nuclear Medicine and Biology

SN - 0969-8051

IS - 4

ER -

Radiobromination of anti-HER2/neu/ErbB-2 monoclonal antibody using the p-isothiocyanatobenzene derivative of the [76Br]undecahydro-bromo-7, 8-dicarba-nido-undecaborate(1-) ion

Abstract

Keywords

ASJC Scopus subject areas

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Radiobromination of anti-HER2/neu/ErbB-2 monoclonal antibody using the p-isothiocyanatobenzene derivative of the [⁷⁶Br]undecahydro-bromo-7, 8-dicarba-nido-undecaborate(1-) ion