Chiral resolution of some environmental pollutants by capillary electrophoresis

Ali, Imran; Gupta, Vinod K.; Aboul‐Enein, Hassan Y.

doi:10.1002/elps.200390175

Cited by 30 publications

(15 citation statements)

References 58 publications

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“…Although chiral separations by CE have been recently reviewed in food analysis [7], drugs [4,5], peptides [8], in nonaqueous media [9,10], etc., few articles have reviewed the chiral separation of pollutants [11][12][13]. The most recent of these articles [13] reports the chiral resolution of some environmental pollutants, mainly pesticides, without compiling the published articles concerning this topic (in that paper, special emphasis was put on the influence of different parameters as type of chiral selector, pH of BGE, applied voltage, temperature, etc., on the chiral resolution).…”

Section: Introductionmentioning

confidence: 99%

“…The most recent of these articles [13] reports the chiral resolution of some environmental pollutants, mainly pesticides, without compiling the published articles concerning this topic (in that paper, special emphasis was put on the influence of different parameters as type of chiral selector, pH of BGE, applied voltage, temperature, etc., on the chiral resolution). In view of the importance of the separation of chiral contaminants, the goal of this work is, therefore, to review the chiral separation of pollutants and metabolites by capillary electromigration methods, with special emphasis on those articles published in the last 10 years.…”

Section: Introductionmentioning

confidence: 99%

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Chiral analysis of pollutants and their metabolites by capillary electromigration methods

et al. 2005

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Chiral analysis of pollutants and their metabolites by capillary electromigration methodsChiral separation of enantiomers is one of the most challenging tasks for any analytical technique including CE. Since the first report in 1985 showing the great possibilities of CE for the separation of chiral compounds, the amount of publications concerning this topic has quickly increased. Although chiral electromigration methods have mainly been used for enantioseparation of drugs and pharmaceuticals, they have also been applied to analyze chiral pollutants. This article intends to provide an updated overview, including works published till January 2005, on the principal applications of CE to the chiral analysis of pollutants and their metabolites, with especial emphasis on articles published in the last 10 years. The main advantages and drawbacks regarding the use of CE for chiral separation of pollutants are addressed including some discussion on the foreseen trends of electromigration procedures applied to chiral analysis of contaminants. IntroductionSeparation of chiral compounds is an interesting and challenging topic of research in many analytical chemistry areas, especially in the biomedical, pharmaceutical, and environmental fields where pure enantiomeric forms are widely required. It is already well-known that enantiomers, in spite of their very similar structure, when exposed to an identical biological environment can show very different biological activity. Furthermore, as a general rule, when the toxicological effect of an active substance is directly related to its desired biological activity, the most active isomer is usually the most toxic one Abbreviations: Allyl-TER, 1-allylterguride; ANDSA, 7-aminonaphthalene-1,3-disulfonic acid; ANSA, 5-aminonaphthalene-1-sulfonic acid; ANTS, 8-aminonaphthalene-1,3,6-trisulfonic acid; CA, chrysanthemic acid; CM-ª-CD, carboxymethylated-g-CD; CMBA, 2-(4-chlorophenyl)-3-methylbutanoic acid; 2,2-CPPA, 2-(2-chlorophenoxy)-propionic acid; 2,3-CPPA, 2-(3-chlorophenoxy)-propionic acid; 2,4-CPPA, 2-(4-chlorophenoxy)-propionic acid; â-CD-NH 2 , 6-monodeoxy-6-monoamino-b-CD; â-CD- (NH 3 )

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chiral analysis of pollutants and their metabolites by capillary electromigration methods

et al. 2005

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“…The agrochemical industry and government regulators are beginning to take enantioselectivity into account and several papers have been reported showing differences in the toxicities and the biodegradation behaviour between enantiomers [4 -6]. To obtain information on the toxicity and biotransformation of the chiral pollutants it is necessary to develop suitable methods for the chiral resolution of pollutants [7]. In bibliography, some references about the enantiomeric separation of some pesticides have been reported [7 -10].…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of nuarimol by affinity electrokinetic chromatography‐partial filling technique using human serum albumin as chiral selector

