DNA‐binding activity and cytotoxic and cell‐cycle arrest properties of some new coumarin derivatives: a multispectral and computational investigation

Khosravifar, Fariba; Dehghan, Gholamreza; Bidoki, Seyed Kazem; Mahdavi, Majid

doi:10.1002/bio.3702

Cited by 12 publications

(7 citation statements)

References 39 publications

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“…The alternation in the absorption spectra at maximum wavelength caused by interaction with small molecules plays an important role as it provides information about the ligand’s binding mode, which is either a groove binder or an intercalator. According to the recent research, enhancement in intensity or a red shift is observed when small molecules interact through groove binding mode, whereas intercalation of small molecules into the DNA base pairs imparts intensity reduction or a blue shift …”

Section: Resultsmentioning

confidence: 99%

Visible Light-Prompted Regioselective Synthesis of Novel 5-Aroyl/hetaroyl-2′,4-dimethyl-2,4′-bithiazoles as DNA- and BSA-Targeting Agents

Aggarwal,

Jain,

Dubey

et al. 2023

Biomacromolecules

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Organic transformations mediated by visible light have gained popularity in recent years as they are green, renewable, inexpensive, and clean and yield excellent products. The present study describes cyclo-condensation of 2-methylthiazole-4-carbothioamide with differently substituted α-bromo-1,3-diketones achieved by utilizing a white light-emitting diode (LED) (9W) to accomplish the regioselective synthesis of novel 5-aroyl/hetaroyl-2′,4-dimethyl-2,4′-bithiazole derivatives as DNA/bovine serum albumin (BSA)-targeting agents. The structure characterization of the exact regioisomer was achieved unequivocally by heteronuclear two-dimensional nuclear magnetic resonance (2D-NMR) spectroscopy [1H–13C] HMBC; [1H–13C] HMQC; and [1H–15N] HMBC. In silico toxicity studies indicated that the synthesized compounds exhibit low toxicity risks and adhere to the rules of oral bioavailability without any exception. Computational molecular modeling of the bithiazole derivatives with the dodecamer sequence of the DNA duplex and BSA identified 5-(4-chlorobenzoyl)-2′,4-dimethyl-2,4′-bithiazole 7g as the most suitable derivative that can interact effectively with these biomolecules. Furthermore, theoretical results concurred with the ex vivo binding mode of the 7g with calf thymus DNA (ct-DNA) and BSA through a variety of spectroscopic techniques, viz., ultraviolet–visible (UV–visible), circular dichroism (CD), steady-state fluorescence, and competitive displacement assay, along with viscosity measurements.

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Section: Resultsmentioning

confidence: 99%

Visible Light-Prompted Regioselective Synthesis of Novel 5-Aroyl/hetaroyl-2′,4-dimethyl-2,4′-bithiazoles as DNA- and BSA-Targeting Agents

Aggarwal,

Jain,

Dubey

et al. 2023

Biomacromolecules

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“…We undertook molecular docking using the DNA oligonucleotide 1DNE to investigate the mechanism that might allow the formation of DNA–PHMG-Cl complexes. 1DNE has been previously used in several studies to investigate the interaction of various ligands with DNA [ 39 , 40 , 41 ]. As we were interested in identifying PHMG-Cl interactions in both AT- and CG-rich regions, we modeled PHMG-Cl as a dimer following the approach used in studying DNA–PHMB dimer interactions [ 42 ].…”

Section: Resultsmentioning

confidence: 99%

eDNA Inactivation and Biofilm Inhibition by the PolymericBiocide Polyhexamethylene Guanidine Hydrochloride (PHMG-Cl)

