Spectroscopic investigation (FT-IR, FT-Raman), HOMO-LUMO, NBO, and molecular docking analysis of N -ethyl- N -nitrosourea, a potential anticancer agent

Singh, Priyanka; Islam, S. S.; Ahmad, Hilal; Prabaharan, A.

doi:10.1016/j.molstruc.2017.10.012

Cited by 35 publications

(19 citation statements)

References 28 publications

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“…The high value of E HOMO and low value of E LUMO show that the compounds are highly reactive with nucleophilic molecules. The energy gap ΔE depends on the van der Waals interaction between molecules and its value could be correlated with the biological activity of the compounds [ 62 , 63 ]. The hybrids 1 , 5 , 9 , and 13 are characterized by the lowest chemical hardness and the highest negative value of chemical potential, which means they are comparatively soft with high polarizability compared with other compounds in this series.…”

Section: Resultsmentioning

confidence: 99%

Lipophilicity, Pharmacokinetic Properties, and Molecular Docking Study on SARS-CoV-2 Target for Betulin Triazole Derivatives with Attached 1,4-Quinone

et al. 2021

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A key parameter in the design of new active compounds is lipophilicity, which influences the solubility and permeability through membranes. Lipophilicity affects the pharmacodynamic and toxicological profiles of compounds. These parameters can be determined experimentally or by using different calculation methods. The aim of the research was to determine the lipophilicity of betulin triazole derivatives with attached 1,4-quinone using thin layer chromatography in a reverse phase system and a computer program to calculate its theoretical model. The physiochemical and pharmacokinetic properties were also determined by computer programs. For all obtained parameters, the similarity analysis and multilinear regression were determined. The analyses showed that there is a relationship between structure and properties under study. The molecular docking study showed that betulin triazole derivatives with attached 1,4-quinone could inhibit selected SARS-CoV-2 proteins. The MLR regression showed that there is a correlation between affinity scoring values (ΔG) and the physicochemical properties of the tested compounds.

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Section: Resultsmentioning

confidence: 99%

Lipophilicity, Pharmacokinetic Properties, and Molecular Docking Study on SARS-CoV-2 Target for Betulin Triazole Derivatives with Attached 1,4-Quinone

et al. 2021

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“…Hence, the closer the HOMO energy level of guanine (biological target) to the LUMO energy level of the electrophile [toxicants or drugs like N -ethyly- N -nitrosourea (ENU) or N -methyl- N -nitrosourea (MNU)], the higher will be the relative reactivity of the toxicant. For example, LUMO of ENU (−2.309 eV) is lower compared to LUMO of MNU (−0.681 eV) . Therefore, ENU can form an adduct with guanine more readily compared to MNU, which is also observed experimentally. ,, The LUMO energy level is also useful in predicting the mutagenicity of the guanine adduct.…”

Section: Resultsmentioning

confidence: 97%

Detecting DNA Methylation Using Surface-Enhanced Raman Spectroscopy

Hasan

Chang

et al. 2018

J. Phys. Chem. C

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Among all of the epigenetic events that are responsible for various diseases such as cancer, lupus, and several birth defects, DNA methylation is one of the crucial ones. It occurs because of the alkylation of various bases. These modifications of genes carried through altered creations of proteins ultimately lead to various diseases. For example, a vital cause behind canine lymphoma is found to be DNA methylation in the guanine base. In this work, we analyzed the methylated and nonmethylated guanine structure with the assistance of surface-enhanced Raman spectroscopy and density functional theory (DFT). Because of their vulnerability for causing DNA methylation, the N7 and O6 positions of the guanine structure were the positions of interest with the addition of various adducts such as methyl, hydroxyethyl, and deuterated methyl groups. To distinguish the methylated samples from the nonmethylated ones, principal component analysis was performed, and the same analysis was used to distinguish their methylated positions and added adducts. The experimental results were then explained by structure optimization and frequency calculation of the molecules based on DFT calculations. To understand the charge distribution and detect the possible locations of alkylation of DNA bases, electrostatic potential, highest occupied molecular orbital, and lowest unoccupied molecular orbital for each of the molecules were analyzed, and the reactivity was discussed in the light of electronic structure calculations. The results presented in this study demonstrate a potential label-free technique to examine epigenetic modification of DNA.

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“…The experimental values are taken from similar C-Cl bond length is observed in 1.8200 Å by Vanasundari et al[19]. The magnitude of the length N-N bond is described in 1.38 Å assigned by Priyanka Singh et al[20] and is found in the center to be 1.3963/1.3946Å for the CPTBN molecule. The angle formed between two adjacent bonds shows the internal bond angles N 25 -C 42 -N 43 , C 1 -N 24 -N 25 , C 39 -C 40 -O 44 and N 43 -C 40 -O 44 are found around the range to be 123 , 108 , 124 , and 122 in the CPTBN respectively.…”

mentioning

confidence: 74%

“…The CH 2 asymmetric stretching modes are computed at 2955, 2915 cm À1 for B3LYP/6-31G and 2953, 2912 cm À1 for B3LYP/6-311G, but no peak can be seen in this region on a recorded spectrum. The bending mode, which involves a hydrogen atom attached to the core carbon, is between 1450 and 875 cm À1 , although there is a coupling of vibration modes that generally occurs, especially CH 2 scissoring and rocking, which are more sensitive to the molecular Ref [17,18,19,20].…”

Section: Ch 2 Vibrationsmentioning

confidence: 99%