Recent applications of stereoselective chromatography

Chirality

Volumn 14, Issue 5, 2002, Pages 417-435

  Szymura Oleksiak, Joanna ^a   Bojarski, Jacek ^a   Aboul Enein, Hassan Y ^b  

^a JAGIELLONIAN UNIVERSITY   (Poland)

^b KING FAISAL SPECIALIST HOSPITAL AND RESEARCH CENTER   (Saudi Arabia)

Author keywords

Applications; Clinical pharmacy; Drug analysis; Food and natural products; Review; Stereoselective chromatography

Indexed keywords

4 HYDROXYDEBRISOQUINE; 4 PHOSPHONOMETHYLPIPECOLIC ACID; ACEBUTOLOL; AMPHETAMINE; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; ANTIINFLAMMATORY AGENT; BETA ADRENERGIC RECEPTOR BLOCKING AGENT; BISOPROLOL; CHOLECYSTOKININ; CLOPIDOGREL; DIACETOLOL; FLUMEQUINE; FLUOXETINE; IBUPROFEN; INDOBUFEN; KETAMINE; LICARBAZEPINE; LORAZEPAM; METHAMPHETAMINE; MEXILETINE; NATURAL PRODUCT; NORFLUOXETINE; PHOLEDRINE; POSACONAZOLE; PROPRANOLOL; PROTEINASE INHIBITOR; SALSOLINOL; TRAMADOL; UNINDEXED DRUG;

ARTICLE; CHIRALITY; CHROMATOGRAPHY; COLUMN CHROMATOGRAPHY; DEVICE; DRUG DETERMINATION; FOOD ANALYSIS; MEDICAL LITERATURE; PHARMACY; PRIORITY JOURNAL; RESEARCH; STEREOCHEMISTRY;

BIOLOGICAL PRODUCTS; BODY FLUIDS; CHROMATOGRAPHY; FOOD ANALYSIS; HUMANS; PHARMACEUTICAL PREPARATIONS; PHARMACOLOGY, CLINICAL; STEREOISOMERISM;

EID: 0036249824     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10110     Document Type: Article

References (187)

