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 journalArticle

8 Citations (Scopus)

Abstract

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
Volume350
Issue number1
DOIs
Publication statusPublished - Jan 1 2017

Fingerprint

Naphthoquinones
Type I DNA Topoisomerase
Antineoplastic Agents
Lithospermum
Boraginaceae
Topoisomerase I Inhibitors
Wound Healing
Oxidation-Reduction
Neoplasms
Anti-Inflammatory Agents
Coloring Agents
Cell Line
Pharmaceutical Preparations
naphthalene
alkannin
shikonin
naphthazarin

Keywords

  • Alkannin
  • Anticancer
  • Camptothecin
  • Naphthoquinones
  • Topoisomerase

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery

Cite this

Beretta, G. L., Ribaudo, G., Menegazzo, I., Supino, R., Capranico, G., Zunino, F., & Zagotto, G. (2017). Synthesis and Evaluation of New Naphthalene and Naphthoquinone Derivatives as Anticancer Agents. Archiv der Pharmazie, 350(1), [e1600286]. https://doi.org/10.1002/ardp.201600286

Synthesis and Evaluation of New Naphthalene and Naphthoquinone Derivatives as Anticancer Agents. / Beretta, Giovanni L.; Ribaudo, Giovanni; Menegazzo, Ileana; Supino, Rosanna; Capranico, Giovanni; Zunino, Franco; Zagotto, Giuseppe.

In: Archiv der Pharmazie, Vol. 350, No. 1, e1600286, 01.01.2017.

Research output: Contribution to journalArticle

Beretta, GL, Ribaudo, G, Menegazzo, I, Supino, R, Capranico, G, Zunino, F & Zagotto, G 2017, 'Synthesis and Evaluation of New Naphthalene and Naphthoquinone Derivatives as Anticancer Agents', Archiv der Pharmazie, vol. 350, no. 1, e1600286. https://doi.org/10.1002/ardp.201600286
Beretta GL, Ribaudo G, Menegazzo I, Supino R, Capranico G, Zunino F et al. Synthesis and Evaluation of New Naphthalene and Naphthoquinone Derivatives as Anticancer Agents. Archiv der Pharmazie. 2017 Jan 1;350(1). e1600286. https://doi.org/10.1002/ardp.201600286
Beretta, Giovanni L. ; Ribaudo, Giovanni ; Menegazzo, Ileana ; Supino, Rosanna ; Capranico, Giovanni ; Zunino, Franco ; Zagotto, Giuseppe. / Synthesis and Evaluation of New Naphthalene and Naphthoquinone Derivatives as Anticancer Agents. In: Archiv der Pharmazie. 2017 ; Vol. 350, No. 1.
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