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

doi:10.1002/chem.202000833

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

Department of Applied Chemistry

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

2 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	14351-14358
Number of pages	8
Journal	Chemistry - A European Journal
Volume	26
Issue number	63
DOIs	https://doi.org/10.1002/chem.202000833
Publication status	Published - 2020 Nov 11

Keywords

cytotoxicity
neocarzinostatin chromophore
peroxides
photodegradation
photosensitizer

ASJC Scopus subject areas

Catalysis
Organic Chemistry

UN SDGs

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

Access to Document

10.1002/chem.202000833

Cite this

@article{4e1c375d0dea4cffb07741dddd8eb51b,

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

abstract = "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.",

keywords = "cytotoxicity, neocarzinostatin chromophore, peroxides, photodegradation, photosensitizer",

author = "Takashi Kitamura and Saori Shiroshita and Daisuke Takahashi and Kazunobu Toshima",

note = "Funding Information: Bovine serum albumin (BSA) and hen egg lysozyme (Lyso) were purchased from Sigma–Aldrich Co. LLC. Concanavalin A (Con A) was purchased from Wako Pure Chemical Industries, LTD. The mouse melanoma cell line, B16F10 (RCB2630), was provided by the RIKEN BRC through the National Bio‐Resource Project of the MEXT, Japan. The normal human lung fibroblast cell line, WI‐38 (IFO50075), was purchased from the Japanese Collection of Research Bioresources (JCRB) Cell Bank (Osaka, Japan). Funding Information: This research was supported in part by a grant for Scientific Research (B) (No. JP19H02724) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT), and the Sasagawa Scientific Research Grant (No. 2019–3022) from the Japan Science Society. Publisher Copyright: {\textcopyright} 2020 Wiley-VCH GmbH",

year = "2020",

month = nov,

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doi = "10.1002/chem.202000833",

language = "English",

volume = "26",

pages = "14351--14358",

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AU - Kitamura, Takashi

AU - Shiroshita, Saori

AU - Takahashi, Daisuke

AU - Toshima, Kazunobu

N1 - Funding Information: Bovine serum albumin (BSA) and hen egg lysozyme (Lyso) were purchased from Sigma–Aldrich Co. LLC. Concanavalin A (Con A) was purchased from Wako Pure Chemical Industries, LTD. The mouse melanoma cell line, B16F10 (RCB2630), was provided by the RIKEN BRC through the National Bio‐Resource Project of the MEXT, Japan. The normal human lung fibroblast cell line, WI‐38 (IFO50075), was purchased from the Japanese Collection of Research Bioresources (JCRB) Cell Bank (Osaka, Japan). Funding Information: This research was supported in part by a grant for Scientific Research (B) (No. JP19H02724) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT), and the Sasagawa Scientific Research Grant (No. 2019–3022) from the Japan Science Society. Publisher Copyright: © 2020 Wiley-VCH GmbH

PY - 2020/11/11

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N2 - 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.

AB - 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.

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