Sugammadex analogue cyclodextrins as chiral selectors for enantioseparation of cathinone derivatives by capillary electrophoresis

Ujj, Dóra; Kalydi, Eszter; Varga, Erzsébet; Sohajda, Tamás; Béni, Szabolcs; Benkovics, Gábor

doi:10.1016/j.chroma.2022.463506

Cited by 6 publications

(6 citation statements)

References 20 publications

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“…As CE does not provide any molecular-level information on the interaction between host and guest molecules, NMR measurements were carried out according to previous works [ 29 , 32 , 33 , 34 ]. The CD complexation of different cathinone analogs was previously studied by our group in the case of the heptakis(6- O -methyl)-β-CD—MDPV system [ 34 ] and with the SBX— N -ethylbuphedrone [ 29 ] complex.…”

Section: Resultsmentioning

confidence: 99%

Cyclodextrin-Enabled Enantioselective Complexation Study of Cathinone Analogs

Dohárszky,

Kalydi,

Völgyi

et al. 2024

Molecules

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The characteristic alkaloid component of the leaves of the catnip shrub (Catha edulis) is cathinone, and its synthetic analogs form a major group of recreational drugs. Cathinone derivatives are chiral compounds. In the literature, several chiral methods using cyclodextrins (CDs) have been achieved so far for diverse sets of analogs; however, a comprehensive investigation of the stability of their CD complexes has not been performed yet. To characterize the enantioselective complex formation, a systematic experimental design was developed in which a total number of 40 neutral, positively, and negatively charged CD derivatives were screened by affinity capillary electrophoresis and compared according to their cavity size, substituent type, and location. The functional groups responsible for the favorable interactions were identified in the case of para-substituted cathinone analog mephedrone, flephedrone, and 4-methylethcathinone (4-MEC) and in the case of 3,4-methylendioxy derivative butylone and methylenedioxypyrovalerone (MDPV). The succinylated-β-CD and subetadex exhibited the highest complex stabilities among the studied drugs. The complex stoichiometry was determined using the Job’s plot method, and the complex structures were further studied using ROESY NMR measurements. The results of our enantioselective complex formation study can facilitate chiral method development and may lead to evaluate potential CD-based antidotes for cathinone analogs.

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Section: Resultsmentioning

confidence: 99%

Cyclodextrin-Enabled Enantioselective Complexation Study of Cathinone Analogs

Dohárszky,

Kalydi,

Völgyi

et al. 2024

Molecules

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“…A variety of CyDs and their derivatives have been extensively applied as chiral selectors owing to their wide diversity, nontoxicity, and biodegradable properties. [136][137][138][139][140] Integrating conductive NMs with b-CyD and the sensing film is a desirable strategy to enhance the conductivity of b-CyD, further improving the sensing efficiency. Carbon NMs such as graphene and CNTs have been utilized to modify electrodes for enhancing the detection sensitivity.…”

Section: Creating a Cooperative Relationship Between Polysaccharides ...mentioning

confidence: 99%

A cooperation tale of biomolecules and nanomaterials in nanoscale chiral sensing and separation

Hong,

Zhou,

Tan

et al. 2023

Nanoscale Horiz.

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“…It is used in the clinical practice as the first selective antidote of steroidal neuromuscular blocking agents rocuronium and vecuronium during surgical 2 of 17 interventions [12]. In addition, Suγ-CD was patented for the selective sequestration of cortisol [13] and fentanyl-related compounds [14] and applied as a selector in an affinity capillary electrophoresis method for penicillins [15] and cathinones [16]. The monosubstituted analogue of Suγ-CD, mono-Suγ-CD in Figure 1 has also been synthesized [17], without assessing its potential applications.…”

Section: Introductionmentioning

confidence: 99%

“…The monosubstituted analogue of Suγ-CD, mono-Suγ-CD in Figure 1 has also been synthesized [17], without assessing its potential applications. In addition to the expanding utilization of Suγ-CD, there is also a growing interest in its α-and β-CD homologues sualphadex and subetadex [16,17], abbreviated as Suα-CD and Suβ-CD in Figure 1. Besides interaction studies with fentanyl [14], rocuronium bromide [18] and azobenzenes [19], their applicability as chiral selectors was also explored recently [16].…”

Section: Introductionmentioning

confidence: 99%

“…In addition to the expanding utilization of Suγ-CD, there is also a growing interest in its α-and β-CD homologues sualphadex and subetadex [16,17], abbreviated as Suα-CD and Suβ-CD in Figure 1. Besides interaction studies with fentanyl [14], rocuronium bromide [18] and azobenzenes [19], their applicability as chiral selectors was also explored recently [16]. A thorough physicochemical profiling of CD derivatives is essential in order to deepen our understanding and improve the modeling perspectives on their intermolecular interactions upon inclusion complex formation.…”

Section: Introductionmentioning

confidence: 99%

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Fully Symmetric Cyclodextrin Polycarboxylates: How to Determine Reliable Protonation Constants from NMR Titration Data

Kalydi

Ujj

Benkovics

et al. 2022

IJMS

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Acid-base properties of cyclodextrins (CDs), persubstituted at C-6 by 3-mercaptopropionic acid, sualphadex (Suα-CD), subetadex (Suβ-CD) and sugammadex (Suγ-CD, the antidote of neuromuscular blocking steroids) were studied by 1H NMR-pH titrations. For each CD, the severe overlap in protonation steps prevented the calculation of macroscopic pKa values using the standard data fitting model. Considering the full symmetry of polycarboxylate structures, we reduced the number of unknown NMR parameters in the “Q-fitting” or the novel “equidistant macroscopic” evaluation approaches. These models already provided pKa values, but some of them proved to be physically unrealistic, deceptively suggesting cooperativity in carboxylate protonations. The latter problem could be circumvented by adapting the microscopic site-binding (cluster expansion) model by Borkovec, which applies pairwise interactivity parameters to quantify the mutual basicity-decreasing effect of carboxylate protonations. Surprisingly, only a single averaged interactivity parameter could be calculated reliably besides the carboxylate ‘core’ microconstant for each CD derivative. The speciation of protonation isomers hence could not be resolved, but the optimized microscopic basicity parameters could be converted to the following sets of macroscopic pKa values: 3.84, 4.35, 4.81, 5.31, 5.78, 6.28 for Suα-CD; 3.82, 4.31, 4.73, 5.18, 5.64, 6.06, 6.54 for Suβ-CD and 3.83, 4.28, 4.65, 5.03, 5.43, 5.81, 6.18, 6.64 for Suγ-CD. The pH-dependent charge of these compounds can now be accurately calculated, in support of designing new analytical methods to exploit their charge-dependent molecular recognition such as in cyclodextrin-aided chiral capillary electrophoresis.

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Sugammadex analogue cyclodextrins as chiral selectors for enantioseparation of cathinone derivatives by capillary electrophoresis

Cited by 6 publications

References 20 publications

Cyclodextrin-Enabled Enantioselective Complexation Study of Cathinone Analogs

Cyclodextrin-Enabled Enantioselective Complexation Study of Cathinone Analogs

A cooperation tale of biomolecules and nanomaterials in nanoscale chiral sensing and separation

Fully Symmetric Cyclodextrin Polycarboxylates: How to Determine Reliable Protonation Constants from NMR Titration Data

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