Synthesis, spectroscopic and computational evaluation of a xanthene-based fluorogenic derivatization reagent for the determination of primary amines. (December 2021)

• Record Type: Journal Article
• Authors: 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.
• Is Part Of: Dyes and pigments. Volume 196(2022)
• Publication Date: 2021-12
• Subjects: Amine derivatization -- Colorimetric detection -- Fluorogenic sensing -- Chromatographic analysis -- Quantum calculations; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2021.109798
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: To detect an analyte, typically at the sub-nanomolar scale, extremely sensitive analytical tools are required. Fluorescence is the spectroscopy of choice to achieve such a level due to its non-invasive nature and efficiency in accurately probing the sub-nanomolar concentration range. Here, we report the design, synthesis and photophysical characterization of a fluorogenic derivatization reagent with exclusive selectivity for primary amines. This xanthene-based dye owns an exacerbated fluorogenic character making the derivatized amine absorbing in yellow and emitting in the vermilion edge. In addition to being fluorogenic, this derivatization method also has the crucial advantage of being chromogenic (colorless => fuchsia). Chemical quantum calculations give an insight into the dye's molecular properties, while the development of an LC analytical method provides proof of concept regarding its application for the analysis of primary amines in a complex matrix. Graphical abstract: MAGENTA or RED : select your 1° amine detection colorȦ .☺ Image 1 Highlights: The identification of challenging amines in complex extracts of natural products requires more and more innovative and sensitive spectroscopic methods. A xanthene-based derivatization reagent was engineered for the exclusive detection of primary amines. Thanks to its chromogenic nature (colorless => magenta), the derivatization process becomes accessible to a broader audience. The developed fluorogenic sensing (non-fluorescent => red) allows the method to reach an exquisite sensitivity level, approaching the picomolar range.