Analysis of interactions between calf thymus DNA and 1,5-di(piperazin-1-yl)anthracene-9,10-dione using spectroscopic and electrochemical methods

Białobrzeska, Wioleta; Niedziałkowski, Paweł; Malinowska, Natalia; Cebula, Zofia; Ossowski, Tadeusz

doi:10.1016/j.molliq.2019.111080

Cited by 22 publications

(13 citation statements)

References 48 publications

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“…The concentration of the freshly prepared CT-DNA was calculated based on the absorbance value at 260 nm and the calibration curve [3 DNA 6600 (base pairs) per M per cm]. 53 2HP was dissolved in Tris-HCl to give 10 mL of solution at a mass concentration equal to 0.18 mM, which was used as the initial and pure pyrazine derivative sample for both types of titration.…”

Section: Affinity To Biomolecule Assaymentioning

confidence: 99%

When biomolecules meet 2-hydrazinopyrazine: from theory through experiment to molecular levels using a wide spectrum of techniques

et al. 2020

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Section: Affinity To Biomolecule Assaymentioning

confidence: 99%

When biomolecules meet 2-hydrazinopyrazine: from theory through experiment to molecular levels using a wide spectrum of techniques

et al. 2020

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“…S11 ; SI) and based on the calibration curve [ɛ DNA 6,600 (base pairs) M −1. cm −1 ] 45 , 46 . The 3,6-PIRAMICAR was dissolved in Tris–HCl to give 10 mL of the solution at mass concentration equal 2.36·10 –4 M, which was used as an initial and pure carbazole derivative sample for both types of titration.…”

Section: Methodsmentioning

confidence: 99%

Photosensitive and pH-dependent activity of pyrazine-functionalized carbazole derivative as promising antifungal and imaging agent

Chylewska

Dąbrowska

Ramotowska

et al. 2020

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Carbazole skeleton plays a significant role as a structural scaffold of many pharmacologically active compounds. Pyrazine-functionalized carbazole derivative was constructed by coupling 2-amino-5-bromo-3-methylaminepyrazine (ABMAP) into 3 and 6 positions of the carbazole ring. Multiexperimental methods were used, e.g., potentiometric, spectroscopic (ATR, UV, XRD powder, 1 H and 13 C NMR), electrochemical (cyclic voltammetry), and optical techniques, to receive the complete structural analysis, physicochemical (pKa, logP) and biological profile of a new carbazole derivative with acronym 3,6-PIRAMICAR. the interaction ability of the compound studied with potential cellular targets like Calf Thymus DNA (CT-DNA), or BovineSerumAlbumin (BSA) were also taken into account. experiments showed the existence of strong binding, but no DnA or BSA cleavage was observed. the comparative analyzes of compounds anti-Candida action clearly show pH-dependent antifungal activity of 3,6-PIRAMICAR , which was strongly stimulated in the acidic media. Surprisingly, the titled compound turn out to be much more effective (14 times by MIC50; 8 times by MIC; c.a. 4 times by MFC) against Candidakrusei than fluconazole at pH 4. The emergence of multidrug-resistant microorganisms, as well as fungal infectious diseases, is a major global problem, especially for immuno-deficient populations. The development of new antifungal agents in clinical trials is problematic inferior to the incidence of drug resistance, and the available antifungal agents are restricted. Their mechanisms are based on certain characteristics of the fungus in order to avoid biological similarities with the host 1. Fungi in the Candida genus are the most common fungal pathogens which can colonize various host niches (stomach, vagina and oral mucosa) with varying ambient pH range 2-6. Carbazoles and derivatives with carbazole skeleton are currently tested intensively according to their antimicrobial properties which is directly relating with their structure or in more details with anaromatic N-heterocyclic ring inside 7. Carbazole derivatives have been reported to be potential agents against tumor 8 or opportunistic infections of AIDS 9,10. The studies about high active DNA intercalators show the significance of the carbazole structural agents like planarity or aromaticity 11,12. Interestingly, the mentioned parameters are described as responsible for the high affinity of carbazoles substituted at 3,6-or 2,7-positions by amine, amidine, or imidazoline groups to GC or AT-rich sequences of DNA 13,14. However, chemistry of especially di-substituted 3,6-derivatives of carbazole is still not very extensively explored due to problems with synthesis of such compounds. Mainly nitrogen atom was a hot spot for carbazole derivatives 14. The first concept of the studies was to check the basic design structures assumptions to predict pharmaceuticals activity, like presented carbazole functionalized by pyrazines-our previous research objects. Consequently, the confirmation of the possibili...

