Absorption spectra and spectral-kinetic characteristics of the fluorescence of Sanguinarine in complexes with polyelectrolytes and DNA

Motevich, I. G.; Strekal, N. D.; Nowicky, J. W.; Маскевич, С. А.

doi:10.1007/s10812-010-9344-2

Cited by 3 publications

(4 citation statements)

References 13 publications

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“…Fluorescence of iminium form of QBA is quenched except for sanguinarine and chelerythrine, but only the sanguinarine lifetime could be reliably measured. The measured value of 2.4 ns is the same as that reported previously [ 22 , 37 ]. The addition of DNA causes a decrease of sanguinarine steady-state fluorescence.…”

Section: Resultssupporting

confidence: 83%

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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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Section: Resultssupporting

confidence: 83%

“…The lifetime of DNA-bound sanguinarine increases to 10.1 ns with another component of 2.4 ns attributable to its free form in solution ( S1 Fig ). Again, lifetime of sanguinarine-DNA complex is the same as reported earlier [ 37 ]. Steady-state fluorescence of other QBAs increases in the presence of DNA.…”

Section: Resultssupporting

confidence: 78%

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

et al. 2015

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“…But the same for alkanolamine exists only at 285 and 326 nm devoid of any band at higher wavelength. 40 In CTAB and OBG micelles, the characteristic peaks for the iminium form (peaks at 396 and 475 nm) are reduced indicating the lesser ground state population of the iminium form (Fig. S1b and c, ESI †), whereas in the SDS micelle it exhibits a small red shift (396 and 475 nm peak) suggesting the stabilization of the iminium form of SANG (Fig.…”

Section: Steady State Studymentioning

confidence: 99%

“…40 In CTAB and OBG micelles, the characteristic peaks for the iminium form (peaks at 396 and 475 nm) are reduced indicating the lesser ground state population of the iminium form ( Fig. iminium and alkanolamine form (Scheme 1) and the conversion between these two forms is largely dependent on the pH of medium.…”

Section: Steady State Studymentioning

confidence: 99%

Fluorescence switching of sanguinarine in micellar environments

Satpathi

Gavvala

Hazra

2015

Phys. Chem. Chem. Phys.

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Sanguinarine (SANG), a key member of the benzylisoquinoline alkaloid family, is well-known for its various therapeutic applications such as antimicrobial, antitumor, anticancer, antifungal and anti-inflammatory etc. Depending on the medium pH, SANG exists in the iminium or alkanolamine form, which emits at 580 nm and 420 nm, respectively. Nucleophilic attack on the C6 carbon atom converts the iminium form to the alkanolamine form of SANG, and these two forms are equally important for the medicinal activities of SANG. To improve its potency as a drug, it is essential to get a physical insight into this conversion process. In this study, we have deployed steady sate and time-resolved spectroscopic techniques to probe this conversion process inside different micellar environments. We have observed that the conversion from the iminium to alkanolamine form takes place in neutral OBG (octyl-β-d-glucopyranoside) and positively charged CTAB micelles, whereas the iminium form exclusively exists in negatively charged SDS micelles. This conversion from the iminium to alkanolamine form in the case of OBG and CTAB micelles may be attributed to the reduced pKa of this conversion process owing to the enhanced hydrophobicity experienced by the iminium form in between the surfactant head groups. On the other hand, the electrostatic attraction between positively charged iminium and negatively charged surfactant head groups stabilizes the iminium form in the stern layer of the SDS micelle. We believe that our observations are useful for selective transportation of any particular form of the drug into the active site. Moreover, loading of any particular form of drug can be easily monitored with the help of fluorescence color switch from orange (iminium) to violet (alkanolamine) without pursuing any sophisticated or complex technique.

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Use of Confocal Microscopy to Monitor Structural Transformations in Nanopillars Based on DNA and CdSe/CdZnSe/ZnS Quantum Dots

Motevich,

Erdem,

Akrema

et al. 2023

J Appl Spectrosc

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Absorption spectra and spectral-kinetic characteristics of the fluorescence of Sanguinarine in complexes with polyelectrolytes and DNA

Abstract: The absorption spectra and stationary and time resolved fluorescence spectra of the isoquinoline alkaloid sanguinarine are studied in aqueous media and during interactions with synthetic polyelectrolytes (polystyrene sulfonate and polyallylamine) and a natural polyelectrolyte (DNA).

Cited by 3 publications

References 13 publications

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

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

Fluorescence switching of sanguinarine in micellar environments

Use of Confocal Microscopy to Monitor Structural Transformations in Nanopillars Based on DNA and CdSe/CdZnSe/ZnS Quantum Dots

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