Role of chemical structure in stereoselective recognition of beta‐blockers and H<sub>1</sub>‐antihistamines by human serum transferrin in capillary zone electrophoresis

Gagyi, László; Gyéresi, Árpád; Kilár, Ferenc

doi:10.1002/elps.200500787

Cited by 14 publications

(7 citation statements)

References 17 publications

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“…Higher transferrin concentration and ionic strength, as well as longer residence time in the protein zone was necessary for successful stereoselective differentiation of TME enantiomers. Further studies will, however, be necessary to clarify the precise role of the structural components in molecular recognition by proteins (Gagyi et al, 2006).…”

Section: Discussionmentioning

confidence: 99%

Role of chemical structure in molecular recognition by transferrin

Takátsy¹,

Hodrea²,

Majdik³

et al. 2006

J of Molecular Recognition

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Studies of molecular recognition of chiral compounds by proteins are of importance from many points of view. The biological role of proteins in their interaction with small molecules is of fundamental interest and can be used in many different fields, for instance for in vitro analysis of optically active compounds. Studies in these areas need a detailed study of the interaction sites on the protein surface and the relationship between chemical structure and the complex formation ability of small molecules, such as drugs. The electrophoretic migration of charged compounds through a protein zone may provide information about the surface properties of the macromolecule in the interaction site. The interaction of human serum transferrin with tryptophan-methyl- (TME), ethyl- (TEE) and butyl-esters (TBE) has been investigated by capillary electrophoresis (CE) and model calculations. Differences in the separation of tryptophan derivatives were obtained by varying experimental parameters such as, pH, ionic strength of background electrolyte and the length of transferrin zone. Limited separation of the enantiomer pairs were observed at pH 5 and 7 with a maximum resolution at pH 6. The size of the ligands coupled to the chiral centre has importance in stereoselective recognition; however, a direct comparison of resolution different in same runs may lead to false conclusion if the experimental conditions are not comparable. With a careful evaluation of the data we obtained significant differences between the resolution of the smallest enantiomer pair compared to those of tryptophan derivatives with longer alkyl chains.

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Section: Discussionmentioning

confidence: 99%

Role of chemical structure in molecular recognition by transferrin

Takátsy¹,

Hodrea²,

Majdik³

et al. 2006

J of Molecular Recognition

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“…[6][7][8][9][10] In CE, the enantioselectivity is based on the chiral selector, which is dissolved in the running buffer. During the last decade, various types of chiral selectors, such as cyclodextrins (CDs) and their derivatives, 11,12 crown ethers, 13 chiral surfactants, 14,15 polysaccharides, 16,17 macrocyclic antibiotics, 18 proteins, 19 and metal complexes 20,21 have been widely used in CE. Among them, CDs and their various derivatives are the most popularly used chiral selectors with about 90% of the applications.…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of Palonosetron Hydrochloride by Capillary Zone Electrophoresis with High-concentration β-CD as Chiral Selector

