Design and synthesis of a series of truncated neplanocin fleximers

Zimmermann, S. C., O'Neill, E., Ebiloma, G. U., Wallace, L. J.M., De Koning, H. P. and Seley-Radtke, K. L. (2014) Design and synthesis of a series of truncated neplanocin fleximers. Molecules, 19(12), pp. 21200-21214. (doi:10.3390/molecules191221200)

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Abstract

In an effort to study the effects of flexibility on enzyme recognition and activity, we have developed several different series of flexible nucleoside analogues in which the purine base is split into its respective imidazole and pyrimidine components. The focus of this particular study was to synthesize the truncated neplanocin A fleximers to investigate their potential anti-protozoan activities by inhibition of S-adenosylhomocysteine hydrolase (SAHase). The three fleximers tested displayed poor anti-trypanocidal activities, with EC50 values around 200 μM. Further studies of the corresponding ribose fleximers, most closely related to the natural nucleoside substrates, revealed low affinity for the known T. brucei nucleoside transporters P1 and P2, which may be the reason for the lack of trypanocidal activity observed.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:De Koning, Professor Harry and Wallace, Dr Lynsey
Authors: Zimmermann, S. C., O'Neill, E., Ebiloma, G. U., Wallace, L. J.M., De Koning, H. P., and Seley-Radtke, K. L.
College/School:College of Medical Veterinary and Life Sciences > Institute of Infection Immunity and Inflammation
Journal Name:Molecules
Publisher:MDPI AG
ISSN:1420-3049
ISSN (Online):1420-3049
Copyright Holders:Copyright © 2014 The Authors
First Published:First published in 19(12):21200-21214
Publisher Policy:Reproduced under a Creative Commons License
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