Synthesis, characterization, and anticancer potency of coumarin-derived thiosemicarbazones and their Copper(II) complexes

Shrestha, Ramina Maharjan; Mahiya, Kuldeep; Shrestha, Asmita; Mohanty, Soumya Ranjan; Yadav, Sanjeev Kumar; Yadav, Paras Nath

doi:10.1016/j.inoche.2024.112142

Inorganic Chemistry Communications

2024

DOI: 10.1016/j.inoche.2024.112142

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Synthesis, characterization, and anticancer potency of coumarin-derived thiosemicarbazones and their Copper(II) complexes

Ramina Maharjan Shrestha,

Kuldeep Mahiya,

Asmita Shrestha

et al.

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Cited by 11 publications

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Synthesis, structural characterization, density functional theory, anticancer, and antimicrobic studies of Ni²⁺ and Cu²⁺ complexes encompassing tridentate ONS‐donor azo‐thiosemicarbazone

Hassan,

Ebrahium,

Al‐Hakimi

2024

Applied Organom Chemis

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This study focuses on the synthesis of azo‐thiosemicarbazone ligand, which is designed by reacting 2‐hydroxy‐5‐(phenyldiazenyl)benzaldehyde with hydrazine carbothioamide. Hence, this ligand was exploited for chelation with nickel and cupric salts in (1 M:1 L) molar ratio. These synthetics were structurally investigated using a variety of physical, analytical, and spectroscopic (1D/2D‐NMR, UV–Vis, FT‐IR, and E‐mass) tools as well as theoretically. The finding demonstrated that the resulting azo‐thiosemicarbazone (H4Azo‐TSC) bonded with the nickel and cupric ions as mono/di‐basic tridentate chelators, binding them via deprotonated phenolic oxygen, imino nitrogen, and thionic/thiol sulfur atoms adopting square planar geometry. The theoretical investigation was examined by DFT/B3LYP/LanL2dZ, including energetic parameters, HOMO‐LUMO energy gap, dipole moment, and geometrical optimization, which were applied to support the complexes' geometrical structure. The in vitro microbicidal activities of the azo‐thiosemicarbazone, compared with its Ni2+ and Cu2+ complexes, display superior activity over the metal complexes against different bacterial and fungal species. The anticancer efficacy of the synthetics was tested against human lung fibroblast (WI38) and mammary gland breast cancer (MCF‐7) compared with Doxorubicin as a standard drug. The cytotoxic efficiency of metallic complexes exceeded that of un‐chelated azo‐thiosemicarbazone. The most effective complex is Ni2+ complex with IC50 equal to 11.75 and 14.05 μg/ml, respectively. It has been demonstrated that Ni2+ and Cu2+ complexes are more biocompatible than free azo‐thiosemicarbazone; this finding may be related to the chelation process.

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Synthesis, structural characterization, density functional theory, anticancer, and antimicrobic studies of Ni²⁺ and Cu²⁺ complexes encompassing tridentate ONS‐donor azo‐thiosemicarbazone

Hassan,

Ebrahium,

Al‐Hakimi

2024

Applied Organom Chemis

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Novel Mononuclear Cu(II), Ni(II), and Co(II) Complexes of Coumarinyl‐Pyrazolyl‐Thiazole Thiosemicarbazone: Synthesis, Characterization, and Biological Evaluation

