Truncated S-MGBs: towards a parasite-specific and low aggregation chemotype

Brooke, D. P. et al. (2021) Truncated S-MGBs: towards a parasite-specific and low aggregation chemotype. RSC Medicinal Chemistry, 12(8), pp. 1391-1401. (doi: 10.1039/D1MD00110H)

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This paper describes the design and synthesis of Strathclyde minor groove binders (S-MGBs) that have been truncated by the removal of a pyrrole ring in order to mimic the structure of the natural product, disgocidine. S-MGBs have been found to be active against many different organisms, however, selective antiparasitic activity is required. A panel of seven truncated S-MGBs was prepared and the activities examined against a number of clinically relevant organisms including several bacteria and parasites. The effect of the truncation strategy on S-MGB aggregation in aqueous environment was also investigated using 1H inspection and DOSY experiments. A lead compound, a truncated S-MGB, which possesses significant activity only against trypanosomes and Leishmania has been identified for further study and was also found to be less affected by aggregation compared to its full-length analogue.

Item Type:Articles
Additional Information:This research is part funded by the MSD Scottish Life Sciences Fund. Funding was also provided by BBSRC grant BB/N007638/1 and the Carnegie Trust for the Universities of Scotland Ref-70260.
Glasgow Author(s) Enlighten ID:Giordani, Dr Federica and Barrett, Professor Michael
Authors: Brooke, D. P., McGee, L. M. C., Giordani, F., Cross, J. M., Khalaf, A. I., Irving, C., Gillingwater, K., Shaw, C. D., Carter, K. C., Barrett, M. P., Suckling, C. J., and Scott, F. J.
College/School:College of Medical Veterinary and Life Sciences > School of Infection & Immunity
Journal Name:RSC Medicinal Chemistry
Publisher:Royal Society of Chemistry (RSC)
ISSN (Online):2632-8682
Published Online:06 July 2021
Copyright Holders:Copyright © 2021 The Royal Society of Chemistry
First Published:First published in RSC Medicinal Chemistry 12(8): 1391-1401
Publisher Policy:Reproduced under a Creative Commons License
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