Absorption, fluorescence, and SERS spectra of sanguinarine at different pH values

Abstract

We have studied the absorption, fluorescence, and surface-enhanced Raman scattering (SERS) spectra of sanguinarine using a silver hydrosol and an electrochemical cell with a silver working electrode for different pH values in the medium. We carried out quantum chemical calculations in order to interpret the electronic and vibrational spectra and to establish their correlations with the structure of the molecules. We optimized the structure and determined the spectral characteristics of the cationic and neutral forms of the sanguinarine molecules in solution and adsorbed on the surface of an anodized Ag electrode for different potentials.Introduction. Sanguinarine belongs to the class of quaternary benzophenanthridine alkaloids. It is encountered in many plant species in the family Papaveraceae (Sanguinaria Canadensis, Dicranostigma lactucoides, Macleaya microcarpa, etc.) [1]. A large amount of sanguinarine is found in the roots of greater celandine (Chelidonium majus). Medicinal drugs have been created on the basis of sanguinarine. Thus the drug Chelivag (Poland) is used to treat trichomonas vaginitis. This alkaloid is also a component of such anti-tumor drugs as UKRAIN [2], which has pronounced immunostimulating properties [3,4].Since besides having antimicrobial and fungicidal action [5], sanguinarine also has a narcotic effect, inducing excitation of the central nervous system, its detection in different substances and study of the structure/function states are important for forensics and biomedicine. One of the methods sensitive to a change in molecular structure and making it possible to study aqueous media is Raman light scattering. However, rather large amounts and high (up to molar) concentrations of the original solutions are needed to record the Raman spectra, which considerably limits the analytical possibilities for this method. Surface-enhanced Raman scattering (SERS) spectroscopy with its inherent high sensitivity and selectivity, making it possible to determine the presence of a specific compound in trace amounts [6,7], is devoid of this disadvantage. An important advantage of SERS spectroscopy is the possibility of studying the structural transformations of molecules on a phase interface and under conditions of varying potential during their sorption.In this work, we have studied the UV absorption, fluorescence, and SERS spectra of sanguinarine using a silver hydrosol and an electrochemical cell in aqueous salt solutions at different pH values. We carried out quantum chemical calculations in order to interpret the electronic and vibrational spectra and their correlation with the structure of the molecules.Objects of Investigation, Study Methods, and Calculation Methods. As the test object, we used the drug sanguinarine (SIGMA), a bright orange powder.The sanguinarine molecules are characterized by the sensitivity of the polar C=N + bond to nucleophilic attack, as a result of which adducts at the carbon atom at the 4 position are rather easily formed [8,9]. Depending on the pH of the medium, the sa...

Crystal structure of norcoclaurine‐6‐O‐methyltransferase, a key rate‐limiting step in the synthesis of benzylisoquinoline alkaloids

“…The analysis of the sigma‐A weighed F o − F c electron density map in the active site of the ternary complex with sanguinarine is indicative of a planar molecule (Figures c,e and S3b). The ionic form of sanguinarine (Motevich et al ., ) can be refined at this position with 80% occupancy (Figures c and S3b). The D, E and F rings can be localized without ambiguity so that the A and B rings match the other part of the density.…”

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

“…They exhibit very characteristic spectral features that can be used for their direct determination, for studies of their interactions with biomacromolecules using UV-VIS spectrophotometry, fluorimetry, mass spectrometry etc. [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.…”

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

“…These bands are also caused by electronic π → π * transitions. An acid solution of sanguinarine has faint luminosity with a maximum at ~600 nm, while in a highly alkaline medium, it has a high relative luminous intensity with a peak at λ = 418 nm [7].…”