Determination of Acid Dissociation Constants of Compounds Active at Neuronal Nicotinic Acetylcholine Receptors by Means of Electrophoretic and Potentiometric Techniques

Roda, Gabriella; Dallanoce, Clelia; Grazioso, Giovanni; Liberti, Vincenzo; Amici, Marco De

doi:10.2116/analsci.26.51

Cited by 28 publications

(19 citation statements)

References 19 publications

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“…Recently published papers about applications of CE methods to p K a determination bring some methodological innovation (e.g., temperature and ionic strength corrections of measured effective mobilities, determination of very low or very high p K a values, pressure assisted accelerated measurement of EOF and effective mobilities, and determination of p K a in nonaqueous solvents) . The determination of the p K a of 22 frequently used pharmaceuticals using CE was presented .…”

Section: Separation and Analysis Of Small Moleculesmentioning

confidence: 99%

Recent advances in capillary electrophoretic migration techniques for pharmaceutical analysis (2013–2015)

et al. 2016

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This review updates and follows-up a previous review by highlighting recent advancements regarding capillary electromigration methodologies and applications in pharmaceutical analysis. General approaches such as quality by design as well as sample injection methods and detection sensitivity are discussed. The separation and analysis of drug-related substances, chiral CE, and chiral CE-MS in addition to the determination of physicochemical constants are addressed. The advantages of applying affinity capillary electrophoresis in studying receptor-ligand interactions are highlighted. Finally, current aspects related to the analysis of biopharmaceuticals are reviewed. The present review covers the literature between January 2013 and December 2015.

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Section: Separation and Analysis Of Small Moleculesmentioning

confidence: 99%

Recent advances in capillary electrophoretic migration techniques for pharmaceutical analysis (2013–2015)

et al. 2016

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“…Intermediate mobility is a function of the dissociation equilibrium, and pK a values are determined by regression analysis [14]. In a previous paper, we reported the measure of the acid-base dissociation constants for a set of nAChR ligands with both potentiometric and electrophoretic methods [15]. Herein, we describe a parallel study on the determination of the dissociation constants of the group of new nicotinic ligands 2-9.…”

Section: Introductionmentioning

confidence: 99%

Determination of Acid Dissociation Constants of Poorly Water-Soluble Nicotinic Ligands by Means of Electrophoretic and Potentiometric Techniques

Roda¹,

Dallanoce²,

Gambaro³

et al. 2015

Pharm Anal Acta

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Objectives: Acid-base dissociations constants of a series of poorly water-soluble nicotinic ligands designed as anti-inflammatory agents were determined in order to characterize the pharmacokinetic profile of this kind of ligands.Methods: pK a s values were assessed by means of potentiometric and electrophoretic methods and investigated by computational protocols.Results: Both electrophoretic and potentiometric measurements produced reliable results. However, with the electrophoretic technique only an average value for close pK a s was found, whereas the potentiometric method allowed determination of each pK a value in water-cosolvent mixtures. A theoretical treatment with various prediction programs -i.e. ADME Boxes v. 4.1, ACD/pK a DB and ACD/pK a GALAS -led in most cases to values which were not in accordance with the experimental ones. Conclusion:Electrophoretic and potentiometric techniques showed complementary features. Indeed, with capillary electrophoresis, the problem associated with the low water solubility of the studied samples could be easily overcome, although this technique did not allow to measuring all dissociation constants. In contrast, application of the potentiometric method afforded all the theoretical pK a values, although we had to perform the titrations in watercosolvent mixtures, a less precise, more laborious and time-consuming approach.

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“…Acid dissociation constants are important physicochemical parameters, which can provide critical information about drug properties such as solubility, lipophilicity, acidity [1–3], transport behavior, bonding to receptors [2–4], and permeability [5]. Hence, the relationship between the acid dissociation constants and structure in drug design studies is important [2, 3, 6].…”

Section: Introductionmentioning

confidence: 99%

“…Hence, the relationship between the acid dissociation constants and structure in drug design studies is important [2, 3, 6]. Acid dissociation constants are also important parameters for the selection of the optimum conditions in the development of analytical methods [5, 7] and provide information about the stereochemical and conformational structures of active centers of enzymes [8].…”

Section: Introductionmentioning

confidence: 99%

“…Acid dissociation constants are also important parameters for the selection of the optimum conditions in the development of analytical methods [5, 7] and provide information about the stereochemical and conformational structures of active centers of enzymes [8]. Acid dissociation constants are determined by various methods such as potentiometric [5, 9], spectroscopic [6], and electrophoretic methods [2, 10]. …”

Section: Introductionmentioning

confidence: 99%

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Determination of Acid Dissociation Constants (pKa) of Bicyclic Thiohydantoin-Pyrrolidine Compounds in 20% Ethanol-Water Hydroorganic Solvent

Nural

Döndaş

Sarı

et al. 2014

International Journal of Analytical Chemistry

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The acid dissociation constants of potential bioactive fused ring thiohydantoin-pyrrolidine compounds were determined by potentiometric titration in 20% (v/v) ethanol-water mixed at 25 ± 0.1°C, at an ionic background of 0.1 mol/L of NaCl using the HYPERQUAD computer program. Proton affinities of potential donor atoms of the ligands were calculated by AM1 and PM3 semiempiric methods. We found, potentiometrically, three different acid dissociation constants for 1a–f. We suggest that these acid dissociation constants are related to the carboxyl, enol, and amino groups.

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Determination of Acid Dissociation Constants of Compounds Active at Neuronal Nicotinic Acetylcholine Receptors by Means of Electrophoretic and Potentiometric Techniques

Cited by 28 publications

References 19 publications

Recent advances in capillary electrophoretic migration techniques for pharmaceutical analysis (2013–2015)

Recent advances in capillary electrophoretic migration techniques for pharmaceutical analysis (2013–2015)

Determination of Acid Dissociation Constants of Poorly Water-Soluble Nicotinic Ligands by Means of Electrophoretic and Potentiometric Techniques

Determination of Acid Dissociation Constants (pKa) of Bicyclic Thiohydantoin-Pyrrolidine Compounds in 20% Ethanol-Water Hydroorganic Solvent

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