Martínez-Gómez

Escuder-Gilabert

Villanueva-Camañas

et al. 2008

J of Separation Science

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The present paper deals with the enantiomeric separation of nuarimol enantiomers by affinity EKC-partial filling technique using HSA as chiral selector. Firstly, a study of nuarimol interactions with HSA by CE-frontal analysis was performed. The binding parameters obtained for the first site of interaction were n(1) = 0.84; K(1) = 9.7 +/- 0.3x10(3 )M(-1) and the protein binding percentage of nuarimol at physiological concentration of HSA was 75.2 +/- 0.2%. Due to the moderate affinity of nuarimol towards HSA the possibility of using this protein as chiral selector for the separation of nuarimol using the partial filling technique was evaluated. A multivariate optimization approach of the most critical experimental variables in enantioresolution, running pH, HSA concentration and plug length was carried out. Separation of nuarimol enantiomers was obtained under the following selected conditions: electrophoretic buffer composed of 50 mM Tris at pH 7.3; 160 muM HSA solution applied at 50 mbar for 156 s as chiral selector; nuarimol solutions in the range of 2-8x10(-4) M injected hydrodynamically at 30 mbar for 2 s and the electrophoretic runs performed at 30 degrees C applying 15 kV voltage. Resolution, accuracy, reproducibility speed and cost of the proposed method make it suitable for quality control of the enantiomeric composition of nuarimol in formulations and for further toxicological studies. The results showed a different affinity between nuarimol enantiomers towards HSA.

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“…The formation of CDbased guest-host complexes is a simple model for studying molecular recognition processes and has been employed in many applications (see [1,5,6] and the references cited therein) in, for example, pharmaceutical, cosmetic and food industries. In separation methods, CDs are frequently used as buffer modifiers to increase selectivity, and are especially used as chiral selectors to optimize the separation of enantiomers in CZE (see [7][8][9][10][11] and the references cited therein). Theoretically, a simple guest-host complex model based on binding equilibria has been shown to excellently explain the effect of changing the concentration of selectors on the resolution of enantiomer separation [12][13][14].…”

Section: Introductionmentioning

confidence: 99%

“…The apparent binding constants of these guest analytes were evaluated by a simple nonlinear regression model, which showed that b-CD is the better complex-forming host CDs with NS anions. Determining the binding constants between the charged guest compounds and the neutral CDs (native or derivatized) by CE method has been studied extensively (see [7][8][9][10][11]25] and the references cited therein). The binding constants of ionic analytes are relatively low because the analytes are hydrophilic.…”

Section: Introductionmentioning

confidence: 99%

Application of cyclodextrin-mediated capillary electrophoresis to determine the apparent binding constants and thermodynamic parameters of the alkylnaphthalene derivatives

Wang

2005

Electrophoresis

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The separation and migration behavior of seven positional and structural neutral alkylnaphthalene derivatives in cyclodextrin-mediated capillary electrophoresis were systematically investigated. The effective separation conditions were to use 10 mM phosphate buffer with negatively charged carboxymethyl-beta-cyclodextrin (CM-beta-CD) at pH 6.0. The guest-host interactions with 1:1 or both 1:1 and 1:2 binding stoichiometries for various derivatives were evaluated by comparing their apparent binding constants. The results reveal that the substituent group(s) attached to the naphthalene ring significantly affected the inclusion stoichiometric behaviors. Alkylnaphthalene derivatives with the substituent(s) at the 1-position(s), such as 1-ethylnaphthalene, 1,4-dimethylnaphthalene, may undergo complexation with one and two CM-beta-CD molecules. The binding constants of these derivatives were consistent with the data obtained by a spectrophotometric method. The thermodynamic parameters were also calculated in order to improve our understanding of the interaction between the neutral alkylnaphthalene derivatives and CM-beta-CD at various temperatures. The positive entropy (deltaS degrees) values of the alkylnaphthalenes with the substituent(s) at the 2-position(s) indicate that the inclusion of the guest molecule into the cavity of CM-beta-CD is favored at all temperatures.

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Chiral resolution of some environmental pollutants by capillary electrophoresis

Cited by 30 publications

References 58 publications

Chiral analysis of pollutants and their metabolites by capillary electromigration methods

Chiral analysis of pollutants and their metabolites by capillary electromigration methods

Enantioseparation of nuarimol by affinity electrokinetic chromatography‐partial filling technique using human serum albumin as chiral selector

Application of cyclodextrin-mediated capillary electrophoresis to determine the apparent binding constants and thermodynamic parameters of the alkylnaphthalene derivatives

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