Synthesis, Structural Investigations, DNA/BSA Interactions, Molecular Docking Studies, and Anticancer Activity of a New 1,4-Disubstituted 1,2,3-Triazole Derivative

Göktürk, Tolga; Sakallı Çetin, Esin; Hökelek, Tuncer; Pekel, Hanife; Şensoy, Özge; Aksu, Ebru Nur; Güp, Ramazan

doi:10.1021/acsomega.3c03355

Cited by 20 publications

(1 citation statement)

References 93 publications

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“…This intercalation is one of the most important interactions substantial to DNA-binding mechanisms, which may be related to some of the compound's biological activity. 27,68,69…”

Section: Hirshfeld Surface (Hs) Analysismentioning

confidence: 99%

Experimental and theoretical studies on (2E,5E)-2,5-bis(2-methoxybenzylidene)cyclopentanone: Structural, electrochemical, spectroscopic features, solid-state interactions, molecular docking and adsorption studies onto 2D carbon nanomaterials

Thaçi,

Reka,

Ristovska

et al. 2023

Maced. J. Chem. Chem. Eng.

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A monocarbonyl analog of curcumin, (2E,5E)-2,5-bis(2-methoxybenzylidene)-cyclopentanone (B2MBCP), was prepared and characterized via spectroscopic methods (NMR, UV-Vis, FT-IR, and MS). Furthermore, density functional calculations were implemented to study the molecular structure and spectroscopic features, as well as adsorption properties. In addition, Hirshfeld surface and NBO theoretical analysis were carried out. The reduced density gradient (RDG) analysis via non-covalent interactions (NCI) and interaction region indicator (IRI) indicate the presence of extensive Van der Waals interactions. These interactions are classified in different contributions and energy stabilization from Hirshfeld surface analysis where the dominant type of contacts are H···H contacts. The molecular docking studies of B2MBCP with DNA revealed cooperative interactions that led to intercalation. The results from the cyclic voltammetry (CV) measurements agreed with the calculated energies of the frontier orbitals and the compound structure. Theoretical studies indicated that the relatively flat B2MBCP is adsorbed onto a graphene surface, with a significant adsorption energy of –41.19 kcal/mol. The results of this study provide a better overall picture of the properties of MAC with a cyclopentanone core and can be taken as a useful guide in the search for new biologically active compounds and new possible means of delivery.

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“…This intercalation is one of the most important interactions substantial to DNA-binding mechanisms, which may be related to some of the compound's biological activity. 27,68,69…”

Section: Hirshfeld Surface (Hs) Analysismentioning

confidence: 99%

Experimental and theoretical studies on (2E,5E)-2,5-bis(2-methoxybenzylidene)cyclopentanone: Structural, electrochemical, spectroscopic features, solid-state interactions, molecular docking and adsorption studies onto 2D carbon nanomaterials

Thaçi,

Reka,

Ristovska

et al. 2023

Maced. J. Chem. Chem. Eng.

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Crystal structure, Hirshfeld surface analysis, molecular modeling, electrochemical properties, and potential medicinal activity of a novel binuclear Co(II) complex

