Atomic electronegativities in molecules

Tognetti, Vincent; Morell, Christophe; Joubert, Laurent

doi:10.1016/j.cplett.2015.05.057

Cited by 22 publications

(13 citation statements)

References 47 publications

(55 reference statements)

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“…The higher the TDM, the greater the polarity of the molecule and consequently greater a tendency to dissolve and interact in polar environment [ 25 , 26 ]. The electronegativity (χ), is directly related to TDM, and is described as the capacity that an atom has to attract to itself electrons of a bond that it makes with another atom [ 27 ]. It can be used to estimate the tendency of a molecule to attract electrons from another molecule with which it performs interaction [ 28 ].…”

Section: Resultsmentioning

confidence: 99%

An In Silico Study of the Antioxidant Ability for Two Caffeine Analogs Using Molecular Docking and Quantum Chemical Methods

et al. 2018

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The antioxidant activity of molecules constitutes an important factor for the regulation of redox homeostasis and reduction of the oxidative stress. Cells affected by oxidative stress can undergo genetic alteration, causing structural changes and promoting the onset of chronic diseases, such as cancer. We have performed an in silico study to evaluate the antioxidant potential of two molecules of the zinc database: ZINC08706191 (Z91) and ZINC08992920 (Z20). Molecular docking, quantum chemical calculations (HF/6-31G**) and Pearson’s correlation have been performed. Molecular docking results of Z91 and Z20 showed both the lower binding affinity (BA) and inhibition constant (Ki) values for the receptor-ligand interactions in the three tested enzymes (cytochrome P450—CP450, myeloperoxidase—MP and NADPH oxidase—NO) than the control molecules (5-fluorouracil—FLU, melatonin—MEL and dextromethorphan—DEX, for each receptor respectively). Molecular descriptors were correlated with Ki and strong correlations were observed for the CP450, MP and NO receptors. These and other results attest the significant antioxidant ability of Z91 and Z20, that may be indicated for further analyses in relation to the control of oxidative stress and as possible antioxidant agents to be used in the pharmaceutical industry.

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Section: Resultsmentioning

confidence: 99%

An In Silico Study of the Antioxidant Ability for Two Caffeine Analogs Using Molecular Docking and Quantum Chemical Methods

et al. 2018

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“…In view of these results, one may wonder which atomic energy definition is the most suitable for chemical applications. As a first test, we will consider carbocations of the benzhydrylium family (represented in Scheme ), which were theoretically studied by Liu from an information theory point of view, and by us from dual descriptor and atomic electronegativities perspectives . The reactivity of the electrophilic carbon was experimentally investigated by using accurate kinetic measurements, and incorporated in Mayr's electrophilicity scale [Eq.…”

Section: Resultsmentioning

confidence: 99%

“…Consistent with Refs. and , the M06‐2X exchange‐correlation functional was used. The atomic energies for the central carbon atom and the corresponding Mayr electrophilicity values ( E Mayr ) are reported in Table .…”

Section: Resultsmentioning

confidence: 99%

On Atoms‐in‐Molecules Energies from Kohn–Sham Calculations

Tognetti

Joubert

2017

ChemPhysChem

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Herein, we discuss three methods to partition the total molecular energy into additive atomic contributions within the framework of Bader's atoms‐in‐molecules theory and in the particular context of Kohn–Sham density functional theory. The first method is derived from the virial theorem, whereas the two other schemes, termed “standard” and “model”, are based on Pendás’ interacting‐quantum‐atoms decomposition. The methods are then compared for a dataset of molecules of interest for direct application in organic chemistry and biochemistry. Finally, the relevance of the three methods for the prediction of intrinsic reactivity properties (e.g., electrophilicity) or for unravelling the nature of chemical bonding (e.g., in halogen bonds, beyond the pure electrostatic point of view), is examined and paves the way for their more systematic use for the in silico design of new reactants.

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“…Its higher values of TSA and MV (457.63 Å 2 and 831. The electronegativity (χ) is described as the capacity that an atom has to attract to itself electrons of a bond that it makes with another atom [16]. It can be used to estimate the tendency of a molecule to attract electrons from another molecule with which it performs interaction [17].…”

Section: Molecular Descriptors and Antioxidant Potentialmentioning

confidence: 99%

In Silico Evaluation of the Antioxidant Potential of Two Caffeine Analogs with Recognized Epithelial Anticancer Potential

Costa¹,

C²,

K³

et al. 2018

Preprint

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The antioxidant activity of molecules constitutes an important factor for the regulation of redox homeostasis and reduction of oxidative stress. Cells affected by oxidative stress can undergo genetic alteration, causing structural changes and promoting the onset of chronic diseases, such as cancer. The in silico study performed here was developed to evaluate the antioxidant potential of two molecules, ZINC08706191 (Z91) and ZINC08992920 (Z20), with recognized epithelial anticancer potential. Molecular docking, chemical-quantum calculations and Pearson's correlation were performed. The Z91 and Z20 molecules showed lower binding free energy (ΔG) values for the receptor-ligand interaction than the reference molecules (caffeine – CAF and ascorbic acid – AA), and better results for values of molecular descriptors correlated with ΔG, resulting in a decrease of ΔG. Strong correlations were observed between ΔG values for the five receptors evaluated and ΔG values of the potential epithelial anticancer activity available in literature. These results attest to the significant antioxidant potential of the Z91 and Z20 molecules and their strong relation with the potential epithelial anticancer activity and may be indicated for further analysis in relation to the control of oxidative stress and epithelial anticancer activity.

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Atomic electronegativities in molecules

Cited by 22 publications

References 47 publications

An In Silico Study of the Antioxidant Ability for Two Caffeine Analogs Using Molecular Docking and Quantum Chemical Methods

An In Silico Study of the Antioxidant Ability for Two Caffeine Analogs Using Molecular Docking and Quantum Chemical Methods

On Atoms‐in‐Molecules Energies from Kohn–Sham Calculations

In Silico Evaluation of the Antioxidant Potential of Two Caffeine Analogs with Recognized Epithelial Anticancer Potential

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