A study of azopyrimidine photoswitches and their interactions with cyclodextrins: When the guest governs the type of accommodation at the host

Hruzíková, Anna; Čechová, Lucie; Štěpánová, Sille; Tučková, Lucie; Tichotová, Markéta; Růžička, Aleš; Kašička, Václav; Procházková, Eliška

doi:10.1016/j.dyepig.2023.111099

Cited by 3 publications

(4 citation statements)

References 83 publications

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“…CDN binding with HP‐β‐CD has been investigated assuming a 1:1 stoichiometry of their complexes based on a previously published study with structurally similar compounds [39, 40]. In the case of the 1:1 stoichiometry, the interaction of a chiral analyte, A, with a stereoselector, S, and the formation of an analyte‐stereoselector complex, AS, can be described by the following equilibrium:

\begin{equation}\text{A}+\text{S}\rightleftarrows \text{AS}\end{equation}

…”

Section: The Theoretical Background Of Acementioning

confidence: 99%

“…The mobilities are the average values from three measurements. The viscosity-corrected and viscosity-uncorrected values of the average apparent binding constants, K b , the average actual ionic mobilities, µ AS , of the complexes of the cyclic dinucleotides (CDNs) 1-4, with 2-hydroxypropyl-β-cyclodextrin (HP-β-CD), and the effective mobilities, µ A , of free (non-complexed) CDNs in the background electrolytes (BGE) composed of40 mM tris[hydroxymethyl]aminomethane (Tris), 40 mM N-[Tris(hydroxymethyl)methyl]glycine (tricine), pH 8.1, at 25 • C.…”

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confidence: 99%

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The separation of cyclic diadenosine diphosphorothioate and the diastereomers of its difluorinated derivative and the estimation of the binding constants and ionic mobilities of their complexes with 2‐hydroxypropyl‐β‐cyclodextrin by affinity capillary electrophoresis

Štěpánová,

Břehová,

Kašička

2024

Electrophoresis

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The incorporation of phosphorothioate linkages has recently been extensively employed in therapeutic oligonucleotides. For their separation and quality control, new high‐efficient and high‐sensitive analytical methods are needed. In this work, a new affinity capillary electrophoresis method has been developed and applied for the separation of a potential anticancer drug, 2′,3′‐cyclic diadenosine diphosphorothioate (Rp, Rp) (ADU‐S100), and three recently newly synthesized diastereomers of its difluorinated derivative, 3′,3′‐cyclic di(2′‐fluoro, 2′‐deoxyadenosine phosphorothioate). The separation was performed in the various background electrolytes (BGEs) within a pH range 5–9 using several native and derivatized cyclodextrins (CDs) as chiral additives of the BGE. Relatively good separations were obtained with β‐, γ‐, and 2‐hydroxypropyl‐γ‐CDs in some of the BGEs tested. However, the best separation was achieved using the 2‐hydroxypropyl‐β‐CD chiral selector at 43.5 mM average concentration in the BGE composed of 40 mM Tris, 40 mM tricine, pH 8.1. Under these conditions, all the previous four cyclic dinucleotides (CDNs) were baseline separated within 4 min. Additionally, the average apparent binding constants and the average actual ionic mobilities of the complexes of all four CDNs with 2‐hydroxypropyl‐β‐CD in the above BGE were determined. The formed complexes were found to be relatively weak, with the average apparent binding constants in the range of 12.2–94.1 L mol−1 and with the actual ionic mobilities spanning the interval (−7.8 to −12.7) × 10−9 m2 V−1 s−1. The developed method can be applied for the separation, analysis, and characterization of the above and similar CDNs.

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\begin{equation}\text{A}+\text{S}\rightleftarrows \text{AS}\end{equation}

…”

Section: The Theoretical Background Of Acementioning

confidence: 99%

mentioning

confidence: 99%

The separation of cyclic diadenosine diphosphorothioate and the diastereomers of its difluorinated derivative and the estimation of the binding constants and ionic mobilities of their complexes with 2‐hydroxypropyl‐β‐cyclodextrin by affinity capillary electrophoresis

