Cyano-Hydrol green derivatives: Expanding the 9-cyanopyronin-based resonance Raman vibrational palette

Hiroyoshi Fujioka; Yuta Murao; Momoko Okinaka; Spencer John Spratt; Jingwen Shou; Minoru Kawatani; Ryosuke Kojima; Ryo Tachibana; Yasuteru Urano; Yasuyuki Ozeki; Mako Kamiya

doi:10.1016/j.bmcl.2024.129757

Cyano-Hydrol green derivatives: Expanding the 9-cyanopyronin-based resonance Raman vibrational palette

Bioorg Med Chem Lett. 2024 Jul 1:106:129757. doi: 10.1016/j.bmcl.2024.129757. Epub 2024 Apr 16.

Authors

Affiliations

¹ Department of Life Science and Technology, Tokyo Institute of Technology, 4259 Nagatsuta-cho. Midori-ku, Yokohama, Kanagawa 226-8501, Japan.
² Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
³ Research Center for Advanced Science and Technology, The University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo 153-8904, Japan.
⁴ Department of Electrical Engineering and Information Systems, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan.
⁵ Department of Life Science and Technology, Tokyo Institute of Technology, 4259 Nagatsuta-cho. Midori-ku, Yokohama, Kanagawa 226-8501, Japan; Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
⁶ Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
⁷ Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan; Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
⁸ Research Center for Advanced Science and Technology, The University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo 153-8904, Japan; Department of Electrical Engineering and Information Systems, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan.
⁹ Department of Life Science and Technology, Tokyo Institute of Technology, 4259 Nagatsuta-cho. Midori-ku, Yokohama, Kanagawa 226-8501, Japan; Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan; Research Center for Autonomous Systems Meterialogy (ASMat), Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta-cho. Midori-ku, Yokohama, Kanagawa 226-8501, Japan. Electronic address: kamiya.m.ad@m.titech.ac.jp.

PMID: 38636718
DOI: 10.1016/j.bmcl.2024.129757

Abstract

9-cyanopyronin is a promising scaffold that exploits resonance Raman enhancement to enable sensitive, highly multiplexed biological imaging. Here, we developed cyano-Hydrol Green (CN-HG) derivatives as resonance Raman scaffolds to expand the color palette of 9-cyanopyronins. CN-HG derivatives exhibit sufficiently long wavelength absorption to produce strong resonance Raman enhancement for near-infrared (NIR) excitation, and their nitrile peaks are shifted to a lower frequency than those of 9-cyanopyronins. The fluorescence of CN-HG derivatives is strongly quenched due to the lack of the 10th atom, unlike pyronin derivatives, and this enabled us to detect spontaneous Raman spectra with high signal-to-noise ratios. CN-HG derivatives are powerful candidates for high performance vibrational imaging.

Keywords: Michler’s Hydrol Blue; Multiplex detection; Resonance Raman; Spontaneous Raman scattering; Stimulated Raman scattering.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Molecular Structure
Nitriles / chemical synthesis
Nitriles / chemistry
Spectrum Analysis, Raman*
Vibration

Substances

Nitriles