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<p>The development of acid-responsive fluorescent probes with additional chemical functionality remains of considerable interest in chemical biology. Herein, we report an acid-responsive rhodamine-based fluorescent probe, 2PCA-RhB, which exhibits a pronounced fluorescence “turn-on” response under acidic aqueous conditions through spirolactam ring opening. The probe displays favorable photophysical properties, good aqueous compatibility, and enables fluorescence imaging in living cells. Beyond its fluorescence response, 2PCA-RhB incorporates a 2-pyridinecarboxaldehyde (2PCA) moiety that enables <i>N</i>-terminal-selective protein labeling, while its allyl carbonate functionality is compatible with palladium-catalyzed Tsuji–Trost allylic alkylation under aqueous conditions. These studies establish 2PCA-RhB as an acid-responsive fluorescent probe with both <i>N</i>-terminal labeling capability and compatibility with aqueous transition-metal-mediated transformation. The present work provides a versatile molecular scaffold for the future development of fluorescent chemical tools for protein modification and bioorthogonal applications in complex biological environments.</p>

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An acid-responsive rhodamine-based fluorescent probe for N-terminal protein labeling and aqueous Tsuji–Trost allylic alkylation

  • 期刊论文

  • 发表日期：

    2026年7月16日

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  • Yonghua Tan,
  • Kaiyuan Hui,
  • Raphaël Frédérick,
  • Oliver Riant,
  • Xiaodong Jiang

摘要

The development of acid-responsive fluorescent probes with additional chemical functionality remains of considerable interest in chemical biology. Herein, we report an acid-responsive rhodamine-based fluorescent probe, 2PCA-RhB, which exhibits a pronounced fluorescence “turn-on” response under acidic aqueous conditions through spirolactam ring opening. The probe displays favorable photophysical properties, good aqueous compatibility, and enables fluorescence imaging in living cells. Beyond its fluorescence response, 2PCA-RhB incorporates a 2-pyridinecarboxaldehyde (2PCA) moiety that enables N-terminal-selective protein labeling, while its allyl carbonate functionality is compatible with palladium-catalyzed Tsuji–Trost allylic alkylation under aqueous conditions. These studies establish 2PCA-RhB as an acid-responsive fluorescent probe with both N-terminal labeling capability and compatibility with aqueous transition-metal-mediated transformation. The present work provides a versatile molecular scaffold for the future development of fluorescent chemical tools for protein modification and bioorthogonal applications in complex biological environments.