1. Recent developments in liquid chromatographic enantioseparations
2. Stereoisomers and drug toxicity
3. Chirality in new drug development
4. Pharmacological importance of stereochemical resolution of enantiomeric drugs
5. Importance of stereospecific bioanalytical monitoring in drug development
6. Validation of liquid chromatographic and gas chromatographic methods. Applications to pharmacokinetics
7. Enantioselectivity in the metabolism of mexiletine by conjugation in female patients with the arrhythmic form of chronic Chagas' heart disease
8. Enantioselective analysis of N-hydroxymexiletine glucuronide in human plasma for pharmacokinetic studies
9. Stereoselective disposition of the antiarrhythmic agent mexiletine during the concomitant administration of caffeine
10. Pharmacokinetics of single oral and multiple intravenous and oral administration of acebutolol enantiomers in a rat model
11. Stereoselective metabolism of tazofelone, an anti-inflammatory bowel disease agent, in rats and dogs and in human liver microsomes
12. Very slow chiral inversion of clopidogrel in rats: A pharmacokinetic and mechanistic investigation
13. Determination of ibuprofen in human plasma by high-performance liquid chromatography: Validation and application in pharmacokinetic study
14. LC procedure with SPE for quantification of indobufen enantiomers: Pharmacokinetic studies
15. Stereoselective pharmacokinetics of indobufen from tablets and intramuscular injections in man
16. Effect of dosage form on stereoisomeric inversion of ibuprofen in volunteers
17. Quantification of influmequine enantiomers in plasma by high-performance liquid chromatography
18. Assessment of the metabolic chiral inversion of D-leucine in rat by gas chromatography-mass spectrometry combined with a stable isotope dilution analysis
19. 7]leucine in plasma by capillary gas chromatography-mass spectrometry
20. Stereospecific analysis and enantiomeric disposition of 3,4-methylenedioxymethamphetamine (Ecstasy) in humans
21. Quantitative determination of endogenous tetrahydroisoquinoline salsolinol in peripheral blood mononuclear cells by gas chromatography-mass spectrometry
22. Species-dependent enantioselective pharmacokinetics of PNU-103017, a pyrone HIV protease inhibitor
23. HPLC methodology for determination of ibuprofen enantiomers to be used in pharmacokinetics
24. Stereoselective pharmacokinetics of ibuprofen and its lysinate from suppositories in rabbits
25. Use of chiral liquid chromatography-tandem mass spectrometry to investigate the metabolism of racemic cholecystokinin B antagonists
26. Achiral and chiral high-performance liquid chromatographic methods for clinafloxacin, a fluoroquinolone antibacterial, in human plasma
27. Stereoselective pharmacokinetics of RS-8359, a selective and reversible inhibitor of A-type monoamine oxidase, in rats, mice, dogs and monkeys
28. Stereoselective pharmacokinetic analysis of the antiepileptic 10-hydroxycarbamazepine in dogs
29. Stereoselective high-performance liquid chromatographic determination of ketamine and its active metabolite, norketamine in human plasma
30. Pharmacokinetics and metabolism of bisoprolol enantiomers in humans
31. Stereoselective metabolism of bisoprolol enantiomers in dogs and humans
32. Chiral high-performance liquid chromatographic analysis of antifungal SCH 56592 and evaluation of its stereoselective inversion in animals and humans
33. Stereospecific analysis of lorazepam in plasma by chiral column chromatography with a circular dichroism-based detector
34. Steady-state pharmacokinetics of propranolol enantiomers in healthy male volunteers
35. Stereoselective determination of R,S-2-[4-(3-methyl-2-thienyl)phenyl] propionic acid and its taurine conjugates in dog urine by high-performance liquid chromatography
36. In vivo studies on chiral inversion and amino acid conjugation of 2-[4-(3-methyl-2-thienyl)phenyl] propionic acid in rats and dogs
37. Issues in methodology and applications for therapeutic drug monitoring of fluoxetine and norfluoxetine enantiomers
38. Enantiomeric separation of tramadol and its active metabolite in human plasma by chiral high-performance liquid chromatography: Application to pharmacokinetic studies
39. Differential permeation of propranolol enantiomers across human skin in vitro from formulations containing an enantioselective excipient
40. Enantioselectivity of debrisoquine 4-hydroxylation in Brazilian Caucasian hypertensive patients phenotyped as extensive metabolizers
41. Enantioselective determination of selfotel in human urine by high-performance liquid chromatography on a chiral stationary phase after derivatization with 9-fluorenylmethyl chloroformate