et al. 2009

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The enantioseparation of four stereoisomers of palonosetron hydrochloride (PALO) by capillary zone electrophoresis using high concentration β-CD as chiral selector was described in this study. For optimization of the method of enantioseparation, several parameters such as β-CD concentration, separation buffer pH and concentration, the types and concentration of organic modifiers, and the applied voltage were evaluated. The optimum conditions were obtained as follows: 30 mmol L -1 NaH2PO4 (pH 3.0) containing 150 mmol L -1 β-CD and 10% (v/v) methanol with an applied voltage of 15 kV. Under these conditions, baseline separation of the four PALO stereoisomers was achieved within 35 min, and the reproducibility (expressed as relative standard deviation, RSD) of the migration times and the peak areas were below 0.5, 2.5% (intra-day), and 1.9, 4.4% (inter-day), respectively. hydrochloride, is a pharmacologically distinct and highly selective, secondgeneration 5-hydroxytryptamine type-3 (5-HT3) receptor antagonist approved for prevention of chemotherapy-and radiotherapy-induced nausea and vomit (CINV) after highly emetogenic chemotherapy. 1-4 Chemotherapy-and radiotherapyinduced nausea and vomit will have a series of related complications if they lack control; these are the most feared adverse reactions in cancer patients. 5-HT3 receptor antagonized mainly through competing to block the release of 5-HT and 5-HT3 receptor-binding of digestive tract mucosa in order to have a role in anti-vomit treatment.Chiral drugs include a large proportion of drugs at present; they generate different pharmacological effects through combining with different stereo structure molecules in the body in the processes of drug absorption, distribution, metabolism and excretion. Consequently, the separation and measurement of chiral drugs have great significance in the pharmacokinetics, pharmacological and toxicological mechanisms as well as in quality control of chiral drugs. Palonosetron hydrochloride contains two chiral centers and four stereoisomers: (3aR, 2R), (3aS, 2S), (3aR, 2S) and (3aS, 2R), among which only (3aS, 2S) possesses pharmacological activity. 5 Therefore, it is necessary to establish an appropriate enantiomeric separation method for PALO.Capillary electrophoresis (CE) is now recognized as a powerful tool for enantioseparation due to its high separation efficiency, low operational cost, simplicity and versatility. [6][7][8][9][10] In CE, the enantioselectivity is based on the chiral selector, which is dissolved in the running buffer. During the last decade, various types of chiral selectors, such as cyclodextrins (CDs) and their derivatives, 11,12 crown ethers, 13 chiral surfactants, 14,15 polysaccharides, 16,17 macrocyclic antibiotics, 18 proteins, 19 and metal complexes 20,21 have been widely used in CE. Among them, CDs and their various derivatives are the most popularly used chiral selectors with about 90% of the applications. 10 CDs, which obtained from amylum enzymatic conversion, can form inclusion compounds with many ...

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“…Ethamsylate, tramadol, and lidocaine are partially excreted by kidneys, and are generally used as hemostatic, analgesic, and local anesthetic in surgery. Antihistamines [127], antidepressants [128], morphine and related compounds [127], protease inhibitors [129], antibiotics [40,133,134,138,139], and amino acids [140,141] are a few examples of drugs that have been detected by CE.…”

Section: Ce In Pharmaceuticsmentioning

confidence: 99%

CE at the omics level: Towards systems biology – An update

Song

Babar

et al. 2007

Electrophoresis

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This review provides an updated overview of recent developments and applications of CE based on previously published reports in the field of omic research. The increased number of published articles on omics shows that the field is growing and attracting the attention of many life science researchers. Due to developments in the omics sciences, many researchers have been studying systems biology, in which biological events in organisms are systematically interpreted through the combination of complex measurements from various methods resulting in high-throughput data. Given the challenges of such complex forms of analysis, CE is a strong candidate for generating omics data useful for acquiring the qualitative and quantitative knowledge necessary for systems-level investigation. By emphasizing CE for systems biology, this review will discuss and focus on the applicability of CE to systems-based analytical data at the genomic, transcriptomic, proteomic, and metabolomic levels from 2005 to the present.

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Role of chemical structure in stereoselective recognition of beta‐blockers and H₁‐antihistamines by human serum transferrin in capillary zone electrophoresis

Cited by 14 publications

References 17 publications

Role of chemical structure in molecular recognition by transferrin

Role of chemical structure in molecular recognition by transferrin

Enantioseparation of Palonosetron Hydrochloride by Capillary Zone Electrophoresis with High-concentration β-CD as Chiral Selector

CE at the omics level: Towards systems biology – An update

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Role of chemical structure in stereoselective recognition of beta‐blockers and H1‐antihistamines by human serum transferrin in capillary zone electrophoresis

Cited by 14 publications

References 17 publications

Role of chemical structure in molecular recognition by transferrin

Role of chemical structure in molecular recognition by transferrin

Enantioseparation of Palonosetron Hydrochloride by Capillary Zone Electrophoresis with High-concentration β-CD as Chiral Selector

CE at the omics level: Towards systems biology – An update

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Role of chemical structure in stereoselective recognition of beta‐blockers and H₁‐antihistamines by human serum transferrin in capillary zone electrophoresis