Comparative evaluation of the chiral recognition potential of single-isomer sulfated beta-cyclodextrin synthesis intermediates in non-aqueous capillary electrophoresis

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F16%3A10336411" target="_blank" >RIV/00216208:11310/16:10336411 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.chroma.2016.07.033" target="_blank" >http://dx.doi.org/10.1016/j.chroma.2016.07.033</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.chroma.2016.07.033" target="_blank" >10.1016/j.chroma.2016.07.033</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Comparative evaluation of the chiral recognition potential of single-isomer sulfated beta-cyclodextrin synthesis intermediates in non-aqueous capillary electrophoresis

Popis výsledku v původním jazyce

The enantioselectivity of neutral single-isomer synthetic precursors of sulfated-beta-cyclodextrins was studied. Four neutral single-isomer cyclodextrins substituted on the secondary side with acetyl and/or methyl functional groups, heptakis(2-O-methyl-3,6-dihydroxy)-beta-cyclodextrin (HM-beta-CD), heptakis(2,3-di-O-acetyl-6-hydroxy)-beta-cyclodextrin (HDA-beta-CD), heptakis(2,3-di-O-methyl-6-hydroxy)-beta-cyclodextrin (HDM-beta-CD), heptakis(2-O-methyl-3-O-acetyl-6-hydroxy)-beta-cyclodextrin (HMA-beta-CD), and their sulfated analogs the negatively charged heptakis(2,3-di-O-methyl-6-sulfato)-beta-cyclodextrin (HDMS-beta-CD) and heptakis(2,3-di-O-acetyl-6-sulfato)-beta-cyclodextrin (HDAS-beta-CD) were investigated by non-aqueous capillary electrophoresis in the view of enantiodiscrimination for various drugs and related pharmaceutical compounds. The focus of the present work was on the chiral selectivity studies of the neutral derivatives, which are the synthesis intermediates of the sulfated products. The chiral recognition experiments proved that among the neutral compounds the HMA-beta-CD shows remarkable enantioselectivity towards chiral guests in non-aqueous capillary electrophoresis, while HM-beta-CD, HDA-beta-CD and HDM-beta-CD failed to resolve any of the 25 studied racemates under the applied experimental conditions. In order to get deeper insight into the molecular interactions between the studied single-isomer cyclodextrin and chiral fluoroquinolones (ofloxacin, gatifloxacin and lomefloxacin) and beta-blockers (propranolol), H-1 and ROESY NMR experiments were performed. The 2-O-methylation in combination with the 3-O-acetylation of the host was evidenced to exclusively carry the essential spatial arrangement for chiral recognition.

Název v anglickém jazyce

Comparative evaluation of the chiral recognition potential of single-isomer sulfated beta-cyclodextrin synthesis intermediates in non-aqueous capillary electrophoresis

Popis výsledku anglicky

The enantioselectivity of neutral single-isomer synthetic precursors of sulfated-beta-cyclodextrins was studied. Four neutral single-isomer cyclodextrins substituted on the secondary side with acetyl and/or methyl functional groups, heptakis(2-O-methyl-3,6-dihydroxy)-beta-cyclodextrin (HM-beta-CD), heptakis(2,3-di-O-acetyl-6-hydroxy)-beta-cyclodextrin (HDA-beta-CD), heptakis(2,3-di-O-methyl-6-hydroxy)-beta-cyclodextrin (HDM-beta-CD), heptakis(2-O-methyl-3-O-acetyl-6-hydroxy)-beta-cyclodextrin (HMA-beta-CD), and their sulfated analogs the negatively charged heptakis(2,3-di-O-methyl-6-sulfato)-beta-cyclodextrin (HDMS-beta-CD) and heptakis(2,3-di-O-acetyl-6-sulfato)-beta-cyclodextrin (HDAS-beta-CD) were investigated by non-aqueous capillary electrophoresis in the view of enantiodiscrimination for various drugs and related pharmaceutical compounds. The focus of the present work was on the chiral selectivity studies of the neutral derivatives, which are the synthesis intermediates of the sulfated products. The chiral recognition experiments proved that among the neutral compounds the HMA-beta-CD shows remarkable enantioselectivity towards chiral guests in non-aqueous capillary electrophoresis, while HM-beta-CD, HDA-beta-CD and HDM-beta-CD failed to resolve any of the 25 studied racemates under the applied experimental conditions. In order to get deeper insight into the molecular interactions between the studied single-isomer cyclodextrin and chiral fluoroquinolones (ofloxacin, gatifloxacin and lomefloxacin) and beta-blockers (propranolol), H-1 and ROESY NMR experiments were performed. The 2-O-methylation in combination with the 3-O-acetylation of the host was evidenced to exclusively carry the essential spatial arrangement for chiral recognition.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Chromatography A

ISSN

0021-9673

e-ISSN

—

Svazek periodika

1467

Číslo periodika v rámci svazku

October

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

9

Strana od-do

454-462

Kód UT WoS článku

000385323800044

EID výsledku v databázi Scopus

2-s2.0-84979518936