Phthalimide: a potential warhead for switchable and bioorthogonal conjugation
4-Azidophthalimide, previously reported as a photoaffinity labeling (PAL) tag, was repurposed as a post-conjugation warhead. Using the phthalimide-amine reaction, cyanine amines were successfully conjugated to target proteins after PAL and later replaced with other amines, demonstrating its "switchable" nature. These findings highlight phthalimide's unique characteristics as a novel chemical tool for bioorthogonal conjugations.
Authors
- Minoru Ishikawa (ORCID: https://orcid.org/0000-0002-3937-2261)
- Takao Yamaguchi (ORCID: https://orcid.org/0000-0003-3180-0257)
- Kosuke Chiba (ORCID: https://orcid.org/0000-0002-8074-4549)
- Satoshi Obika (ORCID: https://orcid.org/0000-0002-6842-6812)
- Kana Okada
- Yuichi Hashimoto (ORCID: https://orcid.org/0009-0005-9070-9439)
- T. YOSHIDA
Institutions
- The University of Tokyo (JP)
- The University of Osaka (JP)
Publication Details
- Journal
- Chemical Communications
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5cc03171k
- Primary Topic
- Click Chemistry and Applications
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Japan Agency for Medical Research and Development
- Hoansha Foundation
- Japan Society for the Promotion of Science