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Nonsymmetrical Near-Infrared Rhodamines for Carboxylesterase-Activatable Tumor Imaging and Photodynamic Therapy.

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Researchers developed novel near-infrared rhodamine fluorophores for bioimaging and therapy. These new probes enable specific detection of carboxylesterase activity and targeted tumor ablation via photodynamic therapy (PDT).

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Area of Science:

  • Organic Chemistry
  • Biomedical Engineering
  • Photochemistry

Background:

  • Developing activatable probes with large Stokes shifts, high quantum yields, and tunable near-infrared (NIR) wavelengths is crucial for bioimaging and biomedical applications.
  • Existing fluorophores often lack the ideal combination of these properties, limiting their utility.
  • Nonsymmetrical rhodamine-based fluorophores offer a promising avenue for creating advanced imaging and therapeutic agents.

Purpose of the Study:

  • To engineer novel nonsymmetrical near-infrared (NIR) rhodamine-based fluorophores.
  • To investigate their utility as activatable probes for fluorogenic imaging and targeted photodynamic therapy (PDT).
  • To develop a specific probe for carboxylesterase (CE) activity and demonstrate its in vivo tumor ablation capabilities.

Main Methods:

  • Synthesized nonsymmetrical NIR rhodamine derivatives incorporating phenothiazine moieties as auxochromes.
  • Characterized their photophysical properties, including absorption/emission profiles and Stokes shifts.
  • Engineered an activatable probe by conjugating a furan substrate to the rhodamine secondary amine for CE detection.
  • Evaluated probe performance in vitro for CE activity imaging and apoptosis induction via PDT.
  • Assessed the probe's efficacy for in vivo tumor imaging and PDT-mediated ablation.

Main Results:

  • Rhodamine incorporated with phenoselenazine showed red-shifted absorption/emission, large Stokes shift, and efficient reactive oxygen species (ROS) production.
  • The engineered CE-activatable probe transitioned from spirolactone to zwitterion form upon CE hydrolysis, enabling specific CE imaging.
  • The probe successfully induced apoptosis in CE-positive cells via PDT.
  • A polyethylene glycol-modified probe facilitated specific in vivo tumor imaging and PDT-mediated ablation.

Conclusions:

  • Nonsymmetrical NIR rhodamine fluorophores can be engineered with desirable photophysical properties for theranostic applications.
  • The developed CE-activatable probe is effective for specific bioimaging and targeted photodynamic therapy.
  • These findings highlight the potential of these novel fluorophores for advancing theranostics in cancer treatment and other biomedical fields.