Deciphering the DNA-binding affinity, cytotoxicity and apoptosis induce as the anticancer mechanism of Bavachinin: An experimental and computational investigation

Dehkordi, Mahvash Farajzadeh; Farhadian, Sadegh; Abdolvand, Mohammad; Soureshjani, Ehsan Heidari; Rahmani, Babak; Darzi, Sina

doi:10.1016/j.molliq.2021.117373

Cited by 19 publications

(12 citation statements)

References 52 publications

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“…Generally, native Ct-DNA shows two distinct peaks, a positive peak at 275 nm due to DNA helicity and a negative peak at 245 nm due to π–π base stacking. 70 Figure 12 shows that compounds binding to DNA have only a significant result on a negative peak location of 245 nm and also a slight shift at 275 nm. The results demonstrate that the compounds 3a and 3h interact with Ct-DNA by intercalative mode, which in turn causes conformational alterations in the DNA structure.…”

Section: Results and Discussionmentioning

confidence: 99%

“…To explore the structural modification found throughout compound–DNA binding interaction, a CD spectrum of Ct-DNA was used without and with active compounds ( 3a , 3h ). Generally, native Ct-DNA shows two distinct peaks, a positive peak at 275 nm due to DNA helicity and a negative peak at 245 nm due to π–π base stacking Figure shows that compounds binding to DNA have only a significant result on a negative peak location of 245 nm and also a slight shift at 275 nm.…”

Section: Results and Discussionmentioning

confidence: 99%

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Design and Synthesis of Carbothioamide/Carboxamide-Based Pyrazoline Analogs as Potential Anticancer Agents: Apoptosis, Molecular Docking, ADME Assay, and DNA Binding Studies

et al. 2022

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To discover anticancer drugs with novel structures and expand our research scope, pyrazoline derivatives ( 3a – 3l ) were designed and synthesized through cyclization of chalcones with thiosemicarbazide/semicarbazide in CH 3 COOH as a solvent. All newly synthesized pyrazoline derivatives were fully characterized using several spectroscopic experiments such as 1 H, 13 C NMR, FT-IR spectroscopy, and mass analysis. By HPLC , the purity of all analogs was found above 95% and both lead compounds ( 3a and 3h ) were also validated by HRMS . Anticancer activity of synthesized pyrazoline derivatives ( 3a – 3l ) was investigated by the MTT assay against the human lung cancer cell (A549), human cervical cancer cell (HeLa), and human primary normal lung cells (HFL-1). Staurosporine (STS) was used as a standard drug. The anticancer results showed that two potent analogs 3a and 3h exhibit excellent activity against A549 (IC 50 = 13.49 ± 0.17 and 22.54 ± 0.25 μM) and HeLa cells (IC 50 = 17.52 ± 0.09 and 24.14 ± 0.86 μM) and low toxicity against the HFL-1 (IC 50 = 114.50 ± 0.01 and 173.20 ± 10 μM). The flow cytometry was further used to confirm the anticancer activity of potent derivatives against the A549 cancer cell line. DNA binding interaction of anticancer agents 3a and 3h with Ct-DNA has been carried out by absorption, fluorescence, EtBr (dye displacement assay), circular dichroism, cyclic voltammetry and time-resolved fluorescence, which showed noncovalent binding mode of interaction. Anticancer activity of both lead compounds ( 3a and 3h ) may be attributed to DNA binding. The evaluation of the antioxidant potential of pyrazoline analogs 3a and 3h by 2,2-diphenyl-1-picrylhydrazyl free radical showed promising antioxidant activity with IC 50 values of 0.132 ± 0.012 and 0.215 ± 0.025 μg/mL, respectively. In silico molecular docking of pyrazoline derivatives was also performed using autodock vina software against the DNA hexamer with PDB ID: 1Z3F and ADMET properties to explore their best hits.

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Section: Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

Design and Synthesis of Carbothioamide/Carboxamide-Based Pyrazoline Analogs as Potential Anticancer Agents: Apoptosis, Molecular Docking, ADME Assay, and DNA Binding Studies

et al. 2022

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“…In this case, higher temperature values result in faster diffusion and a higher K sv value. Static quenching results from forming a stable non‐fluorescent complex between the fluorophore and the quencher [11,27] . Hence, higher temperature leads to reduced complex stability and lower values for K sv .…”

Section: Resultsmentioning

confidence: 99%

“…binders. [11,12,27] Based on the results, it is most likely to conclude that the binding mode is groove binding.…”

Section: Chemistryselectmentioning

confidence: 99%

“…In addition, interactions between small molecules and DNA can disrupt the transcription or repression of specific genes, offering diverse options for various downstream processes with biological or medical implications. [5,7,8,[10][11][12] As a result, studying the interaction between DNA and small molecules can help us better understand how they interact and supply more context for developing new DNA-targeted therapies. Small molecules can bind to DNA in three ways that are non-covalent: intercalation, groove binding, and electrostatic binding.…”

Section: Introductionmentioning

confidence: 99%

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DNA‐Binding Studies of Ofloxacin Using a Series of Spectroscopic, Electrochemical Techniques and in Silico Approaches

Çeşme¹,

Özaltay²

2022

ChemistrySelect

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Ofloxacin (OFL), a quinolone antibiotic, shows a bactericidal effect by inhibiting the DNA gyrase enzyme in bacteria. In addition to its use in various infections has a wide range of benefits from urinary system disorders to pneumonia and bronchitis. DNA is the main molecular target for many small molecules of therapeutic importance. In this article, the interaction between OFL and fsDNA (fish sperm DNA) is reported using a combination of biophysical (spectroscopic and electrochemical) and in silico techniques (molecular docking and molecular dynamics). The interaction and complex formation were studied using UV-visible and steady-state fluorescence spectroscopy. Ethidium bromide (EtBr), Rhodamine B (RB) competitive displacement, potassium iodide quenching, and ionic strength assays confirmed the binding mode between OFL and DNA via minor groove binding. Thermodynamic parameters at various temperatures supported the enthalpically driven, exothermic, and spontaneous reaction between OFL and fsDNA. It was found that hydrogen bond interaction and van der Waals forces play a dominant role in forming the complex form. DNA melting experiments corroborated these findings. In-silico molecular docking and molecular dynamics simulation studies revealed the interaction mode, major stabilizing forces, and the nucleotide sequences OFL binds and dock into the GC-rich region of the DNA minor groove, confirming the in vitro experiment results.

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Evidence for paraquat-pepsin interaction: In vitro and silico study

Farokhvand,

Shareghi,

Farhadian

2024

Chemosphere

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Deciphering the DNA-binding affinity, cytotoxicity and apoptosis induce as the anticancer mechanism of Bavachinin: An experimental and computational investigation

Cited by 19 publications

References 52 publications

Design and Synthesis of Carbothioamide/Carboxamide-Based Pyrazoline Analogs as Potential Anticancer Agents: Apoptosis, Molecular Docking, ADME Assay, and DNA Binding Studies

Design and Synthesis of Carbothioamide/Carboxamide-Based Pyrazoline Analogs as Potential Anticancer Agents: Apoptosis, Molecular Docking, ADME Assay, and DNA Binding Studies

DNA‐Binding Studies of Ofloxacin Using a Series of Spectroscopic, Electrochemical Techniques and in Silico Approaches

Evidence for paraquat-pepsin interaction: In vitro and silico study

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