27th International symposium: Synthesis in organic chemistry

Synthesis, characterization, and investigation of the role of antibiotic metabolites in the development of bacterial AMR Mairéad Gallagher, Gordon Cooke, and Fintan Kelleher TU Dublin Tallaght, Ireland Bacterial antimicrobial resistance (AMR), also known as antibiotic resistance, occurs when bacteria develop the ability to resist or combat previously effective antibiotic treatments. 1 Ciprofloxacin ( 1 ) and amoxicillin ( 2 ) are commonly prescribed antibiotics belonging to the fluoroquinolone (FQ) and β-lactam classes, respectively. Both antibiotics are included in the World Health Organization’s list of essential medicines. 2 Although the human metabolites of these antibiotics are available commercially, they are costly for very small quantities.

Figure 1: Structure of 1 and 2 with main areas of human metabolism highlighed We have adapted and improved existing literature methodologies to obtain these compounds. We have successfully synthesized and characterized a number of the human metabolites of 1 and 2 , in quantities sufficient for biological studies. Notably, we employed microwave assisted synthesis (MAS) to obtain two of the ciprofloxacin metabolites, which has not been reported previously for these compounds. Thus far, we have conducted microbiological studies with the ESKAPE pathogen Pseudomonas aeruginosa ; the results of these studies will be presented. References 1. World Health Organization. Antibiotic Resistance . World Health Organization. https://www.who.int/news-room/fact-sheets/ detail/antibiotic-resistance WHO model list of essential medicines - 22nd list, 2021 . www.who.int. https://www.who.int/ publications/i/item/WHO-MHP-HPS-EML-2021.02

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© The Author(s), 2023

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