Exploring Glycosylated Soy Isoflavones Affinities toward G‐tetrads as Studied by Survival Yield Method

Stężycka, Olga; Frańska, Magdalena; Beszterda, Monika

doi:10.1002/cphc.202300056

Cited by 5 publications

(13 citation statements)

References 58 publications

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“…In other words, the methylation of 3-OH substantially increases the flavonol affinity toward G-tetrads. If there is a free 3-OH group, the C4O···HO–C3 hydrogen bond can exist (which interferes with C4O···HO–C5). , Methylation of 3-OH yields C4O, making them more available to form hydrogen bonds with G-tetrads, which may increase the adduct stabilities, similarly, as observed for isoflavone glycosides …”

Section: Resultsmentioning

confidence: 92%

“…25,26 Methylation of 3-OH yields C4�O, making them more available to form hydrogen bonds with G-tetrads, which may increase the adduct stabilities, similarly, as observed for isoflavone glycosides. 38 Guanosine tetrad yielded 2:1 adducts with all M molecules, whereas deoxyguanosine tetrad did not yield 2:1 adducts with quercetin and isorhamnetin. The determined values of E comδ50 of 2:1 adducts are shown in Figure 4.…”

Section: ■ Materials and Methodsmentioning

confidence: 89%

“…The survival yield of the precursor ion subjected to the collision-induced dissociation is defined as SY = I normalp I p + ∑ I f where I p stands for the intensity of the peak of precursor ion and I f for the intensities of the peaks of fragment ions. Collision energy expressed in terms of the center-of-mass E comδ (the maximum kinetic energy available for transfer into internal energy) is defined as E com δ = δ E lab m normalg m p + m g where E lab stands for laboratory collision energy, m g stands for the mass of the neutral target gas, m p stands for the mass of precursor ion, and δ is the correction factor, which reflects the number of degrees of freedom (DOF = 3 N – 6, N stands for the number of atoms in the analyzed ions). − The ion [4G dr + Na + Que] + is the smallest from among the analyzed ions, this ion was selected as a reference (DOF ref = 477), so for this ion δ = 1, and for the other ones δ = DOF ref /DOF ion . The plot of the SY against E comδ gives the curve of the precursor ion fragmentation.…”

Section: Methodsmentioning

confidence: 99%

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Binding of Quercetin Derivatives toward G-Tetrads as Studied by the Survival Yield Method

Stężycka,

Frańska

2023

ACS Omega

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Recently, much interest has been devoted to finding effective G-quadruplex ligands, both of synthetic or natural origins, which may be of potential use in the field of cancer therapy. Among compounds of natural origin, a common flavonol quercetin has attracted notable attention. Yet, only a modest number of papers have been concerned with a comparison of quercetin conjugates binding to G-quadruplexes. In this study, we applied the survival yield (SY) method in order to compare the stability of G-tetrad complexes with quercetin and its conjugates, namely, 3-Oglycosides and O-methylated conjugates. According to the determined values of E comδ50 , flavonol glycosides bind most effectively with G-tetrads, whereas, among flavonols, 3-O-methylquercetin makes the most effective bonds. Because the aglycone structure is of crucial importance for biological processes, 3-O-methylquercetin seems to be a suitable candidate for anticancer therapeutics, and the extracts from the plants, which contain high amounts of 3-O-methylquercetin or its glycosides, should be considered as interesting materials for preparation of pharmaceuticals or dietary supplements.

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Section: Resultsmentioning

confidence: 92%

Section: ■ Materials and Methodsmentioning

confidence: 89%

Section: Methodsmentioning

confidence: 99%

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Binding of Quercetin Derivatives toward G-Tetrads as Studied by the Survival Yield Method

Stężycka,

Frańska

2023

ACS Omega

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“…The SY of the precursor ion subjected to the CID is defined as

SY goodbreak= \frac{I_{normalp}}{I_{p} + \sum I_{f}}

where I p is the intensity of the peak of the precursor ions and I f the intensity of the peak of the fragment ions. CE expressed in terms of the center‐of‐mass E comδ (the maximum kinetic energy available for transfer into internal energy) is defined as

E_{comδ} goodbreak= {δE}_{lab} \frac{m_{normalg}}{m_{p} + m_{g}}

where E lab is the laboratory CE, m g is the mass of the neutral target gas, m p is the mass of the precursor ions, and δ is the correction factor that reflects the number of degrees of freedom (DOF = 3 N – 6, where N is the number of atoms in the analyzed ions) 24–26 . The ion [2C + H] + is the smallest of the analyzed ions; therefore, this ion was selected as reference (DOF ref = 75); for this ion δ = 1, and for the other ions δ = DOF ref /DOF ion .…”