Štěpánová,

Břehová,

Kašička

2024

Electrophoresis

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“…The ways how to improve the accuracy and precision of ms-ACE measurements have been thoroughly discussed in [186]. ms-ACE has been applied to determine binding constants of many (bio)molecular complexes, for example, the complexes of rotamers of nitrosopyrimidines with β-CD [185], the complexes of azopyrimidines with β-CD [187], the complexes of the enantiomers of the metal-polypyridyl associates, [Ru(bpy) 3 ] 2+ , [Ru(phen) 3 ] 2+ , and [Fe(phen) 3 ] 2+ with the single-isomer 2,3-diacetylated-6-sulfated-CDs (12Ac-6S-α-CD, 14Ac-7S-β-CD, and 16Ac-8S-γ-CD) [188], the crown ether complexes with potassium ion [189], drug enantiomers complexes with human serum albumin (HSA) [190].…”

Section: Mobility Shift Acementioning

confidence: 99%

Determination of physicochemical parameters of (bio)molecules and (bio)particles by capillary electromigration methods

Štěpánová,

Kašička

2024

J of Separation Science

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The review provides an overview of recent developments and applications of capillary electromigration (CE) methods for the determination of important physicochemical parameters of various (bio)molecules and (bio)particles. These parameters include actual and limiting (absolute) ionic mobilities, effective electrophoretic mobilities, effective charges, isoelectric points, electrokinetic potentials, hydrodynamic radii, diffusion coefficients, relative molecular masses, acidity (ionization) constants, binding constants and stoichiometry of (bio)molecular complexes, changes of Gibbs free energy, enthalpy and entropy and rate constants of chemical reactions and interactions, retention factors and partition and distribution coefficients. For the determination of these parameters, the following CE methods are employed: zone electrophoresis in a free solution or in sieving media, isotachophoresis, isoelectric focusing, affinity electrophoresis, electrokinetic chromatography, and electrochromatography. In the individual sections, the procedures for the determination of the above parameters by the particular CE methods are described.

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“…They include electrochemical detection alone [216,217] or in combination with MS [218], direct or indirect chemiluminescence [219], and electrochemiluminescence [220]. NMR spectroscopy is mostly offline combined with CE, especially for the structural analysis of analyte-selector complexes the strength of which was studied by CE [221][222][223].…”

Section: Other Detection Modesmentioning

confidence: 99%

Recent developments in capillary and microchip electroseparations of peptides (2021–mid‐2023)

Kašička

2023

Electrophoresis

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This review article brings a comprehensive survey of developments and applications of high‐performance capillary and microchip electromigration methods (zone electrophoresis in a free solution or in sieving media, isotachophoresis, isoelectric focusing, affinity electrophoresis, electrokinetic chromatography, and electrochromatography) for analysis, micropreparation, and physicochemical characterization of peptides in the period from 2021 up to ca. the middle of 2023. Progress in the study of electromigration properties of peptides and various aspects of their analysis, such as sample preparation, adsorption suppression, electroosmotic flow regulation, and detection, are presented. New developments in the particular capillary electromigration methods are demonstrated, and several types of their applications are reported. They cover qualitative and quantitative analysis of synthetic or isolated peptides and determination of peptides in complex biomatrices, peptide profiling of biofluids and tissues, and monitoring of chemical and enzymatic reactions and physicochemical changes of peptides. They include also amino acid and sequence analysis of peptides, peptide mapping of proteins, separation of stereoisomers of peptides, and their chiral analyses. In addition, micropreparative separations and physicochemical characterization of peptides and their interactions with other (bio)molecules by the above CE methods are described.

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A study of azopyrimidine photoswitches and their interactions with cyclodextrins: When the guest governs the type of accommodation at the host

Cited by 3 publications

References 83 publications

The separation of cyclic diadenosine diphosphorothioate and the diastereomers of its difluorinated derivative and the estimation of the binding constants and ionic mobilities of their complexes with 2‐hydroxypropyl‐β‐cyclodextrin by affinity capillary electrophoresis

The separation of cyclic diadenosine diphosphorothioate and the diastereomers of its difluorinated derivative and the estimation of the binding constants and ionic mobilities of their complexes with 2‐hydroxypropyl‐β‐cyclodextrin by affinity capillary electrophoresis

Determination of physicochemical parameters of (bio)molecules and (bio)particles by capillary electromigration methods

Recent developments in capillary and microchip electroseparations of peptides (2021–mid‐2023)

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