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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
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Coumarin-Caged Nanoparticle for Light-Driven Surface Modification.

Jan Birringer1, Johannes Konrad1, Stephan Melchner1

  • 1Department of Pharmaceutical Technology, University of Regensburg, Regensburg, 93053, Bavaria, Germany.

Chemmedchem
|October 7, 2025
PubMed
Summary
This summary is machine-generated.

Photo-labile protecting groups (PPG) on nanoparticles (NPs) control cell uptake. Light exposure cleaves PPG, restoring NP charge and enhancing cellular uptake for targeted drug delivery.

Keywords:
cell‐penetrating peptidescharge‐mediated uptakenanoparticlesstimuli‐responsivesurface chemistry

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Area of Science:

  • Nanotechnology
  • Materials Science
  • Biomedical Engineering

Background:

  • Photo-labile protecting groups (PPG) enable light-triggered release of caged molecules.
  • Incorporating PPG into nanoparticles (NPs) allows for spatiotemporal control of their surface properties.
  • Modifying NP properties after administration can enhance targeted delivery and therapeutic efficacy.

Purpose of the Study:

  • To investigate the use of PPG-modified nanoparticles (NPs) for light-controlled cellular uptake.
  • To demonstrate spatiotemporal control over NP surface charge and biological interactions using light.
  • To establish a method for triggering enhanced NP cell entry via external light stimuli.

Main Methods:

  • Polymeric core-shell nanoparticles (NPs) were synthesized using poly(D, L-lactide-co-glycolide) and a PEG-PLA block copolymer.
  • NPs were surface-modified with a positively charged cell-penetrating peptide (CPP) and subsequently functionalized with coumarin-derived PPG.
  • Zetapotential measurements and cell uptake assays were performed before and after UV light (365 nm) irradiation.

Main Results:

  • Attachment of PPG to CPP-NPs reduced their surface charge from +23.50 mV to +12.50 mV, significantly decreasing cell uptake.
  • Light irradiation at 365 nm successfully cleaved the PPG, restoring the NP surface charge to +24.67 mV.
  • The restored surface charge led to a significant enhancement in NP cellular uptake.

Conclusions:

  • PPG-functionalized NPs offer a promising platform for light-inducible control over cellular uptake.
  • This approach enables precise spatiotemporal regulation of NP-cell interactions, crucial for targeted drug delivery.
  • The developed method paves the way for future applications in light-activated nanomedicine.