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- 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