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<p>Ferroptosis represents a novel form of cell death distinct from other types, characterized primarily by the accumulation of lipid peroxides (LPO) in the membrane system. The development of specific probes for detecting ferroptosis-associated LPO remains challenging. The widely recognized sensor Liperfluo, for instance, is hampered by poor photostability, underscoring the need for improved molecular tools. Herein, we developed a series of novel fluorescent probes by replacing the conventional light-sensitive perylene with a stable naphthalimide core and systematically tuning the electronic properties of the triphenylphosphine (TPP) recognition head with different substituents (—OCH<sub>3</sub>, —CF<sub>3</sub>). The optimized probe NP-1, incorporating a trifluoromethyl group, demonstrates both superior stability under ambient conditions and specific recognition of lipid hydroperoxides, yielding a robust fluorescence enhancement of &gt;6-fold. It was revealed that the electron-withdrawing —CF<sub>3</sub> group stabilizes the TPP moiety by lowering its electron density, thereby enhancing oxidative resistance. Furthermore, NP-1 enables to monitor RSL3-induced ferroptosis in live cells and the signal is specifically abolished by ferroptosis inhibitor. This work not only delivers a reliable sensor for detecting ferroptosis but, more importantly, establishes a general design principle by electronic modulation of the phosphorus center to develop stable and specific TPP-based probes for redox biology.</p>

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Novel Naphthylamide-based Fluorescent Probe for Detecting Lipid Hydroperoxides in Ferroptosis

  • 期刊论文

  • 发表日期：

    2026年3月21日

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  • Lingxiu Kong,
  • Li Li,
  • Li Zhao,
  • Zhaohu Deng,
  • Luo Bao,
  • Xue Qiu,
  • Yong Wang

摘要

Ferroptosis represents a novel form of cell death distinct from other types, characterized primarily by the accumulation of lipid peroxides (LPO) in the membrane system. The development of specific probes for detecting ferroptosis-associated LPO remains challenging. The widely recognized sensor Liperfluo, for instance, is hampered by poor photostability, underscoring the need for improved molecular tools. Herein, we developed a series of novel fluorescent probes by replacing the conventional light-sensitive perylene with a stable naphthalimide core and systematically tuning the electronic properties of the triphenylphosphine (TPP) recognition head with different substituents (—OCH3, —CF3). The optimized probe NP-1, incorporating a trifluoromethyl group, demonstrates both superior stability under ambient conditions and specific recognition of lipid hydroperoxides, yielding a robust fluorescence enhancement of >6-fold. It was revealed that the electron-withdrawing —CF3 group stabilizes the TPP moiety by lowering its electron density, thereby enhancing oxidative resistance. Furthermore, NP-1 enables to monitor RSL3-induced ferroptosis in live cells and the signal is specifically abolished by ferroptosis inhibitor. This work not only delivers a reliable sensor for detecting ferroptosis but, more importantly, establishes a general design principle by electronic modulation of the phosphorus center to develop stable and specific TPP-based probes for redox biology.