Protolytic equilibria of ACE inhibitors in micellar solution of nonionic surfactant Brij 35
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2023
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The acid–base equilibria of six ACE inhibitors (ACEIs), captopril, cilazapril, enalapril, lisinopril, quinapril, and rami-
pril, were investigated in the presence of micelles of nonionic surfactant Brij 35. The pKa values were potentiometrically
determined at 25 °C and at a constant ionic strength (0.1 M NaCl). The obtained potentiometric data were evaluated in the
computer program Hyperquad. On the basis of the shift in the pKa values (ΔpKa ) determined in micellar media in relation
to the pKa values previously determined in “pure” water, the effect of Brij 35 micelles on ACEIs ionization was estimated.
The presence of nonionic Brij 35 micelles caused a shift in the pKa values of all ionizable groups of the investigated ACEIs
(ΔpKa from − 3.44 to + 1.9) while shifting the protolytic equilibria of both acidic and basic groups toward the molecular
form. The Brij 35 micelles expressed the most pronounced effect on the ionization of captopril among the investigated ACEIs
and stron...ger effect on the ionization of amino than on the ionization of carboxyl groups. The obtained results suggest that
ionizable functional groups of ACEIs are involved in interactions with palisade layer of nonionic Brij 35 micelles, which
potentially can be considered in physiological conditions. Distribution diagrams of the investigated ACEIs equilibrium
forms as a function of pH indicate that the change in distribution is most strongly expressed in pH range 4–8, which includes
biopharmaceutically important pH values.
Ključne reči:
Drug research / Surfactants / Physicochemical properties / Acid–base equilibria / Micelles / BiomimeticsIzvor:
Monatshefte für Chemie - Chemical Monthly, 2023, 154, 615-624Izdavač:
- Springer
Finansiranje / projekti:
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200161 (Univerzitet u Beogradu, Farmaceutski fakultet) (RS-MESTD-inst-2020-200161)
DOI: 10.1007/s00706-023-03059-2
ISSN: 0026-9247
PubMed: 37193115
WoS: 000974814100001
Scopus: 2-s2.0-85153109244
Institucija/grupa
PharmacyTY - JOUR AU - Popović-Nikolić, Marija AU - Nikolić, Katarina AU - Popović, Gordana PY - 2023 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4687 AB - The acid–base equilibria of six ACE inhibitors (ACEIs), captopril, cilazapril, enalapril, lisinopril, quinapril, and rami- pril, were investigated in the presence of micelles of nonionic surfactant Brij 35. The pKa values were potentiometrically determined at 25 °C and at a constant ionic strength (0.1 M NaCl). The obtained potentiometric data were evaluated in the computer program Hyperquad. On the basis of the shift in the pKa values (ΔpKa ) determined in micellar media in relation to the pKa values previously determined in “pure” water, the effect of Brij 35 micelles on ACEIs ionization was estimated. The presence of nonionic Brij 35 micelles caused a shift in the pKa values of all ionizable groups of the investigated ACEIs (ΔpKa from − 3.44 to + 1.9) while shifting the protolytic equilibria of both acidic and basic groups toward the molecular form. The Brij 35 micelles expressed the most pronounced effect on the ionization of captopril among the investigated ACEIs and stronger effect on the ionization of amino than on the ionization of carboxyl groups. The obtained results suggest that ionizable functional groups of ACEIs are involved in interactions with palisade layer of nonionic Brij 35 micelles, which potentially can be considered in physiological conditions. Distribution diagrams of the investigated ACEIs equilibrium forms as a function of pH indicate that the change in distribution is most strongly expressed in pH range 4–8, which includes biopharmaceutically important pH values. PB - Springer T2 - Monatshefte für Chemie - Chemical Monthly T1 - Protolytic equilibria of ACE inhibitors in micellar solution of nonionic surfactant Brij 35 VL - 154 SP - 615 EP - 624 DO - 10.1007/s00706-023-03059-2 ER -
@article{ author = "Popović-Nikolić, Marija and Nikolić, Katarina and Popović, Gordana", year = "2023", abstract = "The acid–base equilibria of six ACE inhibitors (ACEIs), captopril, cilazapril, enalapril, lisinopril, quinapril, and rami- pril, were investigated in the presence of micelles of nonionic surfactant Brij 35. The pKa values were potentiometrically determined at 25 °C and at a constant ionic strength (0.1 M NaCl). The obtained potentiometric data were evaluated in the computer program Hyperquad. On the basis of the shift in the pKa values (ΔpKa ) determined in micellar media in relation to the pKa values previously determined in “pure” water, the effect of Brij 35 micelles on ACEIs ionization was estimated. The presence of nonionic Brij 35 micelles caused a shift in the pKa values of all ionizable groups of the investigated ACEIs (ΔpKa from − 3.44 to + 1.9) while shifting the protolytic equilibria of both acidic and basic groups toward the molecular form. The Brij 35 micelles expressed the most pronounced effect on the ionization of captopril among the investigated ACEIs and stronger effect on the ionization of amino than on the ionization of carboxyl groups. The obtained results suggest that ionizable functional groups of ACEIs are involved in interactions with palisade layer of nonionic Brij 35 micelles, which potentially can be considered in physiological conditions. Distribution diagrams of the investigated ACEIs equilibrium forms as a function of pH indicate that the change in distribution is most strongly expressed in pH range 4–8, which includes biopharmaceutically important pH values.", publisher = "Springer", journal = "Monatshefte für Chemie - Chemical Monthly", title = "Protolytic equilibria of ACE inhibitors in micellar solution of nonionic surfactant Brij 35", volume = "154", pages = "615-624", doi = "10.1007/s00706-023-03059-2" }
Popović-Nikolić, M., Nikolić, K.,& Popović, G.. (2023). Protolytic equilibria of ACE inhibitors in micellar solution of nonionic surfactant Brij 35. in Monatshefte für Chemie - Chemical Monthly Springer., 154, 615-624. https://doi.org/10.1007/s00706-023-03059-2
Popović-Nikolić M, Nikolić K, Popović G. Protolytic equilibria of ACE inhibitors in micellar solution of nonionic surfactant Brij 35. in Monatshefte für Chemie - Chemical Monthly. 2023;154:615-624. doi:10.1007/s00706-023-03059-2 .
Popović-Nikolić, Marija, Nikolić, Katarina, Popović, Gordana, "Protolytic equilibria of ACE inhibitors in micellar solution of nonionic surfactant Brij 35" in Monatshefte für Chemie - Chemical Monthly, 154 (2023):615-624, https://doi.org/10.1007/s00706-023-03059-2 . .