Institute of Bioorganic & Medicinal Chemistry, Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China.
School of Pharmaceutical Sciences, Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Chongqing University, Chongqing, 401331, China.
Eur J Med Chem. 2024 Feb 5;265:116107. doi: 10.1016/j.ejmech.2023.116107. Epub 2023 Dec 30.
Unique benzopyridone cyanoacetates (BCs) as new type of promising broad-spectrum antibacterial candidates were discovered with large potential to combat the lethal multidrug-resistant bacterial infections. Many prepared BCs showed broad antibacterial spectrum with low MIC values against the tested strains. Some highly active BCs exhibited rapid sterilization capacity, low resistant trend and good predictive pharmacokinetic properties. Furthermore, the highly active sodium BCs (NaBCs) displayed low hemolysis and cytotoxicity, and especially octyl NaBC 5g also showed in vivo potent anti-infective potential and appreciable pharmacokinetic profiles. A series of preliminary mechanistic explorations indicated that these active BCs could effectively eliminate bacterial biofilm and destroy membrane integrity, thus resulting in the leakage of bacterial cytoplasm. Moreover, their unique structures might further bind to intracellular DNA, DNA gyrase and topoisomerase IV through various direct noncovalent interactions to hinder bacterial reproduction. Meanwhile, the active BCs also induced bacterial oxidative stress and metabolic disturbance, thereby accelerating bacterial apoptosis. These results provided a bright hope for benzopyridone cyanoacetates as potential novel multitargeting broad-spectrum antibacterial candidates to conquer drug resistance.
独特的苯并吡啶酮氰基乙酸酯 (BCs) 作为一种新型有前途的广谱抗菌候选药物被发现,具有对抗致命的多药耐药细菌感染的巨大潜力。许多制备的 BCs 对测试菌株表现出广谱抗菌活性,MIC 值较低。一些高活性的 BCs 表现出快速杀菌能力、低耐药趋势和良好的预测药代动力学特性。此外,高活性的钠 BCs (NaBCs) 表现出低溶血和细胞毒性,特别是辛基 NaBC 5g 也表现出体内有效的抗感染潜力和可接受的药代动力学特征。一系列初步的机制探索表明,这些活性 BCs 可以有效消除细菌生物膜并破坏膜完整性,从而导致细菌细胞质泄漏。此外,它们独特的结构可能通过各种直接非共价相互作用进一步与细胞内 DNA、DNA 回旋酶和拓扑异构酶 IV 结合,从而阻碍细菌繁殖。同时,活性 BCs 还诱导细菌氧化应激和代谢紊乱,从而加速细菌凋亡。这些结果为苯并吡啶酮氰基乙酸酯作为潜在的新型多靶标广谱抗菌候选药物克服耐药性提供了希望。