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Protolytic Equilibria of Sartans in Micellar Solutions of Differently Charged Surfactants

Authorized Users Only
2016
Authors
Grujić, Maja
Popović, Marija
Popović, Gordana
Nikolić, Katarina
Agbaba, Danica
Article (Published version)
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Abstract
Protolytic equilibria of irbesartan, losartan, and valsartan have been investigated in the presence and absence of differently charged anionic (sodium dodecyl sulfate), cationic (cetyltrimethylammonium bromide), and nonionic (4-octylphenol polyethoxylate and polyoxyethylene (23) lauryl ether) surfactants. Ionization constants were determined by potentiometric titration at a constant ionic strength (0.1 M NaCl) and temperature 25 degrees C. The effect of surfactants was estimated, based on a shift in apparent ionization constants (pK(a)(app)) determined in micellar solutions against the pK(a)(w) values in water. The anionic surfactant caused an increase in the pK(a)(app) values of sartans (up to 1.72 pK units), while the cationic surfactant had an opposite effect and caused a reduction in pK(a)(app) values (up to -1.44 pK units). These results point out to the fact that the ionizable groups of sartans are involved in electrostatic interactions with the charged surface of the ionic micel...les. Shift in the pKa app values in the presence of nonionic surfactants (from -0.86 to +1.30) is a consequence of the interactions of drugs with the hydrophilic palisade layer. Significant changes in the distribution profiles of the equilibrium forms (from -44% to +80%) are observed at the biopharmaceutically important pH 4.5 value and can be considered in terms of the potential influence on intestinal absorption and bioavailability.

Source:
Journal of Pharmaceutical Sciences, 2016, 105, 8, 2444-2452
Publisher:
  • Wiley, Hoboken
Funding / projects:
  • Synthesis, Quantitative Structure and Activity Relationship, Physico-Chemical Characterisation and Analysis of Pharmacologically Active Substances (RS-172033)

DOI: 10.1016/j.xphs.2016.06.007

ISSN: 0022-3549

PubMed: 27422089

WoS: 000381770400025

Scopus: 2-s2.0-84978929438
[ Google Scholar ]
8
8
URI
https://farfar.pharmacy.bg.ac.rs/handle/123456789/2715
Collections
  • Radovi istraživača / Researchers’ publications
Institution/Community
Pharmacy
TY  - JOUR
AU  - Grujić, Maja
AU  - Popović, Marija
AU  - Popović, Gordana
AU  - Nikolić, Katarina
AU  - Agbaba, Danica
PY  - 2016
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2715
AB  - Protolytic equilibria of irbesartan, losartan, and valsartan have been investigated in the presence and absence of differently charged anionic (sodium dodecyl sulfate), cationic (cetyltrimethylammonium bromide), and nonionic (4-octylphenol polyethoxylate and polyoxyethylene (23) lauryl ether) surfactants. Ionization constants were determined by potentiometric titration at a constant ionic strength (0.1 M NaCl) and temperature 25 degrees C. The effect of surfactants was estimated, based on a shift in apparent ionization constants (pK(a)(app)) determined in micellar solutions against the pK(a)(w) values in water. The anionic surfactant caused an increase in the pK(a)(app) values of sartans (up to 1.72 pK units), while the cationic surfactant had an opposite effect and caused a reduction in pK(a)(app) values (up to -1.44 pK units). These results point out to the fact that the ionizable groups of sartans are involved in electrostatic interactions with the charged surface of the ionic micelles. Shift in the pKa app values in the presence of nonionic surfactants (from -0.86 to +1.30) is a consequence of the interactions of drugs with the hydrophilic palisade layer. Significant changes in the distribution profiles of the equilibrium forms (from -44% to +80%) are observed at the biopharmaceutically important pH 4.5 value and can be considered in terms of the potential influence on intestinal absorption and bioavailability.
PB  - Wiley, Hoboken
T2  - Journal of Pharmaceutical Sciences
T1  - Protolytic Equilibria of Sartans in Micellar Solutions of Differently Charged Surfactants
VL  - 105
IS  - 8
SP  - 2444
EP  - 2452
DO  - 10.1016/j.xphs.2016.06.007
ER  - 
@article{
author = "Grujić, Maja and Popović, Marija and Popović, Gordana and Nikolić, Katarina and Agbaba, Danica",
year = "2016",
abstract = "Protolytic equilibria of irbesartan, losartan, and valsartan have been investigated in the presence and absence of differently charged anionic (sodium dodecyl sulfate), cationic (cetyltrimethylammonium bromide), and nonionic (4-octylphenol polyethoxylate and polyoxyethylene (23) lauryl ether) surfactants. Ionization constants were determined by potentiometric titration at a constant ionic strength (0.1 M NaCl) and temperature 25 degrees C. The effect of surfactants was estimated, based on a shift in apparent ionization constants (pK(a)(app)) determined in micellar solutions against the pK(a)(w) values in water. The anionic surfactant caused an increase in the pK(a)(app) values of sartans (up to 1.72 pK units), while the cationic surfactant had an opposite effect and caused a reduction in pK(a)(app) values (up to -1.44 pK units). These results point out to the fact that the ionizable groups of sartans are involved in electrostatic interactions with the charged surface of the ionic micelles. Shift in the pKa app values in the presence of nonionic surfactants (from -0.86 to +1.30) is a consequence of the interactions of drugs with the hydrophilic palisade layer. Significant changes in the distribution profiles of the equilibrium forms (from -44% to +80%) are observed at the biopharmaceutically important pH 4.5 value and can be considered in terms of the potential influence on intestinal absorption and bioavailability.",
publisher = "Wiley, Hoboken",
journal = "Journal of Pharmaceutical Sciences",
title = "Protolytic Equilibria of Sartans in Micellar Solutions of Differently Charged Surfactants",
volume = "105",
number = "8",
pages = "2444-2452",
doi = "10.1016/j.xphs.2016.06.007"
}
Grujić, M., Popović, M., Popović, G., Nikolić, K.,& Agbaba, D.. (2016). Protolytic Equilibria of Sartans in Micellar Solutions of Differently Charged Surfactants. in Journal of Pharmaceutical Sciences
Wiley, Hoboken., 105(8), 2444-2452.
https://doi.org/10.1016/j.xphs.2016.06.007
Grujić M, Popović M, Popović G, Nikolić K, Agbaba D. Protolytic Equilibria of Sartans in Micellar Solutions of Differently Charged Surfactants. in Journal of Pharmaceutical Sciences. 2016;105(8):2444-2452.
doi:10.1016/j.xphs.2016.06.007 .
Grujić, Maja, Popović, Marija, Popović, Gordana, Nikolić, Katarina, Agbaba, Danica, "Protolytic Equilibria of Sartans in Micellar Solutions of Differently Charged Surfactants" in Journal of Pharmaceutical Sciences, 105, no. 8 (2016):2444-2452,
https://doi.org/10.1016/j.xphs.2016.06.007 . .

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