A theoretical study on ionization of sartans in aqueous media and on interactions with surfactant micelles
Само за регистроване кориснике
2018
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
The ionization order of sartans in aqueous media and possible way of interactions between their equilibrium forms and surfactant micelles have been theoretically investigated. The examined sartans are ampholytes (irbesartan and losartan) and a diacid (valsartan) with the close values of ionization constants. In order to get a better insight in the overlapped protolytic equilibria of sartans and to predict an affinity of the equilibrium forms interacting with micelles as biomembrane mimetic systems, the theoretical study was performed. Energy calculation of the optimized structures of the equilibrium forms was performed at the B3LYP/6-31G (d,p) level of the Density Functional Theory (DFT). The results of the theoretical study helped to assign the experimentally determined pK(a) values to the corresponding ionizable centers and confirmed that in all examined compounds, the higher pK(a) values can be attributed to ionization of tetrazole. The molecular descriptor values showed that sartan...s interact predominantly with the micelle surfaces. The equilibrium forms of ampholytes demonstrate higher affinity to the micelles, as compared to the forms of the diprotic acid. Additionally, it was shown that the uncharged molecular forms of ampholytes are more lipophylic then their zwitterionic forms.
Кључне речи:
AT(1) receptor antagonists / pK(a) / Ampholytes / DFT study / Molecular descriptors / B3LYP methodИзвор:
Journal of Molecular Graphics & Modelling, 2018, 82, 67-73Издавач:
- Elsevier Science Inc, New York
Финансирање / пројекти:
- Синтеза, квантитативни однос између структуре и дејства, физичко-хемијска карактеризација и анализа фармаколошки активних супстанци (RS-MESTD-Basic Research (BR or ON)-172033)
DOI: 10.1016/j.jmgm.2018.04.008
ISSN: 1093-3263
PubMed: 29704812
WoS: 000433643100007
Scopus: 2-s2.0-85046074875
Институција/група
PharmacyTY - JOUR AU - Popović-Nikolić, Marija AU - Popović, Gordana AU - Grujić, Maja AU - Nikolić, Katarina AU - Agbaba, Danica PY - 2018 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3167 AB - The ionization order of sartans in aqueous media and possible way of interactions between their equilibrium forms and surfactant micelles have been theoretically investigated. The examined sartans are ampholytes (irbesartan and losartan) and a diacid (valsartan) with the close values of ionization constants. In order to get a better insight in the overlapped protolytic equilibria of sartans and to predict an affinity of the equilibrium forms interacting with micelles as biomembrane mimetic systems, the theoretical study was performed. Energy calculation of the optimized structures of the equilibrium forms was performed at the B3LYP/6-31G (d,p) level of the Density Functional Theory (DFT). The results of the theoretical study helped to assign the experimentally determined pK(a) values to the corresponding ionizable centers and confirmed that in all examined compounds, the higher pK(a) values can be attributed to ionization of tetrazole. The molecular descriptor values showed that sartans interact predominantly with the micelle surfaces. The equilibrium forms of ampholytes demonstrate higher affinity to the micelles, as compared to the forms of the diprotic acid. Additionally, it was shown that the uncharged molecular forms of ampholytes are more lipophylic then their zwitterionic forms. PB - Elsevier Science Inc, New York T2 - Journal of Molecular Graphics & Modelling T1 - A theoretical study on ionization of sartans in aqueous media and on interactions with surfactant micelles VL - 82 SP - 67 EP - 73 DO - 10.1016/j.jmgm.2018.04.008 ER -
@article{ author = "Popović-Nikolić, Marija and Popović, Gordana and Grujić, Maja and Nikolić, Katarina and Agbaba, Danica", year = "2018", abstract = "The ionization order of sartans in aqueous media and possible way of interactions between their equilibrium forms and surfactant micelles have been theoretically investigated. The examined sartans are ampholytes (irbesartan and losartan) and a diacid (valsartan) with the close values of ionization constants. In order to get a better insight in the overlapped protolytic equilibria of sartans and to predict an affinity of the equilibrium forms interacting with micelles as biomembrane mimetic systems, the theoretical study was performed. Energy calculation of the optimized structures of the equilibrium forms was performed at the B3LYP/6-31G (d,p) level of the Density Functional Theory (DFT). The results of the theoretical study helped to assign the experimentally determined pK(a) values to the corresponding ionizable centers and confirmed that in all examined compounds, the higher pK(a) values can be attributed to ionization of tetrazole. The molecular descriptor values showed that sartans interact predominantly with the micelle surfaces. The equilibrium forms of ampholytes demonstrate higher affinity to the micelles, as compared to the forms of the diprotic acid. Additionally, it was shown that the uncharged molecular forms of ampholytes are more lipophylic then their zwitterionic forms.", publisher = "Elsevier Science Inc, New York", journal = "Journal of Molecular Graphics & Modelling", title = "A theoretical study on ionization of sartans in aqueous media and on interactions with surfactant micelles", volume = "82", pages = "67-73", doi = "10.1016/j.jmgm.2018.04.008" }
Popović-Nikolić, M., Popović, G., Grujić, M., Nikolić, K.,& Agbaba, D.. (2018). A theoretical study on ionization of sartans in aqueous media and on interactions with surfactant micelles. in Journal of Molecular Graphics & Modelling Elsevier Science Inc, New York., 82, 67-73. https://doi.org/10.1016/j.jmgm.2018.04.008
Popović-Nikolić M, Popović G, Grujić M, Nikolić K, Agbaba D. A theoretical study on ionization of sartans in aqueous media and on interactions with surfactant micelles. in Journal of Molecular Graphics & Modelling. 2018;82:67-73. doi:10.1016/j.jmgm.2018.04.008 .
Popović-Nikolić, Marija, Popović, Gordana, Grujić, Maja, Nikolić, Katarina, Agbaba, Danica, "A theoretical study on ionization of sartans in aqueous media and on interactions with surfactant micelles" in Journal of Molecular Graphics & Modelling, 82 (2018):67-73, https://doi.org/10.1016/j.jmgm.2018.04.008 . .