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Titolo:
Solubility enhancement of phenol and phenol derivatives in perfluoroocytl bromide
Autore:
Williams, JD; Jay, M; Lehmler, HJ; Clark, ME; Stalker, DJ; Bummer, PM;
Indirizzi:
Univ Kentucky, Coll Pharm, Lexington, KY 40536 USA Univ Kentucky Lexington KY USA 40536 Coll Pharm, Lexington, KY 40536 USA Univ Kentucky, Dept Chem, Lexington, KY 40536 USA Univ Kentucky LexingtonKY USA 40536 , Dept Chem, Lexington, KY 40536 USA Pharmacia & Upjohn Inc, Kalamazoo, MI 49001 USA Pharmacia & Upjohn Inc Kalamazoo MI USA 49001 nc, Kalamazoo, MI 49001 USA
Titolo Testata:
JOURNAL OF PHARMACEUTICAL SCIENCES
fascicolo: 12, volume: 87, anno: 1998,
pagine: 1585 - 1589
SICI:
0022-3549(199812)87:12<1585:SEOPAP>2.0.ZU;2-U
Fonte:
ISI
Lingua:
ENG
Soggetto:
LIQUID VENTILATION; RESPIRATORY-FAILURE; FLUOROCARBON; SURFACTANTS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
18
Recensione:
Indirizzi per estratti:
Indirizzo: Bummer, PM Univ Kentucky, Coll Pharm, Rose St, Lexington, KY 40536 USA Univ Kentucky Rose St Lexington KY USA 40536 gton, KY 40536 USA
Citazione:
J.D. Williams et al., "Solubility enhancement of phenol and phenol derivatives in perfluoroocytl bromide", J PHARM SCI, 87(12), 1998, pp. 1585-1589

Abstract

Perfluorinated solvents are gaining popularity as pulmonary ventilation fluids, but they suffer from poor solvent quality in concurrent drug deliveryapplications. The present study examines the use of a hydrophobic solubilizing agent capable of interacting with model drug solutes by hydrogen bonding with the purpose of enhancing solubility in perfluorooctyl bromide (PFOB). A series of solubilizing agents containing a ketone carbonyl to act as ahydrogen bond acceptor and a perfluoroalkyl chain to maintain the solubility of the putative complex in PFOB are investigated. The solubility of phenol in PFOB is enhanced to the greatest extent by 1-(4-perfluorobutyl phenyl)-1-hexanone (III) where the ketone carbonyl is protected from the electronwithdrawing effects of the perfluorobutyl chain by a phenyl ring. Experiments with solubilizers lacking the ketone group suggest that pi-pi bond interactions of III with phenol do not significantly enhance solubility. For a series of phenol derivatives, a rank-order correlation exists between the magnitude of solubility enhancement by III, as reflected by the calculated association constants, and the Hammett sigma parameter of the phenols. Because the O-methyl-substituted phenols do not have the ability to hydrogen bond, their solubility is not enhanced by the presence of III. The results of the present study indicate that solubility of model drug hydrogen bond donating compounds can be enhanced in PFOB by the presence of fluorocarbon-soluble hydrogen bond accepters.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 30/11/20 alle ore 16:24:33