Degradation of the chemotherapy drug 5-fluorouracil on medical-grade silver surfaces

Abstract

The degradation of the chemotherapy drug 5-Fluorouracil by a non-pristine metal surfaces is studied. Using Density Functional Theory, X-ray Photoelectron Spectroscopy and X-ray Absorption Spectroscopy we show that the drug is entirely degraded by medical-grade silver surfaces, already at body temperature, and that all of the fluorine has left the molecule, presumably as HF. Remarkably, this degradation is even more severe than that reported previously for 5-Fluorouracil on a pristine monocrystalline silver surface (in which case 80% of the drug reacted at body temperature) Mazzola et al. (2015). We conclude that the observed reaction is due to a reaction pathway, driven by H to F attraction between molecules on the surface, which results in the direct formation of HF; a pathway which is favoured when competing pathways involving reactive Ag surface sites are made unavailable by environmental contamination. Our measurements indicate that realistically cleaned, non-pristine silver alloys, which are typically used in medical applications, can result in severe degradation of 5-Fluorouracil, with the release of HF – a finding which may have important implications for the handling of chemotherapy drugs.