Computational and experimental insight into antituberculosis agent, (E)-benzyl-2-(4-hydroxy-2-methoxybenzylidene) hydrazinecarbodithioate: ADME analysis

Pal, Tarun Kumar; Mumit, Mohammad Abdul; Hossen, Jewel; Paul, Subrata; Alam, Md. Ashraful; Islam, M. A. A. A. A.; Sheikh, Md. Chanmiya

doi:10.1016/j.heliyon.2021.e08209

Cited by 8 publications

(3 citation statements)

References 25 publications

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“…The energy gap (HOMO–LUMO) of the PS1 compound is 0.1140, and PS2 has an energy gap of 0.1139, almost identical values in both cases as shown in Figures S1 and S2 (Supporting Information). In this scenario, based on the report, the chemical reactivity of the compounds is also improved, which is directly related to the HOMO–LUMO energy gap (Δ E HOMO–LUMO ), which is smaller than those of S -benzyldithiocarbazate-based Schiff bases (2.43 eV), highlighting that the properties of our developed compounds are improved for multiple applications. In this context, it could be suggested that both PS1 and PS2 have similar reaction-promoting media in chemical reactions.…”

Section: Resultsmentioning

confidence: 75%

“…Based on this previous report, 13 , 14 we synthesized the new compounds PS1 and PS2, which may have more useful functions against bacterial infections. Based on molecular docking studies, the binding free energy for S -benzyldithiocarbazate-based Schiff bases 15 with proteins is higher than the case of our developed compound, the binding free energy for PS compounds; so, the binding affinity is stronger than that of the SBDTC Schiff base, the performance of our developed compound is finally active, and the binding affinity character with the chemical reactivity ratio is also improved based on the HOMO–LUMO energy gap analysis (Δ E HOMO–LUMO ). Based on these facts, we extend our studies and use our analogy to protein-drug interactions, which gives a clear picture of the interaction with the human body.…”

Section: Introductionmentioning

confidence: 99%

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Integrated Approach to Interaction Studies of Pyrene Derivatives with Bovine Serum Albumin: Insights from Theory and Experiment

et al. 2022

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This work aimed to investigate the interaction of bovine serum albumin with newly synthesized potent new pyrene derivatives (PS1 and PS2), which might prove useful to have a better antibacterial character as found for similar compounds in the previous report [ Bioconjugate Chemistry 2014 12 2269 2284 ]. However, to date, binding studies with plasma protein are still unknown. Steady-state fluorescence spectroscopy and lifetime fluorescence studies show that the static interaction binding mode and binding constants of PS1 and PS2 are 7.39 and 7.81 [ K b × 10 5 (M –1 )], respectively. The experimental results suggest that hydrophobic forces play a crucial role in interacting pyrene derivatives with BSA protein. To verify this, molecular docking and molecular dynamics simulations were performed to predict the nature of the interaction and the dynamic behavior of the two compounds in the BSA complex, PS1 and PS2, under physiological conditions of pH = 7.1. In addition, the free energies of binding for the BSA-PS1 and BSA-PS2 complexes were estimated at 300 K based on the molecular mechanics of the Poisson–Boltzmann surface (MMPBSA) with the Gromacs package. PS2 was found to have a higher binding affinity than PS1. To determine the behavior of the orbital transitions in the ground state geometry, we found that both compounds have similar orbital transitions from HOMO–LUMO via π → π* and HOMO–1–LUMO+1 via n → π*, which was included in the FMO analysis. A cytotoxicity study was performed to determine the toxicity of the compounds. Based on the MD study, the stability of the compounds with BSA and the dynamic binding modes were further revealed, as well as the nature of the binding force components involved and the important residues involved in the binding process. From the binding energy analysis, it can be assumed that PS2 may be more active than PS1.

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Section: Resultsmentioning

confidence: 75%

Section: Introductionmentioning

confidence: 99%

Integrated Approach to Interaction Studies of Pyrene Derivatives with Bovine Serum Albumin: Insights from Theory and Experiment

et al. 2022

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“…The blue region corresponds to a positive-charge center (a nucleophilic zone), while the red region corresponds to a negative-charge density (an electrophilic zone). Neutral electrostatic zones are denoted by the color green [ 45 ]. The Schiff base showed the most negative zones on the oxygen atoms (O21, O22, O30) of the sulfamethoxazole portion and the nitrogen atom (N9) of the azomethine group ( Fig.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, quantum chemical calculations, in silico and in vitro bioactivity of a sulfonamide-Schiff base derivative

Abedin,

Pal,

Uddin

et al. 2024

Heliyon

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Investigation on synthesized sulfonamide Schiff base with DFT approaches and in silico pharmacokinetic studies: Topological, NBO, and NLO analyses

Abedin,

Pal,

Chanmiya Sheikh

et al. 2024

Heliyon

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Computational and experimental insight into antituberculosis agent, (E)-benzyl-2-(4-hydroxy-2-methoxybenzylidene) hydrazinecarbodithioate: ADME analysis

Cited by 8 publications

References 25 publications

Integrated Approach to Interaction Studies of Pyrene Derivatives with Bovine Serum Albumin: Insights from Theory and Experiment

Integrated Approach to Interaction Studies of Pyrene Derivatives with Bovine Serum Albumin: Insights from Theory and Experiment

Synthesis, quantum chemical calculations, in silico and in vitro bioactivity of a sulfonamide-Schiff base derivative

Investigation on synthesized sulfonamide Schiff base with DFT approaches and in silico pharmacokinetic studies: Topological, NBO, and NLO analyses

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