Thiahelicene-grafted halloysite nanotubes: Characterization, biological studies and pH triggered release

Tommaso Taroni, Silvia Cauteruccio, Riccardo Vago, Stefano Franchi, Nadia Barbero, Emanuela Licandro, Silvia Ardizzone, Daniela Meroni

Research output: Contribution to journalArticlepeer-review


A novel drug delivery nanosystem was here designed, linking thiahelicenes to halloysite nanotubes. Tetrathia[7]helicenes are very promising DNA intercalators, whose usage in biomedical field has been so far limited by their poor bioavailability. The study of appropriate drug delivery systems is needed to exploit helicenes as therapeutics. In this work, imine chemistry was adopted to covalently attach the bioactive compound and release it in acidic environments such as those surrounding tumour cells. To this aim, halloysite nanotubes were functionalized with (3-aminopropyl)triethoxysilane. The latter acted as linker providing NH2 groups to react with the formyl moiety of the thiahelicene derivative. The nanoconstruct preparation was studied in depth by surface-sensitive spectroscopies and angle-resolved X-ray absorption, to investigate the attachment mode, surface coverage and molecular orientation of the thiahelicene units. Release tests were carried out also in vitro on two tumour cell lines with different extracellular pH values. Mildly acidic pH conditions catalyzed the hydrolysis of the imine bond and promoted the cytotoxic compound release, which proved selective to slight pH differences, confirming the potential of this novel nanoconstruct.

Original languageEnglish
Article number146351
JournalApplied Surface Science
Publication statusPublished - Aug 1 2020


  • Halloysite nanotubes
  • Helicene
  • Nanocarrier
  • Triggered release

ASJC Scopus subject areas

  • Chemistry(all)
  • Condensed Matter Physics
  • Physics and Astronomy(all)
  • Surfaces and Interfaces
  • Surfaces, Coatings and Films

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