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<p>This study presents a multi-faceted investigation into the structural, electronic, and therapeutic profiles of the crown and chair conformers of CPRA, 2HPRA, 3HPRA, and 4HPRA macrocycles. A dispersion corrected standard density functional theory (DFT/B3LYP-D3) calculations were utilized for geometric optimization, Mulliken atomic charge analysis, and to evaluate conformational stability based on relative energy values. Frontier Molecular Orbital (FMO) analysis, global reactivity descriptors, and dipole moments reveal that the crown conformers exhibit significantly elevated chemical reactivity compared to their chair counterparts. Thermodynamic assessments further delineate the reaction pathways, confirming the kinetic and thermodynamic stability of the products. These theoretical insights are corroborated by topological mapping include Molecular Electrostatic Potential (MESP), Electron Localization Function (ELF), and Localization of Electron Density (LOL) analyses which map the reactive sites, electron distribution, and intramolecular hydrogen bonding networks. Experimentally, the macrocycles were rapidly synthesized within 30–60&#xa0;min, and their crown-chair conformations were confirmed via <sup>1</sup>H-NMR and <sup>13</sup>C-NMR spectroscopy. UV-Visible and fluorescence analyses indicate that phenyl and hydroxyphenyl substitutions on the methine bridges pivotally modulate charge-transfer and proton-transfer transitions, yielding distinct photophysical properties and Stokes shift values. Biologically, blind molecular docking (CB-Dock2) underscores the medicinal potential of these macrocycles, demonstrating high binding affinity and specific interactions with the p53 cellular tumor antigen. Furthermore, phosphomolybdate and Kirby-Bauer assays reveal potent antioxidant and antibacterial activities against both Gram-positive and Gram-negative bacteria. Collectively, these computational and experimental findings position these macrocycles as promising candidates for novel anticancer and antibacterial drug development, as well as high-sensitivity molecular probes for advanced photophysical sensing.</p>

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Computational Density Functional Theory and Kinetic-Thermodynamic Stable Crown-Chair Conformers of Hydroxyphenyl Calix[4]resorcinarene Macrocycles: Molecular Docking, Antioxidant, Antibacterial and Photophysical Applications

  • 期刊论文

  • 发表日期：

    2026年7月31日

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  • Kasi Sathiyaseelan,
  • Albert Antony Muthu Prabhu

摘要

This study presents a multi-faceted investigation into the structural, electronic, and therapeutic profiles of the crown and chair conformers of CPRA, 2HPRA, 3HPRA, and 4HPRA macrocycles. A dispersion corrected standard density functional theory (DFT/B3LYP-D3) calculations were utilized for geometric optimization, Mulliken atomic charge analysis, and to evaluate conformational stability based on relative energy values. Frontier Molecular Orbital (FMO) analysis, global reactivity descriptors, and dipole moments reveal that the crown conformers exhibit significantly elevated chemical reactivity compared to their chair counterparts. Thermodynamic assessments further delineate the reaction pathways, confirming the kinetic and thermodynamic stability of the products. These theoretical insights are corroborated by topological mapping include Molecular Electrostatic Potential (MESP), Electron Localization Function (ELF), and Localization of Electron Density (LOL) analyses which map the reactive sites, electron distribution, and intramolecular hydrogen bonding networks. Experimentally, the macrocycles were rapidly synthesized within 30–60 min, and their crown-chair conformations were confirmed via 1H-NMR and 13C-NMR spectroscopy. UV-Visible and fluorescence analyses indicate that phenyl and hydroxyphenyl substitutions on the methine bridges pivotally modulate charge-transfer and proton-transfer transitions, yielding distinct photophysical properties and Stokes shift values. Biologically, blind molecular docking (CB-Dock2) underscores the medicinal potential of these macrocycles, demonstrating high binding affinity and specific interactions with the p53 cellular tumor antigen. Furthermore, phosphomolybdate and Kirby-Bauer assays reveal potent antioxidant and antibacterial activities against both Gram-positive and Gram-negative bacteria. Collectively, these computational and experimental findings position these macrocycles as promising candidates for novel anticancer and antibacterial drug development, as well as high-sensitivity molecular probes for advanced photophysical sensing.