Simultaneous stereoselective analysis of tramadol and its main phase I metabolites by on-line capillary zone electrophoresis–electrospray ionization mass spectrometry

Rudaz, Serge; Cherkaoui, Samir; Dayer, P.; Fanali, Salvatore; Veuthey, Jean‐Luc

doi:10.1016/s0021-9673(99)01257-1

Cited by 80 publications

(53 citation statements)

References 52 publications

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“…Thus, two different derivatization protocols for amino acids using dansyl chloride (DNS) and FITC were compared observing better mass sensitivity for FITC-amino acids (LODs in the mM range) [139]. CE-ESI-MS has also been used for the sensitive determination of chiral compounds in biological samples such as urine [135,140,141], plasma [142], serum [143], and in vivo samples [144], and for the identification of drugs and their metabolites [145,140].…”

Section: Alternative Detection Systems To On-column Uv-vis Absorptionmentioning

confidence: 99%

Sensitive chiral analysis by capillary electrophoresis

García-Ruiz

Marina

2006

Electrophoresis

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Sensitive chiral analysis by capillary electrophoresisIn this review, an updated view of the different strategies used up to now to enhance the sensitivity of detection in chiral analysis by CE will be provided to the readers. With this aim, it will include a brief description of the fundamentals and most of the recent applications performed in sensitive chiral analysis by CE using offline and online sample treatment techniques (SPE, liquid-liquid extraction, microdialysis, etc.), on-column preconcentration techniques based on electrophoretic principles (ITP, stacking, and sweeping), and alternative detection systems (spectroscopic, spectrometric, and electrochemical) to the widely used UV-Vis absorption detection.

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Section: Alternative Detection Systems To On-column Uv-vis Absorptionmentioning

confidence: 99%

Sensitive chiral analysis by capillary electrophoresis

García-Ruiz

Marina

2006

Electrophoresis

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“…Tramadol (TMD) is a centrally acting drug that possesses an analgesic action. TMD is formulated as a racemic mixture, where each enantiomer displays different binding properties for various receptors [16][17][18]. Methadone (MTD) is a synthetic opiate largely used as an analgesic drug [19].…”

Section: Introductionmentioning

confidence: 99%

Enhanced method performances for conventional and chiral CE‐ESI/MS analyses in plasma

et al. 2006

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Due to its high efficiency, selectivity, and sensitivity, CE-ESI/MS has evolved as an efficient technique for the drugs and metabolites analysis in biological matrices. However, a sample preparation is mandatory prior to CE-ESI/MS analysis. To achieve fast and simplified sample preparation of plasma samples, protein precipitation (PP) and liquid-liquid extraction (LLE) were used with two injection techniques: hydrodynamic (HD) and electrokinetic (EK) injection. CE-ESI/MS analyses of pharmaceutical compounds and amphetamine derivatives were developed. Detection limits of 1 ppm were reached with PP and HD injection whereas 1 ppb was detected when samples were prepared with LLE and injected by EK. Same experiments were performed for stereoselective determinations in partial-filling mode and detection limits achieved were equivalent to conventional analysis (0.5 ppb per enantiomer). When complex matrices are analyzed, MS signal suppression or enhancement effects are generally not reproducible and could compromise results with ESI. Therefore, matrix effect was investigated in CE-ESI/MS with a commercially available coaxial sheath-liquid ESI interface used as postcapillary infusion system to determine MS signal alterations. Matrix effects were differentially evidenced according to the selected sample preparation. With PP, signal suppression was observed out of the analyses migration window, while for LLE no relevant matrix effect occurred in all experiments.

