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The effects of micelles of differently charged surfactants on the equilibrium between (Z)- and (E)-diastereomers of five ACE inhibitors in aqueous media

Authorized Users Only
2015
Authors
Popović, Marija
Popović, Gordana
Filipić, Slavica
Nikolić, Katarina
Agbaba, Danica
Article (Published version)
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Abstract
The (Z)/(E) equilibria in water solutions of five ACE inhibitors (captopril, enalapril, lisinopril, perindopril, and ramipril) in presence and in absence of surfactants (anionic sodium dodecyl sulfate, cationic cetyltrimethyl ammonium bromide, and non-ionic 4-octylphenol polyethoxylate) were analyzed by reversed-phase high-performance liquid chromatography. The results showed that the (Z)/(E) equilibrium of lisinopril and captopril was the least sensitive to the effect of the examined surfactants. 4-Octylphenol polyethoxylate expressed the weakest effect on isomerization of the ACE inhibitors, while the (Z)/(E) equilibria of enalapril, ramipril, and perindopril were the most sensitive to the presence of sodium dodecyl sulfate and cetyltrimethyl ammonium bromide. In addition, the response of two structurally very close compounds, such as enalapril and ramipril to the presence of sodium dodecyl sulfate and cetyltrimethyl ammonium bromide was opposite, and these two ACE inhibitors had dif...ferent chromatographic behavior. To provide a better insight into the reasons for the differences in order of elution of (Z)- and (E)-diastereomers and the possible molecular mechanism underlying their retention, (Z)- and (E)-diastereomers of enalapril and ramipril were subjected to a theoretical study optimized at the B3LYP/6-31G (d,p) level of density functional theory. The Connolly solvent-excluded volume was taken as the most significant parameter that can be connected to differences in chromatographic behavior of the (Z)- and (E)-diastereomers of enalapril and ramipril. [GRAPHICS]

Keywords:
Isomers / Proline peptide bond / High-pressure liquid chromatography / Density functional theory
Source:
Monatshefte für Chemie Chemical Monthly, 2015, 146, 6, 913-921
Publisher:
  • Springer Wien, Wien
Funding / projects:
  • Synthesis, Quantitative Structure and Activity Relationship, Physico-Chemical Characterisation and Analysis of Pharmacologically Active Substances (RS-172033)

