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

Absolínová, Helena; Jančář, Luděk; Jančářová, Irena; Vičar, Jaroslav; Kubáň, Vlastimil

doi:10.2478/s11532-010-0038-7

Cited by 7 publications

(6 citation statements)

References 14 publications

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“…Similarly as in the case of CV measurement, SWV analyses confirmed that SG current responses are higher than DHSG ones. This is probably related to the lower solubility and stability of DHSG in aqueous environments from which the alkaloids are adsorbed (see stability study 50). Moreover, DHSG in contrast to SG does not have a strictly planar structure and positive charge and this may partially limit its adsorption onto the surface of PGE.…”

Section: Resultssupporting

confidence: 80%

Oxidation of Sanguinarine and Its Dihydro‐Derivative at a Pyrolytic Graphite Electrode Using Ex Situ Voltammetry. Study of the Interactions of the Alkaloids with DNA

et al. 2011

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This study describes the oxidation of sanguinarine (SG) and its metabolite dihydrosanguinarine (DHSG) on the surface of a basal-plane pyrolytic graphite electrode (PGE). Since both alkaloids strongly adsorb onto the surface of pyrolytic graphite, measurements were performed using ex situ voltammetric methods, adsorptive transfer (AdT) cyclic voltammetry (CV) and square-wave voltammetry (SWV). Oxidation peaks of SG (peak A) and DHSG (peak A*) were observed around the potential of + 0.7 V (vs. Ag/AgCl/3 M KCl), depending on the experimental conditions. The voltammetric peaks A and A* are probably related to the oxidation of N-methylphenanthridine nitrogenous heterocycle of SG and oxidation of DHSG back to SG, respectively. The electrochemical results and optimized AdT SWV were subsequently applied to the study of the interactions of SG and DHSG with DNA in vitro. Analysis of the alkaloid/DNA interactions was based on observing heights of oxidation peaks A and A* after incubation of SG and/or DHSG with supercoiled (sc) DNA [pBSK (À) ]. Electrochemical study of the interactions was supported and complemented with measurements using gel electrophoresis (Topoisomerase I scDNA relaxation assay) and steady-state and time-resolved fluorescence spectroscopy. The results suggest that SG intercalates into the doublestranded structure of scDNA (the SG/base pair ratio is max. 1/4) while increased binding affinity was observed for quaternary cation (SG + ). DHSG which, unlike SG + , does not possess a strictly planar molecular structure, did not show intercalative DNA binding in any of the three methods applied.

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Section: Resultssupporting

confidence: 80%

Oxidation of Sanguinarine and Its Dihydro‐Derivative at a Pyrolytic Graphite Electrode Using Ex Situ Voltammetry. Study of the Interactions of the Alkaloids with DNA

et al. 2011

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“…Previous studies of sanguinarine and chelerythrine showed that the fluorescence of QBAs comes from two distinct species–neutral alkanolamine and positively charged iminium [ 20 , 21 ]. In aqueous solution typical values of pK ROH for QBAs are between 7.7 (chelirubine) and 9 (chelerythrine) [ 30 ].…”

Section: Discussionmentioning

confidence: 99%

Influence of Solvent Polarity and DNA-Binding on Spectral Properties of Quaternary Benzo[c]phenanthridine Alkaloids

et al. 2015

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Quaternary benzo[c]phenanthridine alkaloids are secondary metabolites of the plant families Papaveraceae, Rutaceae, and Ranunculaceae with anti-inflammatory, antifungal, antimicrobial and anticancer activities. Their spectral changes induced by the environment could be used to understand their interaction with biomolecules as well as for analytical purposes. Spectral shifts, quantum yield and changes in lifetime are presented for the free form of alkaloids in solvents of different polarity and for alkaloids bound to DNA. Quantum yields range from 0.098 to 0.345 for the alkanolamine form and are below 0.033 for the iminium form. Rise of fluorescence lifetimes (from 2–5 ns to 3–10 ns) and fluorescence intensity are observed after binding of the iminium form to the DNA for most studied alkaloids. The alkanolamine form does not bind to DNA. Acid-base equilibrium constant of macarpine is determined to be 8.2–8.3. Macarpine is found to have the highest increase of fluorescence upon DNA binding, even under unfavourable pH conditions. This is probably a result of its unique methoxy substitution at C12 a characteristic not shared with other studied alkaloids. Association constant for macarpine-DNA interaction is 700000 M-1.

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“…The solvents chosen were rich in methanol to avoid degradation of the compounds observable in aqueous solutions [20].…”

Section: Esi Ion-trap Ms and Liquid Chromatography Of The Alkaloidsmentioning

confidence: 99%

Identification of benzo[c]phenanthridine metabolites in human hepatocytes by liquid chromatography with electrospray ion-trap and quadrupole time-of-flight mass spectrometry

Kosina

Vacek

Papoušková

et al. 2011

Journal of Chromatography B

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

Cited by 7 publications

References 14 publications

Oxidation of Sanguinarine and Its Dihydro‐Derivative at a Pyrolytic Graphite Electrode Using Ex Situ Voltammetry. Study of the Interactions of the Alkaloids with DNA

Oxidation of Sanguinarine and Its Dihydro‐Derivative at a Pyrolytic Graphite Electrode Using Ex Situ Voltammetry. Study of the Interactions of the Alkaloids with DNA

Influence of Solvent Polarity and DNA-Binding on Spectral Properties of Quaternary Benzo[c]phenanthridine Alkaloids

Identification of benzo[c]phenanthridine metabolites in human hepatocytes by liquid chromatography with electrospray ion-trap and quadrupole time-of-flight mass spectrometry

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