Chiral derivatization reagents for drug enantioseparation by high‐performance liquid chromatography based upon pre‐column derivatization and formation of diastereomers: enantioselectivity and related structure

Sun, Xian Xiang; Sun, Lijuan; Aboul‐Enein, Hassan Y.

doi:10.1002/bmc.41

Cited by 52 publications

(20 citation statements)

References 77 publications

(81 reference statements)

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“…With respect to pharmaceutical applications, the indirect techniques have been used extensively for the enantioselective analysis of drugs in biological fluids. Review about precolumn derivatization and diastereomer formation has been published [13,69,70].…”

Section: Indirect Methodsmentioning

confidence: 99%

Role of biological matrices during the analysis of chiral drugs by liquid chromatography

Mislanova

Hutta

2003

Journal of Chromatography B

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Section: Indirect Methodsmentioning

confidence: 99%

Role of biological matrices during the analysis of chiral drugs by liquid chromatography

Mislanova

Hutta

2003

Journal of Chromatography B

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“…The acetyl groups might also contribute to the difference between the selectivities of the two CDR. As discussed in a review paper by Sun et al [6], the magnitude of relative diastereomer chromatographic resolvability is directly related to the conformational and configurational properties of the molecules; in this respect the most important feature is the structural characteristic of a CDR. Further, in establishing the conformational differences between the diastereomers, the formation of intramolecular hydrogen-bonds might play a significant role, as proposed for several CDR [24 30].…”

Section: Comparative Analysismentioning

confidence: 99%

Comparison of isothiocyanate chiral derivatizing reagents for high-performance liquid chromatography

Mamiro

Fülöp

2002

Chromatographia

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SummaryThis paper describes the synthesis of a new chiraJ derivatizing reagent, (1S,2R)-l-acetoxy-1-phenyl-2-propyl isothiocyanate ((S,R)-APPI), which is readily available in both enantiomeric forms after a straightforward f,,vo-step synthesis, and compares its separating properties with those of (1S,2S)-l,3-diacetoxy-l-(4-nitrophenyl)-2-propyl isothiocyanate in the indirect highperformance liquid chromatographic separation of the enantiomers of amino compounds. The thiourea diastereomers formed were analysed on a reversed-phase column with methanol as organic mobile-phase modifier. Comparison of the resolution achieved by use of the f,,vo reagents revealed that their enantioselectivity might be very different, despite their structural similarity. (S,R)-APPI usually proved to be an excellent chiral derivatizing agent.

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“…Since the analytical field as a whole has shown significant technological advancement not only in the field of separation science but also in the availability of sensitive instruments, reagents, accessories such as chromatographic columns, novel stationary phases, column switching options, automation tools, improvement in extraction procedures, novel derivatization reagents and enhancement in detection systems with MS interfaces permitting different ionization schemes and approaches to increase the throughput of analysis and availability of trained and skilled personnel, the task of developing sound bioanalytical assay(s) can be achieved very easily (Toyo'oka, 2005;Kataoka, 2005;Paull and Nesterenko, 2005;Halket et al, 2005;Trivedi et al, 2005;Locatelli et al, 2005;Taylor PJ, 2004;Veuthey et al, 2004;Herron et al, 2004;Bhushan and Bruckner, 2004;Claessens and van Straten, 2004;Marshall et al, 2004;Kostiaimen et al, 2003;Deng et al, 2003;Naidong, 2003;Tiller et al, 2003;Li et al, 2003;Hoptgartner and Bourgogne, 2003;Huikko et al, 2003;Srinivas and Mamidi, 2003;Schellen et al, 2003;Cserhati, 2002;Williams and Wainer, 2002;Toyo'oka, 2002;Lim and Lord, 2002;Morrand et al, 2001;Plumb et al, 2001;Sun et al, 2001;Meguro et al, 2001;Xia et al, 2000).…”

Section: Introductionmentioning

confidence: 98%

Applicability of bioanalysis of multiple analytes in drug discovery and development: review of select case studies including assay development considerations

Srinivas

2006

Biomed. Chromatogr.

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The development of sound bioanalytical method(s) is of paramount importance during the process of drug discovery and development culminating in a marketing approval. Although the bioanalytical procedure(s) originally developed during the discovery stage may not necessarily be fit to support the drug development scenario, they may be suitably modified and validated, as deemed necessary. Several reviews have appeared over the years describing analytical approaches including various techniques, detection systems, automation tools that are available for an effective separation, enhanced selectivity and sensitivity for quantitation of many analytes. The intention of this review is to cover various key areas where analytical method development becomes necessary during different stages of drug discovery research and development process. The key areas covered in this article with relevant case studies include: (a) simultaneous assay for parent compound and metabolites that are purported to display pharmacological activity; (b) bioanalytical procedures for determination of multiple drugs in combating a disease; (c) analytical measurement of chirality aspects in the pharmacokinetics, metabolism and biotransformation investigations; (d) drug monitoring for therapeutic benefits and/or occupational hazard; (e) analysis of drugs from complex and/or less frequently used matrices; (f) analytical determination during in vitro experiments (metabolism and permeability related) and in situ intestinal perfusion experiments; (g) determination of a major metabolite as a surrogate for the parent molecule; (h) analytical approaches for universal determination of CYP450 probe substrates and metabolites; (i) analytical applicability to prodrug evaluations-simultaneous determination of prodrug, parent and metabolites; (j) quantitative determination of parent compound and/or phase II metabolite(s) via direct or indirect approaches; (k) applicability in analysis of multiple compounds in select disease areas and/or in clinically important drug-drug interaction studies. A tabular representation of select examples of analysis is provided covering areas of separation conditions, validation aspects and applicable conclusion. A limited discussion is provided on relevant aspects of the need for developing bioanalytical procedures for speedy drug discovery and development. Additionally, some key elements such as internal standard selection, likely issues of mass detection, matrix effect, chiral aspects etc. are provided for consideration during method development.

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Chiral derivatization reagents for drug enantioseparation by high‐performance liquid chromatography based upon pre‐column derivatization and formation of diastereomers: enantioselectivity and related structure

Cited by 52 publications

References 77 publications

Role of biological matrices during the analysis of chiral drugs by liquid chromatography

Role of biological matrices during the analysis of chiral drugs by liquid chromatography

Comparison of isothiocyanate chiral derivatizing reagents for high-performance liquid chromatography

Applicability of bioanalysis of multiple analytes in drug discovery and development: review of select case studies including assay development considerations

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