Synthesis, characterisation and anticancer activity screening of lanthanide(III) acetate complexes with benzohydrazone and nicotinohydrazone ligands

Madanhire, Tatenda; Davids, Hajierah; Pereira, Melanie C.; Hosten, Eric C.; Abrahams, Abubak’r

doi:10.1016/j.poly.2020.114560

Cited by 21 publications

(6 citation statements)

References 58 publications

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“…The two metal centers are finally bridged by a pair of chelating-bridging acetato ligands which are acting in η 1 :η 2 :µ 2 -OOCCH 3 mode. 7)°] is in the range expected for η 1 :η 2 :µ 2 -acetate groups [34]. The dihedral angle formed by the planes of the two terminal pyridine rings is 15.61°.…”

Section: Molecular Structure Of Complex (2)mentioning

confidence: 70%

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Synthesis, Characterization and Single Crystal X–ray Crystallography of Nd(III) and Pr(III) Complexes with the Tridentate Schiff Base Ligand N'–(1–(pyridin–2–yl)ethylidene)nicotinohydrazide

Faye

Gaye

Sow

et al. 2021

EJCS

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The use of N'–(1–(pyridin–2–yl)ethylidene)nicotinohydrazide (HL) in lanthanide(III) chemistry has yielded one mononuclear and one dinuclear complexes. The 1:1 Nd(NO3)3.6H2O or Pr(CH3COO)3.6H2O/HL in methanol afforded the complexes [Nd (HL)2(NO3)2(H2O)2].(NO3) (1) and {[Pr(L)(h2–OOCCH3)(H2O)](h1:h2:m–OOCCH3)2[Pr (L)(h2–OOCCH3)(H2O)]} (2). The structures of the complexes were solved by single crystal X–ray crystallography. In the mononuclear complex, the Nd3+ atom is coordinated by two neutral molecules of ligand acting in tridentate fashion, two nitrate anions acting in bidentate manner and two coordinated water molecules yielding a twelve–coordinated Nd atom. In the complex (2) the Pr3+ atoms are doubly bridged by two acetates anions and each metal ion is coordinated by one tridentate monodeprotonated molecule ligand, one bidentate acetate group and one coordinated water molecule. Each Pr3+ atom is nine–coordinated with an environment best described as a tricapped prismatic geometry. Complex 1 crystallizes in the monoclinic space group C2/c with the following parameters: a = 22.7657(8) Å, b = 8.4276(3) Å, c = 18.0831(7) Å, b = 114.851(2)°, V = 3148.2(2) Å3, Z = 4, R1 = 0.032, wR2 = 0.098. Complex 2 crystallizes in the monoclinic space group P21/n with the following parameters: a = 11.5388(6) Å, b = 14.1087(8) Å, c = 12.2833(6) Å, b = 102.211(2)°, V = 1954.45(18) Å3, Z = 2, R1 = 0.029, wR2 = 0.066. The supramolecular structures are consolidated by multiple hydrogen bonds.

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Section: Molecular Structure Of Complex (2)mentioning

confidence: 70%

“…Asymmetric and symmetric bands of COO group in acetic acid are respectively 1585 cm -1 (ν as ) and 1397 cm -1 (ν s ) [34]. Upon coordination to praseodymium ion the IR bands of the acetate groups were shifted.…”

Section: General Studymentioning

confidence: 99%

Synthesis, Characterization and Single Crystal X–ray Crystallography of Nd(III) and Pr(III) Complexes with the Tridentate Schiff Base Ligand N'–(1–(pyridin–2–yl)ethylidene)nicotinohydrazide

Faye

Gaye

Sow

et al. 2021

EJCS

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“…The electrophilicity index ( ω ) can be calculated using the chemical potential and chemical hardness ( Eq. 2 ) [ 52 , 53 ].

…”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of heterocyclic azole based bioactive compounds: Molecular structures, quantum simulation, and mechanistic studies through docking as multi-target inhibitors of SARS-CoV-2 and cytotoxicity

Haribabu

Garisetti

Malekshah

et al. 2022

Journal of Molecular Structure

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Two heterocyclic azole compounds, 3-(2,3-dihydrobenzo[d]thiazol-2-yl)-4H-chromen-4-one ( SVS1 ) and 5-(1H-indol-3-yl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione ( SVS2 ) were obtained unexpectedly from 2-aminothiophenol and 4-oxo-4H-chromene-3-carbaldehyde (for SVS1 ), and ( E )-2-((1H-indol-3-yl)methylene)-N-methylhydrazine-1-carbothioamide in the presence of anhydrous FeCl 3 (for SVS2 ), respectively. The compounds were well characterized by analytical and spectroscopic tools. The molecular structures of both the compounds were determined by single crystal X-ray diffraction (X-RD) study. The results obtained from density functional theory (DFT) study revealed the molecular geometry and electron distribution of the compounds, which were correlated well with the three-dimensional structures obtained from the single crystal X-ray diffraction. DMol 3 was used to calculate quantum chemical parameters [chemical potential ( µ ), global hardness ( η ), global softness ( σ ), absolute electronegativity ( χ ) and electrophilicity index ( ω )] of SVS1 and SVS2 . Molecular docking study was performed to elucidate the binding ability of SVS1 and SVS2 with SARS-CoV-2 main protease and human angiotensin-converting enzyme-2 (ACE-2) molecular targets. Interestingly, the binding efficiency of the compounds with the molecular targets was comparable with that of remdesivir (SARS-CoV-2), chloroquine and hydroxychloroquine. SVS1 showed better docking energy than SVS2 . The molecular docking study was complemented by molecular dynamic simulation study of SARS-CoV-2 main protease- SVS1 complex, which further exemplified the binding ability of SVS1 with the target. In addition, SVS1, SVS2 and cisplatin were assessed for their cytotoxicity against a panel of three human cancer cells such as HepG-2 (hepatic carcinoma), T24 (bladder) and EA.hy926 (endothelial), as well as Vero (kidney epithelial cells extracted from an African green monkey) normal cells using MTT assay. The results showed that SVS2 has significant cytotoxicity against HepG-2 and EA.hy926 cells with the IC 50 values of 33.8 μM (IC 50 = 49.9 μM-cisplatin and 8.6 μM-doxorubicin) and 29.2 (IC 50 = 26.6 μM-cisplatin and 3.8 μM-doxorubicin), respectively.

