2‐Naphthol Moiety of Neocarzinostatin Chromophore as a Novel Protein‐Photodegrading Agent and Its Application as a H2O2‐Activatable Photosensitizer. Issue 63 (6th October 2020)

• Record Type: Journal Article
• Authors: Kitamura, Takashi; Shiroshita, Saori; Takahashi, Daisuke; Toshima, Kazunobu
• Is Part Of: Chemistry. Volume 26:Issue 63(2020)
• Page Start: 14351
• Page End: 14358
• Publication Date: 2020-10-06
• Subjects: cytotoxicity -- neocarzinostatin chromophore -- peroxides -- photodegradation -- photosensitizer; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202000833
• Languages: English
• ISSNs: 0947-6539

Abstract

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 H2 O2 ‐activatable photosensitizer 8 possessing a H2 O2 ‐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 H2 O2 regenerated the photodegradation ability. Compound 8 exhibited selective photo‐cytotoxicity against high H2 O2 ‐expressing cancer cells upon irradiation with long‐wavelength UV light. Abstract : Photo against cancer : A purpose‐designed and synthesized H2 O2 ‐activatable photosensitizer 8 consisting of 2‐naphthol moiety 2 of the neocarzinostatin chromophore showed significantly lower protein photodegradation ability compared to 2. However, release of 2 from 8 by reaction with H2 O2 regenerated the photodegradation ability. Furthermore, 8 exhibited selective and effective photo‐cytotoxicity against target cancer cells upon photoirradiation.