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Correlation between structure, retention and activity of cholic acid derived cis-trans isomeric bis-steroidal tetraoxanes

Authorized Users Only
2011
Authors
Šegan, Sandra
Andrić, Filip
Radoičić, Aleksandra D.
Opsenica, Dejan
Šolaja, Bogdan
Zlatović, Mario
Milojković-Opsenica, Dušanka
Article (Published version)
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Abstract
Both quantitative structure-retention (QSRR) and quantitative structure-activity relationship (QSAR) studies have been performed to correlate the molecular characteristics of seven pairs of cis-trans isomeric bis-steroidal tetraoxanes with their reversed-phase thin-layer chromatography (RPTLC) retention as well as with their antiproliferative activity. 2D and 3D molecular descriptors as whole molecule representations together with retention parameters as well as with biological activity data were subjected to the multivariate statistical analysis (principal component analysis - PCA and hierarchical cluster analysis - HCA) in order to determine the most influential factors governing the retention and activity against human cervix carcinoma (HeLa) and human malignant melanoma (Fem-X) cell lines. Both QSRR and QSAR models were built by means of the partial least-squares (PLS) statistical method. It was found that hydrogen bond donating (HBD), hydrogen bond accepting (HBAcc), hydrophilic s...urface percentage (%HS) and hydrophilic-lipophilic balance (HLB) exhibit the strongest influence on retention. The most prominent factors affecting antiproliferative activity of the investigated substances are those relating to the size and shape of a molecule such as: connectivity indices, refractivity (Ref), surface area (SA), molecular volume and weight, polarizability (Pol) and those regarding the ability of hydrogen bonding (HB).

Keywords:
Bis-steroidal tetraoxanes / Cholic acid derivatives / Quantitative structure-activity relationship (QSAR) / Quantitative structure-retention relationship (QSRR) / Reversed-phase thin-layer chromatography
Source:
Journal of Separation Science, 2011, 34, 19, 2659-2667
Publisher:
  • Wiley-V C H Verlag Gmbh, Weinheim
Funding / projects:
  • The synthesis of aminoquinoline-based antimalarials and botulinum neurotoxin A inhibitors (RS-172008)

DOI: 10.1002/jssc.201100185

ISSN: 1615-9306

PubMed: 21805630

WoS: 000296141200014

Scopus: 2-s2.0-80053203988
[ Google Scholar ]
21
16
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/798
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Šegan, Sandra
AU  - Andrić, Filip
AU  - Radoičić, Aleksandra D.
AU  - Opsenica, Dejan
AU  - Šolaja, Bogdan
AU  - Zlatović, Mario
AU  - Milojković-Opsenica, Dušanka
PY  - 2011
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/798
AB  - Both quantitative structure-retention (QSRR) and quantitative structure-activity relationship (QSAR) studies have been performed to correlate the molecular characteristics of seven pairs of cis-trans isomeric bis-steroidal tetraoxanes with their reversed-phase thin-layer chromatography (RPTLC) retention as well as with their antiproliferative activity. 2D and 3D molecular descriptors as whole molecule representations together with retention parameters as well as with biological activity data were subjected to the multivariate statistical analysis (principal component analysis - PCA and hierarchical cluster analysis - HCA) in order to determine the most influential factors governing the retention and activity against human cervix carcinoma (HeLa) and human malignant melanoma (Fem-X) cell lines. Both QSRR and QSAR models were built by means of the partial least-squares (PLS) statistical method. It was found that hydrogen bond donating (HBD), hydrogen bond accepting (HBAcc), hydrophilic surface percentage (%HS) and hydrophilic-lipophilic balance (HLB) exhibit the strongest influence on retention. The most prominent factors affecting antiproliferative activity of the investigated substances are those relating to the size and shape of a molecule such as: connectivity indices, refractivity (Ref), surface area (SA), molecular volume and weight, polarizability (Pol) and those regarding the ability of hydrogen bonding (HB).
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Journal of Separation Science
T1  - Correlation between structure, retention and activity of cholic acid derived cis-trans isomeric bis-steroidal tetraoxanes
VL  - 34
IS  - 19
SP  - 2659
EP  - 2667
DO  - 10.1002/jssc.201100185
ER  - 
@article{
author = "Šegan, Sandra and Andrić, Filip and Radoičić, Aleksandra D. and Opsenica, Dejan and Šolaja, Bogdan and Zlatović, Mario and Milojković-Opsenica, Dušanka",
year = "2011",
abstract = "Both quantitative structure-retention (QSRR) and quantitative structure-activity relationship (QSAR) studies have been performed to correlate the molecular characteristics of seven pairs of cis-trans isomeric bis-steroidal tetraoxanes with their reversed-phase thin-layer chromatography (RPTLC) retention as well as with their antiproliferative activity. 2D and 3D molecular descriptors as whole molecule representations together with retention parameters as well as with biological activity data were subjected to the multivariate statistical analysis (principal component analysis - PCA and hierarchical cluster analysis - HCA) in order to determine the most influential factors governing the retention and activity against human cervix carcinoma (HeLa) and human malignant melanoma (Fem-X) cell lines. Both QSRR and QSAR models were built by means of the partial least-squares (PLS) statistical method. It was found that hydrogen bond donating (HBD), hydrogen bond accepting (HBAcc), hydrophilic surface percentage (%HS) and hydrophilic-lipophilic balance (HLB) exhibit the strongest influence on retention. The most prominent factors affecting antiproliferative activity of the investigated substances are those relating to the size and shape of a molecule such as: connectivity indices, refractivity (Ref), surface area (SA), molecular volume and weight, polarizability (Pol) and those regarding the ability of hydrogen bonding (HB).",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Journal of Separation Science",
title = "Correlation between structure, retention and activity of cholic acid derived cis-trans isomeric bis-steroidal tetraoxanes",
volume = "34",
number = "19",
pages = "2659-2667",
doi = "10.1002/jssc.201100185"
}
Šegan, S., Andrić, F., Radoičić, A. D., Opsenica, D., Šolaja, B., Zlatović, M.,& Milojković-Opsenica, D.. (2011). Correlation between structure, retention and activity of cholic acid derived cis-trans isomeric bis-steroidal tetraoxanes. in Journal of Separation Science
Wiley-V C H Verlag Gmbh, Weinheim., 34(19), 2659-2667.
https://doi.org/10.1002/jssc.201100185
Šegan S, Andrić F, Radoičić AD, Opsenica D, Šolaja B, Zlatović M, Milojković-Opsenica D. Correlation between structure, retention and activity of cholic acid derived cis-trans isomeric bis-steroidal tetraoxanes. in Journal of Separation Science. 2011;34(19):2659-2667.
doi:10.1002/jssc.201100185 .
Šegan, Sandra, Andrić, Filip, Radoičić, Aleksandra D., Opsenica, Dejan, Šolaja, Bogdan, Zlatović, Mario, Milojković-Opsenica, Dušanka, "Correlation between structure, retention and activity of cholic acid derived cis-trans isomeric bis-steroidal tetraoxanes" in Journal of Separation Science, 34, no. 19 (2011):2659-2667,
https://doi.org/10.1002/jssc.201100185 . .

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