β-Carboline alkaloids bind DNA

Nafisi, Shohreh; Bonsaii, Mahyar; Maali, Pegah; Khalilzadeh, Mohammad A.; Manouchehri, Firouzeh

doi:10.1016/j.jphotobiol.2010.05.005

Cited by 92 publications

(52 citation statements)

References 32 publications

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“…Binding of the alkaloid harmalol to DNA was also shown to be through intercalation, with a binding constant of 4.5 × 10 5 M −1 [33]. To the best of our knowledge, the binding constants estimated for alkaloid-DNA associations have been found to range from 10 3 to 10 7 M −1 [34][35][36][37]. The present study showed that brucine interacted with DNA via both intercalation and electrostatic interaction, similar to most alkaloids.…”

Section: Effects Of Ionic Strength On Fluorescence Propertiessupporting

confidence: 57%

Cytotoxicity and DNA interaction of brucine and strychnine—Two alkaloids of semen strychni

Liu

Wang

Han

et al. 2015

International Journal of Biological Macromolecules

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Section: Effects Of Ionic Strength On Fluorescence Propertiessupporting

confidence: 57%

Cytotoxicity and DNA interaction of brucine and strychnine—Two alkaloids of semen strychni

Liu

Wang

Han

et al. 2015

International Journal of Biological Macromolecules

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“…The interaction of carboline alkaloids with DNA have showed that these compounds intercalate into DNA with different degrees (Smythies and Antun, 1969;Duportail and Lami, 1975;Duportail, 1981;Mc Pherson and Pezzuto, 1983;Funayama et al, 1996;Taira et al, 1996). Recently, we studied the interaction of b-carboline alkaloids with DNA by Fourier transform infrared (FTIR) and UV spectroscopy, and our results showed both interaction and intercalation via groove binding and intercalative modes (Nafisi et al, 2010).…”

Section: Introductionmentioning

confidence: 87%

Interaction of β-Carboline Alkaloids with RNA

Nafisi

Malekabady

Khalilzadeh

2010

DNA and Cell Biology

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β-Carboline alkaloids are present in medicinal plants such as Peganum harmala L., which have been used as folk medicine in anticancer therapy. Recently, they have drawn attention because of their antitumor activities. Despite considerable interest and investigations on alkaloid-DNA complexes, reports on alkaloid-RNA interaction are very limited. This study is the first attempt to investigate the binding of β-carboline alkaloids (harmine, harmane, harmaline, harmalol, and tryptoline) with yeast RNA. The effect of alkaloid complexation on RNA aggregation and condensation was investigated in aqueous solution at physiological conditions, using constant RNA concentration (6.25 mM) and various alkaloid:polynucleotide (phosphate) ratios of 1:240, 1:160, 1:80, 1:40, 1:20, 1:10, 1:5, 1:2, and 1:1. Fourier transform infrared and UV-visible spectroscopic methods were used to determine the ligand-binding modes, the binding constants, and the stability of alkaloid-RNA complexes in aqueous solution. Spectroscopic evidence showed major binding of alkaloids to RNA with overall binding constants of K(harmine)-RNA = 2.95 × 10⁷ M⁻¹, K(harmane)-RNA = 5.62 × 10⁵ M⁻¹, K(harmaline)-RNA = 7.47 × 10⁵ M⁻¹, K(harmalol)-RNA = 4.32 × 10⁵ M⁻¹, and K(tryptoline)-RNA = 3.21 × 10⁵ M⁻¹. The affinity of alkaloids-RNA binding is in the order of harmine > harmaline > harmane > harmalol > tryptoline. No biopolymer secondary structural changes were observed upon alkaloid interaction and RNA remains in the A-family structure in these complexes.

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“…The binding constants obtained for β-carboline derivatives and ctDNA in the present work corroborate some literature data for this class of compounds. 40,41 The K b values ≥ 10 5 indicate high affinity between the evaluated compounds and ctDNA. 3 The Scheme S2 presents a comparative literature reports containing similar compounds to those evaluated in this work and interactions parameters with different nucleic acids.…”

Section: Evaluation Of Ctdna Interaction Applying Spectroscopy Methodsmentioning

confidence: 99%

Interaction of β-Carbolines with DNA: Spectroscopic Studies, Correlation with Biological Activity and Molecular Docking

Silva

Savariz

Silva-Júnior

et al. 2016

Journal of the Brazilian Chemical Society

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Quantitative interaction of twelve β-carboline derivatives with calf thymus deoxyribonucleic acid (ctDNA) using spectroscopic techniques was evaluated. The values of the binding constants (K b ) obtained for the complexes formed with the ctDNA ranged from 3.30 × 10 2 to 1.82 × 10 6 mol L −1 , being the β-carbolines with the N,N-dimethylaminophenyl group at position 1 the ones which presented the highest K b values. The binding mode between the β-carbolines evaluated and ctDNA was proposed from the KI assay, competition with ethidium bromide, and DNA thermal denaturation profile (T m ), where it was possible to infer that the evaluated alkaloids interact with ctDNA preferably via intercalation. Additionally, the correlation of K b values obtained with the IC 50 of seven human cancer cell lines was carried out. From this study, it was possible to observe a linear relation among most of the evaluated derivatives, obtaining r 2 values from 0.5360 to 0.9600. In addition, in silico molecular docking was performed to corroborate the experimental results.

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β-Carboline alkaloids bind DNA

Cited by 92 publications

References 32 publications

Cytotoxicity and DNA interaction of brucine and strychnine—Two alkaloids of semen strychni

Cytotoxicity and DNA interaction of brucine and strychnine—Two alkaloids of semen strychni

Interaction of β-Carboline Alkaloids with RNA

Interaction of β-Carbolines with DNA: Spectroscopic Studies, Correlation with Biological Activity and Molecular Docking

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