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“…21 Although both of the aforementioned techniques avoid the detrimental effects of chiral selector on the MS signal, the former is somewhat limited to the chiral analysis of charged compounds while the latter provides lower resolution and lower peak capacity compared to the standard MEKC-MS. 22 These aforementioned disadvantages have prompted the combined use of counter-migration and PF which demonstrated higher CE resolution and higher MS sensitivity. 23 In the past ten years, polymeric surfactants 24-26 (aka. molecular micelle) has been widely employed as pseudostationary phases for chiral 27-35 and achiral 36-38 separations in MEKC.…”

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Polymeric Sulfated Amino Acid Surfactants: A Class of Versatile Chiral Selectors for Micellar Electrokinetic Chromatography (MEKC) and MEKC-MS

et al. 2006

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In this work, three amino acids derived (L-leucinol, L-isoleucinol and L-valinol) sulfated chiral surfactants are synthesized and polymerized. These chiral sulfated surfactants are thoroughly characterized to determine critical micelle concentration, aggregation number, polarity, optical rotation and partial specific volume. For the first time the morphological behavior of polymeric sulfated surfactants is revealed using cryogenic high-resolution electron microscopy (cryo-HRSEM). The polysodium N-undecenoyl-L-leucine sulfate (poly-L-SUCLS) shows distinct tubular structure, while polysodium N-undecenoyl-L-valine sulfate (poly-L-SUCVS) also shows tubular morphology but without any distinct order of the tubes. On the other hand, polysodium N-undecenoyl-Lisoleucine sulfate (poly-L-SUCILS) displays random distribution of coiled/curved filaments with heavy association of tightly and loosely bound water. All three polymeric sulfated surfactants are compared for enantio-separation of broad range of structurally diverse racemic compounds at very acidic, neutral and basic pH conditions in micellar electrokinetic chromatography (MEKC). A small combinatorial library of 10 structurally related phenylethylamines (PEAs) is investigated for chiral separation under acidic and moderately acidic to neutral pH conditions using an experimental design. In contrast to neutral pH conditions, at acidic pH, significantly enhanced chiral resolution is obtained for class I and class II PEAs due to the compact structure of polymeric sulfated surfactants. It is observed that the presence of hydroxy group on the benzene ring of PEAs resulted in deterioration of enantioseparation. A sensitive MEKC-mass spectrometry (MS) method is developed for one of the PEA (e.g., (±)-pseudoephedrine) in human urine. Very low limit of detection (LOD) is obtained at pH 2.0 (LOD 325 ng/mL), which is ca 16 times better compared to pH 8.0 (LOD 5.2 µg/mL). Other broad range of chiral analytes (β-blockers, phenoxypropionic acid, benzoin derivatives, PTHamino acids, and benzodiazepinones) studied also provided improved chiral separation at low pH compared to high pH conditions. Among the three polymeric sulfated surfactants, poly-L-SUCILS with two chiral centers on the polymer head group provided overall higher enantioresolution for the investigated acidic, basic and neutral compounds. This work clearly demonstrates for the first time the superiority of chiral separation and sensitive MS detection at low pH over conventional high pH chiral separation and detection employing anionic chiral polymeric surfactants in MEKC and MEKC-MS. NIH-PA Author ManuscriptNIH-PA Author Manuscript NIH-PA Author ManuscriptOver the last 20 years, the number of materials and products developed as pure enantiomers (eutomer) has continued to increase. With evidence of problems related to stereoselectivity in drug action, enantioselective analysis by separation are of particular importance for production, therapeutic monitoring or pharmacokinetic studies, and/or to validate the opt...

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Simultaneous stereoselective analysis of tramadol and its main phase I metabolites by on-line capillary zone electrophoresis–electrospray ionization mass spectrometry

Cited by 80 publications

References 52 publications

Sensitive chiral analysis by capillary electrophoresis

Sensitive chiral analysis by capillary electrophoresis

Enhanced method performances for conventional and chiral CE‐ESI/MS analyses in plasma

Polymeric Sulfated Amino Acid Surfactants: A Class of Versatile Chiral Selectors for Micellar Electrokinetic Chromatography (MEKC) and MEKC-MS

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