Recognition of the DNA minor groove by thiazotropsin analogues

Alniss, Hasan Y. and Salvia, Marie Virginie and Sadikov, Mykhailo and Golovchenko, Igor and Anthony, Nahoum G. and Khalaf, Abedawn I. and MacKay, Simon P. and Suckling, Colin J. and Parkinson, John A. (2014) Recognition of the DNA minor groove by thiazotropsin analogues. Chembiochem, 15 (13). 1978–1990. ISSN 1439-4227

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Abstract

Solution-phase self-association characteristics and DNA molecular recognition properties are reported for three close analogues of minor groove binding ligands from the thiazotropsin class of lexitropsin molecules, which incorporate isopropyl thiazole as a lipophilic building block. Thiazotropsin B (AcImPyiPrThDp) shows similar self-assembly characteristics to thiazotropsin A (FoPyPyiPrThDp) although being engineered, by incorporation of imidazole in place of N-methyl pyrrole, to swap its DNA recognition target from 5´-ACTAGT-3´ to 5´-ACGCGT-3´. Replacement of the formamide head-group in thiazotropsin A by nicotinamide in AIK-18/51 results in a measureable difference in solution phase self-assembly character and substantially enhanced DNA association characteristics. The structures and associated thermodynamic parameters of self-assembled ligand aggregates and their complexes with respective DNA targets are considered in the context of cluster targeting of DNA by minor groove complexes.