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 |
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Pages (from-to) | 14351-14358 |
Number of pages | 8 |
Journal | Chemistry - A European Journal |
Volume | 26 |
Issue number | 63 |
DOIs | |
Publication status | Published - 2020 Nov 11 |
Keywords
- cytotoxicity
- neocarzinostatin chromophore
- peroxides
- photodegradation
- photosensitizer
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry