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

Supplementary files

Article information

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

Download Citation

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

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Chemical Communications

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

Abstract

Supplementary files

Article information

Download Citation

Permissions

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

Social activity

Search articles by author

Spotlight

Advertisements