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Titolo:
Conformations of a non-steroidal anti-inflammatory drug nabumetone in aqueous environments
Autore:
Valero, M; Costa, SMB; Santos, MA;
Indirizzi:
Inst Super Tecn, Ctr Quim Estrutural, P-1049001 Lisbon, Portugal Inst Super Tecn Lisbon Portugal P-1049001 al, P-1049001 Lisbon, Portugal Univ Salamanca, Fac Farm, Dept Quim Fis, E-37080 Salamanca, Spain Univ Salamanca Salamanca Spain E-37080 uim Fis, E-37080 Salamanca, Spain
Titolo Testata:
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
fascicolo: 1-2, volume: 132, anno: 2000,
pagine: 67 - 74
SICI:
1010-6030(20000320)132:1-2<67:COANAD>2.0.ZU;2-L
Fonte:
ISI
Lingua:
ENG
Soggetto:
NAPROXEN; DIOXANE; STATE; WATER; SPECTROSCOPY; SULFONATE; MOLECULES; SOLVENT;
Keywords:
cyclodextrin(CD); nabumetone; fluorescence spectra; quantum yield (phi(f)); lifetime (tau(f));
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
29
Recensione:
Indirizzi per estratti:
Indirizzo: Costa, SMB Inst Super Tecn, Ctr Quim Estrutural, Complexo Interdisciplinar,Av RoviscoPais, P-1049001 Lisbon, Portugal Inst Super Tecn Complexo Interdisciplinar,Av Rovisco Pais Lisbon Portugal P-1049001
Citazione:
M. Valero et al., "Conformations of a non-steroidal anti-inflammatory drug nabumetone in aqueous environments", J PHOTOCH A, 132(1-2), 2000, pp. 67-74

Abstract

Spectroscopic and photophysical properties of a non-steroidal anti-inflammatory drug, Nabumetone, were studied in dioxane/water mixtures, cyclodextrins (alpha-CD, beta-CD and HP-beta-CD) and besides that, for comparison, in a wide range of solvents with different polarities, viscosities and hydrogen bonding ability. The fluorescence quantum yields (phi(f)) and lifetimes (tau(f)) in aqueousand in non-aqueous media, present some evidence which points to the existence of two preferred conformations in aqueous media: one with global phi(f)=0.1-0.3 and tau(f)(2)=7 ns, corresponding to the side chain completely extended and the other one, with lower global phi(f)=0.02-0.08 and tau(f)(1)=0.7-2 ns, likely associated with a folded conformation responsible for the fluorescence quenching of the naphthalene moiety by the butanone chain. The formation of one or other conformation is not much affected by the physicalproperties of the solvent. By contrast, the presence of water creates a very favourable environment for the formation of the folded conformation, which is essentially the only one in pure water. This behaviour is explained by a water-structure enforced hydrophobic effect and makes this drug a good water sensitive probe. Inclusion of the drug in the beta-cyclodextrin emphasises the existence of two conformations, whereas in alpha-CD only the extended one is present, with a much higher phi(f)=0.4 and tau(f)=15.7 ns. Molecular mechanics (MM) and molecular orbital (MNDO) calculations also supportthe existence of two possible conformations in Nabumetone. (C) 2000 Elsevier Science S.A. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 13/07/20 alle ore 20:27:59