Intracellular Guest Exchange between Dynamic Supramolecular Hosts

S. Swaminathan, Colin Fowley, Bridgeen McCaughan, J. Cusido, J Callan, F.M. Raymo

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

Decyl and oligo(ethylene glycol) chains were appended to the same poly(methacrylate) backbone to generate an amphiphilic polymer with a ratio between hydrophobic and hydrophilic segments of 2.5. At concentrations greater than 10 μg mL–1 in neutral buffer, multiple copies of this particular macromolecule assemble into nanoparticles with a hydrodynamic diameter of 15 nm. In the process of assembling, these nanoparticles can capture anthracene donors and borondipyrromethene acceptors within their hydrophobic interior and permit the transfer of excitation energy with an efficiency of 95%. Energy transfer is observed also if nanocarriers containing exclusively the donors are mixed with nanoparticles preloaded separately with the acceptors in aqueous media. The two sets of supramolecular assemblies exchange their guests with fast kinetics upon mixing to co-localize complementary chromophores within the same nanostructured container and enable energy transfer. After guest exchange, the nanoparticles can cross the membrane of cervical cancer cells and bring the co-entrapped donors and acceptors within the intracellular environment. Alternatively, intracellular energy transfer is also established after sequential cell incubation with nanoparticles containing the donors first and then with nanocarriers preloaded with the acceptors or vice versa. Under these conditions, the nanoparticles exchange their cargo only after internalization and allow energy transfer exclusively within the cell interior. Thus, the dynamic character of such supramolecular containers offers the opportunity to transport independently complementary species inside cells and permit their interaction only within the intracellular space.
Original languageEnglish
Pages (from-to)7907-7913
Number of pages7
JournalJournal of the American Chemical Society
Volume136
Issue number22
Early online date9 May 2014
DOIs
Publication statusPublished - 4 Jun 2014

Keywords

  • Chromophores
  • Containers
  • Energy transfer
  • Ethylene glycol
  • Hydrophobicity
  • Supramolecular chemistry
  • Amphiphilic polymers
  • Cervical cancer cells
  • Hydrodynamic diameter
  • Hydrophobic and hydrophilic
  • Intracellular spaces
  • Oligo(ethylene glycol)
  • Supramolecular assemblies
  • Supramolecular host
  • Nanoparticles
  • anthracene
  • anthracene derivative
  • dipyrromethene
  • macrogol derivative
  • nanoparticle
  • polymethacrylic acid
  • polymethacrylic acid derivative
  • porphobilinogen
  • article
  • cancer cell
  • chromatophore
  • dynamics
  • energy transfer
  • excitation
  • hydrophobicity
  • internalization
  • intracellular space
  • supramolecular chemistry
  • uterine cervix cancer
  • analogs and derivatives
  • cell membrane
  • chemistry
  • HeLa cell line
  • human
  • metabolism
  • Anthracenes
  • Cell Membrane
  • Energy Transfer
  • HeLa Cells
  • Humans
  • Polyethylene Glycols
  • Polymethacrylic Acids
  • Porphobilinogen

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