Section: Methodsmentioning

confidence: 99%

“…where E lab is the laboratory CE, m g is the mass of the neutral target gas, m p is the mass of the precursor ions, and δ is the correction factor that reflects the number of degrees of freedom (DOF = 3N -6, where N is the number of atoms in the analyzed ions). [24][25][26] The ion [2C + H] + is the smallest of the analyzed ions; therefore, this ion was selected as reference (DOF ref = 75); for this ion δ = 1, and for the other ions δ = DOF ref /DOF ion . The plot of SY against E comδ gives the precursor ion fragmentation curve, which reflects the gas-phase stabilities of the analyzed precursor ions.…”

Section: Sy Methodsmentioning

confidence: 99%

Study of protonated dimers of cytosine, cytidine, and deoxycytidine using survival yield method and quantum mechanics calculations

Jankowski,

Hoffmann,

Półrul

et al. 2023

Rapid Comm Mass Spectrometry

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RationaleCytosine and its conjugates are prone to form protonated, triply‐bonded dimers. Therefore, the nucleic‐acid cytosine‐rich sequence forms the four‐stranded noncanonical secondary structure known as the intercalated motif (i‐motif). This process has resulted in studies on cytosine protonated dimers. This communication focuses on the protonated dimers of cytosine and its nucleoside using the survival yield (SY) method and quantum mechanics calculations.MethodsTo obtain the precursor ion fragmentation curve, the plot of SY against Ecomδ, the product ion spectra of the protonated dimers were obtained using a Waters/Micromass Q‐TOF Premier mass spectrometer. Quantum mechanics calculations were performed using GAUSSIAN 16, and full geometry optimizations and energy calculations were performed within the density functional theory framework at B3LYP/6‐31G(d,p).ResultsThe precursor ion fragmentation curve allowed the rating of the gas‐phase stabilities of the analyzed protonated dimers. Substitution of sugar moiety at N1 cytosine atom decreased the gas‐phase stabilities of the protonated dimers. The deoxycytidine dimer was found to be more stable than the cytidine dimer and cytidine–deoxycytidine dimer. Quantum chemical calculations indicated that cytosine aminohydroxy tautomer may be involved in the formation of protonated cytosine–cytosine nucleoside dimers but not in the formation of cytosine dimers.ConclusionsThe results obtained for nucleoside dimers indicated that the SY method may reflect the i‐motif stabilities observed under physiological conditions. Therefore, the analysis of other protonated dimers of variously substituted cytosine–cytosine nucleoside using the SY method may be important to study the effect of cytosine substitution on the i‐motif stabilities. Cytosine tautomer containing C2‐OH… N(2H)‐C4 moiety may be involved in the formation of protonated cytosine–cytosine nucleoside dimers.

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Oxygen Atom from Carbonyl Group as an Important Binding Agent to the G‐Quadruplex – Study Case of Flavonoids

Stężycka,

Kasperkowiak,

Frańska

et al. 2024

ChemPlusChem

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In the field of anticancer therapy study it is of great interest to find effective G‐quadruplex ligands which may be of potential use in medical treatment or cancer prevention. Since among the compounds of natural origin, flavonoids have attracted notable attention because of their unique properties and promising therapeutic applications, an interesting question was to identify the flavonoid structural features that could provide effective binding properties toward G‐quadruplex. By using electrospray ionization mass spectrometry, followed by the survival yield method, it has been shown that the flavonoid molecules which contain an available C4=O carbonyl group form more stable adducts with G‐tetrads than the other ones. Molecular docking has shown that C4=O carbonyl group can be a source of hydrogen bonds and/or π‐stacking interactions. Therefore, the flavonoid molecules which contain an available C4=O carbonyl group can be regarded as good binders of G‐quadruplexes.

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Exploring Glycosylated Soy Isoflavones Affinities toward G‐tetrads as Studied by Survival Yield Method

Cited by 5 publications

References 58 publications

Binding of Quercetin Derivatives toward G-Tetrads as Studied by the Survival Yield Method

Binding of Quercetin Derivatives toward G-Tetrads as Studied by the Survival Yield Method

Study of protonated dimers of cytosine, cytidine, and deoxycytidine using survival yield method and quantum mechanics calculations

Oxygen Atom from Carbonyl Group as an Important Binding Agent to the G‐Quadruplex – Study Case of Flavonoids

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