Validation of Computational Methods Applied in Molecular Modeling of Caffeine With Epithelial Anticancer Activity: Theoretical Study of Geometric, Thermochemical and Spectrometric Data

Costa, Josivan da Silva; Santos, Cleydson Breno Rodrigues dos; Costa, Karina da Silva Lopes; Ramos, Ryan da Silva; Silva, Carlos Henrique Tomich de Paula da; Macêdo, Williams Jorge da Cruz

doi:10.21577/0100-4042.20170239

Cited by 2 publications

(2 citation statements)

References 27 publications

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“…The method used was the Hartree-Fock in the 6-31G** basis set (HF/6-31G**). The choice of this method was based on the study of Costa et al (2018) [ 64 ], who classified the HF/6-31G** method as the best method for the molecular modeling of caffeine and analogues. The descriptors obtained from calculations were the following: total surface area, molar volume, total dipole moment; molecular hardness (η), molecular softness (1/η), electronegativity (χ), chemical potential (μ), highest occupied molecular orbital energy (HOMO), a level of energy below the highest occupied molecular orbital (HOMO-1), the lowest non-occupied molecular orbital energy (LUMO), and a level of energy above the lowest unoccupied molecular orbital (LUMO+1).…”

Section: Methodsmentioning

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: Methodsmentioning

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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show abstract

“…The method used was Hartree-Fock in the 6-31G** basis set (HF/6-31G**). The choice of this method was based on the study of [35], who classified the HF/6-31G** method as the best method for the molecular modeling of caffeine and analogues. The descriptors obtained from calculations were the following: total surface area, molar volume, total dipole moment; molecular hardness (η), molecular softness(1/η), electronegativity (χ), chemical potential (μ), highest occupied molecular orbital energy (HOMO), a level of energy below the highest occupied molecular orbital (HOMO-1), the lowest non-occupied molecular orbital energy (LUMO), and a level of energy above the lowest unoccupied molecular orbital (LUMO+1).…”

mentioning

confidence: 99%

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

Costa¹,

C²,

K³

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 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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Validation of Computational Methods Applied in Molecular Modeling of Caffeine With Epithelial Anticancer Activity: Theoretical Study of Geometric, Thermochemical and Spectrometric Data

Cited by 2 publications

References 27 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

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

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