Results
Title

2‐Naphthol Moiety of Neocarzinostatin Chromophore as a Novel Protein‐Photodegrading Agent and Its Application as a H<sub>2</sub>O<sub>2</sub>‐Activatable Photosensitizer.

Authors

Kitamura, Takashi; Shiroshita, Saori; Takahashi, Daisuke; Toshima, Kazunobu

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.

Subjects

MOIETIES (Chemistry); PHOTOSENSITIZERS; STRUCTURE-activity relationships; HYDROXYL group; PHOTODEGRADATION; BIOMARKERS; CANCER cells

Publication

Chemistry - A European Journal, 2020, Vol 26, Issue 63, p14351

ISSN

0947-6539

Publication type

Academic Journal

DOI

10.1002/chem.202000833