42. Enantioselective high-performance liquid chromatography with fluorescence detection of methamphetamine and its metabolites in human urine
43. Enantiomer-specific high-performance liquid chromatography with fluorescence detection of methamphetamines in abusers' hair and urine
44. Quantification of methamphetamine, amphetamine and enantiomers by semi-micro column HPLC with fluorescence detection; applications on abusers single hair analyses
45. Simultaneous HPLC analysis of S- and R-verapamil and metabolites, S- and R-norverapamil in human plasma
46. Stereoselective determination of cisapride, a prokinetic agent, in human plasma by chiral high-performance liquid chromatography with ultraviolet detection: Application to pharmacokinetic study
47. Enantioselective determination of isradipine in human serum using stereoselective stationary phase liquid chromatography and gas chromatography with nitrogen selective detection
48. Stereoselective inversion of pantoprazole enantiomers after separate doses to rats
49. Enantiomer-selective pharmacokinetics and metabolism of ketorolac in children
50. Enantiomers of thalidomide: Blood distribution and the influence of serum albumin on stereoselective inversion and hydrolysis
51. Intravenous formulation of the enantiomers of thalidomide: Pharmacokinetic and initial pharmacodynamic characterization in man
52. Chiral determination of mirtazapine in human blood plasma by high-performance liquid chromatography
53. High-performance liquid chromatographic analysis of the anti-tumor agent SCH 66336 in cynomolgus monkey plasma and evaluation of its chiral inversion in animals
54. Determination of the enantiomers of omeprazole in blood plasma by normal-phase liquid chromatography and detection by atmospheric pressure ionization tandem mass spectrometry
55. Enantioselectivity in the steady-state pharmacokinetics of metoprolol in hypertensive patients
56. Enantioselective kinetic disposition of Albendazole sulfoxide in patients with neurocysticercosis
57. Enantioselective analysis of disopyramide and mono-N-dealkyldisopyramide in plasma and urine by high-performance liquid chromatography on an amylose-derived chiral stationary phase
58. Enantiomeric determination of tramadol and its main metabolite O-desmethyltramadol in human plasma by liquid chromatography-tandem mass spectrometry
59. Determination of the enantiomers of chlorpheniramine and its main monodesmethyl metabolite in urine using achiral-chiral liquid chromatography
60. Binding of chlorpheniramine enantiomers to human plasma proteins
61. Enantioselective high performance liquid chromatographic assay of acebutolol and its active metabolite diacetolol in human serum
62. Cyclodextrins and enantiomeric separation of drugs by liquid chromatography and capillary electrophoresis: Basic principles and new developments
63. Steady state concentrations of the enantiomers of mianserin and desmethylmianserin in poor and in homozygous and heterozygous extensive metabolizers of debrisoquine
64. Development and application of a chiral high performance liquid chromatography assay for pharmacokinetic studies of methadone
65. Enantiospecific determination of PNU-83894 and its major metabolite, PNU-83892, in plasma and its application to the characterization of the enantioselective pharmacokinetics of PNU-83894 in the dog
66. Chiral high-performance liquid chromatographic analysis of fluoxetine and norfluoxetine in rabbit plasma, urine and vitreous humor using an acetylated β-cyclodextrin column
67. Development and validation of a sensitive and robust LC-tandem MS method for the analysis of warfarin enantiomers in human plasma
68. Determination of S/R ratio of mephenytoin in human urine by chiral HPLC and ultraviolet detection and its comparison with gas chromatography
69. Stereospecific analysis of ecstasy-like N-ethyl-3,4-methylenedioxyamphetamine and its metabolites in humans
70. Stereoselective pharmacokinetic analysis of valnoctamide, a CNS-active chiral amide analogue of valproic acid in dogs, rats and mice
71. Quantitative determination of isoflurane enantiomers in blood samples during and after surgery via headspace gas chromatography-mass spectrometry
72. Enantioselective analysis of ketone bodies in patients with β-ketothiolase deficiency, medium-chain acyl coenzyme A dehydrogenase deficiency and ketonemic vomiting
73. Stereodifferentiation of 3-hydroxyisobutyric- and 3-aminoisobutyric acid in human urine by enantioselective multidimensional capillary gas chromatography-mass spectrometry
74. Pharmacokinetics of (R)- and (S)-cyclophosphamide and their dechloroethylated metabolites in cancer patients
75. Enantioselective induction of cyclophosphamide metabolism by phenytoin
