A simple, inexpensive but effective approach for visual chiral recognition of ketoprofen enantiomers was developed using L-cysteine capped silver nanoparticles (L-Cys-AgNPs) as a colorimetric sensor. Upon the addition of R-ketoprofen to L-Cys-AgNPs, rapid aggregation occurred, and the solution changed color from yellow to green. However, the presence of S-ketoprofen did not induce any color change. The results were characterized using UV-Vis, FESEM, FT-IR, SERS, and zeta potential measurements. The chiral assay described in this work is easily distinguished with the naked eyes or using a UV-Vis spectrometer. The sensor revealed a good linear response to ketoprofen enantiomers in the concentration range of 8.33-33.3 μM with a detection limit of 4.52 μM and relative standard deviation of 3.73%. The proposed method was utilized for the determination of ketoprofen racemic mixtures in water samples and commercial tablets. The method excels by its simplicity, low cost, and good availability of materials.
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http://dx.doi.org/10.1002/chir.23354 | DOI Listing |
Biomed Chromatogr
December 2024
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, India.
The synthesis of optically active compounds requires determination of ee, er, and enantiomeric purity. The aim of the present paper is to review the synthesis of several chiral derivatizing reagents (CDRs) in a rational manner, which were successful for the separation and isolation of enantiomers of a variety of active pharmaceutical ingredients and other important and useful racemates. Besides, the application of (i) certain enantiomerically pure amines, either directly or by incorporating each of them as chiral auxiliary in difluorodinitrobenzene or cyanuric chloride moieties to construct the CDR, (ii) (S)-ketoprofen and (S)-levofloxacin as chiral platforms, and (iii) a few isothiocyanates, have been suitably included.
View Article and Find Full Text PDFJ Chromatogr B Analyt Technol Biomed Life Sci
August 2024
Shanxi Eye Hospital, Taiyuan 030002, PR China. Electronic address:
Profenoid drugs are a kind of common non-steroidal anti-inflammatory drugs and their chiral enantiomers often have huge differences in pharmacological activities. In this work, a novel chiral separation system by capillary electrophoresis (CE) was constructed using gold nanoparticles (AuNPs) functionalized with bovine serum albumin (BSA) as a quasi-stationary phase (QSP), and the enantioseparation of six profenoid drugs was efficiently accomplished. Under optimal chromatographic conditions, the enantioseparation performance of the AuNP@BSA-based chiral separation system was greatly improved compared with that of free BSA (Resolutions, Ibuprofen: 0.
View Article and Find Full Text PDFChemistry
April 2024
Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell'Insubria, Via Valleggio 11, 22100, Como, Italy.
Among inherently chiral selectors of axial stereogenicity, usually resulting in very good enantiodiscrimination performances, the biindole-based family has the additional advantage of very easy functionalization of the two nitrogen atoms with a variety of substituents with desirable properties. Aiming to evaluate the possibility of exploiting such feature to enhance the enantiodiscrimination ability of the archetype structure, a series of three inherently chiral monomers were designed and synthesized, characterised by a 2,2'-biindole atropisomeric core conjugated to bithiophene wings enabling fast and regular electrooligomerization, and functionalised at the nitrogen atoms with an ethyl, a methoxyethyl, or a hydroxyethyl substituent. Nitrogen alkylation was also exploited to obtain for the first time the chemical resolution of the biindole selectors without employing chiral HPLC.
View Article and Find Full Text PDFInt J Mol Sci
February 2024
Department of Pharmaceutical Chemistry, Semmelweis University, Hogyes 9, H-1092 Budapest, Hungary.
A reversed-phase high-performance liquid chromatographic (HPLC) method was developed for the simultaneous determination of the potential impurities of dexketoprofen, including the distomer R-ketoprofen. After screening the separation capability of four polysaccharide columns (Lux Amylose-1, Lux Amylose-2, Lux Cellulose-1 and Lux Cellulose-2) in polar organic and in reversed-phase modes, appropriate enantioseparation was observed only on the Lux Amylose-2 column in an acidified acetonitrile/water mixture. A detailed investigation of the mobile phase composition and temperature for enantio- and chemoselectivity showed many unexpected observations.
View Article and Find Full Text PDFKetoprofen, a bicyclic non-steroidal anti-inflammatory drug commonly used in human and veterinary medicine, has recently been cited as an environmental contaminant that raises concerns for ecological well-being. It poses a growing threat due to its racemic mixture, enantiomers, and transformation products, which have ecotoxicological effects on various organisms, including invertebrates, vertebrates, plants, and microorganisms. Furthermore, ketoprofen is bioaccumulated and biomagnified throughout the food chain, threatening the ecosystem function.
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