DNA Interaction Studies and In Vitro Cytotoxicity of Newly Synthesized Steroidal Imidazolidinones

Dar, Ayaz Mahmood; Gatoo, Manzoor Ahmad; Ahmad, Ajaz; Ahmad, Mir Shabeer; Najar, Muzaffar Hussain; Shamsuzzaman, _

doi:10.1007/s10895-015-1628-8

Cited by 7 publications

(3 citation statements)

References 45 publications

(63 reference statements)

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“…The cytotoxic activity of the complexes can be due to the presence of N,N‐chelating ligands, which increase the solubility and introduce electrostatic interactions in the complexes . The electrostatic interaction of the complexes with DNA can induce deleterious effects on cell cycle and growth . Furthermore, the SI values were calculated by comparing the cytotoxic activity (IC 50 ) of the complexes against each cancer cell type with that of the normal cell line to evaluate the selective effect of the tested complexes against cancer cells .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization and biological activities of two novel orthopalladated complexes: Interactions with DNA and bovine serum albumin, antitumour activity and molecular docking studies

Karami

Hashemi

Lipkowski

et al. 2017

Applied Organom Chemis

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[Pd(L 1 )(C,N)]CF 3 SO 3 and [Pd(L 2 )(C,N)]CF 3 SO 3 (L 1 = 2,2′-bipyridine, L 2 = 1,10-phenanthroline and C,N = benzylamine) novel orthopalladated complexes have been synthesized and characterized using various techniques. The binding of the complexes with native calf thymus DNA (CT-DNA) was monitored using UVvisible absorption spectrophotometry, fluorescence spectroscopy and thermal denaturation studies. Our results indicate that these complexes can strongly bind to CT-DNA via partial intercalative mode. In addition, fluorescence spectrometry of bovine serum albumin (BSA) with the complexes shows that the fluorescence quenching mechanism of BSA is a static process. The results of site-competitive replacement experiments with specific site markers clearly indicate that the complexes bind to site I of BSA. Notably, the complexes exhibit significant in vitro cytotoxicity against two human cancer cell lines (Jurkat and MCF-7) with IC 50 values varying from 37 to 53 μM. Finally, a molecular docking experiment effectively proves the binding of the Pd(II) complexes to DNA and BSA.

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Section: Resultsmentioning

confidence: 99%

Synthesis, characterization and biological activities of two novel orthopalladated complexes: Interactions with DNA and bovine serum albumin, antitumour activity and molecular docking studies

Karami

Hashemi

Lipkowski

et al. 2017

Applied Organom Chemis

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“…Metronidazole and nitrofurantoin for instance are commercial imidazole-based antibiotics which target DNA and modify its structure. Many other imidazole and thiazolidinone based molecules reported in literature have shown strong affinity towards DNA thereby inhibiting its function [20][21][22]. Encouraged by these reports, we decided to probe DNA as possible target for the synthesized molecules.…”

Section: Introductionmentioning

confidence: 99%

Rationale design and synthesis of some novel imidazole linked thiazolidinone hybrid molecules as DNA minor groove binders

War

Srivastava

2020

Eur J Chem

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A new series of imidazole linked thiazolidinone hybrid molecules was designed and subsequently synthesized through a feasible, three step reaction protocol. The structures of these molecules were established using FT-IR, 1H NMR, 13C NMR and HRMS techniques. In vitro susceptibility tests against some Gram positive (Staphylococcus aureus and Bacillus subtilis) and Gram negative bacteria (Escherichia coli and Pseudomonas aeruginosa) exhibited broad spectrum potency of the molecules. The most potent molecule (S2A7) amongst the screened molecules, showed minimum inhibitory concentration (MIC) value not less than 2.0 µg/mL which was at par with the reference drug Streptomycin. Structure activity relationships revealed nitro and chloro groups being crucial for bioactivity when present at meta position of arylidene ring in 3-(3-(imidazol-1-yl)propyl)-5-(benzylidene)-2-(phenylimino)thiazolidin-4-one. Deoxyribonucleic acid (DNA)and bovine serum albumin (BSA) binding studies for S2A7 under simulated physiological pH were probed using UV-Visible, fluorescence quenching, gel electrophoresis and molecular docking techniques. These studies established that S2A7 has strong binding affinity towards DNA and binds at the minor groove of DNA with binding constant (Kb) of 0.1287×102 L/mol. Molecular docking simulations of S2A7 with DNA and BSA predicted binding affinity of -9.2 and -7.2 kcal/mol, respectively. Van der Waals forces and hydrogen bonding interactions were predicted as the main forces of interaction. With DNA, S2A7 exhibited specific binding affinity towards adenine-thiamine base pairs. The compound S2A7 forms a stable complex with BSA by binding at subdomain IIIA implying high bio-distribution of the compound.

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“…Metronidazole and nitrofurantoin are commercial imidazole‐based antibiotics that target DNA and modify its structure. Synthetic imidazole‐ and thiazolidinone‐based molecules available in literature have shown strong affinity towards DNA thereby inhibiting its function . Encouraged by these reports we decided to probe DNA as a possible target for the synthesized molecules.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and DNA‐binding study of imidazole linked thiazolidinone derivatives

War

Srivastava

2016

Luminescence

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A novel series of imidazole-linked thiazolidinone hybrid molecules were designed and synthesized through a feasible synthetic protocol. The molecules were characterized with Fourier transform infrared (FT-IR), H nuclear magnetic resonance (NMR), C NMR and high-resolution mass spectrometry (HRMS) techniques. In vitro susceptibility tests against Gram-positive (S. aureus and B. subtilis) and Gram-negative bacteria (E. coli and P. aeruginosa) gave highly promising results. The most active molecule (3e) gave a minimal inhibitory concentration (MIC) value of 3.125 μg/mL which is on par with the reference drug streptomycin. Structure-activity relationships revealed activity enhancement by nitro and chloro groups when they occupied meta position of the arylidene ring in 2-((3-(imidazol-1-yl)propyl)amino)-5-benzylidenethiazolidin-4-ones. DNA-binding study of the most potent molecule 3e with salmon milt DNA (sm-DNA) under simulated physiological pH was probed with UV-visible absorption, fluorescence quenching, gel electrophoresis and molecular docking techniques. These studies established that compound 3e has a strong affinity towards DNA and binds at DNA minor groove with a binding constant (K ) 0.18 × 10 L mol . Molecular docking simulations predicted strong affinity of 3e towards DNA with a binding affinity (ΔG) -8.5 kcal/mol. Van der Waals forces, hydrogen bonding and hydrophobic interactions were predicted as the main forces of interaction. The molecule 3e exhibited specific affinity towards adenine-thiamine base pairs. Copyright © 2016 John Wiley & Sons, Ltd.

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DNA Interaction Studies and In Vitro Cytotoxicity of Newly Synthesized Steroidal Imidazolidinones

Cited by 7 publications

References 45 publications

Synthesis, characterization and biological activities of two novel orthopalladated complexes: Interactions with DNA and bovine serum albumin, antitumour activity and molecular docking studies

Synthesis, characterization and biological activities of two novel orthopalladated complexes: Interactions with DNA and bovine serum albumin, antitumour activity and molecular docking studies

Rationale design and synthesis of some novel imidazole linked thiazolidinone hybrid molecules as DNA minor groove binders

Synthesis and DNA‐binding study of imidazole linked thiazolidinone derivatives

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