Carboxyboranylamino ethanol: unprecedented discovery of boron agents for neutron capture therapy in cancer treatment

Yinghuai Zhu; Jianghong Cai; Narayan S. Hosmane; Minoru Suzuki; Kazuko Uno; Yingjun Zhang; Mao Takagaki

doi:10.1039/D1CC03034E

Carboxyboranylamino ethanol: unprecedented discovery of boron agents for neutron capture therapy in cancer treatment†‡

Yinghuai Zhu,

*^a Jianghong Cai,^b Narayan S. Hosmane,

*^c Minoru Suzuki,

^d Kazuko Uno,^e Yingjun Zhang*^a and Mao Takagaki^ef

Author affiliations

* Corresponding authors

^a The State Key Laboratory of Anti-Infective Drug Development (No. 2015DQ780357), Sunshine Lake Pharma Co. Ltd, Dongguan 523871, China
E-mail: zhuyinghuai@hec.cn, zhangyingjun@hec.cn

^b School of Pharmacy and State Key Laboratory of Quality Research in Chinese Medicine, Macau University of Science and Technology, Avenida Wai Long, Taipa, Macau 999078, China

^c Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, USA
E-mail: hosmane@niu.edu

^d Institute for Integrated Radiation and Nuclear Science, Kyoto University, Osaka 590-0494, Japan

^e Louis Pasteur Centre for Medical Research, 103-5 Nakamonzen-machi, Sakyo-ku, Kyoto 606-8225, Japan

^f Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 604-8232, Japan

Abstract

Carboxyboranylamino ethanol (Me₂N(BH₂CO₂H)CH₂CH₂OH, 1) was prepared in 75.0% yield by an amine-exchange reaction. Compound 1 shows lower cytotoxicity and higher anti-tumor efficacy in vitro towards the SCCVII cell line in comparison with 4-borono-L-phenylalanine (BPA) and methyl 2-hydroxyl-5-(1′-ortho-carbonylmethyl-1′,2′,3′-triazol-4′-yl)-benzonate (2). The bio-enhancement is interpreted using molecular docking calculations.

This article is part of the themed collection: Boron Chemistry in the 21st Century: From Synthetic Curiosities to Functional Molecules

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DOI: https://doi.org/10.1039/D1CC03034E
Article type: Communication
Submitted: 17 Jun 2021
Accepted: 08 Sep 2021
First published: 10 Sep 2021

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Chem. Commun., 2021,57, 10174-10177

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Carboxyboranylamino ethanol: unprecedented discovery of boron agents for neutron capture therapy in cancer treatment

Y. Zhu, J. Cai, N. S. Hosmane, M. Suzuki, K. Uno, Y. Zhang and M. Takagaki, Chem. Commun., 2021, 57, 10174 DOI: 10.1039/D1CC03034E

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Chemical Communications

Carboxyboranylamino ethanol: unprecedented discovery of boron agents for neutron capture therapy in cancer treatment†‡

Abstract

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Carboxyboranylamino ethanol: unprecedented discovery of boron agents for neutron capture therapy in cancer treatment

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