Tuesday, 28 June 2016

Cytotoxicity of synthesized 1,4-naphthoquinone analogues on selected human cancer cell lines

Volume 22, Issue 17, 1 September 2014, Pages 5013–5019

Navneet Kishorea,

  • a Department of Plant Science, Plant Sciences Complex, University of Pretoria, Pretoria 0002, South Africa
  • b Department of Natural Products, National Institute of Pharmaceutical Education and Research, Ahmedabad 380054, India
  • c Department of Biochemistry and Microbiology, Nelson Mandela Metropolitan University, Summerstrand Campus, Port Elizabeth 6031, South Africa
  • d Pharmaceutical Sciences Division, King’s College London, Franklin-Wilkins Building, 150 Stamford Street, London SE1 9NN, UK


In an effort to establish new candidates with enhanced anticancer activity of 5-hydroxy-7-methyl-1,4-naphthoquinone scaffold (7-methyljuglone) previously isolated from the root extract of Euclea natalensis, a series of 7-methyljuglone derivatives have been synthesized and assessed for cytotoxicity on selected human cancer lines. These compounds were screened in vitro for anticancer activity on MCF-7, HeLa, SNO and DU145 human cancer cell lines by MTT assay. Most of them exhibited significant toxicity on cancer cell lines with lower IC50 values. The most potent derivative (19) exhibited the toxicity on HeLa and DU145 cell lines with IC50 value of 5.3 and 6.8 μM followed by compound (5) with IC50 value of 10.1 and 9.3 μM, respectively. Structure–activity relationship reveals that the fluoro substituents at position C-8 while hydroxyl substituents at C-2 and C-5 positions played an important role in toxicity.

Graphical abstract

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  • Euclea natalensis;
  • 7-Methyljuglone derivatives;
  • Cytotoxicity;
  • Cell cycle analysis;
  • Cell apoptosis
Corresponding author. Tel.: +27 12 420 2524; fax: +27 12 420 6668.