Molecular docking, QSAR properties and DNA/BSA binding, anti-proliferative studies of 6-methoxy benzothiozole imine base and its metal complexes

Ravi, Malini; Ushaiah, B.; Prasad, Ch. Kishan; Kunche, Sudeepa; Ravindar, P.; Sunitha, S. N. T.; Devi, Ch. Sarala

doi:10.1080/07391102.2019.1647878

Cited by 15 publications

(3 citation statements)

References 55 publications

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“…The following relation (eq ) was employed to determine the relative viscosities where η o and η refer to the viscosities of DNA in the absence and presence of 3i , respectively, t DNA is the average flow time of pure DNA, t complex refers to the average flow time of DNA in the presence of 3i at varying concentration, and t o is the flow time of Tris-HCl buffer . The data thus obtained were plotted as the ratio of [ 3i ]/[DNA] versus (η/η o ) 1/3 .…”

Section: Methodsmentioning

confidence: 98%

Visible-Light-Prompted Synthesis and Binding Studies of 5,6-Dihydroimidazo[2,1-b]thiazoles with BSA and DNA Using Biophysical and Computational Methods

et al. 2022

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Fused heterocyclic systems containing a bridgehead nitrogen atom have emerged as imperative pharmacophores in the design and development of new drugs. Among these heterocyclic moieties, the imidazothiazole scaffold has long been used in medicinal chemistry for the treatment of various diseases. In this study, we have established a simplistic and environmentally safe regioselective protocol for the synthesis of 5,6-dihydroimidazo[2,1-b]thiazole derivatives from easily available reactants. The reaction proceeds through in situ formation of the α-bromodiketones ensuing trap with imidazolidine-2-thione to provide these versatile bicyclic heterocycles in excellent yields. The synthesized compounds were screened through the molecular docking approach for the most stable complex formation with bovine serum albumin (BSA) and calf thymus deoxyribonucleic acid (ctDNA). The selected compound was further studied using ex vivo binding studies, which revealed moderate interactions with BSA and ctDNA. The binding studies were performed using biophysical approaches including UV–visible spectroscopy, steady-state fluorescence, circular dichroism (CD), and viscosity parameters.

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Section: Methodsmentioning

confidence: 98%

Visible-Light-Prompted Synthesis and Binding Studies of 5,6-Dihydroimidazo[2,1-b]thiazoles with BSA and DNA Using Biophysical and Computational Methods

et al. 2022

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“…This is the case of studies focused on the determination of binding characteristics of potential ligands with albumins . In this regard, bovine serum albumin (BSA) has been applied in numerous studies involving different ligands; and fluorescence quenching is the usual physicochemical approach to study these interactions . BSA is used as a model protein to study the interaction between drugs and albumins .…”

Section: Introductionmentioning

confidence: 99%

Entropy‐driven binding of octyl gallate in albumin: Failure in the application of temperature effect to distinguish dynamic and static fluorescence quenching

Bertozo

Fernandes

Yoguim

et al. 2020

J of Molecular Recognition

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Fluorescence quenching is widely used to obtain association constants between proteins and ligands. This methodology is based on assumption that ground-state complex between protein and ligand is responsible for quenching. Here, we call the attention about the risk of using the temperature criterion for decision of applying or not fluorescence quenching data to measure association constants. We demonstrated that hydrophobic effect can be the major force involved in the interaction and, as such, superposes the well-established rationalization that host/guest com-

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“…[ 55 ] It is observed that the complexes C3 , C7 , C4 , and C8 with 4‐phenyl/napthyl substituted thiosemicarbazone ligand show high binding affinities due to the additional planar aromatic rings present in their ligand scaffolds which facilitate hydrophobic interactions with the nucleobases. [ 56 ] C1 , C5 , C2 , and C6 with 4‐hydrogen/methyl substituted thiosemicarbazone ligand display low binding affinities due to no additional planar aromatic rings. The standard Gibb's free energy for DNA binding was calculated using the following relation.…”

Section: Resultsmentioning

confidence: 99%

Organoruthenium (II) complexes featuring pyrazole‐linked thiosemicarbazone ligands: Synthesis, DNA/BSA interactions, molecular docking, and cytotoxicity studies

Khanvilkar

Dash

Banerjee

et al. 2021

Applied Organom Chemis

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A series of pyrazol-derived thiosemicarbazone ligands (L1-L4) were synthesized and reacted with [Ru(p-cymene)(μ-Cl)Cl] 2 to yield a series of "piano-stool"-type binuclear ruthenium (II)-arene-thiosemicarbazone complexes (C1-C8) of the general type [(Ru(η 6 -p-cym)L) 2 (μ-im/azpy)] Cl 1-2 (L = diphenylpyrazole thiosemicarbazone; cym = p-cymene; im = imidazole; azpy = 4,4 0 -azopyridine). The thiosemicarbazone ligands act as N and S donors binding to the Ru(II) center via the imine nitrogen and the thione sulfur atoms. The complexes were characterized by NMR, FTIR, UV-Vis spectroscopy, and ESI + mass spectrometry. The binding of the complexes to calf thymus deoxyribonucleic acid (CT-DNA) and bovine serum albumin (BSA) was evaluated, and it has been established that the binuclear complexes have good binding efficacies with DNA (K b = 10 4 -10 5 M À1 ) and BSA (K a = 10 5 -10 6 M À1 ). This is attributed to the arene moieties present in the ligands of the complexes that can have hydrophobic interactions with DNA/BSA. Ethidium bromide (EB) displacement studies and DNA viscosity measurements revealed intercalative interaction of the complexes with DNA. Static interaction of the complexes with BSA was revealed by fluorescence quenching studies. Molecular docking studies confirmed base stacking, H-bonding, and hydrophobic interactions with the biomolecules. In vitro antiproliferative studies of the complexes affirmed that the complexes are cytotoxic towards the HeLa (human cervical cancer) cell line with IC 50 values in range of 17.3-41.3 μM. K E Y W O R D S binuclear ruthenium (II) complexes, DNA/BSA binding interactions, HeLa human cervical carcinoma, pyrazole-derived thiosemicarbazone

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Molecular docking, QSAR properties and DNA/BSA binding, anti-proliferative studies of 6-methoxy benzothiozole imine base and its metal complexes

Cited by 15 publications

References 55 publications

Visible-Light-Prompted Synthesis and Binding Studies of 5,6-Dihydroimidazo[2,1-b]thiazoles with BSA and DNA Using Biophysical and Computational Methods

Visible-Light-Prompted Synthesis and Binding Studies of 5,6-Dihydroimidazo[2,1-b]thiazoles with BSA and DNA Using Biophysical and Computational Methods

Entropy‐driven binding of octyl gallate in albumin: Failure in the application of temperature effect to distinguish dynamic and static fluorescence quenching

Organoruthenium (II) complexes featuring pyrazole‐linked thiosemicarbazone ligands: Synthesis, DNA/BSA interactions, molecular docking, and cytotoxicity studies

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