De Luca Laura, Barreca Maria Letizia, Ferro Stefania, Christ Frauke, Iraci Nunzio, Gitto Rosaria, Monforte Anna Maria, Debyser Zeger, Chimirri Alba
Department of Medicinal Chemistry, University of Messina, Viale Annunziata, 98168 Messina, Italy.
ChemMedChem. 2009 Aug;4(8):1311-6. doi: 10.1002/cmdc.200900070.
The cellular protein lens epithelium-derived growth factor, or transcriptional coactivator p75 (LEDGF/p75), plays a crucial role in HIV integration. The protein-protein interactions (PPIs) between HIV-1 integrase (IN) and its cellular cofactor LEDGF/p75 may therefore serve as targets for the development of new anti-HIV drugs. In this work, a structure-based pharmacophore model for potential small-molecule inhibitors of HIV-1 IN-LEDGF/p75 interaction was developed using the LigandScout software. The 3D model obtained was used for virtual screening of our in-house chemical database, CHIME, leading to the identification of compound CHIBA-3002 as an interesting hit for further optimization. The rational design, synthesis and biological evaluation of four derivatives were then carried out. Our studies resulted in the discovery of a new and more potent small molecule (7, CHIBA-3003) that is able to interfere with the HIV-1 IN-LEDGF/p75 interaction at micromolar concentration, representing one of the first compounds to show activity against these specific PPIs. Docking simulations were subsequently performed in order to investigate the possible binding mode of our new lead compound to HIV-1 IN. This study is a valid starting point for the identification of anti-HIV agents with a different mechanism of action from currently available antiviral drugs.
细胞蛋白晶状体上皮衍生生长因子,即转录共激活因子p75(LEDGF/p75),在HIV整合过程中发挥着关键作用。因此,HIV-1整合酶(IN)与其细胞辅因子LEDGF/p75之间的蛋白质-蛋白质相互作用(PPI)可能成为开发新型抗HIV药物的靶点。在这项研究中,使用LigandScout软件构建了一个基于结构的药效团模型,用于筛选潜在的HIV-1 IN-LEDGF/p75相互作用小分子抑制剂。所得的三维模型用于对我们的内部化学数据库CHIME进行虚拟筛选,从而确定化合物CHIBA-3002为值得进一步优化的有价值命中物。随后对四种衍生物进行了合理设计、合成及生物学评价。我们的研究发现了一种新型且更有效的小分子(7,CHIBA-3003),它能够在微摩尔浓度下干扰HIV-1 IN-LEDGF/p75相互作用,是首批显示出针对这些特定PPI具有活性的化合物之一。随后进行了对接模拟,以研究我们新的先导化合物与HIV-1 IN可能的结合模式。这项研究是识别具有与现有抗病毒药物不同作用机制的抗HIV药物的有效起点。