DOI: 10.1007/s00706-014-1400-9

ISSN: 0026-9247

WoS: 000354242200008

Scopus: 2-s2.0-84938294198
[ Google Scholar ]
2
2
URI
https://farfar.pharmacy.bg.ac.rs/handle/123456789/2394
Collections
  • Radovi istraživača / Researchers’ publications
Institution/Community
Pharmacy
TY  - JOUR
AU  - Popović, Marija
AU  - Popović, Gordana
AU  - Filipić, Slavica
AU  - Nikolić, Katarina
AU  - Agbaba, Danica
PY  - 2015
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2394
AB  - The (Z)/(E) equilibria in water solutions of five ACE inhibitors (captopril, enalapril, lisinopril, perindopril, and ramipril) in presence and in absence of surfactants (anionic sodium dodecyl sulfate, cationic cetyltrimethyl ammonium bromide, and non-ionic 4-octylphenol polyethoxylate) were analyzed by reversed-phase high-performance liquid chromatography. The results showed that the (Z)/(E) equilibrium of lisinopril and captopril was the least sensitive to the effect of the examined surfactants. 4-Octylphenol polyethoxylate expressed the weakest effect on isomerization of the ACE inhibitors, while the (Z)/(E) equilibria of enalapril, ramipril, and perindopril were the most sensitive to the presence of sodium dodecyl sulfate and cetyltrimethyl ammonium bromide. In addition, the response of two structurally very close compounds, such as enalapril and ramipril to the presence of sodium dodecyl sulfate and cetyltrimethyl ammonium bromide was opposite, and these two ACE inhibitors had different chromatographic behavior. To provide a better insight into the reasons for the differences in order of elution of (Z)- and (E)-diastereomers and the possible molecular mechanism underlying their retention, (Z)- and (E)-diastereomers of enalapril and ramipril were subjected to a theoretical study optimized at the B3LYP/6-31G (d,p) level of density functional theory. The Connolly solvent-excluded volume was taken as the most significant parameter that can be connected to differences in chromatographic behavior of the (Z)- and (E)-diastereomers of enalapril and ramipril. [GRAPHICS]
PB  - Springer Wien, Wien
T2  - Monatshefte für Chemie Chemical Monthly
T1  - The effects of micelles of differently charged surfactants on the equilibrium between (Z)- and (E)-diastereomers of five ACE inhibitors in aqueous media
VL  - 146
IS  - 6
SP  - 913
EP  - 921
DO  - 10.1007/s00706-014-1400-9
ER  - 
@article{
author = "Popović, Marija and Popović, Gordana and Filipić, Slavica and Nikolić, Katarina and Agbaba, Danica",
year = "2015",
abstract = "The (Z)/(E) equilibria in water solutions of five ACE inhibitors (captopril, enalapril, lisinopril, perindopril, and ramipril) in presence and in absence of surfactants (anionic sodium dodecyl sulfate, cationic cetyltrimethyl ammonium bromide, and non-ionic 4-octylphenol polyethoxylate) were analyzed by reversed-phase high-performance liquid chromatography. The results showed that the (Z)/(E) equilibrium of lisinopril and captopril was the least sensitive to the effect of the examined surfactants. 4-Octylphenol polyethoxylate expressed the weakest effect on isomerization of the ACE inhibitors, while the (Z)/(E) equilibria of enalapril, ramipril, and perindopril were the most sensitive to the presence of sodium dodecyl sulfate and cetyltrimethyl ammonium bromide. In addition, the response of two structurally very close compounds, such as enalapril and ramipril to the presence of sodium dodecyl sulfate and cetyltrimethyl ammonium bromide was opposite, and these two ACE inhibitors had different chromatographic behavior. To provide a better insight into the reasons for the differences in order of elution of (Z)- and (E)-diastereomers and the possible molecular mechanism underlying their retention, (Z)- and (E)-diastereomers of enalapril and ramipril were subjected to a theoretical study optimized at the B3LYP/6-31G (d,p) level of density functional theory. The Connolly solvent-excluded volume was taken as the most significant parameter that can be connected to differences in chromatographic behavior of the (Z)- and (E)-diastereomers of enalapril and ramipril. [GRAPHICS]",
publisher = "Springer Wien, Wien",
journal = "Monatshefte für Chemie Chemical Monthly",
title = "The effects of micelles of differently charged surfactants on the equilibrium between (Z)- and (E)-diastereomers of five ACE inhibitors in aqueous media",
volume = "146",
number = "6",
pages = "913-921",
doi = "10.1007/s00706-014-1400-9"
}
Popović, M., Popović, G., Filipić, S., Nikolić, K.,& Agbaba, D.. (2015). The effects of micelles of differently charged surfactants on the equilibrium between (Z)- and (E)-diastereomers of five ACE inhibitors in aqueous media. in Monatshefte für Chemie Chemical Monthly
Springer Wien, Wien., 146(6), 913-921.
https://doi.org/10.1007/s00706-014-1400-9
Popović M, Popović G, Filipić S, Nikolić K, Agbaba D. The effects of micelles of differently charged surfactants on the equilibrium between (Z)- and (E)-diastereomers of five ACE inhibitors in aqueous media. in Monatshefte für Chemie Chemical Monthly. 2015;146(6):913-921.
doi:10.1007/s00706-014-1400-9 .
Popović, Marija, Popović, Gordana, Filipić, Slavica, Nikolić, Katarina, Agbaba, Danica, "The effects of micelles of differently charged surfactants on the equilibrium between (Z)- and (E)-diastereomers of five ACE inhibitors in aqueous media" in Monatshefte für Chemie Chemical Monthly, 146, no. 6 (2015):913-921,
https://doi.org/10.1007/s00706-014-1400-9 . .

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