Spectroscopic, quantum chemical, molecular docking and molecular dynamics investigations of hydroxylic indole-3-pyruvic acid: a potent candidate for nonlinear optical applications and Alzheimer’s drug

Koyambo-Konzapa, Stève-Jonathan; Kongbonga, Gilbert Yvon Mbesse; Premkumar, R.; Vamhindi, Berthelot Saïd Duvalier Ramlina; Nsangou, Mama; Benial, A. Milton Franklin

doi:10.1080/07391102.2021.1947380

Cited by 17 publications

(7 citation statements)

References 69 publications

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“…The highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) are the two molecular orbitals that are used to analyse how a molecule interacts with other species (LUMO). The HOMO energy represents the capacity to provide electrons, whereas the LUMO energy represents the capacity to carry electrons ( Koyambo-Konzapa et al, 2021 ). Electric and optical properties, UV-Vis spectra, and quantum chemistry all depend on FMOs.…”

Section: Resultsmentioning

confidence: 99%

Targeting potential receptor molecules in non-small cell lung cancer (NSCLC) using in silico approaches

Kirubhanand

Leonora²,

Anitha³

et al. 2023

Front. Mol. Biosci.

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Introduction: Non-Small Cell Lung Cancer is the most prevalent type of cancer in lung cancer. Chemotherapy, radiation therapy, and other conventional cancer treatments have a low success rate. Thus, creating new medications is essential to halt the spread of lung cancer.Methods: In this study bioactive nature of lochnericine against Non-Small Cell Lung Cancer (NSCLC) was analyzed using various computational approaches such as quantum chemical calculations, molecular docking, and molecular dynamic simulation. Furthermore, the MTT assay shows the anti-proliferation activity of lochnericine.Results and Discussion: Using Frontier Molecular Orbital (FMO), the calculated band gap energy value associated with bioactive compounds and the molecule’s potential bioactivity is confirmed. The H38 hydrogen atom and O1 oxygen atom in the molecule are effectively electrophilic, and potential nucleophilic attack sites were confirmed through analysis of the Molecular electrostatic potential surface. Furthermore, the electrons within the molecule were delocalized, which confers bioactivity on the title molecule and was authorized through Mulliken atomic charge distribution analysis. A molecular docking study revealed that lochnericine inhibits non-small cell lung cancer-associated targeted protein. The lead molecule and targeted protein complex were stable during molecular dynamics simulation studies till the simulation period. Further, lochnericine demonstrated remarkable anti-proliferative and apoptotic features against A549 lung cancer cells. The current investigation powerfully suggests that lochnericine is a potential candidate for lung cancer.

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Section: Resultsmentioning

confidence: 99%

Targeting potential receptor molecules in non-small cell lung cancer (NSCLC) using in silico approaches

Kirubhanand

Leonora²,

Anitha³

et al. 2023

Front. Mol. Biosci.

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“…In the calculation of the harmonic IR and Raman vibrational wavenumbers, the B3LYP method was mainly used, which is one of the most cost-effective DFT methods [ 25 , 29 ], and for this reason it is the most widely used [ 30 , 31 , 32 , 33 , 34 ]. This method has been successfully used in many studies of biomolecules [ 35 , 36 , 37 ] and in the drug design field [ 38 , 39 ]. The M06-2X method was also used to optimize the dimer structures in the stacking form of 1b and 2b , because it appears as one of the best options among the meta-generalized gradient functionals for analyzing dispersion-bound systems [ 40 ].…”

Section: Methodsmentioning

confidence: 99%

Study of the Molecular Architectures of 2-(4-Chlorophenyl)-5-(pyrrolidin-1-yl)-2H-1,2,3-triazole-4-carboxylic Acid Using Their Vibrational Spectra, Quantum Chemical Calculations and Molecular Docking with MMP-2 Receptor