76. Enantioselective determination of propafenone and its metabolites in human plasma by liquid chromatography-mass spectrometry
77. Stereoselective pharmacokinetics of propafenone and its major metabolites in healthy Chinese volunteers
78. Stereoselective disposition of tiraprofenic acid enantiomers in rats
79. Development of validated stereoselective methods for methadone determination in clinical samples
80. Enantioselective analysis of methadone in saliva by liquid chromatography-mass spectrometry
81. Stereoselective quantification of methadone and its major oxidative metabolite,2-ethylidene-1,5 dimethyl-3,3-diphenylpyrrolidine, in human urine using high-performance liquid chromatography
82. Enantioselective analysis of methadone in sweat as monitored by liquid chromatography/ion spray-mass spectrometry
83. Synthesis, stereoselective enzymatic hydrolysis and skin permeation of diastereomeric propranolol ester prodrugs
84. Ketamine distribution described by a recirculatory pharmacokinetic model is not stereoselective
85. Stereoselective urinary excretion of bupivacaine and its metabolites during epidural infusion
86. Racemate and enantiomers of ketoprofen; phase diagram thermodynamic studies, skin permeability and use of chiral permeation enhancers
87. Validation of a high-performance liquid chromatographic method for the determination of ibuprofen enantiomers in plasma of broiler chickens
88. Determination of the in vitro metabolism of (+)- and (-)-epibatidine
89. Stereoselective determination of cetirizine and studies on pharmacokinetics in rat plasma
90. Gender differences in labetalol kinetics: Importance of determining stereoisomer kinetics for racemic drugs
91. Application of the restricted-access precolumn packing material alkyl-diol silica in a column-switching system for the determination of ketoprofen enantiomers in horse plasma
92. Studies on concentration-time profiles of nimodipine enantiomers following intravenous and oral administration of nimodipine in patients with subarachnoid hemorrhage
93. Direct high-performance liquid chromatographic determination of (R)- and (S)-propranolol in rat microdialysate using on-line column switching procedures
94. Macrocyclic antibiotics as effective chiral selectors for enantiomeric resolution by liquid chromatography and capillary electrophoresis
95. Chiral separations using the macrocyclic antibiotics: A review
96. Stereoselective HPLC-assay for citalopram and its metabolites
97. Enantiomeric separation of several cyclic imides on a macrocyclic antibiotic (Vancomycin) stereoselective stationary phase under normal and reversed phase conditions
98. Quantitative determination of clenbuterol enantiomers in human plasma by high-performance liquid chromatography using the macrocyclic antibiotic chiral stationary phase teicoplanin
99. β-agonist-induced alterations in organ weights and protein content: Comparison of racemic clenbuterol and its enantiomers
100. Determination of the enantiomers of albuterol in human and canine plasma by enantioselective high-performance liquid chromatography on a teicoplanin-based chiral stationary phase
101. Chiral liquid chromatography tandem mass spectrometry in the determination of the configuration of 2-hydroxyglutaric acid in urine
102. Determination of terbutaline enantiomers in human urine by coupled achiral-chiral high-performance liquid chromatography with fluorescence detection
103. Comparison of packet column supercritical fluid chromatography-tandem mass spectrometry with liquid chromatography-tandem mass spectrometry for bioanalytical determination of (R)- and (S)-ketoprofen in human plasma following automated 96-well solid-phase extraction
104. Pharmaceutical development and specification of stereoisomers
105. Determination of residual amines used in bulk drug synthesis by pre-column derivatization with 3,5-dinitrobenzoyl chloride and high-performance liquid chromatography
106. Direct high-performance liquid chromatographic determination of the enantiomeric purity of levodopa and methyldopa: Comparison with pharmacopoeial polarimetric methods
107. Enantiomeric separation of some pharmaceutical intermediates and reversal of elution orders by high-performance liquid chromatography using cellulose and amylose tris(3,5-dimethylphenylcarbamate) derivatives as stationary phases
108. Determination of the enantiomers of 3-tert-butylamino-1,2-propanediol by high-performance liquid chromatography using mass spectrometric detection
109. Liquid chromatographic separation of the enantiomers of becliconazole and its potential impurities
110. Determination of fluoxetine hydrochloride enantiomeric excess using high-performance liquid chromatography with chiral stationary phases
