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

doi:10.1002/hlca.201000076

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 journal › Article › peer-review

10 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 language	English
Pages (from-to)	2109-2114
Number of pages	6
Journal	Helvetica Chimica Acta
Volume	93
Issue number	11
DOIs	https://doi.org/10.1002/hlca.201000076
Publication status	Published - 2010 Nov 1
Externally published	Yes

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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/hlca.201000076

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title = "Synthesis, physical properties, and cytotoxicity of Nitroxyl-Aziridine hybrid",

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.",

keywords = "Aziridine, Cyclic voltammetry, Cytotoxicity, Electron spin resonance (ESR), Nitroxyl",

author = "Takuya Kumamoto and Kazuya Suzuki and Kim, {Sang Kook} and Katsuyoshi Hoshino and Masahiro Takahashi and Hiromi Sato and Hiroki Iwata and Koichi Ueno and Masahiro Fukuzumi and Tsutomu Ishikawa",

year = "2010",

month = nov,

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doi = "10.1002/hlca.201000076",

language = "English",

volume = "93",

pages = "2109--2114",

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TY - JOUR

T1 - Synthesis, physical properties, and cytotoxicity of Nitroxyl-Aziridine hybrid

AU - Kumamoto, Takuya

AU - Suzuki, Kazuya

AU - Kim, Sang Kook

AU - Hoshino, Katsuyoshi

AU - Takahashi, Masahiro

AU - Sato, Hiromi

AU - Iwata, Hiroki

AU - Ueno, Koichi

AU - Fukuzumi, Masahiro

AU - Ishikawa, Tsutomu

PY - 2010/11/1

Y1 - 2010/11/1

N2 - 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.

AB - 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.

KW - Aziridine

KW - Cyclic voltammetry

KW - Cytotoxicity

KW - Electron spin resonance (ESR)

KW - Nitroxyl

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DO - 10.1002/hlca.201000076

M3 - Article

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SN - 0018-019X

VL - 93

SP - 2109

EP - 2114

JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

IS - 11

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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