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<p>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.</p><p></p>

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Diversification of the 10th core atom of 9-cyanopyronins expands the resonance Raman vibrational palette

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年4月16日

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  • Shun-suke Kanai,
  • Hiroyoshi Fujioka,
  • Minoru Kawatani,
  • Spencer John Spratt,
  • Shun-suke Fukuta,
  • Zhihao Zhan,
  • Yang Ma,
  • Kazuhiro Kuruma,
  • Daisuke Asanuma,
  • Yuichi Asada,
  • Masayasu Taki,
  • Shigehiro Yamaguchi,
  • Yasuyuki Ozeki,
  • Mako Kamiya

摘要

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.