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2‐Naphthol Moiety of Neocarzinostatin Chromophore as a Novel Protein‐Photodegrading Agent and Its Application as a H 2 O 2 ‐Activatable Photosensitizer
Author(s) -
Kitamura Takashi,
Shiroshita Saori,
Takahashi Daisuke,
Toshima Kazunobu
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202000833
Subject(s) - moiety , chemistry , photosensitizer , photodegradation , chromophore , photochemistry , neocarzinostatin , conjugated system , fluorescence , stereochemistry , photocatalysis , dna , organic chemistry , polymer , catalysis , biochemistry , physics , quantum mechanics
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 H 2 O 2 ‐activatable photosensitizer 8 possessing a H 2 O 2 ‐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 H 2 O 2 regenerated the photodegradation ability. Compound 8 exhibited selective photo‐cytotoxicity against high H 2 O 2 ‐expressing cancer cells upon irradiation with long‐wavelength UV light.