Effects of Micelles and Vesicles on the Oximolysis of p-Nitrophenyl Diphenyl Phosphate: A Model System for Surfactant-Based Skin-defensive Formulations against Organophosphates
Contribuinte(s) |
UNIVERSIDADE DE SÃO PAULO |
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Data(s) |
20/10/2012
20/10/2012
2009
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Resumo |
The rates of oximolysis of p-nitrophenyl diphenyl phosphate (PNPDPP) by Acetophenoxime; 10-phenyl-10-hydi-oxyiminodecanoic acid; 4-(9-carboxynonanyl)-1-(9-carboxy-1-hydroyiminononanyl) benzene; 1-dodecyl-2-[(hydroxyimino)methyl]-pyridinium chloride (IV) and N-methylpyridinium-2-aldoxime chloride were determined in micelles of N-hexadecyl-N,N,N-trimethylammonium chloride (CTAC), N-hexadecyl-N,N-dimethylammonium propanesulfonate and dioctadecyldimethylammonium chloride (DODAC) vesicles. The effects of CTAC micelles and DODAC vesicles on the rates of oxymolysis of O,O-Diethyl O-(4-nitrophenyl) phosphate (paraoxon) by oxime IV were also determined. Analysis of micellar and vesicular effects on oximolysis of PNPDPP, using pseudophase or pseudophase with explicit consideration of ion exchange models, required the determination of the aggregate`s effects on the pK(a), of oximes and on the rates of PNPDPP hydrolysis. All aggregates increased the rate of oximolysis of PNPDPP and the results were analyzed quantitatively. In particular, DODAC vesicles catalyzed the reaction and increased the rate of oximolysis of PNPDPP by IV several million fold at pH`s compatible with pharmaceutical formulations. The rate increase produced by DODAC vesicles on the rate of oximolysis paraoxon by IV demonstrates the pharmaceutical potential of this system, since the substrate is used as an agricultural defensive agent and the surfactant is extensively employed in cosmetic formulations. (C) 2008 Wiley-Liss, Inc. and the American Pharmacists Association J Pharm Sci 98:1040-1052, 2009 FAPESP Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) CNPq CNPQ-NSF CNPQ-NSF Universidade de São Paulo - Pro-Reitoria de Pesquisa da USP Universidade de São Paulo - Pro-reitoria de Pesquisa da USP |
Identificador |
JOURNAL OF PHARMACEUTICAL SCIENCES, v.98, n.3, p.1040-1052, 2009 0022-3549 http://producao.usp.br/handle/BDPI/30845 10.1002/jps.21506 |
Idioma(s) |
eng |
Publicador |
JOHN WILEY & SONS INC |
Relação |
Journal of Pharmaceutical Sciences |
Direitos |
restrictedAccess Copyright JOHN WILEY & SONS INC |
Palavras-Chave | #controlled release #drug transport #micelle #surface chemistry #skin #liposomes #IN-VITRO CYTOTOXICITY #EYE IRRITATION TESTS #HYDROXAMATE IONS #INTERLABORATORY VALIDATION #NUCLEOPHILIC-SUBSTITUTION #COSMETIC INGREDIENTS #DEPHOSPHORYLATION #REACTIVITY #EXCHANGE #HYDROLYSIS #Chemistry, Medicinal #Chemistry, Multidisciplinary #Pharmacology & Pharmacy |
Tipo |
article original article publishedVersion |