Synthesis, Physicochemical Characterization, Biological Assessment, and Molecular Docking Study of Some Metal Complexes of Alloxan and Ninhydrin as Alterdentate Ligands

A series of transition metal complexes of alloxan monohydrate (H 2 L 1 ) and ninhydrin (H 2 L 2 ) have been prepared where metal ions are Fe(III), Co(II), Ni(II), Cu(II), Zr(IV), and Mo(VI). Different microanalytical techniques, spectroscopic methods, and magnetic studies were applied to assign the...

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Published in:Journal of inorganic and organometallic polymers and materials 2023-08, Vol.33 (8), p.2252-2269
Main Authors: Masoud, Mamdouh S., Yacout, Galila A., Abd-El-Khalek, Bassant A., Ramadan, Ahmed M.
Format: Article
Language:English
Subjects:
Alloxan
Anticancer properties
Carbonyls
Chemical synthesis
Chemistry
Chemistry and Materials Science
Coordination compounds
Copper
Differential thermal analysis
Fungicides
Inorganic Chemistry
Iron
Ligands
Liver cancer
Metal oxides
Molecular docking
Nickel
Ninhydrin
Organic Chemistry
Oxygen
Polymer Sciences
Stoichiometry
Thermodynamic properties
Transition metal compounds
Zirconium
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Summary:A series of transition metal complexes of alloxan monohydrate (H 2 L 1 ) and ninhydrin (H 2 L 2 ) have been prepared where metal ions are Fe(III), Co(II), Ni(II), Cu(II), Zr(IV), and Mo(VI). Different microanalytical techniques, spectroscopic methods, and magnetic studies were applied to assign the mode of bonding and elucidate the structure of complexes. All solid complexes are of 1:1 (M:L) stoichiometry and octahedral geometry except nickel (II) complexes exist in a tetrahedral geometry. FTIR spectral interpretation reveals that HL 1 coordinates to the central metal ion in a bidentate ON pattern, whereas HL 2 behaves as an alterdentate ligand through hydroxyl oxygen and carbonyl oxygen either C(1) = O or C(3) = O. The thermal behavior of some complexes was followed up to 700 °C by different techniques (TGA, DTA, and DSC) where decomposition stages progress in complicated mechanisms and are ended by the formation of metal oxide residue. Besides, biological screening involving antioxidant, antibacterial, and antifungal for ligands and some of their complexes was done. Moreover, four examined metal complexes displayed anticancer activity against hepatocellular carcinoma cells (HepG-2) but to different degrees. According to the IC 50 values, Cu-ninhydrin complex, [Cu(HL 2 )(H 2 O) 4 ].Cl has a better potency impact in comparison with cisplatin which was used as a reference control. This is in harmony with the molecular docking simulation outcomes that predicted a good binding propensity of the Cu-ninhydrin complex with hepatocellular carcinoma protein ( 2jrs ). Therefore, the Cu-ninhydrin complex should be deemed as a potential chemotherapeutic agent for hepatocellular cancer. Graphical Abstract
ISSN:1574-1443
1574-1451
DOI:10.1007/s10904-023-02661-5