β-cyclodextrin complex formation and protonation equilibria of morphine and other opioid compounds of therapeutic interest.

Analgesics, Opioid Cyclodextrins / chemistry Magnetic Resonance Spectroscopy / methods Molecular Structure Morphine beta-Cyclodextrins / chemistry
(1)H NMR-titration Inclusion complex Morphine ROESY Stability constant β-cyclodextrin

Journal

European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences
ISSN: 1879-0720
Titre abrégé: Eur J Pharm Sci
Pays: Netherlands
ID NLM: 9317982

Informations de publication

Date de publication:
01 Apr 2022
Historique:
received: 21 09 2021
revised: 02 12 2021
accepted: 05 01 2022
pubmed: 10 1 2022
medline: 24 2 2022
entrez: 9 1 2022
Statut: ppublish

Résumé

The inclusion complex formation of morphine and its 18 opioid derivatives with β-cyclodextrin has been studied using nuclear magnetic resonance spectroscopy. Initially, the protonation equilibria and the acid-base properties of dibasic opioid compounds have been fully characterized. Apparent protonation constants and the relative concentration of the microspecies in cyclodextrin excess were also determined. The 1:1 complex stoichiometry was confirmed by the continuous variation method of Job using UV-VIS spectroscopy. The stability constants of the different protonation forms were determined by

Identifiants

DOI: 10.1016/j.ejps.2022.106120 PMID: 34999212
pubmed: 34999212
pii: S0928-0987(22)00005-7
doi: 10.1016/j.ejps.2022.106120
pii:
doi:

Substances chimiques

Analgesics, Opioid 0
Cyclodextrins 0
beta-Cyclodextrins 0
Morphine 76I7G6D29C

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

106120

Informations de copyright

Copyright © 2022. Published by Elsevier B.V.

Auteurs

Boglárka Tűz (B)

Department of Pharmaceutical Chemistry, Semmelweis University, Hőgyes Endre u. 9., Budapest H-1092, Hungary.

Béla Noszál (B)

Department of Pharmaceutical Chemistry, Semmelweis University, Hőgyes Endre u. 9., Budapest H-1092, Hungary.

Sándor Hosztafi (S)

Department of Pharmaceutical Chemistry, Semmelweis University, Hőgyes Endre u. 9., Budapest H-1092, Hungary.

Károly Mazák (K)

Department of Pharmaceutical Chemistry, Semmelweis University, Hőgyes Endre u. 9., Budapest H-1092, Hungary. Electronic address: mazak.karoly@pharma.semmelweis-univ.hu.

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Classifications MeSH

questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Utilisations thérapeutiques › Agents du système nerveux central › Dépresseurs du système nerveux central › Stupéfiants › Analgésiques morphiniques › β-cyclodextrin complex formation and...
questionsmedicales.fr › Glucides › Polyosides › Glucanes › Amidon › Dextrine › Cyclodextrines › β-cyclodextrin complex formation and...
questionsmedicales.fr › Techniques d'investigation › Techniques de chimie analytique › Analyse spectrale › Spectroscopie par résonance magnétique › β-cyclodextrin complex formation and...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › β-cyclodextrin complex formation and...
questionsmedicales.fr › Composés polycycliques › Hydrocarbures aromatiques polycycliques › Phénanthrènes › Morphinanes › Dérivés de la morphine › Morphine › β-cyclodextrin complex formation and...
questionsmedicales.fr › Glucides › Polyosides › Glucanes › Amidon › Dextrine › Cyclodextrines › Cyclodextrines bêta › β-cyclodextrin complex formation and...