Organometallic nucleoside analogues: effect of hydroxylalkyl linker length on cancer cell line toxicity

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Colleges, School and Institutes


A new series of chiral ferrocene derivatives containing both a hydroxyalkyl group and a thyminyl group on one cyclopentadienyl ring have been synthesised in order to probe structure activity relationships in cancer cell-line cytotoxicities. Stereoisomers of enantiomeric pairs of these so-called ferronucleosides have been studied and characterised by a combination of chiral analytical HPLC and single crystal X-Ray diffraction. Biological activity studies reveal that changing the length of the hydroxyalkyl group had marked effects on IC50 values, with compounds having shorter arms that more closely resemble endogenous nucleosides exhibiting lower cytotoxicities. Lipophilicities and electrochemical properties of this compound series have been studied in order to rationalise these trends and indicate future directions of study.


Original languageEnglish
Pages (from-to)466-476
Number of pages11
JournalEuropean Journal of Inorganic Chemistry
Issue number2
Early online date17 Oct 2016
Publication statusPublished - 10 Jan 2017