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. Author manuscript; available in PMC: 2022 Jan 15.
Published in final edited form as: ACS Chem Biol. 2020 Dec 11;16(1):214–224. doi: 10.1021/acschembio.0c00900

Scheme 1. PcephPT cleavage releases PT.

Scheme 1.

As a prodrug that releases a metal-binding agent, PcephPT consists of a β-lactam core (red) that is recognized by β-lactamase enzymes and a masked leaving group (blue) that prevents metal binding by the prochelator form. When cleaved, PcephPT releases the antimicrobial pyrithione (PT, blue), a bidentate metal-binding compound that forms a lipophilic 2:1 complex with Cu2+.