Investigation on the interaction behavior of afatinib, dasatinib, and imatinib docked to the BCR-ABL protein

Rocha, Kelvyn M. L.; Nascimento, Érica C. M.; Martins, João B. L.

doi:10.1007/s00894-021-04925-8

Cited by 5 publications

(2 citation statements)

References 47 publications

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“…Several quantum chemical descriptors have been widely used to characterize intramolecular and intermolecular interactions [18][19][20][21]. Conformational analysis is of interest in these avonoids due to the large degree of freedom of these molecules, in uenced mainly by hydrogen bonding interactions.…”

Section: Introductionmentioning

confidence: 99%

Comparative Analysis of the Reactivity of Anthocyanidins, Leucoanthocyanidins, and Flavonols using a Quantum Chemistry Approach

Farias

Costa

Martins

2023

Preprint

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In the present study, we performed a comparative structural, conformational, electronic, and nuclear magnetic resonance analysis of the reactivity of the chemical structure of primary flavonoids, anthocyanidins, and leucoanthocyanidins. We focused our analysis on the following molecular questions: i) differences in cyanidin catechols (+)-catechin, leucocyanidin and quercetin; ii) the loss of a hydroxyl presents in the R1 radical of leucoanthocyanidin due to possible differences in the functional groups linked to C4 (ring C), and, iii) the electron affinity of the 3-hydroxyl group (R7) in the flavonoids delphinidin, pelargonidin, cyanidin, quercetin and kaempferol. For the analysis of the molecular properties, we used the density functional theory (DFT) to evaluate the formation of the covalent bonds and intermolecular forces. A broad analysis of quantum properties was performed using the assessment of the molecular electrostatic potential (MEP) surface, electron localization function (ELF), Fukui functions, descriptors constructed from frontier orbitals, and nucleus independent chemical shift (NICS).

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Section: Introductionmentioning

confidence: 99%

Comparative Analysis of the Reactivity of Anthocyanidins, Leucoanthocyanidins, and Flavonols using a Quantum Chemistry Approach

Farias

Costa

Martins

2023

Preprint

Self Cite

View full text Add to dashboard Cite

show abstract

“…Several quantum chemical descriptors have been widely used to characterize intramolecular and intermolecular interactions [18][19][20][21]. Conformational analysis is of interest in these flavonoids due to the large degree of freedom of these molecules, influenced mainly by hydrogen bonding interactions.…”

Section: Introductionmentioning

confidence: 99%

Comparative analysis of the reactivity of anthocyanidins, leucoanthocyanidins, and flavonols using a quantum chemistry approach

2023

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Anthocyanidins, leucoanthocyanidins, and flavonols are natural compounds mainly known due to their reported biological activities, such as antiviral, antifungal, anti-inflammatory activities, and antioxidant activity. In the present study, we performed a comparative structural, conformational, electronic, and nuclear magnetic resonance analysis of the reactivity of the chemical structure of primary anthocyanidins, leucoanthocyanidins, and flavonoids. We focused our analysis on the following molecular questions: (i) differences in cyanidin catechols ( +)-catechin, leucocyanidin, and quercetin; (ii) the loss of hydroxyl presents in the R1 radical of leucoanthocyanidin in the functional groups linked to C4 (ring C); and (iii) the electron affinity of the 3-hydroxyl group (R7) in the flavonoids delphinidin, pelargonidin, cyanidin, quercetin, and kaempferol. We show unprecedented results for bond critical point (BCP) of leucopelargonidin and leucodelphirinidin. The BCP formed between hydroxyl hydrogen (R2) and ketone oxygen (R1) of kaempferol has the same degrees of covalence of quercetin. Kaempferol and quercetin exhibited localized electron densities between hydroxyl hydrogen (R2) and ketone oxygen (R1). Global molecular descriptors showed quercetin and leucocyanidin are the most reactive flavonoids in electrophilic reactions. Complementary, anthocyanidins are the most reactive in nucleophilic reactions, while the smallest gap occurs in delphinidin.Local descriptors indicate that anthocyanidins and flavonols are more prone to electrophilic attacks, while in leucoanthocyanidins, the most susceptible to attack are localized in the ring A. The ring C of anthocyanidins is more aromatic than the same found in flavonols and leucoanthocyanidins. Methods For the analysis of the molecular properties, we used the DFT to evaluate the formation of the covalent bonds and intermolecular forces. CAM-B3LYP functional with the def2TZV basis set was used for the geometry optimization. A broad analysis of quantum properties was performed using the assessment of the molecular electrostatic potential surface, electron localization function, Fukui functions, descriptors constructed from frontier orbitals, and nucleus independent chemical shift.

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In silico study of tacrine and acetylcholine binding profile with human acetylcholinesterase: docking and electronic structure

Nascimento

Martins

2022

J Mol Model

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Investigation on the interaction behavior of afatinib, dasatinib, and imatinib docked to the BCR-ABL protein

Cited by 5 publications

References 47 publications

Comparative Analysis of the Reactivity of Anthocyanidins, Leucoanthocyanidins, and Flavonols using a Quantum Chemistry Approach

Comparative Analysis of the Reactivity of Anthocyanidins, Leucoanthocyanidins, and Flavonols using a Quantum Chemistry Approach

Comparative analysis of the reactivity of anthocyanidins, leucoanthocyanidins, and flavonols using a quantum chemistry approach

In silico study of tacrine and acetylcholine binding profile with human acetylcholinesterase: docking and electronic structure

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