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. 2015 Oct 15;25(20):4606-9.
doi: 10.1016/j.bmcl.2015.08.042. Epub 2015 Aug 20.

Synthesis and evaluation of a bis-3-chloropiperidine derivative incorporating an anthraquinone pharmacophore

Ivonne Zuravka  1 , Alice Sosic  2 , Barbara Gatto  3 , Richard Göttlich  4
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Synthesis and evaluation of a bis-3-chloropiperidine derivative incorporating an anthraquinone pharmacophore

Ivonne Zuravka et al. Bioorg Med Chem Lett. .

Abstract

With the aim to attain an alkylating agent with enhanced DNA-affinity, we have successfully synthesised lysine-linked bis-3-chloropiperidine 1 bearing an anthraquinone moiety known to bind double-stranded DNA. Consistent with our expectations, compound 1 appears to intercalate into the DNA double helix, which can be observed by conformational changes of plasmid DNA suggesting alkylation and intercalation-induced DNA unwinding. The results of this work can provide a meaningful starting point for investigating the molecular mechanism of action of this novel DNA alkylating conjugate 1 with improved affinity for DNA.

Keywords: Alkylating agents; Anthraquinone; DNA cleavage; Intercalation; Nitrogen mustard.

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