Electrospray ionization mass spectrometry of mixtures of triterpene glycosides with L-phenylalanine

Lekar, A. V.; Vetrova, E. V.; Borisenko, N. I.; Yakovishin, L. A.; Гришковец, В. И.; Borisenko, S. N.

doi:10.1007/s10812-011-9490-1

Cited by 6 publications

(6 citation statements)

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“…Various physicochemical methods have been applied to get the evidence of complexes formation between GA self-associates and drug molecules in solid state as well as in aqueous and non-aqueous solutions. Such complexes were investigated by Fourier-transform infrared spectroscopy, differential scanning calorimetry, X-ray diffraction and scanning electron microscopy techniques (Lekar et al, 2011a;Yang et al, 2015;Zu et al, 2013;Kong et al, 2017). The physicochemical properties and behavior of GA complexes in solution were characterized by NMR, mass spectroscopy, electrochemical and optical techniques (Baltina, 2003;Apanasenko et al, 2015;Konkina et al, 2015;Polyakov et al, 2005).…”

Section: Complex Formation With Drugsmentioning

confidence: 99%

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Glycyrrhizic acid as a multifunctional drug carrier – From physicochemical properties to biomedical applications: A modern insight on the ancient drug

Selyutina

Polyakov

2019

International Journal of Pharmaceutics

161

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A B S T R A C TGlycyrrhizic acid is the main active component of Licorice root which has been known in traditional Chinese and Japanese medicine since ancient times. In these cultures glycyrrhizic acid (GA) is one of the most frequently used drugs. However, only in 21-st century a novel unusual property of the GA to enhance the activity of other drugs has been discovered. The review describes briefly the experimental evidences of wide spectrum of own biological activities of glycyrrhizic acid as well as discusses the possible mechanisms of the ability of GA to enhance the activity of other drugs. We have shown that due to its amphiphilic nature GA is able to form self-associates in aqueous and non-aqueous media, as well as water soluble complexes with a wide range of lipophilic drugs. The main purpose of our review is to focus reader's attention on physicochemical studies of the molecular mechanisms of GA activity as a drug delivery system (DDS). In our opinion, the most intriguing feature of glycyrrhizic acid which might be the key factor in its therapeutic activity is the ability of GA to incorporate into the lipid bilayer and to increase the membrane fluidity and permeability. The ability of biomolecules and their aggregates to change the properties of cell membranes is of great significance, from both fundamental and practical points of view. monstrated the ability of GA to interact with cell membrane and to https://doi.

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Section: Complex Formation With Drugsmentioning

confidence: 99%

“…In this study the complex formation of GA and chloramphenicol with the ratio 1:1 and 2:1 were registered in the negative ion mode. It was also established that GA derivatives forms complexes with guanine, adenine (Lekar et al, 2011b) and L-phenylalanine (Lekar et al, 2011a).…”

Section: Complex Formation With Drugsmentioning

confidence: 99%

Glycyrrhizic acid as a multifunctional drug carrier – From physicochemical properties to biomedical applications: A modern insight on the ancient drug

Selyutina

Polyakov

2019

International Journal of Pharmaceutics

161

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“…Recently, mass spectrometry (ESI-MS) has been widely used to study supramolecular compounds. It has advantages over other methods for determining the qualitative composition of supramolecular complexes and their properties owing to the mild ionization conditions [11][12][13][14]. …”

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confidence: 99%

Mass Spectrometry of Self-Organizing Supramolecular Structures of Glycyrrhetic Acid and Levomycetin

