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Titolo:
Molecular modelling and H-1-NMR: Ultimate tools for the investigation of tolbutamide : beta-cyclodextrin and tolbutamide : hydroxypropyl-beta-cyclodextrin complexes
Autore:
Veiga, FJB; Fernandes, CM; Carvalho, RA; Geraldes, CFGC;
Indirizzi:
Univ Coimbra, Fac Pharm, Lab Pharmceut Technol, Coimbra, Portugal Univ Coimbra Coimbra Portugal Lab Pharmceut Technol, Coimbra, Portugal Univ Coimbra, Dept Biochem, Coimbra, Portugal Univ Coimbra Coimbra Portugal Coimbra, Dept Biochem, Coimbra, Portugal
Titolo Testata:
CHEMICAL & PHARMACEUTICAL BULLETIN
fascicolo: 10, volume: 49, anno: 2001,
pagine: 1251 - 1256
SICI:
0009-2363(200110)49:10<1251:MMAHUT>2.0.ZU;2-O
Fonte:
ISI
Lingua:
ENG
Soggetto:
NUCLEAR-MAGNETIC-RESONANCE; INCLUSION COMPLEXES; ORAL BIOAVAILABILITY; DISSOLUTION; SPECTROSCOPY; DERIVATIVES; IMPROVEMENT; SOLUBILITY; STABILITY; SYSTEMS;
Keywords:
tolbutamide; cyclodextrin; H-1-NMR; molecular modelling;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
33
Recensione:
Indirizzi per estratti:
Indirizzo: Veiga, FJB Univ Coimbra, Fac Pharm, Lab Pharmceut Technol, Coimbra, Portugal Univ Coimbra Coimbra Portugal eut Technol, Coimbra, Portugal
Citazione:
F.J.B. Veiga et al., "Molecular modelling and H-1-NMR: Ultimate tools for the investigation of tolbutamide : beta-cyclodextrin and tolbutamide : hydroxypropyl-beta-cyclodextrin complexes", CHEM PHARM, 49(10), 2001, pp. 1251-1256

Abstract

A structural study of the inclusion compound of tolbutamide (TBM) with beta -cyclodextrin (beta -CD) and hydroxypropyl-beta -cyclodextrin (HP-beta -CD) was attempted by means of H-1-nuclear magnetic resonance (H-1-NMR) experiments and computer molecular modelling. To establish the stoichiometry andstability constant of the beta -CD:TBM complex, the continuous variation method was used. The presence of true inclusion complexes between TBM and beta -CD or HP-beta -CD in solution was clearly evidenced by the H-1-NMR technique. Changes in chemical shifts of H-3 and H-5 protons, located inside the CD cavity, associated with variations in the chemical shifts of TBM aromatic protons provided clear evidence of inclusion complexation, suggesting that the phenyl moiety of the drug molecule was included in the hydrophobic cavity of CDs. This view was further supported by the observation of intermolecular NOEs between TBM and beta -CD and by the aid of a molecular modelling program, which established the most probable structure of the complex. The molecular graphic computation confirmed that the minimum energy, positioning TBM relative to beta -CD, occurs when the aromatic ring of TBM is included within the beta -CD cavity by its wider side, leaving the aliphatic chain externally, which is in good agreement with the results of H-1-NMR studies.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 04/12/20 alle ore 22:39:38