Electrophoretic separation of multiple chiral center analyte with a three cyclodextrins mixture.
Capillary electrophoresis
Cyclodextrin
Dihydropyridone
Multiple chiral center
Journal
Electrophoresis
ISSN: 1522-2683
Titre abrégé: Electrophoresis
Pays: Germany
ID NLM: 8204476
Informations de publication
Date de publication:
09 2021
09 2021
Historique:
revised:
17
02
2021
received:
18
11
2020
accepted:
22
02
2021
pubmed:
2
3
2021
medline:
10
2
2022
entrez:
1
3
2021
Statut:
ppublish
Résumé
A capillary electrokinetic chromatography method (CEKC) was developed for complete stereoisomeric separation of a neutral, hydrophobic, multiple chiral center dihydropyridone analogue, a drug candidate proposed in type 2 diabetes treatment. A background electrolyte comprising three cyclodextrins was found to successfully separate the eight isomers. First an anionic cyclodextrin, the SBE-β-CD, was selected to allow the chiral separation of our neutral compound and partial resolutions of the eight isomers were obtained. Then, the effects of different parameters such as the nature and concentration of the other cyclodextrins added and pH of the buffer were examined. Finally, a triple CD-system consisted of 15 mM SBE-β-CD plus 15 mM γ-CD and 40 mM HP-γ-CD in a 50 mM borate background electrolyte at pH 10, was found to successfully separate the eight isomers. Last, the selectivity and limits of detection and quantification were evaluated for this optimized method.
Identifiants
pubmed: 33644914
doi: 10.1002/elps.202000342
doi:
Substances chimiques
Anions
0
Cyclodextrins
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
1810-1817Informations de copyright
© 2021 Wiley-VCH GmbH.
Références
Pinto, M.M.M., Fernandes, C., Tiritan, M.E., Molecules 2020, 25, 1931-1947.
Charton, J., Deprez, B., Leroux, F., Picon, S., Aknin, K., Boulahjar, R., Staels, B., Muhr-Tailleux, A., Hennuyer, N., Lestavel, S., Dubanchet, B., 2-Oxo-3,4-dihydropyridine-5-carboxylates and their use, WO2016/016238 2016.
Scriba, G., Methods Mol. Biol. 2019, 1985, 1-33.
Gassmann, E., Kuo, J.E., Zare, R.N., Science 1985, 230, 813-814.
Snopek, J., Jelínek, I., Smolková-Keulemansová, E., J. Chromatogr. A 1988, 438, 211-218.
Fanali, S., J. Chromatogr. A 2000, 875, 89-122.
Chankvetadze, B., J. Chromatogr. A 2007, 1168, 45-70.
Scriba, G.E.K., J. Chromatogr. A 2016, 1467, 56-78.
Fillet, M., Hubert, P., Crommen, J., J. Chromatogr. A 2000, 875, 123-134.
Fejos, I., Kalydi, E., Malanga, M., Benkovics, G., Béni, S., J. Chromatogr. A 2020, 1627, 461375.
Fu, F., Fu, Y., Liu, G., Zhang, M., Qiang, S., Kang, J., J. Chromatogr. A 2020, 1618, 460845.
Lin, J., Tsang, C., Lieu, R., Zhang, K., J. Chromatogr. A 2020, 1620, 460987.
Lin, J., Tsang, C., Lieu, R., Zhang, K., J. Chromatogr. A 2020, 1624, 461244.
Ali, I., Suheil, M., Al-Othman Z.A., Alwarthan, A., Aboul-Enein, H.Y., Biomed. Chromatogr. 2016, 30, 683-694.
Wren, S. A. C., Rowe, R. C., J. Chromatogr. 1992, 603, 235-241.
Wren, S. A. C., Rowe, R. C., J. Chromatogr. 1993, 635, 113-118.
Scriba, G.E.K., Electrophoresis 2003, 24, 4063-4077.
Delplanques, T., Boulahjar, R., Charton, J., Houze, C., Howsam, M., Servais, A.C., Fillet, M., Lipka, E., Electrophoresis 2017, 38, 1922-1931.
Lipka, E., Landagaray, E., Ettaoussi, M., Yous, S., Vaccher, C., Electrophoresis 2014, 35, 2785-2792.
Lipka, E., Danel, C., Yous, S., Bonte, J.P., Vaccher, C., Electrophoresis 2010, 31, 1529-1532.
Fradi, I., Servais, A.C., Lamalle, C., Kallel, M., Abidi, M., Crommen, J., Fillet, M., J. Chromatogr. A 2012, 1267, 121-126.
Németh, K., Varga, E., Iványi, R., Szemán, J., Visya, J., Jicsinszky, L., Szenteb, L., Forróc, E., Fülöpc, F., Péter A., Simonyi, M., J. Pharm. Biomed. Anal. 2010, 53, 382-388.
Holzgrabe, U., Borst, C., Büttner, C., Bitar, Y., in Van Eeckhaut, A., Michotte, Y., (Eds.), Chiral Separations by Capillary Electrophoresis, CRC Press, Boca Raton 2010, pp. 313-340.