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Issue 3, 2017
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Design, synthesis and cytotoxic activity of water-soluble quinones with dibromo-p-benzoquinone cores and amino oligo(ethylene glycol) side chains against MCF-7 breast cancer cells

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Abstract

A series of novel quinones was synthesized by reacting tetrabromo-p-benzoquinone with amino oligo(ethylene glycol) dendrons of generation numbers g = 0–2. According to the performed shake-flask experiments, their aqueous solubility (S = 18 mg l−1–1.6 g ml−1) and partition coefficients (log Poct/wat = 2.53–0.21) can be tuned in a wide range as a function of g. In vitro cytotoxicity assays of tetrabromo-p-benzoquinone and its derivatives against MCF-7 human breast cancer cells showed a concentration- and generation-specific biological activity with IC50-values as low as 0.8 μM. Further investigations revealed a considerable selectivity against cancer cells, as indicated by a weak cytotoxicity against human skin fibroblast cells (>80% survival) within the studied range of concentrations. The results demonstrate that these novel amino oligo(ethylene glycol) dendrons depict versatile tools to ameliorate physical and pharmacological characteristics of extremely hydrophobic molecules and make them susceptible to biological applications.

Graphical abstract: Design, synthesis and cytotoxic activity of water-soluble quinones with dibromo-p-benzoquinone cores and amino oligo(ethylene glycol) side chains against MCF-7 breast cancer cells

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Publication details

The article was received on 31 Dec 2016, accepted on 11 Feb 2017 and first published on 16 Feb 2017


Article type: Research Article
DOI: 10.1039/C6MD00728G
Citation: Med. Chem. Commun., 2017,8, 662-672
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    Design, synthesis and cytotoxic activity of water-soluble quinones with dibromo-p-benzoquinone cores and amino oligo(ethylene glycol) side chains against MCF-7 breast cancer cells

    L. F. Scherz, E. A. Abdel-Rahman, S. S. Ali, A. D. Schlüter and M. A. Abdel-Rahman, Med. Chem. Commun., 2017, 8, 662
    DOI: 10.1039/C6MD00728G

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