Molecular simulation and ADMET analysis of fucoidan derivatives against dengue virus: identification of 3,4-diphospho fucoidan as a promising lead compound

分子模拟和ADMET分析岩藻聚糖衍生物对抗登革病毒的活性:鉴定出3,4-二磷酸岩藻聚糖是一种有前景的先导化合物

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Abstract

Dengue fever, transmitted through mosquito vectors, has emerged as a significant health challenge in India over the past twenty years. This infectious epidemic has demonstrated concerning fatality rates and mortality statistics. The primary objective of this investigation was to conduct molecular simulation studies and evaluate the drug-like properties of marine seaweed fucoidan and five synthetic derivatives against dengue virus (DENV) non-structural proteins. The parent fucoidan compound, along with its acetyl, amino, sulfonyl, phosphate, and benzoyl derivatives, underwent molecular docking analysis against DENV4 NS3 Protease-Helicase (2VBC), DENV2 NS2B/NS3 Protease (2FOM), DENV2 Methyltransferase (1L9K), DENV2 Non-Structural protein NS5 (5ZQK), and DENV2 RNA-dependent RNA polymerase (6IZY). The selected non-structural proteins were analyzed through CDOCKER docking methodology, concentrating on binding sites, with binding energies calculated to assess fucoidan derivative effectiveness. The parent fucoidan, acetylated fucoidan, phosphated fucoidan, and benzoylated fucoidan demonstrated the strongest inhibitory potential against all DENV viral proteins, exhibiting binding affinities of - 13 kcal.mol(-1), - 48 kcal.mol(-1), and 43 kcal.mol(-1), respectively. Pharmacokinetic properties and toxicological profiles were evaluated for all fucoidan compounds using the PreADMET web server simulation software. The comprehensive ligand-binding affinity range for fucoidan and its derivatives spanned from - 146 to - 13 kcal.mol(-1). ADMET analysis confirmed that the parent fucoidan and its acetylated, phosphated, and benzoylated derivatives exhibited non-toxic characteristics with favorable lipophilicity profiles. Molecular dynamics simulation analysis through RMSD and RMSF plots, focusing on the optimized 3,4-diphospho fucoidan, revealed hydrogen bonding patterns and substantial hydrophobic interactions with DENV proteins at allosteric binding sites. In summary, this study establishes that 3,4-diphospho fucoidan represents the most promising lead compound with potential anti-dengue properties among all tested derivatives. Therefore, this molecule warrants additional investigation through in vitro experimental studies.

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