111. Validated chiral high-performance liquid chromatographic method for the determination of trans-(-)-paroxetine and its enantiomer in bulk and pharmaceutical formulations
112. Stereochemistry and enantiomeric purity of a novel anxiolytic agent, deramciclane fumarate
113. Case of enantiomer impurity identification by normal-phase chiral high-performance liquid chromatography with optical rotation and mass spectrometric detection
114. Chromatographic separation of chlorthalidone enantiomers using β-cyclodextrins as chiral additives
115. LC method for the determination of assay and purity of sibutramine hydrochloride and its enantiomers by chiral chromatography
116. Column selection and method development for the determination of the enantiomeric purity of investigational non-nucleoside reverse transcriptase inhibitors
117. Automated determination of amphetamine enantiomers using a two-dimensional column-switching chromatographic system for derivatization and separation
118. Chiral purity test of metoprolol enantiomer after derivatization with (-)-menthyl chloroformate by reversed-phase high performance liquid chromatography
119. Chiral determination of various adrenergic drugs by thin-layer chromatography using molecularly imprinted chiral stationary phases prepared with α-antagonists
120. Evaluation of matrices containing molecularly imprinted polymers in the enantioselective-controlled delivery of β-blockers
121. Optically active synthetic polymers as chiral stationary phases in HPLC
122. Determination of 1-menthol in pharmaceutical products by high performance liquid chromatography with polarized photometric detection
123. Directly coupled HPLC-NMR and HPLC-NMR-MS in pharmaceutical research and development
124. Reliable assay of extreme enantiomeric purity values by a new circular dichroism based HPLC detection system
125. The preparative chromatographic enantioseparation of a racemic morphantridine analog on a chiral stationary phase
126. Direct preparative enantioselective chromatography of propranolol hydrochloride and thioridazine hydrochloride using carbon dioxide based mobile phases
127. Laboratory-developed simulated moving bed for chiral drug separations. Design of the system and separation of tramadol enantiomers
128. Applications of simulated moving-bed chromatography to the separation of the enantiomers of chiral drugs
129. Simulated moving bed chromatographic resolution of a chiral antitussive
130. Evaluation of simulated moving bed chromatography for pharmaceutical process development
131. Chiral separation of a pharmaceutical intermediate by a simulated moving bed process
132. Chromatographic resolution of the enantiomers of a pharmaceutical intermediate from the milligram to the kilogram scale
133. Separation of a racemic pharmaceutical intermediate using closed-loop steady state recycling
134. Enantioselective chromatography as a powerful alternative for the preparation of drug enantiomers
135. Bioanalysis of the enantiomers of (±)-sarin using automated thermal coldtrap injection combined with two-dimensional gas chromatography
136. LC separation of ortho and meta isomers of celecoxib in bulk and formulations using a chiral column
137. Stereochemical analysis of food components
138. Varietal differences in the total and enantiomeric composition of theanine in tea
139. Determination of D-amino acids labeled with fluorescent chiral reagents, R(-)- and S(+)-4-(3isothiocyanatopyrrolidin-1-yl)-7- (N,Ndimethylaminosulfonyl)-2,1,3benzoxadiazoles, in biological and food samples by liquid chromatography
140. Gas chromatographic quantification of amino acid enantiomers in food matrices by their N(O,S)-ethoxycarbonyl heptafluorobutyl ester derivatives
141. Determination of L- and D-amino acids in foodstuffs by coupling of high-performance liquid chromatography with enzyme reactors
142. Chromatographic determination of amino acid enantiomers in beers and raw materials used for their manufacture
143. Multidimensional capillary GC-GC for the analysis of real complex samples. 3. Enantiomeric distribution of monoterpene hydrocarbons and monoterpene alcohols of mandarin oils
144. Multi-dimensional capillary GC-GC for the analysis of real complex samples. 5. Enantiomeric distribution of monoterpene hydrocarbons and monoterpene alcohols and linalyl acetate of bergamot (Citrus bergamia Risso et Poiteau) oils
145. Automatic injection solid-phase microextraction - Chiral-gas chromatography-mass selective detection analyses of essential oils
146. Structure elucidation, enantioselective analysis, and biogenesis of nerol oxide in Pelargonium species
147. Biogenetic studies in Mentha piperita. 2. Stereoselectivity in the bioconversion of pulegone into menthone and isomenthone
