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<p>Salicylic acid (SA) functions as a critical phytohormone coordinating developmental regulation and defense responses in plants. Understanding SA's regulatory roles in both homeostasis and stress adaptation necessitates advanced monitoring platforms. We designed six rhodamine probes (<b>R1</b>–<b>R6</b>) containing spirolactam or spirohydrazone bridges to systematically evaluate five-membered spiro structures for SA detection. Furthermore, through Fourier infrared experiments (FTIR) and density functional theory (DFT) calculations, we performed molecular orbital analysis to disclose the SA-responsive mechanism underlying the rhodamine ring-opening process induced by SA. Comparative analysis revealed that spirohydrazone-modified probes displayed enhanced fluorescence performance and improved molecular recognition specificity for SA. The optimized probe <b>R2</b>, incorporating a quinoline moiety, achieved exceptional sensing performance through synergistic hydrogen bonding and C–H…π interactions, demonstrating high selectivity, rapid response kinetics (&lt; 30&#xa0;s), and excellent sensitivity (LOD = 0.87&#xa0;μM). Overall, this study successfully visualized endogenous SA distribution in living tomato root systems, establishing a novel design framework for acylhydrazone-based rhodamine sensors and elucidating the SA response mechanism through molecular dynamics simulations.</p> Graphic abstract <p></p>

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Rational design of fused-ring-modified rhodamine chemosensors for salicylic acid detection: its mechanistic insights and biological application

  • 期刊论文

  • 发表日期：

    2025年6月27日

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  • Mei-Hong Ge,
  • A-Ling Tang,
  • Feng Gao,
  • Shuai Tan,
  • Wei Niu,
  • Xiang Zhou,
  • Song Yang

摘要

Salicylic acid (SA) functions as a critical phytohormone coordinating developmental regulation and defense responses in plants. Understanding SA's regulatory roles in both homeostasis and stress adaptation necessitates advanced monitoring platforms. We designed six rhodamine probes (R1–R6) containing spirolactam or spirohydrazone bridges to systematically evaluate five-membered spiro structures for SA detection. Furthermore, through Fourier infrared experiments (FTIR) and density functional theory (DFT) calculations, we performed molecular orbital analysis to disclose the SA-responsive mechanism underlying the rhodamine ring-opening process induced by SA. Comparative analysis revealed that spirohydrazone-modified probes displayed enhanced fluorescence performance and improved molecular recognition specificity for SA. The optimized probe R2, incorporating a quinoline moiety, achieved exceptional sensing performance through synergistic hydrogen bonding and C–H…π interactions, demonstrating high selectivity, rapid response kinetics (< 30 s), and excellent sensitivity (LOD = 0.87 μM). Overall, this study successfully visualized endogenous SA distribution in living tomato root systems, establishing a novel design framework for acylhydrazone-based rhodamine sensors and elucidating the SA response mechanism through molecular dynamics simulations.

Graphic abstract