Electrochemical, spectroscopic and molecular docking studies on the interaction of calcium channel blockers with dsDNA

Shahzad, Suniya; Dogan‐Topal, Burcu; Karadurmuş, Leyla; Çağlayan, Mehmet Gökhan; Tok, Tuğba Taşkın; Uslu, Bengi; Shah, Afzal; Özkan, Síbel A.

doi:10.1016/j.bioelechem.2018.12.007

Cited by 23 publications

(8 citation statements)

References 29 publications

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“…A decrease in the peak current of the small molecule by adding some ssDNA or dsDNA solution could be used for the determination of the binding constant and binding site size, while the shift in the peak potential of the small molecule could be used to determine the mode of interaction. In the literature, there are highly explanatory studies based on the interaction of different small molecules with dsDNA. − The possible interaction mechanism between calf thymus dsDNA and three calcium antagonists, nifedipine, lercanidipine, and amlodipine, has published by Shahzad et al In their study, the decrease in the peak current of guanine and adenine was used as an indicator for confirmation of the interaction event in acetate buffer of pH 4.70. Dogan-Topal et al investigated the interaction of efavirenz with fish sperm dsDNA immobilized onto the pencil graphite electrode using the differential pulse voltammetric technique by an electrochemical DNA biosensor.…”

Section: Results and Discussionmentioning

confidence: 99%

Mechanism of Interactions of dsDNA Binding with Apigenin and Its Sulfamate Derivatives Using Multispectroscopic, Voltammetric, and Molecular Docking Studies

et al. 2021

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DNA binding investigations are critical for designing better pharmaceutical compounds since the binding of a compound to dsDNA in the minor groove is critical in drug discovery. Although only one in vitro study on the DNA binding mode of apigenin (APG) has been conducted, there have been no electrochemical and theoretical studies reported. We hereby report the mechanism of binding interaction of APG and a new class of sulfonamide-modified flavonoids, apigenin disulfonamide (ADSAM) and apigenin trisulfonamide (ATSAM), with deoxyribonucleic acid (DNA). This study was conducted using multispectroscopic instrumentation techniques, which include UV–vis absorption, thermal denaturation, fluorescence, and Fourier transform infrared (FTIR) spectroscopy, and electrochemical and viscosity measurement methods. Also, molecular docking studies were conducted at room temperature under physiological conditions (pH 7.4). The molecular docking studies showed that, in all cases, the lowest energy docking poses bind to the minor groove of DNA and the apigenin–DNA complex was stabilized by several hydrogen bonds. Also, π–sulfur interactions played a role in the stabilization of the ADSAM–DNA and ATSAM–DNA complexes. The binding affinities of the lowest energy docking pose (schematic diagram of table of content (TOC)) of APG–DNA, ADSAM–DNA, and ATSAM–DNA complexes were found to be −8.2, −8.5, and −8.4 kcal mol–1, respectively. The electrochemical binding constants K b were determined to be (1.05 × 105) ± 0.04, (0.47 × 105) ± 0.02, and (8.13 × 105) ± 0.03 for APG, ADSAM, and ATSAM, respectively (all of the tests were run in triplicate and expressed as the mean and standard deviation (SD)). The K b constants calculated for APG, ADSAM, and ATSAM are in harmony for all techniques. As a result of the incorporation of dimethylsulfamate groups into the APG structure, in the ADSAM–dsDNA and ATSAM–dsDNA complexes, in addition to hydrogen bonds, π–sulfur interactions have also contributed to the stabilization of the ligand–DNA complexes. This work provides new insights that could lead to the development of prospective drugs and vaccines.

