New bi-phosphonate derivative: Synthesis, characterization, antioxidant activity in vitro and via cyclic voltammetry mode and evaluation of its inhibition of SARS-CoV-2 main protease

Houas, Noudjoud; Kitouni, Siham; Chafai, Nadjib; Ghedjati, Samira; Djenane, Meriem; Tounsi, Assia

doi:10.1016/j.molstruc.2023.135356

Cited by 12 publications

(2 citation statements)

References 31 publications

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“…The docking process aims to determine the energetically most favorable conformation of a molecular entity, upon association with another to form a stable complex [46,47]. Prior to docking, charge allocation, solvent characterization, and fragmental volume assignment to the protein were conducted utilizing AutoDock tools.…”

Section: Molecular Docking Simulationmentioning

confidence: 99%

Integrated quantum chemical calculations, predictive toxicity assessment, absorption, distribution, metabolism, excretion and toxicity profiling and molecular docking analysis to unveil the therapeutic potential of non‐oxovanadium(IV) and organotin(IV) complexes targeting breast cancer cells

Thakur,

Kumari,

Kumar

et al. 2024

Int J of Quantum Chemistry

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In this work, theoretical calculations of o‐phenylphenol‐based non‐oxovanadium(IV) and organotin(IV) complexes, previously prepared and reported by our group, have been carried out by density functional theory (DFT). Density functional theory quantum chemical computations were used to explore the structural and spectroscopic characteristics of the complexes in this study. The inhibitory nature of complexes were revealed via molecular docking research, which were performed against selected breast cancer cell proteins, 5NWH and 3HB5. The optimization and stability of complexes 1–6, were conducted using optimized DFT/B3LYP/6–311++G (d, p) level. Simulated computations of the molecular electrostatic potential surface were also performed to analyze the reactive behavior of the non‐oxovanadium(IV) and organotin(IV) complexes. The stability and molecular reactivity of the molecules were computed using the HOMO‐LUMO energies, energy gap, chemical potential (μ), electronegativity (χ), hardness (η), and softness (S) values. In silico analysis through molecular docking, ADMET properties and toxicity evaluation was used to assess its anticancer activity, drug‐likeness property and toxicity. The binding constant value, evaluated from molecular docking, was found to be very promising, −10.1 kcal mol−1 observed for vanadium complex 5 and the complexes were found to exhibit inhibition constant as low as 0.0378 μMol. Root‐mean‐square deviation (RMSD) has been carried out to validate molecular docking studies, which have been found to be below 2.0 Å for the complexes, indicating successful docking of the ligand‐protein complex by the program. The complexes, evaluated for their toxicity behavior in terms of Lethal Dose, based on Globally Harmonized System (GHS), have been found to be chemical safe falling under the category III and V and hence can find use as future metallo‐based drugs.

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Section: Molecular Docking Simulationmentioning

confidence: 99%

Integrated quantum chemical calculations, predictive toxicity assessment, absorption, distribution, metabolism, excretion and toxicity profiling and molecular docking analysis to unveil the therapeutic potential of non‐oxovanadium(IV) and organotin(IV) complexes targeting breast cancer cells

Thakur,

Kumari,

Kumar

et al. 2024

Int J of Quantum Chemistry

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“…Organophosphorus encompasses various compounds containing carbone-phosphore bond such as α-aminophosphonic acids and their esters α-aminophosphonates, [1][2][3][4] αaminophosphates [5][6] phosphinates and phosphine oxides, [7] αhydrazinophosphonic acid. [8] Amongst the entire organophosphonrus, the α-aminophosphonates analogues of aminocarboxylic acids, possess an important class in biological and therapeutic domains because of their low toxicity.…”

Section: Introductionmentioning

confidence: 99%

SB‐2 cationic resin: an efficient and reusable organocatalyst for the synthesis of α‐aminophosphonates, DFT calculations and, computer aided design in antifungal activity

Touil,

Guezane‐Lakoud,

Boukachabia

et al. 2024

ChemistrySelect

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SB‐2 cationic resin has been employed as an unexpected and reusable heterogeneous organocatalyst in multicomponents reaction for the synthesis of the α‐aminophosphonates derivatives that act as antifungal agents, this reaction proceeds under eco‐friendly and simple procedure by condensation in one pot of substituted aromatic aldehydes, anilines and diethylphosphite. Excellent isolated product yields are obtained (up to 70 %) for (4 a–o) within shorter reaction times in solvent‐free condition. The synthesized compounds were determined by spectroscopic analyses such as: NMR (1H, 13C and 31P), IR and HRMS.Molecular geometries, electronic properties, stability and reactivity such as: HOMO/LUMO, , dipole moment (6.1308<D<10.5829), electronegativity (2.3490<X<3.5892), electrophilicity (1.1046<ω<3.2185) and the calculated thermodynamic descriptors (Zero‐point Energies, Enthalpy and Gibbs Free Energy) of four trimethoxy α‐aminophosphonates derivatives (4 j, 4 k, 4 l and 4 m) were carried by DFT at B3LYP 6‐31G (d, p) basis set. Computer aided design by molecular docking of studied compounds revealed a good binding energy against 5HS1 receptor to be considered as antifungal candidates and compared with Voriconazole. In additionally, druglikeness parameters of selected compounds were found through in silico pharmacological ADME/T properties estimation.

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Design, Synthesis, Cytotoxicity and Docking Evaluation of Novel α‐Aminophosphonates Quinoline Thiohydrazineyl Derivatives

Al Zahrani

2024

ChemistrySelect

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A one‐pot Kabachnik‐Fields reaction is used in the presence of magnesium triflate [Mg(OTf)2] as a catalyst between quinoline, diethyl phosphite (DEP), and substituted aldehydes to synthesize quinoline thioacetohydrazide α‐aminophosphonates (5 a‐f). Analytical and spectroscopic techniques identify the novel compounds. The cytotoxicity properties of the synthesized compounds were examined against HepG2 and MCF7 human cancer cells using the MTT assay. Some of the synthesized compounds exhibit potent anticancer activities. Compounds 5 e and 5 b exhibited the most promising activity against MCF7 human cancer cells, while compounds 5 c and 5 e were potent against HepG2 human cancer cells. Molecular docking experiments on the active compounds showed ring‐stacking interactions between compounds 5 b, 5 c, and 5 e with other proteins, which are compatible with other results.

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New bi-phosphonate derivative: Synthesis, characterization, antioxidant activity in vitro and via cyclic voltammetry mode and evaluation of its inhibition of SARS-CoV-2 main protease

Cited by 12 publications

References 31 publications

Integrated quantum chemical calculations, predictive toxicity assessment, absorption, distribution, metabolism, excretion and toxicity profiling and molecular docking analysis to unveil the therapeutic potential of non‐oxovanadium(IV) and organotin(IV) complexes targeting breast cancer cells

Integrated quantum chemical calculations, predictive toxicity assessment, absorption, distribution, metabolism, excretion and toxicity profiling and molecular docking analysis to unveil the therapeutic potential of non‐oxovanadium(IV) and organotin(IV) complexes targeting breast cancer cells

SB‐2 cationic resin: an efficient and reusable organocatalyst for the synthesis of α‐aminophosphonates, DFT calculations and, computer aided design in antifungal activity

Design, Synthesis, Cytotoxicity and Docking Evaluation of Novel α‐Aminophosphonates Quinoline Thiohydrazineyl Derivatives

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