Synthesis, spectroscopic and computational evaluation of a xanthene-based fluorogenic derivatization reagent for the determination of primary amines

Kalampaliki, Amalia D.; Vincent, Steve; Mallick, Suman; Le, Hoang-Ngoan; Barnoin, Guillaume; More, Yogesh W.; Burger, Alain; Dotsikas, Yannis; Gikas, Evagelos; Michel, Benoît Y.; Kostakis, Ioannis K.

doi:10.1016/j.dyepig.2021.109798

Cited by 2 publications

(3 citation statements)

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“…In order to confirm the formation of the derivatization product following the abovementioned optimal conditions, a UHPLC-MS method was utilized. Initially, our aim was to separate the product from the excess of derivatization reagent by applying a gradient elution program [ 40 ]. The chromatograms presented in Figure 4 demonstrate that a baseline separation was achieved.…”

Section: Resultsmentioning

confidence: 99%

“…Derivatization reagent (1-bromomethyl-2-nitro-9 H -xanthene-9-one, 8 ) was synthesized in our laboratory [ 40 ]. Reference standard of pregabalin was obtained from Pfizer, Inc. (Groton, CT, USA).…”

Section: Methodsmentioning

confidence: 99%

“…In a previous study from our laboratories, a novel xanthene-based reagent for the fluorogenic derivatization of primary amines was designed, synthesized and characterized, and then its application to the derivatization of cyclopropylamine was examined [ 40 ], with the latter acting a model compound. The reagent is selective for primary amines, as the reaction products with secondary amines exhibit no shift in UV absorption and fluorescence.…”

Section: Introductionmentioning

confidence: 99%

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Chemometrically Assisted Optimization of Pregabalin Fluorescent Derivatization Reaction with a Novel Xanthone Analogue and Validation of the Method for the Determination of Pregabalin in Bulk via a Plate Reader

et al. 2022

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Quantitation of chromophore-free analytes is always a challenge. To this purpose, derivatization of the analyte constitutes a common strategy, leading to a product with a strong signal. In the current study, a novel xanthone analogue was utilized for the first time for the derivatization of pregabalin, a model analyte with a primary amine moiety that lacks a chromophore. The fact that only the xanthene-based derivative, formed after the derivatization reaction fluoresces, enables avoiding its chromatographic separation from the reagent and thus reducing the analysis time of a series of samples in 1–2 min via a plate reader. The reaction conditions were optimized via a central composite design (CCD), with fluorescence signal as the measure of the yield. The following factors that affect the derivatization reaction were chosen: (a) temperature, (b) reaction time, and (c) triethylamine solution volume used to drive the reaction to completion. After the identification of the optimal conditions, the method was validated according to ICH guidelines, using a fluorescence plate reader for signal measurement (λex = 540, λem = 615 nm). Finally, the newly developed high-throughput method was applied to the determination of drug content in pregabalin bulk.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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