Pyrithione

Pyrithione (CAS: 1121-30-8) is a transition metal-chelating agent and lipophilic metal ionophore that contains adjacent sulfur and oxygen donor atoms forming a bidentate metal-binding motif. This coordination site enables pyrithione to chelate a variety of divalent metal ions, including Cu²⁺ and Zn²⁺, forming electrically neutral, lipophilic complexes that readily cross biological membranes. Delivery of copper into cells and mitochondria increases the intracellular pool of bioavailable copper and can induce cuproptosis under conditions of copper overload. In contrast, transport of zinc elevates intracellular Zn²⁺ levels and may trigger zinc-mediated cell death or other zinc-dependent cellular responses. Its ability to alter intracellular metal homeostasis has also made it a useful chemical tool for investigating metal transport, metal toxicity, and metal-dependent signaling pathways.

In addition to its metal ionophore activity, pyrithione exhibits potent antibacterial and antifungal properties and has been widely used in biological research and pharmaceutical formulations.

References:

1. Ohji M, Harino H. Comparison of Toxicities of Metal Pyrithiones Including Their Degradation Compounds and Organotin Antifouling Biocides to the Japanese Killifish Oryzias latipes. Arch Environ Contam Toxicol. 2017 Aug;73(2):285-293. doi: 10.1007/s00244-017-0367-z. Epub 2017 May 20. PMID: 28528410.