Elsheemy,

Abdel Aziz,

Ramadan

et al. 2024

Applied Organom Chemis

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A quinoxaline‐based ligand, 6,7‐dimethyl‐2,3‐di(2‐pyridyl)quinoxaline (Me2dpq), and its unique binuclear Co(II)‐Me2dpq complex were prepared and analyzed using single crystal X‐ray diffraction and several spectroscopy techniques. Hirshfeld surface analyses were also used to clarify the Me2dpq ligand and the Co(II)‐Me2dpq crystal packing. The Co(II)‐Me2dpq complex crystallized in triclinic P‐1 space group and exhibited a distorted trigonal bipyramidal geometry around the cobalt(II) ion. Each Co(II) ion coordinated to a Me2dpq ligand through two N donor centers from pyridyl and quinoxaline rings along with a terminal Cl and two bridged Cl atoms. The binding properties of the ligand and its complex with CT‐DNA were studied by several techniques, namely UV–Vis spectroscopy, fluorescence quenching, viscosity measurements, thermal denaturation, and gel electrophoresis. The CT‐DNA binding interaction tests demonstrated that both the Co(II)‐Me2dpq complex and its parent ligand bind to DNA in an intercalative way. The antioxidant studies of the novel Co(II)‐Me2dpq complex illustrated significant activity against DPPH• and radicals. The in vitro cytotoxic effect of Me2dpq ligand and its Co(II)‐complex on MCF‐7 and Hep‐G2 tumor cell lines was evaluated by using the MTT assay. The studies showed that the Co(II)‐Me2dpq complex had superior activity toward the tested cell lines. Molecular docking studies of synthesized compounds were employed to figure out the way they would associate with a biologically macromolecular target B‐DNA (PDB: 1BNA). Thus, this study is anticipated to provide novel opportunities for the successful utilization of the synthesized compounds in many medical domains.

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Anti‐Amyloid Aggregation and Anti‐Hyperglycemic Activities of Novel Ruthenium Uracil Schiff Base Compounds

Makanyane,

Mabuza,

Ngubane

et al. 2024

ChemMedChem

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The formation and characterization of new diamagnetic ruthenium uracil mono‐imine compounds: [(η6‐p‐cymene)RuII(L)Cl][BF4] (L = H2urpda = 5‐((pyridin‐2‐yl)methyleneamino)‐6‐aminouracil) for 1, urdpy = 6‐amino‐1,3‐dimethyl‐5‐((pyridin‐2‐ylmethylene)amino)uracil) for 2 or urqda = 5‐((quinolin‐2‐yl)methyleneamino)‐6‐aminouracil) for 3); cis‐[RuII(L)(bipy)2] (L = urpy = 5‐((pyridin‐2‐yl)methyleneamino)uracil) for 4 and H2dadp = 5,6‐diaminouracil for 5) are described. A paramagnetic ruthenium uracil Schiff base compound, trans‐[RuIV(L)(PPh3)Cl2] (L = H2urpda for 6) was also formed. Various physicochemical techniques were utilized to characterize the novel ruthenium compounds. Similarly, the stabilities of 1 ‐ 3 and 6 monitored in chloro‐containing and the non‐coordinating solvent, dichloromethane show that they are kinetically inert, whereas, in a high nucleophilic environment, the chloride co‐ligands of these ruthenium complexes were rapidly substituted by DMSO. In contrast, the substitution of the labile co‐ligands for these ruthenium complexes by DMSO molecules in a high chloride content was suppressed. Solution chemical reactivities of the different ruthenium complexes were rationalized by density functional theory computations. Furthermore, the binding affinities and strengths between BSA and the respective ruthenium complexes were monitored using fluorescence spectroscopy. In addition, the in vitro anti‐diabetic activities of the novel metal complexes were assessed in selected skeletal muscle and liver cell lines.

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Synthesis, Structural Investigations, DNA/BSA Interactions, Molecular Docking Studies, and Anticancer Activity of a New 1,4-Disubstituted 1,2,3-Triazole Derivative

Cited by 20 publications

References 93 publications

Experimental and theoretical studies on (2E,5E)-2,5-bis(2-methoxybenzylidene)cyclopentanone: Structural, electrochemical, spectroscopic features, solid-state interactions, molecular docking and adsorption studies onto 2D carbon nanomaterials

Experimental and theoretical studies on (2E,5E)-2,5-bis(2-methoxybenzylidene)cyclopentanone: Structural, electrochemical, spectroscopic features, solid-state interactions, molecular docking and adsorption studies onto 2D carbon nanomaterials

Crystal structure, Hirshfeld surface analysis, molecular modeling, electrochemical properties, and potential medicinal activity of a novel binuclear Co(II) complex

Anti‐Amyloid Aggregation and Anti‐Hyperglycemic Activities of Novel Ruthenium Uracil Schiff Base Compounds

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