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“…2b) with 8 coordination numbers. The geometric configuration is calculated in the same way as above 22 . The average bond length of Er-O is 2.327(4) Å, and the shortest bond length is 2.243(6) Å, which is derived from the Er1-O2 with bidentate bridging coordination.…”

Section: [Er(24-dfba)3(phen)]2 (Ii)mentioning

confidence: 99%

“…A muffin-type coordination environment (Fig. 3b) with a coordination number of 9 was calculated by shape 22 software simulation. The adjacent structural units form a 1D chain-like supramolecular structure (Fig.…”

Section: [Er(24-dfba)3(phen)]2 (Ii)mentioning

confidence: 99%

Construction, Thermochemistry, and Fluorescence Properties of Novel Lanthanide Complexes Synthesized from Halogenated Aromatic Carboxylic Acids and Nitrogen-Containing Ligands

Wang¹,

Xu²,

Ren³

et al. 2022

Acta Physico Chimica Sinica

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In this study, new lanthanide complexes were synthesized via the volatilization method in solution at room temperature. The general molecular formulas for the lanthanide complexes are as follows: [Ln(2,4-DFBA)3(phen)]2 (Ln = Sm 1, Eu 2, and Er 3; 2,4-DFBA = 2,4-difluorobenzoate; and phen = 1,10-phenanthroline), as well as [Ln(2-Cl-6-FBA)2(terpy)(NO3)(H2O)]2 (Ln = Tb 4 and Dy 5; 2-Cl-6-FBA = 2chloro-6-fluorobenzoate; and terpy = 2,2':6'2''-tripyridine). Based on single-crystal Xray analysis, the five complexes exhibited a monoclinic crystal structure belonging to the space group P21/n. Even though complexes 1, 2 (I), and 3 (II) share a general molecular formula, their coordination modes were different. For example, complexes 1 and 2 formed a muffin-like structure with nine coordinated atoms, while complex 3 formed a double hat triangular geometry with eight coordinated atoms. The twodimensional (2D) polyhedral structures of complexes 1 and 2 were formed via weak π-π stacking interactions, whereas complex 3 exhibited a 2D faceted supramolecular structure through C-H•••F hydrogen bonds. Complexes 4 and 5 were isostructural, with the presence of nitrate ions in their structure. This occurred through the C-H•••F hydrogen bonds and π-π stacking of the molecules to form a faceted supramolecular crystal structure. A series of characterizations, such as elemental analysis, infrared and Raman spectroscopy, as well as powder X-ray diffraction, were performed on the five complexes. Thermogravimetry-derivative thermogravimetry-differential scanning calorimetry were performed between 299.25 and 1073.15 K to investigate the mechanism for the thermal decomposition of complexes 1-5. The analysis of the escaping gas stacking maps of the five complexes using thermogravimetric and 3D infrared coupling techniques further confirmed the correctness of the thermal decomposition mechanism of each complex. The results obtained revealed that similar structured complexes follow a similar thermal decomposition mechanism, and the end solid products for all complexes were their corresponding metal oxides. During the irradiation of the Xe lamp, the solid fluorescence of complexes 1, 2, 4, and 5 were measured. The characteristic transition peaks were located at 4 G5/2 → 6 H5/2, 4 G5/2 → 6 H7/2, and 4 G5/2 → 6 H9/2 (1); 5 D0 → 7 F0, 5 D0 → 7 F1, 5 D0 → 7 F2, 5 D0 → 7 F3, and 5 D0 → 7 F4 (2); 5 D4 → 7 F6, 5 D4 → 7 F5, 5 D4 → 7 F4, and 5 D4 → 7 F3 (4); and 4 F9/2 → 6 H15/2, 4 F9/2 → 6 H13/2 (5). The peaks observed indicated the characteristic transitions of Ln(III). The lanthanide complexes exhibited characteristic fluorescence due to this fact, which also explained their characteristic color. Furthermore, the fluorescence lifetimes of complexes 2 and 4 were measured, and their fluorescence decay curves indicated fluorescence lifetimes of 1.288 and 0.648 ms, respectively.

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Synthesis, characterisation and anticancer activity screening of lanthanide(III) acetate complexes with benzohydrazone and nicotinohydrazone ligands

Cited by 21 publications

References 58 publications

Synthesis, Characterization and Single Crystal X–ray Crystallography of Nd(III) and Pr(III) Complexes with the Tridentate Schiff Base Ligand N'–(1–(pyridin–2–yl)ethylidene)nicotinohydrazide

Synthesis, Characterization and Single Crystal X–ray Crystallography of Nd(III) and Pr(III) Complexes with the Tridentate Schiff Base Ligand N'–(1–(pyridin–2–yl)ethylidene)nicotinohydrazide

Design and synthesis of heterocyclic azole based bioactive compounds: Molecular structures, quantum simulation, and mechanistic studies through docking as multi-target inhibitors of SARS-CoV-2 and cytotoxicity

Construction, Thermochemistry, and Fluorescence Properties of Novel Lanthanide Complexes Synthesized from Halogenated Aromatic Carboxylic Acids and Nitrogen-Containing Ligands

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