148. Biosynthesis of menthofuran in Mentha piperita: Stereoselective and mechanistic studies
149. Update on enantiomeric composition of (1R)-(+)- and (1S)- (-)-camphor in essential oils by enantioselective gas chromatography
150. Examination of the enantiomeric distribution of certain monoterpene hydrocarbons in selected essential oils by automated solid-phase microextractionchiral gas chromatography-mass selective detection
151. Cyclodextrin derivatives as chiral selectors for direct gas chromatographic separation of enantiomers in the essential oil, aroma and flavour fields
152. Aliphatic β-D-glucosides from fruits of Carica pubescens
153. Analytical and sensory characterization of γ- and δ-thiolactones
154. Vacuum headspace method in aroma research: Flavor chemistry of yellow passion fruits
155. Methyl-branched flavor compounds in fresh and processed apples
156. Enantiomeric purity and odor characteristics of 2- and 3-acetoxy-1,8 cineoles in the rhizomes of Alpina galanga wild
157. Enantiomeric composition of filbertone in hazelnuts in relation to extraction conditions, multidimensional gas chromatography and gas chromatography/mass spectrometry in the single ion monitoring mode of a natural sample
158. Rapid recognition of olive oil adulterated with hazelnut oil by direct analysis of the enantiomeric composition of filbertone
159. Enantiomer analysis of chair lactones in foods by on-line coupled reversed-phase liquid chromatography-gas chromatography
160. Determination of the enantiomeric composition of γ-lactones in edible oils by on-line coupled high performance liquid chromatography and gas chromatography
161. Enantiomeric composition of nornicotine, anatabine, and anabasine in tobacco
162. Elimination of amino acid interferences in the chiral ligand-exchange chromatographic analysis of lactic acid enantiomers in wine
163. Stereochemical composition of clenbuterol residues in edible tissues of swine
164. Determination of the enantiomeric ratios of chiral PCB 95 and 149 in human milk samples by multidimensional gas chromatography with ECD and MS(SIM) detection
165. Enantiomere monoterpene im ätherischen Öl von Achillea millefolium s. I. Eine zusätzliche taxonomische bestimmungshilfe?
166. Chemical polymorphism of the essential oils from populations of Thymus caespititius grown on the island S Jorge (Azores)
167. Sesquiterpene constituents of the liverwort Bazzania trilobata
168. Gymnomitrane-type sesquiterpenes of the liverworts Gymnomitron obtusum and Reboulia hemisphaerica
169. (-)-7-epi-Isojunenol and (+)-7-epi-junenol, constituents of the livewwort Tritomaria quinquedentata
170. Sex pheromone components of pink gypsy moth, Lymantria mathura
171. Synthesis and absolute stereochemistry of spiroacetals in rove bettles (Coleoptera Staphylinidae)
172. Chiral HPLC resolution of monoepoxides derived from 6,9-dienes and its application to stereochemistry assignment of fruit-piercing noctuid pheromone
173. Determination of the absolute configuration of (-)-(3R)-O-β-D-glucopyranosyloxy-5-phenylpentanoic acid from Polygonum salicifolium
174. Separation of the four pairs of enantiomers of vincamine alkaloids by enantioselective high-performance liquid chromatography
175. Enantiomeric excess of a cruciferous phytoalexin, spirobrassinin, and its enantiomeric enrichment in an achiral HPLC system
176. GM-MS analysis of diaminopimelic acid stereoisomers and amino acid enantiomers in rumen bacteria
177. Chromatographic resolution of peptide-like conjugates of jasmonic acid and of cucurbic acid isomers
178. Liquid chromatography of jasmonic acid amine conjugates
179. Trace level determination of enantiomeric monoterpenes in terrestrial plant emission and in the atmosphere using a β-cyclodextrin capillary column coupled with thermal desorption and mass spectrometry
180. Influence of environmental changes on degradation of chiral pollutants in soils
181. Enantioselective behaviour of ethylated γ-cyclodextrins as GC stationary phases for chlorinated pesticides and phase characterisation by HPLC
182. Determination of enantiomeric excess of α-hydroxy-3-phenoxybenzeneacetonitrile and its n-butyl ester by chiral high-performance liquid chromatography
183. Enantiomers separation and preparation of five organophosphorus compounds and their biological activities
184. Isolation and identification of the metolachlor stereoisomers using high-performance liquid chromatography, polarimetric measurements, and enantio-selective gas chromatography
185. Separation of the enantiomers of pyrethroic acids and their esters by high-performance liquid chromatography on a polysaccharide-derived chiral stationary phase