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Section: Results and Discussionmentioning

confidence: 99%

Mechanism of Interactions of dsDNA Binding with Apigenin and Its Sulfamate Derivatives Using Multispectroscopic, Voltammetric, and Molecular Docking Studies

et al. 2021

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“…The presence of a negative induced circular dichroism band, increasing with every added DNA portion with a red shift, again indicates an intercalative binding mode (Garbett, Ragazzon & Chaires, 2007;Thimmaiah et al, 2015). Interestingly, a recent study of the DNA-binding of 1,4-DHP with Ca channel blocker activity, performed mostly by electrochemical methods, also revealed an interaction of the compounds with DNA, although with much lower affinity compared to the AV-153 salts (Shahzad et al, 2019). We also compared the ability of AV-153 salts to interact with the human telomeric G4 repeat and single-stranded DNA.…”

Section: Ftir Spectroscopy Of Av-153 Salts and Their Complexes With Dnamentioning

confidence: 93%

Spectroscopic and electrochemical study of interactions between DNA and different salts of 1,4-dihydropyridine AV-153

Ļeonova

Shvirksts

Borisovs

et al. 2020

PeerJ

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1,4-dihydropyridines (1,4-DHP) possess important biochemical and pharmacological properties, including antimutagenic and DNA-binding activity. The latter activity was first described for water-soluble 1,4-DHP with carboxylic group in position 4, the sodium salt of the 1,4-DHP derivative AV-153 among others. Some data show the modification of physicochemical properties and biological activities of organic compounds by metal ions that form the salts. We demonstrated the different affinity to DNA and DNA-protecting capacity of AV-153 salts, depending on the salt-forming ion (Na, K, Li, Rb, Ca, Mg). This study aimed to use different approaches to collate data on the DNA-binding mode of AV-153-Na and five other AV-153 salts. All the AV-153 salts in this study quenched the ethidium bromide and DNA complex fluorescence, which points to an intercalation binding mode. For some of them, the intercalation binding was confirmed using cyclic voltammetry and circular dichroism spectroscopy. It was shown that in vitro all AV-153 salts can interact with four DNA bases. The FTIR spectroscopy data showed the interaction of AV-153 salts with both DNA bases and phosphate groups. A preference for base interaction was observed as the AV-153 salts interacted mostly with G and C bases. However, the highest differences were detected in the spectral region assigned to phosphate groups, which might indicate either conformational changes of DNA molecule (B form to A or H form) or partial denaturation of the molecule. According to the UV/VIS spectroscopy data, the salts also interact with the human telomere repeat, both in guanine quadruplex (G4) and single-stranded form; Na and K salts manifested higher affinity to G4, Li and Rb –to single-stranded DNA.

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“…Recent data indicate that such widely used 1,4-DHP with Ca blocker activity as nifedipine, lercanidipine and amlodipine can bind minor groove of the DNA, although with a low affinity [23].…”

Section: In Vitro Molecular Interactions and Dna Bindingmentioning

confidence: 99%

Genome protecting and genotoxic effects produced by derivatives of 1,4-dihydropyridine

Ļeonova

Ryabokon

Rostoka

et al. 2022

Preprint

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The review summarizes data on genome protecting and genotoxic action of 1,4-dihydropyridines (DHP) with main focus on the compounds synthesized in the Latvian Institute of Organic synthesis. Most of these compounds manifest very low calcium channel blocking activity, thus considered to be “unusual” 1,4-DHP. Some of these compounds decrease spontaneous mutagenesis and frequency of mutations induced by chemical mutagens. Some water-soluble 1,4-DHP protect DNA against damage produced by hydrogen peroxide, radiation and peroxynitrite. In these molecules capability to protect DNA cohabitates with DNA-binding activity. Possible mechanisms of above effects are discussed.

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Electrochemical, spectroscopic and molecular docking studies on the interaction of calcium channel blockers with dsDNA

Cited by 23 publications

References 29 publications

Mechanism of Interactions of dsDNA Binding with Apigenin and Its Sulfamate Derivatives Using Multispectroscopic, Voltammetric, and Molecular Docking Studies

Mechanism of Interactions of dsDNA Binding with Apigenin and Its Sulfamate Derivatives Using Multispectroscopic, Voltammetric, and Molecular Docking Studies

Spectroscopic and electrochemical study of interactions between DNA and different salts of 1,4-dihydropyridine AV-153

Genome protecting and genotoxic effects produced by derivatives of 1,4-dihydropyridine

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