Journal of Molecular and Pharmaceutical Sciences
Volume 3, Numéro 2, Pages 1-10
2025-04-10

Cu (ii), Fe (ii)-adriamycin Semiquinone Complexes : Computational Investigation And Organometallic Synthesis.



Authors : Kadri Rayene . Bouchekioua Saad . Hasni Nour . Kadri Mekki .

Abstract

Adriamycin semiquinone (ADRS) is an anticancer agent that has been successfully used in chemotherapy since 1963. However, this molecule exhibits a cardiotoxicity as a side effect, which is caused by the radical reactions in which the ADRS molecule is involved. It has also been reported that the presence of Fe (II) and Cu (II) ions catalyses the reaction of ADRS with free radicals. This finding prompted researchers to investigate the role of these ions in radical reactions and their interaction with ADRS. The goal of the current work is to perform a spectroscopic and thermodynamic study of Fe (II) and Cu (II) – ADRS interactions. Distribution diagrams illustrating various chemical species were constructed, followed by the calculation of stability constants for both 1:1 and 1:2 complexes, along with the associated thermodynamic parameters. Solid-state complexes were synthesized in a methanol solution utilizing ultrasonic conditions at a frequency of 20 kHz, and these complexes were subsequently characterized. Additionally, the interactions between ions and ADRS were explored through molecular modelling studies employing DFT/B3LYP-6.311++G(d,p) and DFT/B3LYP-6.311++G(d,p) with Empirical Dispersion=GD3BJ, which incorporates Grimme dispersion effects. The results obtained from these studies were analysed and compared in terms of bond lengths, angles, and dihedral angles. Furthermore, the theoretical FTIR spectra derived from DFT calculations and the UV-vis spectra obtained through time-dependent DFT (TD-DFT) exhibited a strong correlation with the experimental data. The use of Time-Dependent Density Functional Theory (TD-DFT) facilitated the characterization of the properties of frontier orbitals, specifically the Highest Occupied Molecular Orbital (HOMO) and the Lowest Unoccupied Molecular Orbital (LUMO). This approach enabled the calculation of various electronic properties, including the energy gap, hardness, and electrophilicity, among others. Additionally, Natural Bond Orbital (NBO) analysis was performed to clarify the intermolecular interactions occurring between ADRS molecules and metallic ions.

Keywords

Adriamycin semiquinone ; organometallic complexes ; DFT ; TD-DFT ; NBO analysis ; QTAIM analysis

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