Moshynets

Baranovskyi

Iungin

et al. 2022

IJMS

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The choice of effective biocides used for routine hospital practice should consider the role of disinfectants in the maintenance and development of local resistome and how they might affect antibiotic resistance gene transfer within the hospital microbial population. Currently, there is little understanding of how different biocides contribute to eDNA release that may contribute to gene transfer and subsequent environmental retention. Here, we investigated how different biocides affect the release of eDNA from mature biofilms of two opportunistic model strains Pseudomonas aeruginosa ATCC 27853 (PA) and Staphylococcus aureus ATCC 25923 (SA) and contribute to the hospital resistome in the form of surface and water contaminants and dust particles. The effect of four groups of biocides, alcohols, hydrogen peroxide, quaternary ammonium compounds, and the polymeric biocide polyhexamethylene guanidine hydrochloride (PHMG-Cl), was evaluated using PA and SA biofilms. Most biocides, except for PHMG-Cl and 70% ethanol, caused substantial eDNA release, and PHMG-Cl was found to block biofilm development when used at concentrations of 0.5% and 0.1%. This might be associated with the formation of DNA–PHMG-Cl complexes as PHMG-Cl is predicted to bind to AT base pairs by molecular docking assays. PHMG-Cl was found to bind high-molecular DNA and plasmid DNA and continued to inactivate DNA on surfaces even after 4 weeks. PHMG-Cl also effectively inactivated biofilm-associated antibiotic resistance gene eDNA released by a pan-drug-resistant Klebsiella strain, which demonstrates the potential of a polymeric biocide as a new surface-active agent to combat the spread of antibiotic resistance in hospital settings.

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“…We undertook molecular docking using the DNA oligonucleotide 1DNE to investigate the mechanism which might allow the formation of DNA -PHMG-Cl complexes. 1DNE has been previously used in several studies to investigate the interaction of various ligands with DNA [35][36][37]. As we were interested in identifying PHMG-Cl interactions in both AT and CG-rich regions, we modelled PHMG-Cl as a dimer following the approach used in studying DNA -PHMB dimer interactions [38].…”

Section: Dna Docking Assaymentioning

confidence: 99%

eDNA Inactivation and Biofilm Inhibition by the Polymeric Biocide Polyhexamethylene Guanidine Hydrochloride (PHMG-Cl)

Moshynets¹,

Baranovskyi²,

Iungin³

et al. 2021

Preprint

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The choice of effective biocides used for routine hospital practice should consider the role of disinfectants in the maintenance and development of local resistome and how they might affect antibiotic resistance gene transfer within the hospital microbial population. Currently, there is little understanding of how different biocides contribute to eDNA release that may contribute to gene transfer and subsequent environmental retention. Here we investigated how different biocides affected the release of eDNA from mature biofilms of two opportunistic model strains Pseudomonas aeruginosa ATCC 27853 (PA) and Staphylococcus aureus ATCC 25923 (SA) and contribute to the hospital resistome in the form of surface and water contaminants and dust particles. The effect of four groups of biocides including alcohols, hydrogen peroxide, quaternary ammonium compounds, and polymeric guanidines were evaluated using PA and SA biofilms. Most biocides, except for PHMG-Cl and 70% ethanol, caused substantial eDNA release and PHMG-Cl was found to block biofilm development when used at concentrations of 0.5% and 0.1%. This might be associated with the formation of DNA-PHMG-Cl complexes as PHMG-Cl is predicted to bind to AT base pairs by molecular docking assays. PHMG-Cl was found to bind high molecular DNA and plasmid DNA and continued to inactivate DNA on surfaces even after four weeks. PHMG-Cl also effectively inactivated biofilm-associated antibiotic resistance gene eDNA released by a pan-drug-resistant Klebsiella strain which demonstrates the potential of PHMG-Cl as a new surface-active agent to combat the spread of antibiotic resistance in hospital settings.

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DNA‐binding activity and cytotoxic and cell‐cycle arrest properties of some new coumarin derivatives: a multispectral and computational investigation

Cited by 12 publications

References 39 publications

Visible Light-Prompted Regioselective Synthesis of Novel 5-Aroyl/hetaroyl-2′,4-dimethyl-2,4′-bithiazoles as DNA- and BSA-Targeting Agents

Visible Light-Prompted Regioselective Synthesis of Novel 5-Aroyl/hetaroyl-2′,4-dimethyl-2,4′-bithiazoles as DNA- and BSA-Targeting Agents

eDNA Inactivation and Biofilm Inhibition by the PolymericBiocide Polyhexamethylene Guanidine Hydrochloride (PHMG-Cl)

eDNA Inactivation and Biofilm Inhibition by the Polymeric Biocide Polyhexamethylene Guanidine Hydrochloride (PHMG-Cl)

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