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Design, synthesis and antibacterial activity of minor groove binders: the role of non-cationic tail groups

Khalaf, Abedawn I., Bourdin, Claire, Breen, David, Donoghue, Gavin, Scott, Fraser J., Suckling, Colin J., MacMillan, Donna, Clements, Carol, Fox, Keith and Sekibo, Doreen A.T. (2012) Design, synthesis and antibacterial activity of minor groove binders: the role of non-cationic tail groups European Journal of Medicinal Chemistry, 56, pp. 39-47. (doi:10.1016/j.ejmech.2012.08.013).

Record type: Article


The design and synthesis of a new class of minorgroove binder (MGBs) in which, the cationictailgroup has been replaced by a neutral, polar variant including cyanoguanidine, nitroalkene, and trifluoroacetamide groups. Antibacterialactivity (against Gram positive bacteria) was found for both the nitroalkene and trifluoroacetamide groups. For the case of the nitroalkene tailgroup, strong binding of a minorgroove binder containing this tailgroup was demonstrated by both DNA footprinting and melting temperature measurements, showing a correlation between DNA binding and antibacterialactivity. The compounds have also been evaluated for binding to the hERG ion channel to determine whether non-cationic but polar substituents might have an advantage compared with conventional cationictailgroups in avoiding hERG binding. In this series of compounds, it was found that whilst non-cationic compounds generally had lower affinity to the hERG ion channel, all of the compounds studied bound weakly to the hERG ion channel, probably associated with the hydrophobic head groups

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Published date: October 2012
Organisations: Molecular and Cellular


Local EPrints ID: 345237
ISSN: 0223-5234
PURE UUID: a35bd8d0-0ebf-4cba-8c41-609885097658
ORCID for Keith Fox: ORCID iD

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Date deposited: 14 Nov 2012 11:51
Last modified: 18 Jul 2017 05:11

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Author: Abedawn I. Khalaf
Author: Claire Bourdin
Author: David Breen
Author: Gavin Donoghue
Author: Fraser J. Scott
Author: Colin J. Suckling
Author: Donna MacMillan
Author: Carol Clements
Author: Keith Fox ORCID iD
Author: Doreen A.T. Sekibo

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