Shebl,

Ali,

Assiri

2024

Applied Organom Chemis

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Cu(II), Ni(II), and Co(II) acetates reacted with a thiosemicarbazone ligand (CPPTSC; HL) to produce novel solid complexes with the general formula [M(L)(H2O)m]·nH2O, m = 2 or nil, n = 1 or nil, M = Cu(II), Ni(II), and Co(II). Several analytical and spectroscopic techniques have been efficiently used to characterize the synthesized chelates. The investigated CPPTSC ligand functions as a monoanionic tridentate in all chelates. Measurements of molar conductivity showed that all chelates behaved in a non‐electrolytic manner. In contrast to nickel‐CPPTSC and cobalt‐CPPTSC complexes, which showed tetrahedral geometries, the copper‐CPPTSC complex showed a distorted octahedral geometry. The thermal decomposition behaviors of CPPTSC complexes were examined using TG. To assess the molecular structural characteristics of CPPTSC and its complexes, density functional theory (DFT) was applied at the B3LYP/6‐311G(d,p) and LanL2dz levels. The antiproliferative properties of CPPTSC and its chelates against two human cancer cell lines, HepG‐2 (hepatic) and MCF‐7 (breast), were evaluated. The Cu‐CPPTSC and Ni‐CPPTSC complexes displayed the superior IC50 values compared with doxorubicin, suggesting a potentially improved therapeutic index. The bioactive Cu‐CPPTSC and Ni‐CPPTSC complexes markedly increased the late apoptosis of all studied tumor cells. The Cu‐CPPTSC and Ni‐CPPTSC complexes showed great cell cycle arrest in the G2 phase and moderate cell cycle arrest in the S phase. The discovered Cu‐CPPTSC and Ni‐CPPTSC complexes were then subjected to a molecular docking experiment and displayed good interactions with CDK‐2 receptor.

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The current landscape of coumarin hybrids with antibreast cancer therapeutic applications: An updated review

Wang,

Chen,

Huang

et al. 2024

Archiv der Pharmazie

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Globally, breast cancer (BC) has the highest prevalence among malignant diseases. BC is also the primary cause of death among women. Notably, BC morbidity has been increasing continuously at an approximate growth rate of 2.2% per year. Persistent BC is a major public health issue worldwide. Consequently, novel chemotherapeutic agents to combat this lethal disease should be developed urgently. Coumarins with interesting structural and mechanistic variations exhibit promising activity in several forms of BC, including BCs with multidrug resistance. In particular, coumarin hybrids composed of coumarin and one or more anti‐BC pharmacophores can target different biological components in BC cells simultaneously. Thus, coumarin hybrids are useful scaffolds that can help improve the anti‐BC efficacy of coumarins, reduce side effects, improve pharmacokinetics, minimize drug–drug interactions, and circumvent drug resistance. This review, in which articles published from 2020 to the present day have been evaluated, highlights the landscape of coumarin hybrids that exhibit therapeutic effects against breast cancer. These findings can aid further investigations on novel antibreast‐cancer therapeutics.

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Synthesis, characterization, and anticancer potency of coumarin-derived thiosemicarbazones and their Copper(II) complexes

Cited by 11 publications

References 67 publications

Synthesis, structural characterization, density functional theory, anticancer, and antimicrobic studies of Ni²⁺ and Cu²⁺ complexes encompassing tridentate ONS‐donor azo‐thiosemicarbazone

Synthesis, structural characterization, density functional theory, anticancer, and antimicrobic studies of Ni²⁺ and Cu²⁺ complexes encompassing tridentate ONS‐donor azo‐thiosemicarbazone

Novel Mononuclear Cu(II), Ni(II), and Co(II) Complexes of Coumarinyl‐Pyrazolyl‐Thiazole Thiosemicarbazone: Synthesis, Characterization, and Biological Evaluation

The current landscape of coumarin hybrids with antibreast cancer therapeutic applications: An updated review

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Synthesis, characterization, and anticancer potency of coumarin-derived thiosemicarbazones and their Copper(II) complexes

Cited by 11 publications

References 67 publications

Synthesis, structural characterization, density functional theory, anticancer, and antimicrobic studies of Ni2+ and Cu2+ complexes encompassing tridentate ONS‐donor azo‐thiosemicarbazone

Synthesis, structural characterization, density functional theory, anticancer, and antimicrobic studies of Ni2+ and Cu2+ complexes encompassing tridentate ONS‐donor azo‐thiosemicarbazone

Novel Mononuclear Cu(II), Ni(II), and Co(II) Complexes of Coumarinyl‐Pyrazolyl‐Thiazole Thiosemicarbazone: Synthesis, Characterization, and Biological Evaluation

The current landscape of coumarin hybrids with antibreast cancer therapeutic applications: An updated review

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Product

Resources

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Synthesis, structural characterization, density functional theory, anticancer, and antimicrobic studies of Ni²⁺ and Cu²⁺ complexes encompassing tridentate ONS‐donor azo‐thiosemicarbazone

Synthesis, structural characterization, density functional theory, anticancer, and antimicrobic studies of Ni²⁺ and Cu²⁺ complexes encompassing tridentate ONS‐donor azo‐thiosemicarbazone