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<p>Porphyrin aggregation has long been reported to weaken its ability for photosensitizing the generation of <sup>1</sup>O<sub>2</sub> for photodynamic therapy, but cannot be avoided for yet reported single molecule porphyrins. To address this challenge, we here report the design and synthesis of a new series of amphiphilic porphyrin compounds that bear three sulfonate groups and one aliphatic chain. Dynamic light scattering and transmission electron microscopic imaging experiments show that one of the compounds, <b>TSC18P</b>, that bears the longest hydrophobic stearamide unit undergoes ordered H-aggregation to form highly stable uniform single molecule nanomicelles in both water and the solid state. UV-vis, fluorescence and electron spin resonance experiments support that the formation of the single molecule nanomicelles significantly increases the ability of <b>TSC18P</b> in photosensitizing the generation of <sup>1</sup>O<sub>2</sub> and also enables important intracellular self-delivery. <i>In vivo</i> test demonstrates that <b>TSC18P</b> has an excellent biocompatibility, a therapeutic index of 17.5 and can achieve remarkably higher anti-tumor photodynamic therapeutic activity compared with aggregation-free porphyrin control.</p>

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Self-assembly of highly stable uniform single-molecule porphyrin nanomicelles for enhanced photodynamic therapy

  • 期刊论文

  • 发表日期：

    2025年1月23日

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  • Danying Ma,
  • Jiangshan Zhang,
  • Yue-Yang Liu,
  • Lingyu Zhang,
  • Zizhen Zhao,
  • Qihan Lin,
  • Yifei Lei,
  • Jiabin Xing,
  • Hui Wang,
  • Jia Tian,
  • Dan-Wei Zhang,
  • Wei Zhou,
  • Zhan-Ting Li

摘要

Porphyrin aggregation has long been reported to weaken its ability for photosensitizing the generation of 1O2 for photodynamic therapy, but cannot be avoided for yet reported single molecule porphyrins. To address this challenge, we here report the design and synthesis of a new series of amphiphilic porphyrin compounds that bear three sulfonate groups and one aliphatic chain. Dynamic light scattering and transmission electron microscopic imaging experiments show that one of the compounds, TSC18P, that bears the longest hydrophobic stearamide unit undergoes ordered H-aggregation to form highly stable uniform single molecule nanomicelles in both water and the solid state. UV-vis, fluorescence and electron spin resonance experiments support that the formation of the single molecule nanomicelles significantly increases the ability of TSC18P in photosensitizing the generation of 1O2 and also enables important intracellular self-delivery. In vivo test demonstrates that TSC18P has an excellent biocompatibility, a therapeutic index of 17.5 and can achieve remarkably higher anti-tumor photodynamic therapeutic activity compared with aggregation-free porphyrin control.