Correlation between structure, retention and activity of cholic acid derived cis-trans isomeric bis-steroidal tetraoxanes
Само за регистроване кориснике
2011
Аутори
Šegan, SandraAndrić, Filip
Radoičić, Aleksandra D.
Opsenica, Dejan
Šolaja, Bogdan
Zlatović, Mario
Milojković-Opsenica, Dušanka
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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).
Кључне речи:
Bis-steroidal tetraoxanes / Cholic acid derivatives / Quantitative structure-activity relationship (QSAR) / Quantitative structure-retention relationship (QSRR) / Reversed-phase thin-layer chromatographyИзвор:
Journal of Separation Science, 2011, 34, 19, 2659-2667Издавач:
- Wiley-V C H Verlag Gmbh, Weinheim
Финансирање / пројекти:
- Синтеза аминохинолина и њихових деривата као антималарика и инхибитора ботулинум неуротоксина А (RS-172008)
DOI: 10.1002/jssc.201100185
ISSN: 1615-9306
PubMed: 21805630
WoS: 000296141200014
Scopus: 2-s2.0-80053203988
Институција/група
IHTMTY - 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 . .