Diversification of the 10th core atom of 9-cyanopyronins expands the resonance Raman vibrational palette
9-Cyanopyronin derivatives have been used as resonance Raman probes for highly sensitive and multiplexed vibrational biological imaging. Here, we synthesized a series of fourteen 9-cyanopyronin derivatives in which the 10th core atom is substituted with various group 13, 14, 15 or 16 elements, and systematically evaluated their properties using electronic pre-resonance stimulated Raman scattering (EPR-SRS) microscopy. Substitution at the 10th position modulates not only the vibrational frequency of the nitrile (C ≡ N) group in the silent region, but also the conjugated double-bond stretching frequency (C = C) in the fingerprint region, and additionally alters the subcellular localization of the probes. By employing different combinations of probes, we were able to utilize the distinct patterns of C ≡ N or C = C bond vibrations together with the different subcellular localizations of the probes to achieve live-cell three-color imaging. These 9-cyanopyronin derivatives greatly expand the vibrational palette available for multiplexed SRS imaging.
Authors
- Hiroyoshi Fujioka (ORCID: https://orcid.org/0000-0003-1904-0566)
- Yasuyuki Ozeki (ORCID: https://orcid.org/0000-0002-9004-0799)
- Shigehiro Yamaguchi (ORCID: https://orcid.org/0000-0003-0072-8969)
- Masayasu Taki (ORCID: https://orcid.org/0000-0003-2185-4593)
- Zhihao Zhan
- Spencer J. Spratt (ORCID: https://orcid.org/0000-0002-5429-8856)
- Minoru Kawatani (ORCID: https://orcid.org/0000-0002-0192-4366)
- Daisuke Asanuma (ORCID: https://orcid.org/0000-0002-8072-7140)
- Kazuhiro Kuruma (ORCID: https://orcid.org/0000-0002-0830-0230)
- Mako Kamiya (ORCID: https://orcid.org/0000-0002-5592-1849)
- Yang Ma (ORCID: https://orcid.org/0000-0002-9419-6598)
- Yuichi Asada
- Shun-suke Kanai (ORCID: https://orcid.org/0009-0009-6449-2589)
- Shun-suke Fukuta
Institutions
- Tokyo Institute of Technology (JP)
- Life Science Institute (JP)
- Gifu University (JP)
- Nagoya University (JP)
- The University of Tokyo (JP)
Publication Details
- Journal
- Communications Chemistry
- Published
- 2026-04-16
- DOI
- https://doi.org/10.1038/s42004-026-02019-1
- Primary Topic
- Spectroscopy Techniques in Biomedical and Chemical Research
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Japan Agency for Medical Research and Development
- Ministry of Education, Culture, Sports, Science and Technology
- Secom Science and Technology Foundation
- University of Tokyo
- Mochida Memorial Foundation for Medical and Pharmaceutical Research
- Daiichi Sankyo Foundation of Life Science
- Nakatani Foundation for Advancement of Measuring Technologies in Biomedical Engineering
- Research Foundation for Opto-Science and Technology
- Japan Society for the Promotion of Science
- Japan Science and Technology Agency
- Core Research for Evolutional Science and Technology
- ACT-X
- Daiichi Sankyo Europe