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Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy) phenylpiperazine dopamine D2 ligands

Authorized Users Only
2019
Authors
Šegan, Sandra
Penjišević, Jelena
Šukalović, Vladimir
Andrić, Deana
Milojković-Opsenica, Dušanka
Kostić Rajačić, Slađana
Article (Published version)
,
Elsevier
Metadata
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Abstract
Reversed-phase thin-layer chromatography and micellar thin-layer chromatography were used in order to investigate retention behaviour and to determine lipophilicity of series of 2(methoxy)phenylpiperazine dopamine D2 ligands with different size, shape and rigidity. The retention mechanism was discussed. The lipophilicity parameters obtained in conventional reversed-phase systems expressed as RM0 and C0, as well as RM values determined in microemulsion reversed-phase systems were correlated with in silico determined lipophilicity values. In silico pharmacokinetic properties of 2-(methoxy)phenylpiperazine dopamine D2 ligands revealed the importance of experimentally determined lipophilicity values besides the molecular weight, on the blood–brain barrier permeability process. Also, the experimentally determined lipophilicity was found as a very important factor in plasma protein binding process of 2-(methoxy)phenylpiperazine dopamine D2 ligands. Besides, the Lipinski's rule of five indic...ates that examined ligands satisfy the criterion of drug-like molecules. The principal component analysis was performed on the experimentally determined and calculated lipophilicity values as well on the molecular descriptors which describe the pharmacokinetic properties in order to provide basic insights into similarities among the studied ligands.

Keywords:
2-(Methoxy)phenylpiperazine dopamine D2 ligands / Reversed-phase thin-layer chromatography (RPTLC) / Microemulsion thin-layer chromatography (METLC) / Lipophilicity / Blood–brain barrier (BBB) permeability / Protein binding capacity (QPlogKhsa)
Source:
Journal of Chromatography B, 2019, 1124, 146-153
Publisher:
  • Elsevier
Funding / projects:
  • The synthesis of aminoquinoline-based antimalarials and botulinum neurotoxin A inhibitors (RS-172008)
  • Structure-activity relationship of newly synthesized biological active compound (RS-172032)

DOI: 10.1016/j.jchromb.2019.06.006

ISSN: 1570-0232

WoS: 000477685600015

Scopus: 2-s2.0-85067083868
[ Google Scholar ]
5
3
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/2991
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Šegan, Sandra
AU  - Penjišević, Jelena
AU  - Šukalović, Vladimir
AU  - Andrić, Deana
AU  - Milojković-Opsenica, Dušanka
AU  - Kostić Rajačić, Slađana
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2991
AB  - Reversed-phase thin-layer chromatography and micellar thin-layer chromatography were used in order to investigate retention behaviour and to determine lipophilicity of series of 2(methoxy)phenylpiperazine dopamine D2 ligands with different size, shape and rigidity. The retention mechanism was discussed. The lipophilicity parameters obtained in conventional reversed-phase systems expressed as RM0 and C0, as well as RM values
determined in microemulsion reversed-phase systems were correlated with in silico determined lipophilicity values. In silico pharmacokinetic properties of 2-(methoxy)phenylpiperazine dopamine D2 ligands revealed the importance of experimentally determined lipophilicity values besides the molecular weight, on the blood–brain barrier permeability process. Also, the experimentally determined lipophilicity was found as a very important factor in plasma protein binding process of 2-(methoxy)phenylpiperazine dopamine D2 ligands. Besides, the Lipinski's rule of five indicates that examined ligands satisfy the criterion of drug-like molecules. The principal component analysis was performed on the experimentally determined and calculated lipophilicity values as well on the molecular descriptors which describe the pharmacokinetic properties in order to provide basic insights into similarities among the studied ligands.
PB  - Elsevier
T2  - Journal of Chromatography B
T1  - Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy) phenylpiperazine dopamine D2 ligands
VL  - 1124
SP  - 146
EP  - 153
DO  - 10.1016/j.jchromb.2019.06.006
ER  - 
@article{
author = "Šegan, Sandra and Penjišević, Jelena and Šukalović, Vladimir and Andrić, Deana and Milojković-Opsenica, Dušanka and Kostić Rajačić, Slađana",
year = "2019",
abstract = "Reversed-phase thin-layer chromatography and micellar thin-layer chromatography were used in order to investigate retention behaviour and to determine lipophilicity of series of 2(methoxy)phenylpiperazine dopamine D2 ligands with different size, shape and rigidity. The retention mechanism was discussed. The lipophilicity parameters obtained in conventional reversed-phase systems expressed as RM0 and C0, as well as RM values
determined in microemulsion reversed-phase systems were correlated with in silico determined lipophilicity values. In silico pharmacokinetic properties of 2-(methoxy)phenylpiperazine dopamine D2 ligands revealed the importance of experimentally determined lipophilicity values besides the molecular weight, on the blood–brain barrier permeability process. Also, the experimentally determined lipophilicity was found as a very important factor in plasma protein binding process of 2-(methoxy)phenylpiperazine dopamine D2 ligands. Besides, the Lipinski's rule of five indicates that examined ligands satisfy the criterion of drug-like molecules. The principal component analysis was performed on the experimentally determined and calculated lipophilicity values as well on the molecular descriptors which describe the pharmacokinetic properties in order to provide basic insights into similarities among the studied ligands.",
publisher = "Elsevier",
journal = "Journal of Chromatography B",
title = "Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy) phenylpiperazine dopamine D2 ligands",
volume = "1124",
pages = "146-153",
doi = "10.1016/j.jchromb.2019.06.006"
}
Šegan, S., Penjišević, J., Šukalović, V., Andrić, D., Milojković-Opsenica, D.,& Kostić Rajačić, S.. (2019). Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy) phenylpiperazine dopamine D2 ligands. in Journal of Chromatography B
Elsevier., 1124, 146-153.
https://doi.org/10.1016/j.jchromb.2019.06.006
Šegan S, Penjišević J, Šukalović V, Andrić D, Milojković-Opsenica D, Kostić Rajačić S. Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy) phenylpiperazine dopamine D2 ligands. in Journal of Chromatography B. 2019;1124:146-153.
doi:10.1016/j.jchromb.2019.06.006 .
Šegan, Sandra, Penjišević, Jelena, Šukalović, Vladimir, Andrić, Deana, Milojković-Opsenica, Dušanka, Kostić Rajačić, Slađana, "Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy) phenylpiperazine dopamine D2 ligands" in Journal of Chromatography B, 1124 (2019):146-153,
https://doi.org/10.1016/j.jchromb.2019.06.006 . .

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