Mohammed Hashim K K, Manoj E
Department of Applied Chemistry, Cochin University of Science and Technology Kochi Kerala 682 022 India
RSC Adv. 2024 Apr 25;14(19):13654-13668. doi: 10.1039/d4ra00554f. eCollection 2024 Apr 22.
The emission features of a novel bioactive compound, 1,3-bis(2-hydroxy-3,5-diiodophenyl-methylideneamino)guanidine is found impressive with aggregation induced emission enhancement. The nitrogen and iodine rich multidentate proligand was characterized physicochemically. SCXRD and Hirshfeld surface investigation have revealed the presence of significant triangular iodine bonding apart from hydrogen bonding, weak C-H⋯π and π⋯π intermolecular interactions. These interactions collectively contribute to the solid-state packing arrangement of the molecules within the crystal lattice. The band gap of the compound was estimated experimentally and is supported with theoretical calculations. The solid-state fluorescence quantum yield of = 0.36 emphasizes the utility of the proligand and the AIEE characteristics is attributed to restricted intramolecular motions as indicated by fluorescence lifetime decay studies. Strong interaction of the compound with calf thymus DNA was explored experimentally and found to align with docking results. Notably, anticancer assessment on MCF-7 breast cancer cells show an IC value of 181.05 μg mL and signifying its potent cytotoxic properties. Also, the compound is found to have lesser cytotoxicity against L929 normal cell line with an IC value of 356.54 μg mL. Computational studies further underscore the exceptional binding affinity with active sites in the SARS-CoV-2 main protease 3CL, surpassing established repurposed drugs. Furthermore, the proligand demonstrates excellent putative affinity towards the SARS-CoV-2 spike glycoprotein, accompanied by its distinctive AIEE attributes, drug likeness and DNA binding capability rendering it a valuable tool for prospective research investigations.
一种新型生物活性化合物1,3-双(2-羟基-3,5-二碘苯基亚甲基氨基)胍的发射特性令人印象深刻，具有聚集诱导发射增强现象。对富含氮和碘的多齿前体配体进行了物理化学表征。单晶X射线衍射（SCXRD）和 Hirshfeld表面研究表明，除了氢键、弱C-H⋯π和π⋯π分子间相互作用外，还存在显著的三角碘键。这些相互作用共同促成了晶格内分子的固态堆积排列。通过实验估算了该化合物的带隙，并得到了理论计算的支持。固态荧光量子产率为0.36，强调了前体配体的实用性，荧光寿命衰减研究表明，聚集诱导发射增强（AIEE）特性归因于分子内运动受限。通过实验探索了该化合物与小牛胸腺DNA的强相互作用，发现与对接结果一致。值得注意的是，对MCF-7乳腺癌细胞的抗癌评估显示IC值为181.05 μg/mL，表明其具有强大的细胞毒性。此外，该化合物对L929正常细胞系的细胞毒性较小，IC值为356.54 μg/mL。计算研究进一步强调了其与严重急性呼吸综合征冠状病毒2（SARS-CoV-2）主要蛋白酶3CL活性位点的非凡结合亲和力，超过了已有的重新利用药物。此外，前体配体对SARS-CoV-2刺突糖蛋白表现出优异的假定亲和力，同时具有独特的AIEE属性、药物相似性和DNA结合能力，使其成为前瞻性研究调查的有价值工具。
