Hybrid ligand-alkylating agents targeting telomeric G-quadruplex structures

Filippo Doria, Matteo Nadai, Marco Folini, Marco Di Antonio, Luca Germani, Claudia Percivalle, Claudia Sissi, Nadia Zaffaroni, Stefano Alcaro, Anna Artese, Sara N. Richter, Mauro Freccero

Research output: Contribution to journalArticlepeer-review


The synthesis, physico-chemical properties and biological effects of a new class of naphthalene diimides (NDIs) capable of reversibly binding telomeric DNA and alkylate it through an electrophilic quinone methide moiety (QM), are reported. FRET and circular dichroism assays showed a marked stabilization and selectivity towards telomeric G4 DNA folded in a hybrid topology. NDI-QMs' alkylating properties revealed a good reactivity on single nucleosides and selectivity towards telomeric G4. A selected NDI was able to significantly impair the growth of melanoma cells by causing telomere dysfunction and down-regulation of telomerase expression. These findings points to our hybrid ligand-alkylating NDIs as possible tools for the development of novel targeted anticancer therapies.

Original languageEnglish
Pages (from-to)2798-2806
Number of pages9
JournalOrganic and Biomolecular Chemistry
Issue number14
Publication statusPublished - Apr 14 2012

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry
  • Medicine(all)


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