Anticancer metallohelices: nanomolar potency and high selectivity.

Journal: Chemical science
Published Date:

Abstract

A range of new helicate-like architectures have been prepared highly diastereoselective self-assembly using readily accessible starting materials. Six pairs of enantiomers [FeL]Cl·HO (L = various bidentate ditopic ligands NN-NN) show very good water solubility and stability. Their activity against a range of cancer cell lines is structure-dependent and gives IC values as low as 40 nM. In an isogenic pair of HCT116 colorectal cancer cells, preferential activity was observed against cell lines that lack functional p53. Selectivity is also excellent, and against healthy human retinal pigment epithelial (ARPE19) and lung fibroblast (WI38) cells IC values are nearly three orders of magnitude higher. Cisplatin is unselective in the same tests. The compounds also appear to have low general toxicity in a number of models: there is little if any antimicrobial activity against methicillin-resistant and ; is unaffected at 25 μg mL (12.5 μM); larvae showed clear evidence of systemic distribution of the drug, and rather than any observation of adverse effects they exhibited a significant mean weight gain controls. Investigation of the mode of action revealed no significant interaction of the molecules with DNA, and stimulation of substantial cell death by apoptosis.

Authors

  • Rebecca A Kaner
    Department of Chemistry , University of Warwick , Coventry , CV4 7AL , UK . Email: peter.scott@warwick.ac.uk.
  • Simon J Allison
    School of Applied Sciences , University of Huddersfield , Huddersfield , HD1 3DH , UK.
  • Alan D Faulkner
    Department of Chemistry , University of Warwick , Coventry , CV4 7AL , UK . Email: peter.scott@warwick.ac.uk.
  • Roger M Phillips
    School of Applied Sciences , University of Huddersfield , Huddersfield , HD1 3DH , UK.
  • David I Roper
    School of Life Sciences, University of Warwick, Gibbet Hill Road, Coventry, CV4 7AL, United Kingdom.
  • Samantha L Shepherd
    School of Applied Sciences , University of Huddersfield , Huddersfield , HD1 3DH , UK.
  • Daniel H Simpson
    Department of Chemistry , University of Warwick , Coventry , CV4 7AL , UK . Email: peter.scott@warwick.ac.uk.
  • Nicholas R Waterfield
    Warwick Medical School , University of Warwick , Coventry , CV4 7AL , UK.
  • Peter Scott
    Department of Chemistry , University of Warwick , Coventry , CV4 7AL , UK . Email: peter.scott@warwick.ac.uk.

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