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Evaluation of Angiotensin-Converting Enzyme Inhibitor's Absorption with Retention Data of Micellar Thin-Layer Chromatography and Suitable Molecular Descriptor

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2015
2352.pdf (319.2Kb)
Authors
Odović, Jadranka
Marković, Bojan
Vladimirov, Sote
Karljiković-Rajić, Katarina
Article (Published version)
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Abstract
Twelve angiotensin-converting enzyme (ACE) inhibitors were studied to evaluate correlation between their absorption (ABS) data available in the literature (22-96%) and hydrophobicity parameters (k(m) and P-m/w) obtained in micellar thin-layer chromatography (MTLC) using Brij 35. The theoretical considerations showed that the geometric molecular descriptor-volume value (Vol) should be considered as an independent variable simultaneously with calculated hydrophobicity parameters in multiple linear regression analysis to obtain reliable correlation between ACE inhibitor's absorption and lipophilicity (calculated KOWWINlog P) and that captopril should be excluded from further correlations. The results of MTLC confirmed that between the two hydrophobicity parameters k(m) and P-m/w, for absorption prediction of 11 ACE inhibitors, the micelle-water partition coefficient P-m/w provided higher correlation (R-2 = 0.756), while for the k(m) parameter R-2 = 0.612 was obtained. The micelle-water pa...rtition coefficient Pm/w could be considered as analogous to hydrophobicity parameter C-0 from reversed-phase thin-layer chromatography. Dissimilar retention behavior of lisinopril indicated its lowest non-polar interaction with micelle, because of its di-acid form. The proposed model which included ACE inhibitors on the opposite site of lipophilicity-lisinopril and fosinopril (KOWWINlog P = -0.96 and KOWWINlog P = 6.61, respectively), both with similar absorption values (25 and 36%, respectively), could indicate that absorption of investigated compounds occurs via two different mechanisms: active and passive transport.

Source:
Journal of Chromatographic Science, 2015, 53, 10, 1780-1785
Publisher:
  • Oxford Univ Press Inc, Cary
Funding / projects:
  • Development of molecules with antiinflammatory and cardioprotective activity: structural modifications, modelling, physicochemical characterization and formulation investigations (RS-172041)

