Synthesis and Evaluation of New Naphthalene and Naphthoquinone Derivatives as Anticancer Agents

Giovanni L. Beretta, Giovanni Ribaudo, Ileana Menegazzo, Rosanna Supino, Giovanni Capranico, Franco Zunino, Giuseppe Zagotto

Research output: Contribution to journalArticlepeer-review


DNA topoisomerase I inhibitors, both synthetic and of natural origin, are receiving increasing consideration primarily as drugs against refractory tumors. Alkannin and shikonin, two enantiomeric dyes from Alkanna tinctoria and Lithospermum erythrorhizon, have been known over many centuries as dyestuff, wound healing, anti-inflammatory, antibacterial and antitumor substances. Although multiple mechanisms appear to be implicated, their potency is associated with the inhibition of topoisomerase I and with the redox properties of the naphthazarin scaffold. Here, the synthesis of new naphthalene and naphthoquinone derivatives inspired by alkannin and shikonin is described and their structural and biological properties were examined. Different oxidation states of the naphthalene nucleus were examined to observe the effect of this parameter on cytotoxicity. Antiproliferative activities against a panel of human cancer cell lines were evaluated and the implication of topoisomerase I was assessed.

Original languageEnglish
Article numbere1600286
JournalArchiv der Pharmazie
Issue number1
Publication statusPublished - Jan 1 2017


  • Alkannin
  • Anticancer
  • Camptothecin
  • Naphthoquinones
  • Topoisomerase

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery

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