2-Naphthol Moiety of Neocarzinostatin Chromophore as a Novel Protein-Photodegrading Agent and Its Application as a H2O2-Activatable Photosensitizer

Takashi Kitamura, Saori Shiroshita, Daisuke Takahashi, Kazunobu Toshima

研究成果: Article査読

抄録

A 2-naphthol derivative 2 corresponding to the aromatic ring moiety of neocarzinostatin chromophore was found to degrade proteins under photo-irradiation with long-wavelength UV light without any additives under neutral conditions. Structure–activity relationship studies of the derivative revealed that methylation of the hydroxyl group at the C2 position of 2 significantly suppressed its photodegradation ability. Furthermore, a purpose-designed synthetic tumor-related biomarker, a H2O2-activatable photosensitizer 8 possessing a H2O2-responsive arylboronic ester moiety conjugated to the hydroxyl group at the C2 position of 2, showed significantly lower photodegradation ability compared to 2. However, release of the 2 from 8 by reaction with H2O2 regenerated the photodegradation ability. Compound 8 exhibited selective photo-cytotoxicity against high H2O2-expressing cancer cells upon irradiation with long-wavelength UV light.

本文言語English
ページ(範囲)14351-14358
ページ数8
ジャーナルChemistry - A European Journal
26
63
DOI
出版ステータスPublished - 2020 11 11

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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