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“…Such analysis often involves examining the electrochemical behavior of a pharmaceutical in a solution to which DNA is gradually added. Consequently, the impact of the subsequent portions (increasing the DNA concentration) on the redox processes of the examined system is determined [ 24 , 26 , 44 , 46 , 59 , 63 ]. An alternative method is the modification of the electrode, which involves immobilizing one of the analyzed system elements (studied compound with biological activity [ 64 ] or DNA [ 41 , 42 , 57 , 61 , 62 , 63 , 65 , 66 ]) on the surface of the working electrode.…”

Section: Electrochemical Approach To Dna–drug Interaction Descriptionmentioning

confidence: 99%

“…Prior to in vivo research, the interactions between pharmaceutical molecules and DNA can be determined in the chemical laboratory, using the following techniques: spectroscopic methods (NMR [ 17 , 18 , 19 ], IR [ 19 , 20 ], Raman [ 21 , 22 ], and UV–Vis spectroscopy [ 23 , 24 , 25 , 26 , 27 , 28 , 29 ], linear and circular dichroism [ 19 , 20 , 29 ], spectrofluorimetry [ 2 , 25 , 27 , 28 , 29 ]), mass spectrometry [ 30 , 31 ], equilibrium dialysis [ 32 ], surface plasmon resonance (SPR) [ 33 , 34 ], and to some extent, molecular modeling techniques [ 1 , 3 , 6 , 35 , 36 ]. All the above-mentioned methods are generally applicable in the assessment of the position, strength, and mechanism of the interaction, which in turn are crucial to understanding the drug’s mechanism of action.…”

Section: Introductionmentioning

confidence: 99%

“…However, they cannot be used for compounds which do not have absorption maxima in the tested range or their absorption maximum coincides with the maximum absorption of DNA. If the properties of the studied compound allow it, both spectroscopic and electrochemical methods are used to describe the interactions as fully as methodologically possible [ 24 ]. Electrochemical techniques are extremely advantageous in the case of compounds that cannot been studied and described by either UV–Vis or fluorescence spectroscopy because of limitations such as the weak intensity of absorption/fluorescence maxima or the overlap of the electronic transition bands of the studied compound with the electronic transition bands of the DNA.…”

Section: Introductionmentioning

confidence: 99%

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What Can Electrochemical Methods Offer in Determining DNA–Drug Interactions?

2021

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The interactions of compounds with DNA have been studied since the recognition of the role of nucleic acid in organisms. The design of molecules which specifically interact with DNA sequences allows for the control of the gene expression. Determining the type and strength of such interaction is an indispensable element of pharmaceutical studies. Cognition of the therapeutic action mechanisms is particularly important for designing new drugs. Owing to their sensitivity, simplicity, and low costs, electrochemical methods are increasingly used for this type of research. Compared to other techniques, they require a small number of samples and are characterized by a high reliability. These methods can provide information about the type of interaction and the binding strength, as well as the damage caused by biologically active molecules targeting the cellular DNA. This review paper summarizes the various electrochemical approaches used for the study of the interactions between pharmaceuticals and DNA. The main focus is on the papers from the last decade, with particular attention on the voltammetric techniques. The most preferred experimental approaches, the electrode materials and the new methods of modification are presented. The data on the detection ranges, the binding modes and the binding constant values of pharmaceuticals are summarized. Both the importance of the presented research and the importance of future prospects are discussed.

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Analysis of interactions between calf thymus DNA and 1,5-di(piperazin-1-yl)anthracene-9,10-dione using spectroscopic and electrochemical methods

Cited by 22 publications

References 48 publications

When biomolecules meet 2-hydrazinopyrazine: from theory through experiment to molecular levels using a wide spectrum of techniques

When biomolecules meet 2-hydrazinopyrazine: from theory through experiment to molecular levels using a wide spectrum of techniques

Photosensitive and pH-dependent activity of pyrazine-functionalized carbazole derivative as promising antifungal and imaging agent

What Can Electrochemical Methods Offer in Determining DNA–Drug Interactions?

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