Some halogenated anticancer agents, role of halide (-X) and their interaction mechanism with AT/GC base pairs: A computational study

Ahmed, Benzir; Barukial, Pratyashee; Bezbaruah, Bipul

doi:10.1016/j.jics.2023.101027

Cited by 1 publication

(3 citation statements)

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“…Later studies on 5FU interaction with DNA base pairs using quantum chemical tools reveal that the 5FU–GC complexes are more stable than the 5FU–AT complex . Recently, halogen-based anticancer agents with intercalating and groove-binding properties with DNA nucleobases were studied using the DFT method . Very recently, Rezaei-Sameti and Iraji Borojeni studied the interaction of 5FU with nucleobases using DFT and TD-DFT methods …”

Section: Introductionmentioning

confidence: 99%

“…32 Recently, halogen-based anticancer agents with intercalating and groove-binding properties with DNA nucleobases were studied using the DFT method. 33 Very recently, Rezaei-Sameti and Iraji Borojeni studied the interaction of 5FU with nucleobases using DFT and TD-DFT methods. 34 Although there are studies on the adsorption of 5FU drugs on nucleobases and nucleobase pairs, the majority of these studies mainly focus on the energies of absorption.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Unveiling the Intermolecular Interactions between Drug 5-Fluorouracil and Watson–Crick/Hoogsteen Base Pairs: A Computational Analysis

Venkataramanan,

Suvitha,

Sahara

2024

ACS Omega

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The adsorption of 5-fluorouracil (5FU) on Watson–Crick (WC) base pairs and Hoogsteen (HT) base pairs has been studied using the dispersion-corrected density functional theory (DFT). The adsorption, binding energy, and thermochemistry for the drug 5FU on the WC and HT base pairs were determined. The most stable geometries were near planar geometry, and 5FU has a higher preference for WC than HT base pairs. The adsorption energies of 5FU on nucleobase pairs are consistently higher than pristine nucleobase pairs, indicating that nucleobase pair cleavage is less likely during the adsorption of the 5FU drug. The enthalpy change for the formation of 5FU–DNA base pairs is higher than that for the formation of 5FU–nucleobases and is enthalpy-driven. The E gap of AT base pairs is higher, suggesting that their chemical reactivity toward further reaction would be less than that of GC base pairs. The electron density difference (EDD) analysis shows a significant decrease in electron density in aromatic regions on the purine bases (adenine/guanine) compared to the pyrimidine bases. The MESP diagram of the stable 5FU–nucleobase pair complexes shows a directional interaction, with the positive regions in a molecule interacting with the negative region of other molecules. The atoms in molecule analysis show that the ρ(r) values of CO···H–N are higher than those of N···H/N–H···O. The N···H intermolecular bonds between the base pair/drug and nucleobases are weak, closed shell interactions and are electrostatic in nature. The noncovalent interaction analysis shows that several new spikes are engendered along with an increase in their strength, which indicates that the H-bonding interactions are stronger and play a dominant role in stabilizing the complexes. Energy decomposition analysis shows that the drug–nucleobase pair complex has a marginal increase in the electrostatic contributions compared to nucleobase pair complexes.

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Section: Introductionmentioning

confidence: 99%