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Cytotoxicity evaluation and DNA binding studies of 1,3-dihydroxy-2-(4-methoxyphenyl)-4,5-dimethyl-1H-imidazol-3-ium chloride beyond its structural and Hirshfeld surface analysis, spectroscopic investigations, vibrational assignments and theoretical characterizations Mukhia, Munna Tamang, Sumiran Chakraborty, Koushik Habib, Imran Singha, Koustav Dey, Sangita Kumar, Anoop Brahman, Dhiraj Hossain, Mossaraf Pradhan, Kiran DFT Cytotoxicity DNA binding Crystal structure Hirshfeld surface analysis 1,3-Dihydroxy imidazolium chloride 1,3-Dihydroxy-2-(4-methoxyphenyl)-4,5-dimethyl-1H-imidazol-3-ium chloride (DMPDI) was synthesized via a solvent-free protocol and characterized. Crystallographic analyzes reveal that the crystal cation, as a result of steric hindrance, is not planar; the imidazole ring system has a dihedral angle of 44.62° with the plane of the anisole group. The molecule was also optimized using the density functional theory formalism, with the B3LYP functional and 6-31G+(d,2p) basis set. The computationally simulated IR, Raman, and NMR spectra were compared with the corresponding experimental data and detailed frequency assignments were performed. Additionally, frontier molecular orbitals (FMO), molecular electrostatic potential (MEP), and nonlinear optical (NLO) properties were calculated using density functional theory (DFT) methods. Evaluation of the antiproliferative activity of the compound revealed potent anticancer activity with IC50 values of 458.6 µM (124.18 µg/mL) and 645.7 µM (174.78 µg/mL) performed in vitro with A-549 lung cancer and SKOV-3 ovarian cancer cell lines, respectively. The compound was found to be less toxic to the normal hepatic cell line (WRL-68). The selectivity index (SI) of the compound was calculated and found to be 2.5 and 1.8 for A-549 and SKOV3, respectively. Molecular docking studies with human Topoisomerase I (PDB ID: 1RRJ) were carried out to assess binding affinity and investigate the possible mechanism behind the observed anticancer effect. Preliminary binding studies with calf thymus DNA (CT-DNA) by absorption titration and displacement studies with ethidium bromide revealed that DMPDI effectively binds via groove binding. For the theoretical investigation of DNA binding interactions, docking studies of DMPDI with B-DNA dodecamer (PDB ID: 1BNA) were carried out to validate the experimental results. Atlanta Publishing House LLC 2026-03-31 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion application/pdf text/plain application/pdf https://www.eurjchem.com/index.php/eurjchem/article/view/2726 10.5155/eurjchem.17.1.40-61.2726 European Journal of Chemistry; Vol. 17 No. 1 (2026): March 2026; 40-61 2153-2257 2153-2249 eng https://www.eurjchem.com/index.php/eurjchem/article/view/2726/2997 https://www.eurjchem.com/index.php/eurjchem/article/view/2726/2998 https://www.eurjchem.com/index.php/eurjchem/article/view/2726/2999 Copyright (c) 2026 Munna Mukhia, Sumiran Tamang, Koushik Chakraborty, Imran Habib, Koustav Singha, Sangita Dey, Anoop Kumar, Dhiraj Brahman, Mossaraf Hossain, Kiran Pradhan https://creativecommons.org/licenses/by-nc/4.0