Supramolecular nanoreactors for intracellular singlet-oxygen sensitization

Subramani Swaminathan, Colin Fowley, Ek Raj Thapaliya, Bridgeen McCaughan, Sicheng Tang, Aurore Fraix, Burjor Captain, Salvatore Sortino, John F. Callan, Francisco M. Raymo

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)


An amphiphilic polymer with multiple decyl and oligo(ethylene glycol) chains attached to a common poly(methacrylate) backbone assembles into nanoscaled particles in aqueous environments. Hydrophobic anthracene and borondipyrromethene (BODIPY) chromophores can be co-encapsulated within the self-assembling nanoparticles and transported across hydrophilic media. The reversible character of the noncovalent bonds, holding the supramolecular containers together, permits the exchange of their components with fast kinetics in aqueous solution. Incubation of cervical cancer (HeLA) cells with a mixture of two sets of nanoparticles, pre-loaded independently with anthracene or BODIPY chromophores, results in guest scrambling first and then transport of co-entrapped species to the intracellular space. Alternatively, incubation of cells with the two sets of nanocarriers in consecutive steps permits the sequential transport of the anthracene and BODIPY chromophores across the plasma membrane and only then allows their co-encapsulation within the same supramolecular containers. Both mechanisms position the two sets of chromophores with complementary spectral overlap in close proximity to enable the efficient transfer of energy intracellularly from the anthracene donors to the BODIPY acceptors. In the presence of iodine substituents on the BODIPY platform, intersystem crossing follows energy transfer. The resulting triplet state can transfer energy further to molecular oxygen with the concomitant production of singlet oxygen to induce cell mortality. Furthermore, the donor can be excited with two near-infrared photons simultaneously to permit the photoinduced generation of singlet oxygen intracellularly under illumination conditions compatible with applications in vivo. Thus, these supramolecular strategies to control the excitation dynamics of multichromophoric assemblies in the intracellular environment can evolve into valuable protocols for photodynamic therapy. © The Royal Society of Chemistry 2015.
Original languageEnglish
Pages (from-to)14071-14079
Number of pages9
Issue number33
Early online date28 Jul 2015
Publication statusPublished (in print/issue) - 7 Sept 2015


  • Anthracene
  • Cell membranes
  • Chromophores
  • Containers
  • Energy transfer
  • Ethylene
  • Ethylene glycol
  • Infrared devices
  • Lanthanum compounds
  • Nanoparticles
  • Oxygen
  • Photodynamic therapy
  • Solutions
  • Supramolecular chemistry
  • Concomitant production
  • Illumination conditions
  • Inter-system crossings
  • Intracellular spaces
  • Nanoscaled particles
  • Near-infrared photons
  • Oligo(ethylene glycol)
  • Photo-induced generation
  • Molecular oxygen


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