Palafox,

Belskaya,

Kostova

2023

Pharmaceutics

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1,2,3-triazole skeleton is a valuable building block for the discovery of new promising anticancer agents. In the present work, the molecular structure of the synthesized anticancer drug 2-(4-chlorophenyl)-5-(pyrrolidin-1-yl)-2H-1,2,3-triazole-4-carboxylic acid (1b) and its anionic form (2b) was characterized by means of the B3LYP, M06-2X and MP2 quantum chemical methods, optimizing their monomer, cyclic dimer and stacking forms using the Gaussian16 program package. The molecular structure was found to be slightly out of plane. The good agreement between the IR and Raman bands experimentally observed in the solid state with those calculated theoretically confirms the synthesized structures. All of the bands were accurately assigned according to functional calculations (DFT) in the monomer and dimer forms, together with the polynomic scaling equation procedure (PSE). Therefore, the effect of the substituents on the triazole ring and the effect of the chlorine atom on the molecular structure and on the vibrational spectra were evaluated through comparison with its non-substituted form. Through molecular docking calculations, it was evaluated as to how molecule 1b interacts with few amino acids of the MMP-2 metalloproteinase receptor, using Sybyl-X 2.0 software. Thus, the relevance of triazole scaffolds in established hydrogen bond-type interactions was demonstrated.

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“…All optimized structures show only positive harmonic vibrations (local energy minima). B3LYP is one of the most cost-effective DFT methods [ 16 ] and it has been used satisfactorily in many studies of biomolecules [ 32 , 33 , 34 ] and in the drug design field [ 35 , 36 ]. The M06-2X method was used to optimize the dimer structures in stacking form of 2a , because it appears as one of the best options among the meta-generalized gradient functionals for analyzing dispersion–bound systems and it shows good results in non-covalent interactions with broad applicability in chemistry [ 37 , 38 ].…”

Section: Methodsmentioning

confidence: 99%

Peculiarities of the Spatial and Electronic Structure of 2-Aryl-1,2,3-Triazol-5-Carboxylic Acids and Their Salts on the Basis of Spectral Studies and DFT Calculations

Alcolea Palafox,

Belskaya,

Kostova

2023

IJMS

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The molecular structure and vibrational spectra of six 1,2,3-triazoles-containing molecules with possible anticancer activity were investigated. For two of them, the optimized geometry was determined in the monomer, cyclic dimer and stacking forms using the B3LYP, M06-2X and MP2 methods implemented in the GAUSSIAN-16 program package. The effect of the para-substitution on the aryl ring was evaluated based on changes in the molecular structure and atomic charge distribution of the triazole ring. An increment in the positive N4 charge was linearly related to a decrease in both the aryl ring and the carboxylic group rotation, with respect to the triazole ring, and by contrast, to an increment in the pyrrolidine ring rotation. Anionic formation had a larger effect on the triazole ring structure than the electronic nature of the different substituents on the aryl ring. Several relationships were obtained that could facilitate the selection of substituents on the triazole ring for their further synthesis. The observed IR and Raman bands in the solid state of two of these compounds were accurately assigned according to monomer and dimer form calculations, together with the polynomic scaling equation procedure (PSE). The large red-shift of the C=O stretching mode indicates that strong H-bonds in the dimer form appear in the solid state through this group.

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Spectroscopic, quantum chemical, molecular docking and molecular dynamics investigations of hydroxylic indole-3-pyruvic acid: a potent candidate for nonlinear optical applications and Alzheimer’s drug

Cited by 17 publications

References 69 publications

Targeting potential receptor molecules in non-small cell lung cancer (NSCLC) using in silico approaches

Targeting potential receptor molecules in non-small cell lung cancer (NSCLC) using in silico approaches

Study of the Molecular Architectures of 2-(4-Chlorophenyl)-5-(pyrrolidin-1-yl)-2H-1,2,3-triazole-4-carboxylic Acid Using Their Vibrational Spectra, Quantum Chemical Calculations and Molecular Docking with MMP-2 Receptor

Peculiarities of the Spatial and Electronic Structure of 2-Aryl-1,2,3-Triazol-5-Carboxylic Acids and Their Salts on the Basis of Spectral Studies and DFT Calculations

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