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Cytotoxicity, alpha-glucosidase inhibition and molecular docking studies of hydroxamic acid chromium(III) complexes

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Abstract

Hydroxamic acids [R(CO)N(OH)R’] are flexible compounds for organic and inorganic analyses due to their frailer structures compared to the carboxylic acid. The syntheses and characterization of benzohydroxamic acid (BHA), its CH3–, OCH3–, Cl– para-substituted derivatives and their Cr(III) complexes are reported herein. The metal complexes were synthesized by reacting the hydroxamic acids with chromium(III) chloride hexahydrate in 2:1 molar ratio. The compounds were characterized via melting point, elemental analysis, FTIR, 1H and 13C NMR, TGA, mass spectrometry, molar conductance and UV–Visible. Data analysis suggests that each complex has the Cr(III) center coordinated to the carbonyl and hydroxy oxygen atoms of the hydroxamic acids in bidentate O,O manner and two water molecules to form octahedral geometry. Non-electrolytic behavior of the complexes was shown through their low molar conductivity. Cytotoxicity study against HCT116 and alpha-glucosidase inhibition test revealed that all complexes have higher activity than their parent ligands. Molecular docking study shows that the docking of active complexes is thermodynamically favorable and the inhibition efficiency may depend on the types and the numbers of molecular interactions established in the corresponding stable conformers.

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Funding

This work was funded by the Ministry of Higher Education of Malaysia for the research fund; 600-IRMI 5/3/GIP (004/2018), Universiti Teknologi MARA and AuRIns for research facilities and Faculty of Pharmacy for the facilities on cytotoxicity study.

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Authors and Affiliations

  1. Faculty of Applied Sciences, Universiti Teknologi MARA, Shah Alam, 40450, Selangor, Malaysia

    Latifah Robbaniyyah Hassan, Hadariah Bahron & Amalina Mohd Tajuddin

  2. Department of Chemistry, College of Science and Humanities in Al-Kharj, Prince Sattam Bin Abdulaziz University, Al-Kharj, 11942, Saudi Arabia

    El Hassane Anouar

  3. University of Malaya Centre for Ionic Liquid (UMCIL), Universiti Malaya, 50603, Kuala Lumpur, Malaysia

    Hadariah Bahron

  4. Centre of Foundation Studies, Universiti Teknologi MARA, Dengkil, 43800, Selangor, Malaysia

    Faiezah Abdullah

  5. Atta-ur-Rahman Institute for Natural Product Discovery (AuRIns), Universiti Teknologi MARA, Level 9, FF3 Building, 42300 Puncak Alam, Selangor, Malaysia

    Amalina Mohd Tajuddin

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  1. Latifah Robbaniyyah Hassan
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  2. El Hassane Anouar
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Correspondence to El Hassane Anouar or Amalina Mohd Tajuddin.

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Hassan, L.R., Anouar, E.H., Bahron, H. et al. Cytotoxicity, alpha-glucosidase inhibition and molecular docking studies of hydroxamic acid chromium(III) complexes. J Biol Inorg Chem 25, 239–252 (2020). https://doi.org/10.1007/s00775-020-01755-6

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  • DOI: https://doi.org/10.1007/s00775-020-01755-6

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