School of Science, STEM College, Engineering and Health, RMIT University, GPO Box 2476, Melbourne, VIC, 3001, Australia.
Combi-Chem Bio-Resource Centre, Organic Chemistry Division, CSIR-National Chemical Laboratory, Pune, Maharashtra, 411 008, India.
Mol Divers. 2022 Oct;26(5):2535-2548. doi: 10.1007/s11030-021-10351-y. Epub 2021 Nov 25.
Herein, we identified a potent lead compound RRA2, within a series of 54 derivatives of 1,2,4-triazolethiols (exhibit good potency as an anti-mycobacterial agents) against intracellular Mycobacterium tuberculosis (Mtb). Compound RRA2 showed significant mycobactericidal activity against active stage Mycobacterium bovis BCG and Mtb with minimum inhibitory concentration (MIC) values of 2.3 and 2.0 µg/mL, respectively. At MIC value, RRA2 compound yielded 0.82 log reduction of colony-forming unit (cfu) against non-replicating Mtb. Furthermore, RRA2 compound was selected for further target identification due to the presence of alkyne group, showing higher selectivity index (> 66.66 ± 0.22, in non-replicating stage). Using "click" chemistry, we synthesized the biotin linker-RRA2 conjugate, purified with HPLC method and confirmed the conjugation of biotin linker-RRA2 complex by HR-MS analysis. Furthermore, we successfully pulled down and identified a specific target protein GroEl2, from Mtb whole-cell extract. Furthermore, computational molecular modeling indicated RRA2 could interact with GroEl2, which explains the structure-activity relationship observed in this study. GroEL-2 identified a potent and specific target protein for RRA 2 compound in whole cell extract of Mtb H37Ra.
在此,我们在一系列 54 个 1,2,4-三唑硫醇衍生物中鉴定出一种有效的先导化合物 RRA2(对细胞内结核分枝杆菌(Mtb)具有良好的抗菌活性)。化合物 RRA2 对处于活跃期的牛分枝杆菌 BCG 和 Mtb 具有显著的杀菌活性,最低抑菌浓度(MIC)值分别为 2.3 和 2.0μg/mL。在 MIC 值时,RRA2 化合物对非复制 Mtb 的菌落形成单位(cfu)减少了 0.82 对数。此外,由于存在炔基,RRA2 化合物显示出更高的选择性指数(>66.66±0.22,在非复制阶段),因此被选为进一步的靶标鉴定。我们使用“点击”化学合成了生物素连接物-RRA2 缀合物,通过 HPLC 方法进行纯化,并通过 HR-MS 分析确认了生物素连接物-RRA2 复合物的缀合。此外,我们成功地从 Mtb 全细胞提取物中拉下并鉴定出一种特定的靶蛋白 GroEl2。此外,计算分子建模表明 RRA2 可以与 GroEl2 相互作用,这解释了本研究中观察到的结构-活性关系。GroEL-2 在 Mtb H37Ra 的全细胞提取物中鉴定出 RRA2 化合物的一种潜在和特异性靶蛋白。