Crystal structure and polymorphic forms of auranofin revisited

Ziemniak, Marcin; Trzybiński, Damian; Pawlędzio, Sylwia; Filipowicz, Gabriela; Pająk-Tarnacka, Beata; Priebe, Waldemar; Woźniak, Krzysztof

doi:10.1039/D5RA00196J

Crystal structure and polymorphic forms of auranofin revisited

Journal Article · Thu Apr 03 00:00:00 EDT 2025 · RSC Advances

DOI:https://doi.org/10.1039/D5RA00196J· OSTI ID:2573287

^[1]; ^[1]; ^[2]; Filipowicz, Gabriela ^[3]; ^[4]; Priebe, Waldemar ^[5]; ^[1]

Univ. of Warsaw (Poland)
Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)
Univ. of Chicago, IL (United States)
Univ. of Warsaw (Poland); WPD Pharmaceuticals Inc, Warsaw (Poland)
Univ. of Texas, Houston, TX (United States)

Auranofin, initially developed as a treatment for rheumatoid arthritis, is currently under extensive investigation as a potential drug for various conditions, including cancer, bacterial infections, and parasitic infections. The compound is a known inhibitor of thioredoxin reductase (TXNRD1) and related selenoproteins. Although preliminary studies on the auranofin crystal polymorphism exist, and a low-quality crystal structure has been reported, a comprehensive crystallographic characterization remains unexplored. Utilizing X-ray crystallography techniques, we conducted detailed structural analysis of auranofin and compared our findings with related organogold compounds. Implementation of Hirshfeld atom refinement (HAR) enabled a more accurate hydrogen atom positioning in the structure. The crystal packing reveals a layered arrangement stabilised by numerous weak hydrogen bonds and dispersive interactions. Notably, our attempts to reproduce the previously reported polymorphic form of auranofin, purportedly more water-soluble, were unsuccessful despite following published protocols. To our knowledge, this is the first study describing a “disappearing polymorph” phenomenon of any pharmaceutically relevant transition metal coordination compound. Our findings may have significant implications for medicinal chemistry and pharmacology of coordination complexes, suggesting the need for systematic revision of historical crystallographic data in this field.

View Accepted Manuscript (DOE)

Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 2573287

Journal Information:: RSC Advances, Journal Name: RSC Advances Journal Issue: 13 Vol. 15; ISSN 2046-2069

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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