Poster Presentation 11th Annual Conference of the International Chemical Biology Society 2022

Development of a Novel Chemotype of Formyl Peptide Receptors Biased Agonists for the Preventing Myocardial Reperfusion Injury   (#176)

Xiangyan Yi 1 , Jephthah Odiba 1 , Mia De Seram 2 , Elizabeth Vecchio 3 , Chengxue Qin 3 , Rebecca Ritchie 3 , Jonathan Baell 1
  1. Medicinal chemistry, Faculty of Pharmacy and Pharmaceutical Sciences, Monash University (Parkville Campus), Melbourne, VIC, Australia
  2. Heart Failure Pharmacology Group, Monash Institute of Pharmaceutical Sciences , Monash University (Parkville Campus), Melbourne, VIC, Australia
  3. Drug Discovery Biology, Monash Institute of Pharmaceutical Sciences , Monash University (Parkville Campus), Melbourne, VIC, Australia

Cardiovascular diseases (CVDs), especially myocardial infarction (MI) and stroke, are prevalent diseases leading to high mortality worldwide. Reperfusion therapy as the current standard of care is able to efficiently restore blood into jeopardized myocardium. The earlier this is applied, the more that myocardium is rescued. Nevertheless, oxidative damage and a subsequent inflammatory response occurs later during the treatment of MI with reperfusion therapy. Such reperfusion injury is thought to contribute to up to 50% of the final infarct size, and is a major driver of arrhythmia, as well as impaired contractile function and heart failure. Despite the improvements in rapid triage of patients, and technical advances in reperfusion, there is a major unmet clinical need for treatments to protect against ischaemia-reperfusion (IR) injury. Previous research has demonstrated that subtype-selective or dual formyl peptide receptor (FPR1/2) agonism may represent a novel therapeutic strategy for attenuating IR injury. However, activation alone is insufficient and it has been recently shown that activation of cardioprotective signalling of extracellular signal-regulated kinases (ERK1/2) phosphorylation with a bias away from the detrimental calcium mobilisation is critical to achieve the net cardioprotective effect. Hence, two broad series of compounds were designed and synthesised, followed by the testing for agonism and bias profile at FPR1 and FPR2 in FPR1/2-expressing CHO cells. One series of compounds was broadly derived from literature-reported substituted benzimidazoles, while the other series was broadly derived from published pyrazinone anilides. One of these compounds, which was hybridised from substituted benzimidazoles and anilides, exhibits an improved potency of FPR1 than its prototype in cell-based assays. The SAR emerging from this project is setting clear synthetic targets going forward. Further modelling studies revealed new insights for subtype selectivity and receptor activation mechanisms. These experiments are allowing us to build up a library of biased FPR1/2 agonists and understand the cardioprotective mechanisms of biased FPR1/2 agonists, which will facilitate the development of FPR-biased strategies for improving outcomes after MI.

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