A One-Pot Three-Component Double-Click Method for Synthesis of [67Cu]-Labeled Biomolecular Radiotherapeutics

Abstract A one-pot three-component double-click process for preparing tumor-targeting agents for cancer radiotherapy is described here. By utilizing DOTA (or NOTA) containing tetrazines and the TCO-substituted aldehyde, the two click reactions, the tetrazine ligation (an inverse electron-demand Diel...

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Autores principales:	Katsumasa Fujiki, Shinya Yano, Takeshi Ito, Yuki Kumagai, Yoshinori Murakami, Osamu Kamigaito, Hiromitsu Haba, Katsunori Tanaka
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/9c0c018d43294658b790d101729d8a05
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spelling	oai:doaj.org-article:9c0c018d43294658b790d101729d8a052021-12-02T11:40:50ZA One-Pot Three-Component Double-Click Method for Synthesis of [67Cu]-Labeled Biomolecular Radiotherapeutics10.1038/s41598-017-02123-22045-2322https://doaj.org/article/9c0c018d43294658b790d101729d8a052017-05-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-02123-2https://doaj.org/toc/2045-2322Abstract A one-pot three-component double-click process for preparing tumor-targeting agents for cancer radiotherapy is described here. By utilizing DOTA (or NOTA) containing tetrazines and the TCO-substituted aldehyde, the two click reactions, the tetrazine ligation (an inverse electron-demand Diels-Alder cycloaddition) and the RIKEN click (a rapid 6π-azaelectrocyclization), could simultaneously proceed under mild conditions to afford covalent attachment of the metal chelator DOTA or NOTA to biomolecules such as to albumin and anti-IGSF4 antibody without altering their activities. Subsequently, radiolabeling of DOTA- or NOTA-attached albumin and anti-IGSF4 antibody (an anti-tumor-targeting antibody) with [67Cu], a β−-emitting radionuclide, could be achieved in a highly efficient manner via a simple chelation with DOTA proving to be a more superior chelator than NOTA. Our work provides a new and operationally simple method for introducing the [67Cu] isotope even in large quantities to biomolecules, thereby representing an important process for preparations of clinically relevant tumor-targeting agents for radiotherapy.Katsumasa FujikiShinya YanoTakeshi ItoYuki KumagaiYoshinori MurakamiOsamu KamigaitoHiromitsu HabaKatsunori TanakaNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-9 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Katsumasa Fujiki Shinya Yano Takeshi Ito Yuki Kumagai Yoshinori Murakami Osamu Kamigaito Hiromitsu Haba Katsunori Tanaka A One-Pot Three-Component Double-Click Method for Synthesis of [67Cu]-Labeled Biomolecular Radiotherapeutics
description	Abstract A one-pot three-component double-click process for preparing tumor-targeting agents for cancer radiotherapy is described here. By utilizing DOTA (or NOTA) containing tetrazines and the TCO-substituted aldehyde, the two click reactions, the tetrazine ligation (an inverse electron-demand Diels-Alder cycloaddition) and the RIKEN click (a rapid 6π-azaelectrocyclization), could simultaneously proceed under mild conditions to afford covalent attachment of the metal chelator DOTA or NOTA to biomolecules such as to albumin and anti-IGSF4 antibody without altering their activities. Subsequently, radiolabeling of DOTA- or NOTA-attached albumin and anti-IGSF4 antibody (an anti-tumor-targeting antibody) with [67Cu], a β−-emitting radionuclide, could be achieved in a highly efficient manner via a simple chelation with DOTA proving to be a more superior chelator than NOTA. Our work provides a new and operationally simple method for introducing the [67Cu] isotope even in large quantities to biomolecules, thereby representing an important process for preparations of clinically relevant tumor-targeting agents for radiotherapy.
format	article
author	Katsumasa Fujiki Shinya Yano Takeshi Ito Yuki Kumagai Yoshinori Murakami Osamu Kamigaito Hiromitsu Haba Katsunori Tanaka
author_facet	Katsumasa Fujiki Shinya Yano Takeshi Ito Yuki Kumagai Yoshinori Murakami Osamu Kamigaito Hiromitsu Haba Katsunori Tanaka
author_sort	Katsumasa Fujiki
title	A One-Pot Three-Component Double-Click Method for Synthesis of [67Cu]-Labeled Biomolecular Radiotherapeutics
title_short	A One-Pot Three-Component Double-Click Method for Synthesis of [67Cu]-Labeled Biomolecular Radiotherapeutics
title_full	A One-Pot Three-Component Double-Click Method for Synthesis of [67Cu]-Labeled Biomolecular Radiotherapeutics
title_fullStr	A One-Pot Three-Component Double-Click Method for Synthesis of [67Cu]-Labeled Biomolecular Radiotherapeutics
title_full_unstemmed	A One-Pot Three-Component Double-Click Method for Synthesis of [67Cu]-Labeled Biomolecular Radiotherapeutics
title_sort	one-pot three-component double-click method for synthesis of [67cu]-labeled biomolecular radiotherapeutics
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/9c0c018d43294658b790d101729d8a05
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A One-Pot Three-Component Double-Click Method for Synthesis of [67Cu]-Labeled Biomolecular Radiotherapeutics

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