Estimation of lipophilicity and retention behavior of some alpha adrenergic and imidazoline receptor ligands using rp-tlc
Abstract
The chromatographic behavior of 16 alpha adrenergic and imidazoline receptor ligands has been studied by reversed-phase thin-layer chromatography (RP-TLC) on RP-18 and CN stationary phases. Retention constant R-M(0) was determined for all tested compounds in three different chromatographic systems: methanol-water/RP-18, tetrahydrofuran-ammonia-water/RP-18, and tetrahydrofuran-ammonia-water/CN. Good correlations between determined hydrophobic parameters R-M(0) and calculated log P values were obtained for the system tetrahydrofuran-ammonia-water on both RP-18 and CN stationary phases. Experimentally obtained R-M(0) values and computed molecular parameters of the examined compounds were further used for the quantitative structure-retention relationship (QSRR) study, in order to determine the most important properties governing retention. The QSRR modeling was performed with use of the partial least squares regression, and predictive performances of the developed QSRR models were tested b...y use of the cross-validation and external test set prediction. The created models revealed that apart from lipophilicity, constitutional descriptors, the amount of van der Waals surface area having a property P (P_VSA-like descriptors), and hydrogen bonding properties of the tested compounds were important for the retention behavior in the RP-TLC systems.
Keywords:
guanidine derivatives / imidazoline derivatives / lipophilicity / PLS / QSRR / RP-TLCSource:
Journal of Liquid Chromatography & Related Technologies, 2014, 37, 20, 2829-2845Publisher:
- Taylor & Francis Inc, Philadelphia
Funding / projects:
DOI: 10.1080/10739149.2014.906880
ISSN: 1082-6076
WoS: 000337971200003
Scopus: 2-s2.0-84903189900
Collections
Institution/Community
PharmacyTY - JOUR AU - Shenger, Musbah Salem Mohamed AU - Filipić, Slavica AU - Nikolić, Katarina AU - Agbaba, Danica PY - 2014 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2207 AB - The chromatographic behavior of 16 alpha adrenergic and imidazoline receptor ligands has been studied by reversed-phase thin-layer chromatography (RP-TLC) on RP-18 and CN stationary phases. Retention constant R-M(0) was determined for all tested compounds in three different chromatographic systems: methanol-water/RP-18, tetrahydrofuran-ammonia-water/RP-18, and tetrahydrofuran-ammonia-water/CN. Good correlations between determined hydrophobic parameters R-M(0) and calculated log P values were obtained for the system tetrahydrofuran-ammonia-water on both RP-18 and CN stationary phases. Experimentally obtained R-M(0) values and computed molecular parameters of the examined compounds were further used for the quantitative structure-retention relationship (QSRR) study, in order to determine the most important properties governing retention. The QSRR modeling was performed with use of the partial least squares regression, and predictive performances of the developed QSRR models were tested by use of the cross-validation and external test set prediction. The created models revealed that apart from lipophilicity, constitutional descriptors, the amount of van der Waals surface area having a property P (P_VSA-like descriptors), and hydrogen bonding properties of the tested compounds were important for the retention behavior in the RP-TLC systems. PB - Taylor & Francis Inc, Philadelphia T2 - Journal of Liquid Chromatography & Related Technologies T1 - Estimation of lipophilicity and retention behavior of some alpha adrenergic and imidazoline receptor ligands using rp-tlc VL - 37 IS - 20 SP - 2829 EP - 2845 DO - 10.1080/10739149.2014.906880 ER -
@article{ author = "Shenger, Musbah Salem Mohamed and Filipić, Slavica and Nikolić, Katarina and Agbaba, Danica", year = "2014", abstract = "The chromatographic behavior of 16 alpha adrenergic and imidazoline receptor ligands has been studied by reversed-phase thin-layer chromatography (RP-TLC) on RP-18 and CN stationary phases. Retention constant R-M(0) was determined for all tested compounds in three different chromatographic systems: methanol-water/RP-18, tetrahydrofuran-ammonia-water/RP-18, and tetrahydrofuran-ammonia-water/CN. Good correlations between determined hydrophobic parameters R-M(0) and calculated log P values were obtained for the system tetrahydrofuran-ammonia-water on both RP-18 and CN stationary phases. Experimentally obtained R-M(0) values and computed molecular parameters of the examined compounds were further used for the quantitative structure-retention relationship (QSRR) study, in order to determine the most important properties governing retention. The QSRR modeling was performed with use of the partial least squares regression, and predictive performances of the developed QSRR models were tested by use of the cross-validation and external test set prediction. The created models revealed that apart from lipophilicity, constitutional descriptors, the amount of van der Waals surface area having a property P (P_VSA-like descriptors), and hydrogen bonding properties of the tested compounds were important for the retention behavior in the RP-TLC systems.", publisher = "Taylor & Francis Inc, Philadelphia", journal = "Journal of Liquid Chromatography & Related Technologies", title = "Estimation of lipophilicity and retention behavior of some alpha adrenergic and imidazoline receptor ligands using rp-tlc", volume = "37", number = "20", pages = "2829-2845", doi = "10.1080/10739149.2014.906880" }
Shenger, M. S. M., Filipić, S., Nikolić, K.,& Agbaba, D.. (2014). Estimation of lipophilicity and retention behavior of some alpha adrenergic and imidazoline receptor ligands using rp-tlc. in Journal of Liquid Chromatography & Related Technologies Taylor & Francis Inc, Philadelphia., 37(20), 2829-2845. https://doi.org/10.1080/10739149.2014.906880
Shenger MSM, Filipić S, Nikolić K, Agbaba D. Estimation of lipophilicity and retention behavior of some alpha adrenergic and imidazoline receptor ligands using rp-tlc. in Journal of Liquid Chromatography & Related Technologies. 2014;37(20):2829-2845. doi:10.1080/10739149.2014.906880 .
Shenger, Musbah Salem Mohamed, Filipić, Slavica, Nikolić, Katarina, Agbaba, Danica, "Estimation of lipophilicity and retention behavior of some alpha adrenergic and imidazoline receptor ligands using rp-tlc" in Journal of Liquid Chromatography & Related Technologies, 37, no. 20 (2014):2829-2845, https://doi.org/10.1080/10739149.2014.906880 . .