School of Computing, Engineering and Physical Sciences, University of the West of Scotland, PA12BE Paisley, UK.
Drug Discovery Unit, Wellcome Centre for Anti-infective Research, University of Dundee, Dow Street, Dundee DD1 5EH, UK.
Bioorg Chem. 2021 Oct;115:105215. doi: 10.1016/j.bioorg.2021.105215. Epub 2021 Jul 29.
Global health concern regarding malaria has increased since the first report of artemisinin-resistant Plasmodium falciparum (Pf) two decades ago. The current therapies suffer various drawbacks such as low efficacy and significant side effects, alarming for an urgent need of more effective and less toxic drugs with higher patient compliance. Chemical entities with natural origins become progressively attractive as new drug leads due to their structural diversity and bio-compatibility. This study initially aimed at the targeted isolation of hydroxyquinoline derivatives following our published genomics and metabolomics study of Pantoea agglomerans (Pa). Fermentation of Pa on a pre-selected medium followed by chromatographic isolation, NMR and HRMS analyses led to the characterisation of one new hydroxyquinoline alkaloid together with another six known congeners and two known hydroxyquinolone derivatives. When screened for their antimalarial activity by high throughput screening against asexual blood-stage parasites, almost all compounds showed potent and selective sub-micromolar activities. Computational investigation was performed to identify the antiplasmodial potential targets. Ligand-based similarity search predicted the tested compounds to act as hemozoin inhibitors. Computational target identification results were further validated by competitive hemozoin inhibitory properties of hydroxyquinoline and hydroxyquinolone derivatives in vitro. The overall results suggest this natural scaffold is of potential to be developed as antimalarial drug lead.
自二十年前首次报告青蒿素耐药疟原虫(Pf)以来,全球对疟疾的健康关注日益增加。目前的治疗方法存在各种缺点,如疗效低和副作用大,这令人警惕地需要更有效和毒性更低的药物,同时需要更高的患者依从性。具有天然来源的化学实体由于其结构多样性和生物相容性,成为新药物先导的吸引力越来越大。本研究最初旨在根据我们之前对聚生泛菌(Pa)的基因组学和代谢组学研究,进行羟基喹啉衍生物的靶向分离。Pa 在预先选择的培养基上发酵,然后通过色谱分离、NMR 和 HRMS 分析,鉴定出一种新的羟基喹啉生物碱,以及另外六种已知的同系物和两种已知的羟基喹啉衍生物。当通过高通量筛选针对无性血期寄生虫进行抗疟活性筛选时,几乎所有化合物都表现出强大而选择性的亚微米级活性。进行了计算研究以确定抗疟原虫的潜在靶标。基于配体的相似性搜索预测,测试化合物将作为亚铁血红素抑制剂发挥作用。计算靶标鉴定结果进一步通过羟基喹啉和羟基喹啉衍生物在体外的竞争性亚铁血红素抑制特性得到验证。总体结果表明,这种天然支架具有作为抗疟药物先导的潜力。