DNA groove binder and significant cytotoxic activity on human colon cancer cells: Potential of a dimeric zinc (II) phthalocyanine derivative

Batibay, Gonul S.; Karaoğlan, Gülnur Keser; Köse, Gülşah Gümrükçü; Kazancioglu, Elif Ozcelik; Metin, Eyup; Kalındemirtaş, Ferdane Danışman; Kuruca, Serap Erdem; Arsu, Nergis

doi:10.1016/j.bpc.2023.106974

Cited by 2 publications

(6 citation statements)

References 51 publications

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“…These fluorescent dye tests were conducted to confirm how a small molecule binds to natural polymeric DNA. Fluorescent active dyes having documented DNA binding mechanisms are introduced. , For instance, ethidium bromide attaches to DNA through an intercalative association, while rhodamine-B binds via a groove binding mode. , The most common groove binding markers and intercalative binding markers are rhodamine-B and ethidium bromide, respectively. , Rhodamine-B and ethidium bromide were utilized as binding indicators in competitive binding studies to even further confirm the binding mechanism of YH with CT-DNA . The shift in the emission spectra of such dye–DNA complex formation is monitored when the dye–DNA complex would be enabled to bind to YH; its binding mechanism needs to be determined.…”

Section: Resultsmentioning

confidence: 99%

“…Information regarding the drug′s interaction with DNA upon binding is revealed through molecular modeling study . To understand the binding interactions, docking of the lowest-energy conformer of YH was performed with CT-DNA (PDB-ID: 1BNA) using the AutoDock 1.5.6 program. , …”

Section: Resultsmentioning

confidence: 99%

“…Fluorescent active dyes having documented DNA binding mechanisms are introduced. 50,69 For instance, ethidium bromide attaches to DNA through an intercalative association, while rhodamine-B binds via a groove binding mode. 70,71 The most common groove binding markers and intercalative binding markers are rhodamine-B and ethidium bromide, respectively.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…Information regarding the drug′s interaction with DNA upon binding is revealed through molecular modeling study. 69 To understand the binding interactions, docking of the lowest-energy conformer of YH was performed with CT-DNA (PDB-ID: 1BNA) 88 using the AutoDock 1.5.6 program. 80,89 In each instance, docking was employed to highlight the YH binding interaction with the CT-DNA and to comprehend the underlying forces that are involved.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

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Structural Insight into Groove Binding of Yohimbine with Calf Thymus DNA: A Spectroscopic, Calorimetric, and Computational Approach

et al. 2023

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A variety of anticancer and antibacterial drugs target DNA as one of their primary intracellular targets. Understanding ligand−DNA interactions and developing new, promising bioactive molecules for clinical use are greatly aided by elucidating the interaction between small molecules and natural polymeric DNAs. Small molecules′ ability to attach to and inhibit DNA replication and transcription provides more information on how drugs impact the expression of genes. Yohimbine has been broadly studied in pharmacological properties, while its binding mode to DNA has not been explicated so far. In this study, an attempt was made to explore the interaction between Yohimbine (YH) and calf thymus (CT-DNA) by using varying thermodynamics and in silico approaches. Minor hypochromic and bathochromic shifts of fluorescence intensity were observed, suggesting the binding of YH to CT-DNA. The Scatchard plot analysis using the McGhee−von Hipple method revealed noncooperative binding and affinities in the range of 10 5 M −1 . The binding stoichiometry value is 2:1 (2 molecules of YH were span by 1 base pair) and was determined by Job's plot. The thermodynamic parameters suggested exothermic binding, which was favored by negative enthalpy and positive entropy changes from both isothermal titration calorimetry and temperature-dependent fluorescence experiment. Salt-dependent fluorescence suggested that the interaction between the ligand and DNA was governed by nonpolyelectrolytic forces. Kinetics experiment confirmed the static type of quenching. The results of iodide quenching, urea denaturation assay, dye displacement, DNA melting, and in silico molecular docking (MD) suggested groove binding of YH to CT-DNA. Circular dichroism spectra confirmed minimal perturbation of CT-DNA with YH binding via groove region. Therefore, the groove binding mechanism of interaction was validated by biophysical techniques and in silico, MD approaches. The findings supported here may contribute to the development of new YH therapeutics possessing better efficacy and lesser side effects.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: ■ Materials and Methodsmentioning

confidence: 99%

Section: ■ Materials and Methodsmentioning

confidence: 99%

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Structural Insight into Groove Binding of Yohimbine with Calf Thymus DNA: A Spectroscopic, Calorimetric, and Computational Approach

et al. 2023

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“…chloroform series, 7 toluene, 8 nitrite, 9 and nitrate 10 ), spintronic and quantum computing, 11 catalysis, 12 semiconductors, 13 electrochromic and optical limiting materials, 14 nonlinear optics, 15 liquid crystals, 16 sensitizers for photodynamic cancer therapy (PDCT) 17 and optical data storage, 18 organic and polymer electronic materials, 19 and DNA binders as potential chemotherapeutic agents. 20,21 There are many articles, reviews, and books in the literature on the synthesis and purification methods of Pcs with excellent and unique properties, and on their physical, chemical, and spectral properties. [22][23][24][25] Even chiral porphyrins and Pcs have been synthesized by Kobayashi et al, and the stereochemistry of these compounds has been studied.…”

Section: Introductionmentioning

confidence: 99%

Novel methoxyphenylthio-substituted phthalocyanines: synthesis, characterization, proton-transfer, and acid-sensing properties

Ağcaabat,

Seslikaya,

Fındık

et al. 2024

New J. Chem.

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DNA groove binder and significant cytotoxic activity on human colon cancer cells: Potential of a dimeric zinc (II) phthalocyanine derivative

Cited by 2 publications

References 51 publications

Structural Insight into Groove Binding of Yohimbine with Calf Thymus DNA: A Spectroscopic, Calorimetric, and Computational Approach

Structural Insight into Groove Binding of Yohimbine with Calf Thymus DNA: A Spectroscopic, Calorimetric, and Computational Approach

Novel methoxyphenylthio-substituted phthalocyanines: synthesis, characterization, proton-transfer, and acid-sensing properties

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