Synthesis, physical properties, and cytotoxicity of Nitroxyl-Aziridine hybrid

Takuya Kumamoto, Kazuya Suzuki, Sang Kook Kim, Katsuyoshi Hoshino, Masahiro Takahashi, Hiromi Sato, Hiroki Iwata, Koichi Ueno, Masahiro Fukuzumi, Tsutomu Ishikawa

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Nitroxyl-aziridine hybrid, a candidate for a magnetic resonance imaging (MRI) probe and an anticancer drug, was synthesized by aziridine formation reaction of nitroxyl-introduced aldehyde and guanidinium ylide in good diastereoselectivity. The relative configuration at aziridine C(2)-C(3) bond of the major diastereoisomer was determined to be cis by X-ray crystallographic analysis. Application of chiral guanidinium ylide resulted in the formation of the corresponding optically active aziridine in 84% ee. Reversible one-electron redox potential and quantitative spin yield of the hybrid were observed in cyclic voltammogram and electron spin resonance, respectively. However, cytotoxicity of the hybrid against cancer cell lines used was not observed.

Original languageEnglish
Pages (from-to)2109-2114
Number of pages6
JournalHelvetica Chimica Acta
Volume93
Issue number11
DOIs
Publication statusPublished - 2010 Nov 1
Externally publishedYes

Keywords

  • Aziridine
  • Cyclic voltammetry
  • Cytotoxicity
  • Electron spin resonance (ESR)
  • Nitroxyl

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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    Kumamoto, T., Suzuki, K., Kim, S. K., Hoshino, K., Takahashi, M., Sato, H., Iwata, H., Ueno, K., Fukuzumi, M., & Ishikawa, T. (2010). Synthesis, physical properties, and cytotoxicity of Nitroxyl-Aziridine hybrid. Helvetica Chimica Acta, 93(11), 2109-2114. https://doi.org/10.1002/hlca.201000076