Near-Infrared Coumarin-Hemicyanine Hybrid Dyes Bearing an Intramolecular Nucleophile for Activatable Fluorescence and Raman Imaging

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Abstract
Coumarin-hemicyanine (CHC) hybrid fluorophores bearing an intramolecular nucleophile have been reported as ratiometric fluorescent probes based on the equilibrium between the π-conjugated open and cyclic closed forms. Here, we report red-shifted CHC derivatives that can serve as scaffold dyes of activated fluorescent probes and activated Raman probes. We prepared a series of cyano-substituted CHC derivatives and found that substitution at C-4 of the coumarin moiety is effective in extending the absorption wavelength. The near-infrared (NIR) emission of these 4CN-CHC derivatives exhibits high tissue penetration. Dual-color imaging with 4CN-CHC enabled ratiometric monitoring of the lysosomal pH changes. Furthermore, the coherent anti-Stokes Raman scattering (CARS) signals of 4CN-CHC derivatives could be regulated by modifying the open/closed equilibrium, and the different patterns of CARS spectra enabled us to perform multicomponent imaging. Thus, these 4CN-CHC derivatives expand the repertoire of functional probes for NIR and multiplexed vibrational imaging.
Funding Information
  • JST-Mirai Program (JPMJMI21G5, JPMJMI22G5)
  • Konica Minolta Imaging Science Foundation
  • Core Research for Evolutional Science and Technology (JPMJCR2331)
  • Astellas Foundation for Research on Metabolic Disorders
  • Research Foundation for Opto-Science and Technology
  • Keio University
  • Daiichi Sankyo Foundation of Life Science
  • ACT-X (JPMJAX2328)
  • Moonshot Research and Development Program (JPMJMS2022-12)
  • Japan Society for the Promotion of Science (JP22H02193, JP23gm1910004, JP23K19240, JP23K23297, JP24H00050, JP24zf012701)
  • Fusion Oriented REsearch for disruptive Science and Technology (JPMJFR216R, JPMJFR221M)
  • Secom Science and Technology Foundation
  • Mochida Memorial Foundation for Medical and Pharmaceutical Research

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