Effect of Two-Photon Excitation to 8-Azacoumarin Derivatives as Photolabile Protecting Groups

Takuya Kobayakawa; Hikaru Takano; Takahiro Ishii; Peter Bolah; Kohei Tsuji; Nami Ohashi; Wataru Nomura; Toshiaki Furuta; Hirokazu Tamamura

doi:10.1248/cpb.c24-00013

Note

Effect of Two-Photon Excitation to 8-Azacoumarin Derivatives as Photolabile Protecting Groups

Takuya Kobayakawa ^†, Hikaru Takano ^†, Takahiro Ishii, Peter Bolah, Kohei Tsuji, Nami Ohashi, Wataru Nomura, Toshiaki Furuta, Hirokazu Tamamura

Author information

Takuya Kobayakawa ^†
Department of Medicinal Chemistry, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU)
Hikaru Takano ^†
Department of Medicinal Chemistry, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU)
Takahiro Ishii
Department of Medicinal Chemistry, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU)
Peter Bolah
Department of Medicinal Chemistry, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU)
Kohei Tsuji
Department of Medicinal Chemistry, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU)
Nami Ohashi
Department of Laboratory of Drug Design and Medicinal Chemistry, Showa Pharmaceutical University
Wataru Nomura
Department of Genome and Biomolecular Engineering for Drug Discovery, School of Pharmaceutical Sciences and Graduate School of Biomedical & Health Sciences, Hiroshima University
Toshiaki Furuta
Department of Biomolecular Science, Faculty of Science, Toho University
Hirokazu Tamamura Corresponding author
Department of Medicinal Chemistry, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU)
Author contributions

†These authors contributed equally: Takuya Kobayakawa, Hikaru Takano

Keywords: azacoumarin, caged compound, photolabile protecting group, two-photon excitation

JOURNAL OPEN ACCESS FULL-TEXT HTML

2024 Volume 72 Issue 3 Pages 311-312

DOI https://doi.org/10.1248/cpb.c24-00013

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Abstract

An improvement of the two-photon excitation was achieved using 8-azacoumarin-type caged compounds, which showed large values of the two-photon uncaging action cross-section (δ_u >0.1 Goeppert–Mayer (GM)). In particular, the 7-hydroxy-6-iodo-8-azacoumarin (8-aza-Ihc)-caged compound showed an excellent uncaging action cross-section value (δ_u = 1.28 GM). Therefore, 8-azacoumarin-type photolabile protecting groups (PPGs) can be used as two-photon excitation sources.

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