Synthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution

Abstract Astatine-211 (211At)-labeled phenylalanine is expected to be a promising agent for targeted alpha-particle therapy for the treatment of patients with glioma. The existing reactions to prepare the labeled compound usually require organic solvents and metals that are toxic and hazardous to th...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Yoshifumi Shirakami, Tadashi Watabe, Honoka Obata, Kazuko Kaneda, Kazuhiro Ooe, Yuwei Liu, Takahiro Teramoto, Atsushi Toyoshima, Atsushi Shinohara, Eku Shimosegawa, Jun Hatazawa, Koichi Fukase
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2021
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/c725b93b6496492c9ff9377e5a3890d6
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:doaj.org-article:c725b93b6496492c9ff9377e5a3890d6
record_format	dspace
spelling	oai:doaj.org-article:c725b93b6496492c9ff9377e5a3890d62021-12-02T17:12:18ZSynthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution10.1038/s41598-021-92476-62045-2322https://doaj.org/article/c725b93b6496492c9ff9377e5a3890d62021-06-01T00:00:00Zhttps://doi.org/10.1038/s41598-021-92476-6https://doaj.org/toc/2045-2322Abstract Astatine-211 (211At)-labeled phenylalanine is expected to be a promising agent for targeted alpha-particle therapy for the treatment of patients with glioma. The existing reactions to prepare the labeled compound usually require organic solvents and metals that are toxic and hazardous to the environment. In this study, we developed a novel method wherein astatination was realized via the substitution of 211At for a dihydroxyboryl group coupled to phenylalanine. [211At]4-astato-L-phenylalanine was obtained as the carrier-free product in aqueous medium in high radiochemical yields (98.1 ± 1.9%, n = 5). The crude reaction mixture was purified by solid-phase extraction, and the radiochemical purity of the product was 99.3 ± 0.7% (n = 5). The high yield and purity were attributed to the formation of [211At]AtI and AtI2 − as the reactive intermediates in the astatination reaction. The reaction did not require any organic solvents or toxic reagents, suggesting that this method is suitable for clinical applications.Yoshifumi ShirakamiTadashi WatabeHonoka ObataKazuko KanedaKazuhiro OoeYuwei LiuTakahiro TeramotoAtsushi ToyoshimaAtsushi ShinoharaEku ShimosegawaJun HatazawaKoichi FukaseNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 11, Iss 1, Pp 1-7 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Yoshifumi Shirakami Tadashi Watabe Honoka Obata Kazuko Kaneda Kazuhiro Ooe Yuwei Liu Takahiro Teramoto Atsushi Toyoshima Atsushi Shinohara Eku Shimosegawa Jun Hatazawa Koichi Fukase Synthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution
description	Abstract Astatine-211 (211At)-labeled phenylalanine is expected to be a promising agent for targeted alpha-particle therapy for the treatment of patients with glioma. The existing reactions to prepare the labeled compound usually require organic solvents and metals that are toxic and hazardous to the environment. In this study, we developed a novel method wherein astatination was realized via the substitution of 211At for a dihydroxyboryl group coupled to phenylalanine. [211At]4-astato-L-phenylalanine was obtained as the carrier-free product in aqueous medium in high radiochemical yields (98.1 ± 1.9%, n = 5). The crude reaction mixture was purified by solid-phase extraction, and the radiochemical purity of the product was 99.3 ± 0.7% (n = 5). The high yield and purity were attributed to the formation of [211At]AtI and AtI2 − as the reactive intermediates in the astatination reaction. The reaction did not require any organic solvents or toxic reagents, suggesting that this method is suitable for clinical applications.
format	article
author	Yoshifumi Shirakami Tadashi Watabe Honoka Obata Kazuko Kaneda Kazuhiro Ooe Yuwei Liu Takahiro Teramoto Atsushi Toyoshima Atsushi Shinohara Eku Shimosegawa Jun Hatazawa Koichi Fukase
author_facet	Yoshifumi Shirakami Tadashi Watabe Honoka Obata Kazuko Kaneda Kazuhiro Ooe Yuwei Liu Takahiro Teramoto Atsushi Toyoshima Atsushi Shinohara Eku Shimosegawa Jun Hatazawa Koichi Fukase
author_sort	Yoshifumi Shirakami
title	Synthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution
title_short	Synthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution
title_full	Synthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution
title_fullStr	Synthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution
title_full_unstemmed	Synthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution
title_sort	synthesis of [211at]4-astato-l-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution
publisher	Nature Portfolio
publishDate	2021
url	https://doaj.org/article/c725b93b6496492c9ff9377e5a3890d6
work_keys_str_mv	AT yoshifumishirakami synthesisof211at4astatolphenylalaninebydihydroxyborylastatinesubstitutionreactioninaqueoussolution AT tadashiwatabe synthesisof211at4astatolphenylalaninebydihydroxyborylastatinesubstitutionreactioninaqueoussolution AT honokaobata synthesisof211at4astatolphenylalaninebydihydroxyborylastatinesubstitutionreactioninaqueoussolution AT kazukokaneda synthesisof211at4astatolphenylalaninebydihydroxyborylastatinesubstitutionreactioninaqueoussolution AT kazuhiroooe synthesisof211at4astatolphenylalaninebydihydroxyborylastatinesubstitutionreactioninaqueoussolution AT yuweiliu synthesisof211at4astatolphenylalaninebydihydroxyborylastatinesubstitutionreactioninaqueoussolution AT takahiroteramoto synthesisof211at4astatolphenylalaninebydihydroxyborylastatinesubstitutionreactioninaqueoussolution AT atsushitoyoshima synthesisof211at4astatolphenylalaninebydihydroxyborylastatinesubstitutionreactioninaqueoussolution AT atsushishinohara synthesisof211at4astatolphenylalaninebydihydroxyborylastatinesubstitutionreactioninaqueoussolution AT ekushimosegawa synthesisof211at4astatolphenylalaninebydihydroxyborylastatinesubstitutionreactioninaqueoussolution AT junhatazawa synthesisof211at4astatolphenylalaninebydihydroxyborylastatinesubstitutionreactioninaqueoussolution AT koichifukase synthesisof211at4astatolphenylalaninebydihydroxyborylastatinesubstitutionreactioninaqueoussolution
_version_	1718381461752512512

Synthesis of [211At]4-astato-L-phenylalanine by dihydroxyboryl-astatine substitution reaction in aqueous solution

Ejemplares similares