DOI: 10.1093/chromsci/bmv091

ISSN: 0021-9665

PubMed: 26123666

WoS: 000368427200022

Scopus: 2-s2.0-84947711105
[ Google Scholar ]
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2
URI
https://farfar.pharmacy.bg.ac.rs/handle/123456789/2354
Collections
  • Radovi istraživača / Researchers’ publications
Institution/Community
Pharmacy
TY  - JOUR
AU  - Odović, Jadranka
AU  - Marković, Bojan
AU  - Vladimirov, Sote
AU  - Karljiković-Rajić, Katarina
PY  - 2015
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2354
AB  - Twelve angiotensin-converting enzyme (ACE) inhibitors were studied to evaluate correlation between their absorption (ABS) data available in the literature (22-96%) and hydrophobicity parameters (k(m) and P-m/w) obtained in micellar thin-layer chromatography (MTLC) using Brij 35. The theoretical considerations showed that the geometric molecular descriptor-volume value (Vol) should be considered as an independent variable simultaneously with calculated hydrophobicity parameters in multiple linear regression analysis to obtain reliable correlation between ACE inhibitor's absorption and lipophilicity (calculated KOWWINlog P) and that captopril should be excluded from further correlations. The results of MTLC confirmed that between the two hydrophobicity parameters k(m) and P-m/w, for absorption prediction of 11 ACE inhibitors, the micelle-water partition coefficient P-m/w provided higher correlation (R-2 = 0.756), while for the k(m) parameter R-2 = 0.612 was obtained. The micelle-water partition coefficient Pm/w could be considered as analogous to hydrophobicity parameter C-0 from reversed-phase thin-layer chromatography. Dissimilar retention behavior of lisinopril indicated its lowest non-polar interaction with micelle, because of its di-acid form. The proposed model which included ACE inhibitors on the opposite site of lipophilicity-lisinopril and fosinopril (KOWWINlog P = -0.96 and KOWWINlog P = 6.61, respectively), both with similar absorption values (25 and 36%, respectively), could indicate that absorption of investigated compounds occurs via two different mechanisms: active and passive transport.
PB  - Oxford Univ Press Inc, Cary
T2  - Journal of Chromatographic Science
T1  - Evaluation of Angiotensin-Converting Enzyme Inhibitor's Absorption with Retention Data of Micellar Thin-Layer Chromatography and Suitable Molecular Descriptor
VL  - 53
IS  - 10
SP  - 1780
EP  - 1785
DO  - 10.1093/chromsci/bmv091
ER  - 
@article{
author = "Odović, Jadranka and Marković, Bojan and Vladimirov, Sote and Karljiković-Rajić, Katarina",
year = "2015",
abstract = "Twelve angiotensin-converting enzyme (ACE) inhibitors were studied to evaluate correlation between their absorption (ABS) data available in the literature (22-96%) and hydrophobicity parameters (k(m) and P-m/w) obtained in micellar thin-layer chromatography (MTLC) using Brij 35. The theoretical considerations showed that the geometric molecular descriptor-volume value (Vol) should be considered as an independent variable simultaneously with calculated hydrophobicity parameters in multiple linear regression analysis to obtain reliable correlation between ACE inhibitor's absorption and lipophilicity (calculated KOWWINlog P) and that captopril should be excluded from further correlations. The results of MTLC confirmed that between the two hydrophobicity parameters k(m) and P-m/w, for absorption prediction of 11 ACE inhibitors, the micelle-water partition coefficient P-m/w provided higher correlation (R-2 = 0.756), while for the k(m) parameter R-2 = 0.612 was obtained. The micelle-water partition coefficient Pm/w could be considered as analogous to hydrophobicity parameter C-0 from reversed-phase thin-layer chromatography. Dissimilar retention behavior of lisinopril indicated its lowest non-polar interaction with micelle, because of its di-acid form. The proposed model which included ACE inhibitors on the opposite site of lipophilicity-lisinopril and fosinopril (KOWWINlog P = -0.96 and KOWWINlog P = 6.61, respectively), both with similar absorption values (25 and 36%, respectively), could indicate that absorption of investigated compounds occurs via two different mechanisms: active and passive transport.",
publisher = "Oxford Univ Press Inc, Cary",
journal = "Journal of Chromatographic Science",
title = "Evaluation of Angiotensin-Converting Enzyme Inhibitor's Absorption with Retention Data of Micellar Thin-Layer Chromatography and Suitable Molecular Descriptor",
volume = "53",
number = "10",
pages = "1780-1785",
doi = "10.1093/chromsci/bmv091"
}
Odović, J., Marković, B., Vladimirov, S.,& Karljiković-Rajić, K.. (2015). Evaluation of Angiotensin-Converting Enzyme Inhibitor's Absorption with Retention Data of Micellar Thin-Layer Chromatography and Suitable Molecular Descriptor. in Journal of Chromatographic Science
Oxford Univ Press Inc, Cary., 53(10), 1780-1785.
https://doi.org/10.1093/chromsci/bmv091
Odović J, Marković B, Vladimirov S, Karljiković-Rajić K. Evaluation of Angiotensin-Converting Enzyme Inhibitor's Absorption with Retention Data of Micellar Thin-Layer Chromatography and Suitable Molecular Descriptor. in Journal of Chromatographic Science. 2015;53(10):1780-1785.
doi:10.1093/chromsci/bmv091 .
Odović, Jadranka, Marković, Bojan, Vladimirov, Sote, Karljiković-Rajić, Katarina, "Evaluation of Angiotensin-Converting Enzyme Inhibitor's Absorption with Retention Data of Micellar Thin-Layer Chromatography and Suitable Molecular Descriptor" in Journal of Chromatographic Science, 53, no. 10 (2015):1780-1785,
https://doi.org/10.1093/chromsci/bmv091 . .

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