Fluorescence properties of selected benzo[c]phenantridine alkaloids and studies of their interaction with CT DNA

Urbanová, Jana; Lubal, Přemysl; Slaninová, Iva; Táborská, Eva; Táborský, Petr

doi:10.1007/s00216-009-2601-7

Cited by 44 publications

(36 citation statements)

References 19 publications

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“…QBAs, a group of low molecular compounds with N-heteroatom, belong to the highly bioactive substances [1]. Some side effects were reported (toxic effect on some cellular level [2][3][4][5]) in addition to the beneficial pharmacological actions (antimicrobial, antiapoptotic, antiinflamatory etc. effects [6,7]).…”

Section: Introductionmentioning

confidence: 99%

“…[12][13][14][15] The exact knowledge of physico-chemical characteristics is very important for correct interpretation of experiments concerning studies of interactions and behavior of the alkaloids at nearly physiological conditions. It is evident that the study of interactions [3][4][5][6] with biologically important macromolecules (i.e., receptors, transport proteins, nucleic acids etc. ), as Amresco ® , Solon, Ohio, USA) and sodium hydroxide (reagent grade purity, Penta, Chrudim, Czech Republic) solutions were used for the pH adjustment in a pH interval pH = 2 -11 with steps ∆pH = 0.2 -0.5.…”

Section: Introductionmentioning

confidence: 99%

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Spectrophotometric study of time stability and acid-base characteristics of chelerythrine and dihydrochelerythrine

et al. 2010

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Time stability, acid-base and UV-VIS spectral properties of dihydrochelerythrine (DHCHE) were studied spectrophotometrically in water:methanol and water:ethanol media. DHCHE is stable in strongly acid milieu (pH < 3) and at the higher amounts (60% v/v) alcohol. Acid-base characteristics and UV-VIS spectral properties of chelerythrine (CHE) were studied in aqueous solutions in the presence of different concentrations of HCl, HNO 3 , H 2 SO 4 , H 3 PO 4 and their mixtures. Remarkable shifts of formation parts of absorbance-pH (A-pH) curves to the alkaline medium were observed depending on the type and concentration of inert electrolyte (most remarkable for HNO 3 and HCl). The corresponding equilibrium constants pK R+ of the transition reaction between charged iminium Q + and uncharged QOH (pseudo-base, 6-hydroxy-dihydro derivative) forms of chelerythine were calculated using a numerical interpretation of A-pH curves by a SQUAD-G computer program which ranged from 8.51-9.31. The highest changes of ∆pK R+ (0.75 and 0.53) were observed for H 3 PO 4 and H 2 SO 4 , respectively. The priority effect of ionic species and ionic strength was confirmed in the presence of additions of NaCl and KCl. The strength of interaction of CHE with biomacromolecular compounds (i.e., peptides, proteins, nucleic acids etc.) may be affected because of the observed influence of both cation and anion of the inert electrolyte on acid-base behavior.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Spectrophotometric study of time stability and acid-base characteristics of chelerythrine and dihydrochelerythrine

et al. 2010

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“…For instance, whereas sanguilutine and chelilutine exhibit antiproliferative and anti-microtubular activities (Slaninova et al 2001), sanguirubine, chelirubine, and macarpine are antiproliferative and pro-apoptotic, as has been well documented (Slaninova et al 2007). Macarpine and sanguirubine show a considerable fluorescence shift when bound to deoxyribonucleic acid (DNA), a property which makes them useful as fluorescent probes (Urbanova et al 2009). Macarpine seems to be a promising novel cell-permeant DNA dye for livecell imaging and flow cytometry sorting (Slaninova et al 2016).…”

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confidence: 99%

The capability of minor quaternary benzophenanthridine alkaloids to inhibit TNF-α secretion and cyclooxygenase activity

et al. 2017

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Quaternary benzophenanthridine alkaloids are known to have a wide range of biological effects, including antimicrobial, antifungal, anti-inflammatory, and antitumour activities. However, only sanguinarine and chelerythrine have been studied intensively. The aim of this study was to evaluate the anti-inflammatory potential of the five minor quaternary benzophenanthridine alkaloids sanguilutine, sanguirubine, chelirubine, chelilutine, and macarpine in vitro and to compare them with more thoroughly studied sanguinarine and chelerythrine. Before making cellbased assays, the cytotoxicity of the alkaloids was evaluated. The anti-inflammatory potential of the chosen alkaloids was evaluated as for their ability to modulate the lipopolysaccharideinduced secretion of tumour necrosis factor α (TNF-α) in the macrophage-like cell line THP-1. The cyclooxygenase (COX)-1 and COX-2 inhibitory activities were also measured. The results indicate that the presence of a methylenedioxy ring attached at carbon (C)7-C8 is important for reducing the secretion of TNF-α. Interestingly, this effect did not show a simple dependence on concentration. The selected alkaloids showed little or no anti-COX activity. The results obtained from the present experiments may provide additional information useful in understanding the structure-to-activity relationship of the quaternary benzophenanthridine alkaloids. The antiinflammatory potential and the cytotoxic effect are driven by the presence of a methylenedioxy ring attached at C7-C8 and C2-C3, respectively.

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“…Prado et al (2004) reported that nitidine and fagaronine bind to duplex DNA by the mechanism of intercalation. Recently a comparative study on the binding of sanguinarine, nitidine, and chelerythrine with calf thymus DNA, poly(dG-dC).poly(dG-dC), poly (dA-dT).poly(dA-dT), and several sequence-designed double-stranded oligonucleotides was performed using spectrophotometric and spectrofluorimetric techniques to elucidate their sequence selectivity for DNA binding (Bai et al 2006;Urbanova et al 2009). Fluorescence titration of DNA with three alkaloids was performed in acidic buffer at pH 5.30 to ensure that these alkaloids exist exclusively as the iminium form (Bai et al 2006).…”

Section: Sanguinarine (Iminium)-triplex Dna Interactionmentioning

confidence: 99%

Biophysical aspects and biological implications of the interaction of benzophenanthridine alkaloids with DNA

Maiti

Kumar

2009

Biophys Rev

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Benzophenanthridine alkaloids represent a very interesting and significant group of natural products that exhibit a broad range of biological and pharmacological properties. Among this group of alkaloids, sanguinarine, nitidine, fagaronine, and chelerythrine have the potential to form molecular complexes with DNA structures and have attracted recent attention for their possible clinical and pharmacological utility. This review focuses on the interaction of these alkaloids with polymorphic DNA structures (B-form, Z-form, H-form, and triple helical form) reported by several research groups employing various physical techniques such as spectrophotometry, spectrofluorimetry, circular dichroism, NMR spectroscopy, thermal melting, viscometry as well as thermodynamic analysis by isothermal titration calorimetry and differential scanning calorimetry to elucidate the mode and mechanism of action at the molecular level to determine the structure-activity relationship. DNA binding properties of these alkaloids are interpreted in relation to their biological activity.

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Fluorescence properties of selected benzo[c]phenantridine alkaloids and studies of their interaction with CT DNA

Cited by 44 publications

References 19 publications

Spectrophotometric study of time stability and acid-base characteristics of chelerythrine and dihydrochelerythrine

Spectrophotometric study of time stability and acid-base characteristics of chelerythrine and dihydrochelerythrine

The capability of minor quaternary benzophenanthridine alkaloids to inhibit TNF-α secretion and cyclooxygenase activity

Biophysical aspects and biological implications of the interaction of benzophenanthridine alkaloids with DNA

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