Characterization studies of 1-butyl-3-methyl-imidazolium bis(2-ethylhexyl) sulfosuccinate vesicles at different pH values have been carried out by using liquid surface tension, transmission electron microscopy, and dynamic light scattering. The results show that there are no vesicle changes in its size and negative Z potential at pH 3, 6, and 10. Furthermore, indomethacin and 1-naphthol, both pH-dependent, electroactive, and fluorescence probes, were used to further characterize the bilayer employing electrochemical and emission techniques. The partition of indomethacin and 1-naphthol between the water and bilayer pseudophases only occurs for the neutral species and does not happen for the anionic species because the highly negative Z bilayer potential prevents incorporation due to negative repulsion. For the neutral species, the partition constant values were evaluated by square wave voltammetry and emission spectroscopy. Finally, for the indomethacin incorporated into the vesicle bilayer at pH 3, the release profile was monitored over time at pH 6. It was found that a change in the pH values causes the complete release of indomethacin after 25 min, which led us to think that the vesicles presented in this work can be used as a pH-sensitive nanocarrier for neutral pH-sensitive drugs.
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http://dx.doi.org/10.1021/acs.langmuir.3c03263 | DOI Listing |
Langmuir
January 2024
Instituto para el desarrollo agroindustrial y de la salud (IDAS, CONICET-UNRC), Departamento de Química, Universidad Nacional de Río Cuarto, Agencia Postal #3. C.P. , Río Cuarto X5804BYA, Argentina.
Characterization studies of 1-butyl-3-methyl-imidazolium bis(2-ethylhexyl) sulfosuccinate vesicles at different pH values have been carried out by using liquid surface tension, transmission electron microscopy, and dynamic light scattering. The results show that there are no vesicle changes in its size and negative Z potential at pH 3, 6, and 10. Furthermore, indomethacin and 1-naphthol, both pH-dependent, electroactive, and fluorescence probes, were used to further characterize the bilayer employing electrochemical and emission techniques.
View Article and Find Full Text PDFToxicol In Vitro
December 2012
Center for Drug Research, University of Helsinki, Finland.
In vitro glucuronidation assays of diclofenac and indomethacin at pH 7.4 are biased by the instability of the glucuronides due to acyl migration. The extent of this acyl migration may be reduced significantly by performing the glucuronidation reaction at pH 6.
View Article and Find Full Text PDFDrug Metab Dispos
March 2011
Centre for Drug Research, Faculty of Pharmacy, University of Helsinki, Helsinki, Finland.
Cell differentiation increases UDP-glucuronosyltransferase (UGT) gene expression in Caco-2 cells. Glucuronidation of 13 UGT substrates, 1-naphthol, diclofenac, epitestosterone, estradiol, ethinylestradiol, indomethacin, oxazepam, R- and S-propranolol, propofol, testosterone, trifluoperazine, and zidovudine, were studied to derive a broad view on the effect of cell differentiation on the glucuronidation activities of different human UGTs. In parallel, the glucuronidation of these compounds in human liver microsomes (HLM) and human intestinal microsomes (HIM) was analyzed.
View Article and Find Full Text PDFInt J Pharm
January 2010
Division of Pharmaceutical Technology, Faculty of Pharmacy, University of Helsinki, Finland.
The human intestinal cell line, Caco-2, was used to study compounds - indomethacin, paracetamol and 1-naphthol - that undergo intestinal phase II metabolism followed by apical and/or basolateral efflux of the metabolites and/or parent compounds. The interplay was studied during permeability experiments across fully differentiated Caco-2 cell monolayers. The parent compounds and their glucuronide and/or sulfate metabolites were detected by LC-MS/MS.
View Article and Find Full Text PDFJ Pharmacol Exp Ther
November 2000
Pharmaceutical Research Center, Meiji Seika Kaisha, Ltd., Yokohama, Japan.
ME3229 is an ester-type prodrug of a glycoprotein IIb/IIIa receptor antagonist ME3277. In our previous study, it was shown that only a small part of the drug taken up into the enterocytes reached the mesenteric vein, mainly due to transporter-mediated efflux of its hydrolyzed metabolites formed in the cells. To characterize the efflux transport system for the metabolites, the transport of the diacid metabolite ME3277 and the monoacid metabolites PM-10 and PM-11 were studied.
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