論文

査読有り 国際誌
2017年9月15日

Photosensitization of Fluorofuroxans and Its Application to the Development of Visible Light-Triggered Nitric Oxide Donor.

The Journal of organic chemistry
  • Christopher Peter Seymour
  • ,
  • Rei Tohda
  • ,
  • Motonari Tsubaki
  • ,
  • Masahiko Hayashi
  • ,
  • Ryosuke Matsubara

82
18
開始ページ
9647
終了ページ
9654
記述言語
英語
掲載種別
研究論文(学術雑誌)
DOI
10.1021/acs.joc.7b01709
出版者・発行元
AMER CHEMICAL SOC

Nitric oxide (NO) is an endogenous signaling molecule used in multiple biochemical processes. The development of switchable NO donors that deliver an NO payload under spatiotemporal control harbors many medicinal benefits. Previously, 4-fluorofuroxans were found to function as a UV light-induced NO donor under physiological conditions based on the photoinduced isomerization mechanism; however, the isomerization of fluorofuroxans with longer wavelength light is desired for further application into living systems. Herein, we report the use of photosensitizers in the photochemical isomerization of fluorofuroxan, enabling the use of visible light to induce isomerization. Among the tried photosensitizers, anthraquinone derivatives showed a good sensitizing ability to isomerize 4-fluorofuroxan to 3-fluorofuroxan using visible light. This new phenomenon was applied to the synthesis of a water-soluble anthraquinone-fluorofuroxan all-in-one molecule, which demonstrated promising NO-releasing ability using 400-500 nm irradiation. A high level of control is displayed with "on" and "off" NO-release functionality suggesting that photosensitizer-furoxan hybrids would make valuable donors. Furthermore, unlike most furoxans, NO is released in the absence of thiol cofactor.

Web of Science ® 被引用回数 : 7

リンク情報
DOI
https://doi.org/10.1021/acs.joc.7b01709
PubMed
https://www.ncbi.nlm.nih.gov/pubmed/28837775
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000411304500038&DestApp=WOS_CPL