Hypocrellin B-based activatable photosensitizers for specific photodynamic effects against high H2O2-expressing cancer cells

Takashi Kitamura; Hirotaka Nakata; Daisuke Takahashi; Kazunobu Toshima

doi:10.1039/d1cc05823a

Hypocrellin B-based activatable photosensitizers for specific photodynamic effects against high H₂O₂-expressing cancer cells

Takashi Kitamura, Hirotaka Nakata, Daisuke Takahashi, Kazunobu Toshima

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

A novel tumor-related biomarker, a H₂O₂-activatable photosensitizer4based on the 1,3-dicarbonyl enol moieties of hypocrellin B (3), was designed and synthesized. The photosensitizer4showed a blue-shifted absorption band compared with3, and showed negligible photosensitizing ability without H₂O₂. However, the release of3from4by the reaction with H₂O₂regenerated the photosensitizing ability. Furthermore,4exhibited selective and effective photo-cytotoxicity against high H₂O₂-expressing cancer cells upon photo-irradiation with 660 nm light, which is inside the phototherapeutic window.

Original language	English
Pages (from-to)	242-245
Number of pages	4
Journal	Chemical Communications
Volume	58
Issue number	2
DOIs	https://doi.org/10.1039/d1cc05823a
Publication status	Published - 2022 Jan 7

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

UN SDGs

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

Access to Document

10.1039/d1cc05823a

Cite this

@article{84c877763566477dbb10496119396815,

title = "Hypocrellin B-based activatable photosensitizers for specific photodynamic effects against high H2O2-expressing cancer cells",

abstract = "A novel tumor-related biomarker, a H2O2-activatable photosensitizer4based on the 1,3-dicarbonyl enol moieties of hypocrellin B (3), was designed and synthesized. The photosensitizer4showed a blue-shifted absorption band compared with3, and showed negligible photosensitizing ability without H2O2. However, the release of3from4by the reaction with H2O2regenerated the photosensitizing ability. Furthermore,4exhibited selective and effective photo-cytotoxicity against high H2O2-expressing cancer cells upon photo-irradiation with 660 nm light, which is inside the phototherapeutic window.",

author = "Takashi Kitamura and Hirotaka Nakata and Daisuke Takahashi and Kazunobu Toshima",

note = "Funding Information: This research was supported in part by the JSPS KAKENHI Grant Number JP19H02724 in Scientific Research (B), JP20J12227 in JSPS Fellows, the JST CREST Grant Number JPMJCR20R3, Keio University Academic Development Funds, and the Keio Gijuku Fukuzawa Memorial Fund for the Advancement of Education and Research. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021.",

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doi = "10.1039/d1cc05823a",

language = "English",

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T1 - Hypocrellin B-based activatable photosensitizers for specific photodynamic effects against high H2O2-expressing cancer cells

AU - Kitamura, Takashi

AU - Nakata, Hirotaka

AU - Takahashi, Daisuke

AU - Toshima, Kazunobu

N1 - Funding Information: This research was supported in part by the JSPS KAKENHI Grant Number JP19H02724 in Scientific Research (B), JP20J12227 in JSPS Fellows, the JST CREST Grant Number JPMJCR20R3, Keio University Academic Development Funds, and the Keio Gijuku Fukuzawa Memorial Fund for the Advancement of Education and Research. Publisher Copyright: © The Royal Society of Chemistry 2021.

PY - 2022/1/7

Y1 - 2022/1/7

N2 - A novel tumor-related biomarker, a H2O2-activatable photosensitizer4based on the 1,3-dicarbonyl enol moieties of hypocrellin B (3), was designed and synthesized. The photosensitizer4showed a blue-shifted absorption band compared with3, and showed negligible photosensitizing ability without H2O2. However, the release of3from4by the reaction with H2O2regenerated the photosensitizing ability. Furthermore,4exhibited selective and effective photo-cytotoxicity against high H2O2-expressing cancer cells upon photo-irradiation with 660 nm light, which is inside the phototherapeutic window.

AB - A novel tumor-related biomarker, a H2O2-activatable photosensitizer4based on the 1,3-dicarbonyl enol moieties of hypocrellin B (3), was designed and synthesized. The photosensitizer4showed a blue-shifted absorption band compared with3, and showed negligible photosensitizing ability without H2O2. However, the release of3from4by the reaction with H2O2regenerated the photosensitizing ability. Furthermore,4exhibited selective and effective photo-cytotoxicity against high H2O2-expressing cancer cells upon photo-irradiation with 660 nm light, which is inside the phototherapeutic window.

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