Improved synthesis of biotinol-5'-AMP: implications for antibacterial discovery

Date

2015

Authors

Tieu, W.
Polyak, S.
Paparella, A.
Yap, M.
Soares Da Costa, T.
Ng, B.
Wang, G.
Lumb, R.
Bell, J.
Turnidge, J.

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Journal article

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ACS Medicinal Chemistry Letters, 2015; 6(2):216-220

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William Tieu, Steven W. Polyak, Ashleigh S. Paparella, Min Y. Yap, Tatiana P. Soares da Costa, Belinda Ng, Geqing Wang, Richard Lumb, Jan M. Bell, John D. Turnidge, Matthew C. J. Wilce, Grant W. Booker, and Andrew D. Abell

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Abstract

An improved synthesis of biotinol-5'-AMP, an acyl-AMP mimic of the natural reaction intermediate of biotin protein ligase (BPL), is reported. This compound was shown to be a pan inhibitor of BPLs from a series of clinically important bacteria, particularly Staphylococcus aureus and Mycobacterium tuberculosis, and kinetic analysis revealed it to be competitive against the substrate biotin. Biotinol-5'-AMP also exhibits antibacterial activity against a panel of clinical isolates of S. aureus and M. tuberculosis with MIC values of 1-8 and 0.5-2.5 μg/mL, respectively, while being devoid of cytotoxicity to human HepG2 cells.

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Copyright © 2014 American Chemical Society

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