Quantitative structure retention/activity relationships of biologically relevant 4-amino-7-chloroquinoline based compounds
Samo za registrovane korisnike
2016
Autori
Šegan, Sandra B.Opsenica, Igor
Zlatović, Mario
Milojković-Opsenica, Dušanka
Šolaja, Bogdan A.
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
The chromatographic behaviour of series of 4-amino-7-chloroquinoline (4,7-ACQ) based compounds was studied by reversed-phase thin-layer chromatography (RPTLC) with binary mobile phases containing water and the organic modifiers, DMSO or acetone. The lipophilicity of the studied compounds was determined by extrapolation of retention parameters R-M to pure water content in mobile phase. In order to obtain some basic insight into the chromatographic behaviour and structural features of investigated compounds, PCA was performed on both chromatographic data (R-M values) and calculated 2D and 3D structural descriptors. Both QSRR and QSAR models were built by means of the partial least squares (PLS) statistical method. It was found that descriptors which encode hydrophobic (dispersive) interactions have positive influence on retention, while influence of descriptors encoding polar interactions was negative. According to the obtained PLS model for inhibition of botulinum neurotoxin serotype A ...light chain, hydrophobic interactions influence positively on the mechanism of action of the investigated 4,7-ACQ while polar interactions are less favoured. Contrary, the results of PLS modelling of activity against Plasmodium falciparum strains (W2, D6 and TM91C235) indicate that higher polarity of 4,7-ACQ contribute to their higher antimalarial activity. (C) 2016 Elsevier B.V. All rights reserved.
Ključne reči:
4-Amino-7-chloroquinoline / Reversed-phase thin-layer chromatography (RPTLC) / Lipophilicity / Quantitative structure-retention relationship (QSRR) / Quantitative structure activity relationship (QSAR)Izvor:
Journal of Chromatography B: Analytical Technologies in the Biomedical and L, 2016, 1012, 144-152Izdavač:
- Elsevier Science Bv, Amsterdam
Finansiranje / projekti:
- Sinteza aminohinolina i njihovih derivata kao antimalarika i inhibitora botulinum neurotoksina A (RS-172008)
Napomena:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3603
DOI: 10.1016/j.jchromb.2016.01.033
ISSN: 1570-0232
PubMed: 26827282
WoS: 000370882800020
Scopus: 2-s2.0-84955618060
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Šegan, Sandra B. AU - Opsenica, Igor AU - Zlatović, Mario AU - Milojković-Opsenica, Dušanka AU - Šolaja, Bogdan A. PY - 2016 UR - https://cherry.chem.bg.ac.rs/handle/123456789/2059 AB - The chromatographic behaviour of series of 4-amino-7-chloroquinoline (4,7-ACQ) based compounds was studied by reversed-phase thin-layer chromatography (RPTLC) with binary mobile phases containing water and the organic modifiers, DMSO or acetone. The lipophilicity of the studied compounds was determined by extrapolation of retention parameters R-M to pure water content in mobile phase. In order to obtain some basic insight into the chromatographic behaviour and structural features of investigated compounds, PCA was performed on both chromatographic data (R-M values) and calculated 2D and 3D structural descriptors. Both QSRR and QSAR models were built by means of the partial least squares (PLS) statistical method. It was found that descriptors which encode hydrophobic (dispersive) interactions have positive influence on retention, while influence of descriptors encoding polar interactions was negative. According to the obtained PLS model for inhibition of botulinum neurotoxin serotype A light chain, hydrophobic interactions influence positively on the mechanism of action of the investigated 4,7-ACQ while polar interactions are less favoured. Contrary, the results of PLS modelling of activity against Plasmodium falciparum strains (W2, D6 and TM91C235) indicate that higher polarity of 4,7-ACQ contribute to their higher antimalarial activity. (C) 2016 Elsevier B.V. All rights reserved. PB - Elsevier Science Bv, Amsterdam T2 - Journal of Chromatography B: Analytical Technologies in the Biomedical and L T1 - Quantitative structure retention/activity relationships of biologically relevant 4-amino-7-chloroquinoline based compounds VL - 1012 SP - 144 EP - 152 DO - 10.1016/j.jchromb.2016.01.033 ER -
@article{ author = "Šegan, Sandra B. and Opsenica, Igor and Zlatović, Mario and Milojković-Opsenica, Dušanka and Šolaja, Bogdan A.", year = "2016", abstract = "The chromatographic behaviour of series of 4-amino-7-chloroquinoline (4,7-ACQ) based compounds was studied by reversed-phase thin-layer chromatography (RPTLC) with binary mobile phases containing water and the organic modifiers, DMSO or acetone. The lipophilicity of the studied compounds was determined by extrapolation of retention parameters R-M to pure water content in mobile phase. In order to obtain some basic insight into the chromatographic behaviour and structural features of investigated compounds, PCA was performed on both chromatographic data (R-M values) and calculated 2D and 3D structural descriptors. Both QSRR and QSAR models were built by means of the partial least squares (PLS) statistical method. It was found that descriptors which encode hydrophobic (dispersive) interactions have positive influence on retention, while influence of descriptors encoding polar interactions was negative. According to the obtained PLS model for inhibition of botulinum neurotoxin serotype A light chain, hydrophobic interactions influence positively on the mechanism of action of the investigated 4,7-ACQ while polar interactions are less favoured. Contrary, the results of PLS modelling of activity against Plasmodium falciparum strains (W2, D6 and TM91C235) indicate that higher polarity of 4,7-ACQ contribute to their higher antimalarial activity. (C) 2016 Elsevier B.V. All rights reserved.", publisher = "Elsevier Science Bv, Amsterdam", journal = "Journal of Chromatography B: Analytical Technologies in the Biomedical and L", title = "Quantitative structure retention/activity relationships of biologically relevant 4-amino-7-chloroquinoline based compounds", volume = "1012", pages = "144-152", doi = "10.1016/j.jchromb.2016.01.033" }
Šegan, S. B., Opsenica, I., Zlatović, M., Milojković-Opsenica, D.,& Šolaja, B. A.. (2016). Quantitative structure retention/activity relationships of biologically relevant 4-amino-7-chloroquinoline based compounds. in Journal of Chromatography B: Analytical Technologies in the Biomedical and L Elsevier Science Bv, Amsterdam., 1012, 144-152. https://doi.org/10.1016/j.jchromb.2016.01.033
Šegan SB, Opsenica I, Zlatović M, Milojković-Opsenica D, Šolaja BA. Quantitative structure retention/activity relationships of biologically relevant 4-amino-7-chloroquinoline based compounds. in Journal of Chromatography B: Analytical Technologies in the Biomedical and L. 2016;1012:144-152. doi:10.1016/j.jchromb.2016.01.033 .
Šegan, Sandra B., Opsenica, Igor, Zlatović, Mario, Milojković-Opsenica, Dušanka, Šolaja, Bogdan A., "Quantitative structure retention/activity relationships of biologically relevant 4-amino-7-chloroquinoline based compounds" in Journal of Chromatography B: Analytical Technologies in the Biomedical and L, 1012 (2016):144-152, https://doi.org/10.1016/j.jchromb.2016.01.033 . .