et al. 2015

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The formation of supramolecular complexes of glycyrrhetic acid (GLA) and levomycetin was detected and studied for the first time using electrospray-ionization mass spectrometry (ESI-MS). It was shown that the intermolecular complexes detected in the mass spectra were formed most effectively for a 1:1 host-guest ratio and less effectively for a 1:2 ratio. GLA aggregates (dimers and trimers) bound one or two levomycetin molecules and formed several singly and doubly charged cationic complexes. A comparison of the mass spectra of supramolecular complexes of glycyrrhizic acid (GA) and its aglycon (GLA) indicated that GLA self-aggregates and complexes with levomycetin formed more effectively than those of GA.Glycyrrhizic acid (GA, 1c), the principal bioactive constituent from roots of Glycyrrhiza glabra L. and G. uralensis Fisch. ex DC. and a natural drug of folk medicine, is a natural compound with significant medicinal value as the basis for formulating new highly effective preparations. GA and its aglycon glycyrrhetic acid (GLA, 1) are known to exhibit high antiinflammatory, antiulcer, anti-allergic, hepatoprotective, antiviral, and other types of biological activity and are currently the subjects of numerous investigations [1,2]. Despite that facts that the complexing properties of GA are rather well known [3][4][5][6][7][8][9] and that drug substances based on modified natural compounds often have biological activities surpassing those of the starting compounds [5,10], the ability of GLA to form complexes with drugs is practically unstudied [4].The goal of the present work was to study the formation of supramolecular complexes of 1 with the widely used drug levomycetin (2) using electrospray-ionization mass spectrometry. Understanding the reaction mechanisms of plant metabolites and drugs on the molecular level is one of the most important problems of biochemistry and medicinal chemistry because it can reveal the drug mechanism of action and facilitate the development of methods for monitoring it and minimizing possible in vivo side effects. Recently, mass spectrometry (ESI-MS) has been widely used to study supramolecular compounds. It has advantages over other methods for determining the qualitative composition of supramolecular complexes and their properties owing to the mild ionization conditions [11][12][13][14].

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“…ESI-MS can be used not only to elucidate the structures of the complexes but also to study the mechanisms of intermolecular interactions because ions are generated directly from solution with retention of the complex structure under electrospray-ionization conditions [1,2]. These features of ESI-MS make it possible to study the binding and dissociation of ligand-receptor complexes [3,4], which enables methods for controlling drugs to be developed and possible side effects to be minimized. Knowledge of the correlations among the intermolecular-interaction mechanisms and the therapeutic effects of drugs on the molecular level provides a fundamental basis for developing new drugs.…”

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confidence: 99%

Study of Simvastatin Self-Association Using Electrospray-Ionization Mass Spectrometry

et al. 2015

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Self-association of simvastatin, which is widely used to treat coronary heart disease, was investigated using electrospray-ionization mass spectrometry. Formation of simvastatin self-associates in various solvents was demonstrated using mass spectrometry. Solvation effects were shown to play a special role in the formation of the self-associates. Self-associates containing from two to fi ve simvastatin molecules were detected in mass spectra of an aqueous MeOH (20%) solution of simvastatin. The formation of simvastatin self-associates could compete with the complexation of supramolecular structures during the synthesis of new generation drugs.Introduction. Electrospray-ionization mass spectrometry (ESI-MS) is a modern method for studying the structures of drugs and supramolecular complexes based on them that are used for targeted delivery and increased bioavailability. The mild ionization conditions of ESI-MS provide advantages over other methods for determining the qualitative and quantitative composition of supramolecular complexes [1, 2]. ESI-MS can be used not only to elucidate the structures of the complexes but also to study the mechanisms of intermolecular interactions because ions are generated directly from solution with retention of the complex structure under electrospray-ionization conditions [1,2]. These features of ESI-MS make it possible to study the binding and dissociation of ligand-receptor complexes [3,4], which enables methods for controlling drugs to be developed and possible side effects to be minimized. Knowledge of the correlations among the intermolecular-interaction mechanisms and the therapeutic effects of drugs on the molecular level provides a fundamental basis for developing new drugs.Herein, simvastatin {1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl-2,2-dimethylbutanoate, C 25 H 38 O 5 , MW = 418.57}, which is widely used to treat coronary heart disease [5], was selected for the ESI-MS studies:

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Electrospray ionization mass spectrometry of mixtures of triterpene glycosides with L-phenylalanine

Cited by 6 publications

References 7 publications

Glycyrrhizic acid as a multifunctional drug carrier – From physicochemical properties to biomedical applications: A modern insight on the ancient drug

Glycyrrhizic acid as a multifunctional drug carrier – From physicochemical properties to biomedical applications: A modern insight on the ancient drug

Mass Spectrometry of Self-Organizing Supramolecular Structures of Glycyrrhetic Acid and Levomycetin

Study of Simvastatin Self-Association Using Electrospray-Ionization Mass Spectrometry

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