Hydrolysis and Enantiodiscrimination of (R)- and (S)-Oxazepam Hemisuccinate by Methylated β-Cyclodextrins: An NMR Investigation

Partially and exhaustively methylated β-cyclodextrins [(2-methyl)-β-CD (MCD), heptakis-(2,6-di-O-methyl)-β-CD (DIMEB), and heptakis-(2,3,6-tri-O-methyl)-β-CD (TRIMEB)] have been compared in the hydrolysis and enantiodiscrimination of benzodiazepine derivative (&...

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Autores principales:	Andrea Cesari, Federica Balzano, Gloria Uccello Barretta, Alessandra Recchimurzo
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	NMR chiral discrimination methylated cyclodextrins benzodiazepines hydrolysis inclusion complexes Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/3ac1ca906f9f41d6a0ff19419f437a35
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spelling	oai:doaj.org-article:3ac1ca906f9f41d6a0ff19419f437a352021-11-11T18:22:51ZHydrolysis and Enantiodiscrimination of (<i>R</i>)- and (<i>S</i>)-Oxazepam Hemisuccinate by Methylated β-Cyclodextrins: An NMR Investigation10.3390/molecules262163471420-3049https://doaj.org/article/3ac1ca906f9f41d6a0ff19419f437a352021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6347https://doaj.org/toc/1420-3049Partially and exhaustively methylated β-cyclodextrins [(2-methyl)-β-CD (MCD), heptakis-(2,6-di-<i>O</i>-methyl)-β-CD (DIMEB), and heptakis-(2,3,6-tri-<i>O</i>-methyl)-β-CD (TRIMEB)] have been compared in the hydrolysis and enantiodiscrimination of benzodiazepine derivative (<i>R</i>)- or (<i>S</i>)-oxazepam hemisuccinate (OXEMIS), using nuclear magnetic resonance (NMR) spectroscopy as an investigation tool. After 6 h, MCD induced an 11% hydrolysis of OXEMIS, remarkably lower in comparison with underivatized β-CD (48%), whereas no hydrolysis was detected in the presence of DIMEB or TRIMEB after 24 h. DIMEB showed greater ability to differentiate OXEMIS enantiomers in comparison to TRIMEB, by contrast MCD did not produce any splitting of racemic OXEMIS resonances. Both enantiomers of OXEMIS underwent deep inclusion of their phenyl pendant into cyclodextrins cavities from their wider rims, but tighter complexes were formed by DIMEB with respect to TRIMEB.Andrea CesariFederica BalzanoGloria Uccello BarrettaAlessandra RecchimurzoMDPI AGarticleNMRchiral discriminationmethylated cyclodextrinsbenzodiazepineshydrolysisinclusion complexesOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6347, p 6347 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	NMR chiral discrimination methylated cyclodextrins benzodiazepines hydrolysis inclusion complexes Organic chemistry QD241-441
spellingShingle	NMR chiral discrimination methylated cyclodextrins benzodiazepines hydrolysis inclusion complexes Organic chemistry QD241-441 Andrea Cesari Federica Balzano Gloria Uccello Barretta Alessandra Recchimurzo Hydrolysis and Enantiodiscrimination of (<i>R</i>)- and (<i>S</i>)-Oxazepam Hemisuccinate by Methylated β-Cyclodextrins: An NMR Investigation
description	Partially and exhaustively methylated β-cyclodextrins [(2-methyl)-β-CD (MCD), heptakis-(2,6-di-<i>O</i>-methyl)-β-CD (DIMEB), and heptakis-(2,3,6-tri-<i>O</i>-methyl)-β-CD (TRIMEB)] have been compared in the hydrolysis and enantiodiscrimination of benzodiazepine derivative (<i>R</i>)- or (<i>S</i>)-oxazepam hemisuccinate (OXEMIS), using nuclear magnetic resonance (NMR) spectroscopy as an investigation tool. After 6 h, MCD induced an 11% hydrolysis of OXEMIS, remarkably lower in comparison with underivatized β-CD (48%), whereas no hydrolysis was detected in the presence of DIMEB or TRIMEB after 24 h. DIMEB showed greater ability to differentiate OXEMIS enantiomers in comparison to TRIMEB, by contrast MCD did not produce any splitting of racemic OXEMIS resonances. Both enantiomers of OXEMIS underwent deep inclusion of their phenyl pendant into cyclodextrins cavities from their wider rims, but tighter complexes were formed by DIMEB with respect to TRIMEB.
format	article
author	Andrea Cesari Federica Balzano Gloria Uccello Barretta Alessandra Recchimurzo
author_facet	Andrea Cesari Federica Balzano Gloria Uccello Barretta Alessandra Recchimurzo
author_sort	Andrea Cesari
title	Hydrolysis and Enantiodiscrimination of (<i>R</i>)- and (<i>S</i>)-Oxazepam Hemisuccinate by Methylated β-Cyclodextrins: An NMR Investigation
title_short	Hydrolysis and Enantiodiscrimination of (<i>R</i>)- and (<i>S</i>)-Oxazepam Hemisuccinate by Methylated β-Cyclodextrins: An NMR Investigation
title_full	Hydrolysis and Enantiodiscrimination of (<i>R</i>)- and (<i>S</i>)-Oxazepam Hemisuccinate by Methylated β-Cyclodextrins: An NMR Investigation
title_fullStr	Hydrolysis and Enantiodiscrimination of (<i>R</i>)- and (<i>S</i>)-Oxazepam Hemisuccinate by Methylated β-Cyclodextrins: An NMR Investigation
title_full_unstemmed	Hydrolysis and Enantiodiscrimination of (<i>R</i>)- and (<i>S</i>)-Oxazepam Hemisuccinate by Methylated β-Cyclodextrins: An NMR Investigation
title_sort	hydrolysis and enantiodiscrimination of (<i>r</i>)- and (<i>s</i>)-oxazepam hemisuccinate by methylated β-cyclodextrins: an nmr investigation
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/3ac1ca906f9f41d6a0ff19419f437a35
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Hydrolysis and Enantiodiscrimination of (<i>R</i>)- and (<i>S</i>)-Oxazepam Hemisuccinate by Methylated β-Cyclodextrins: An NMR Investigation

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