Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters
Autori
Šegan, Sandra
Terzić-Jovanović, Nataša

Milojković-Opsenica, Dušanka

Trifković, Jelena

Šolaja, Bogdan

Opsenica, Dejan

Članak u časopisu (Recenzirana verzija)

Metapodaci
Prikaz svih podataka o dokumentuApstrakt
The chromatographic behavior of mixed 1,2,4,5-tetraoxanes, cholic and deoxycholic acid derivatives with distinct biological activity, was examined by high-performance thin-layer chromatography in order to correlate their structure and retention. Chromatographic systems were consisted of RP-18 or CN-silica as stationary phase, and binary mixtures of water with methanol, dioxane or acetone as mobile phase. Based on the respective retentions, the lipophilicity of the investigated compounds was determined. Multiple linear regression and partial least squares have been used to select variables that best describe the behavior of the investigated compounds in chromatographic systems and to quantify influences of most important parameters. The validation and cross-validation of the QSRR model suggest its applicability for prediction and understanding of retention of congeners. The models indicate the importance of nonpolar properties of the solutes and their ability for hydrophobic interaction...s, as well as the importance of proton donating abilities, hydrophilic and,pi interactions pointing out on that way the possible separation mechanism in the studied chromatographic systems. Observed correlations between structure and biological activity of mixed 1,2,4,5-tetraoxanes, indicate that the antimalarial activity against W2 and D6 Plasmodium falciparum strains, is governed by hydrophobic feature (measured with lipophilicity parameter), hydrophilic feature (measured with HLB, %HS, HB and HBA descriptors), and electronic feature (HOMO).
Ključne reči:
Mixed 1,2,4,5-tetraoxanes / Lipophilicity / Quantitative structure-retention relationship (QSRR) / Quantitative structure activity relationship (QSAR) / Reversed-phase thin layer chromatography (RPTLC)Izvor:
Journal of Pharmaceutical and Biomedical Analysis, 2014, 97, 178-183Izdavač:
- Elsevier
Finansiranje / projekti:
- Sinteza aminohinolina i njihovih derivata kao antimalarika i inhibitora botulinum neurotoksina A (RS-172008)
Napomena:
- This is the peer-reviewed version of the article: S. Segan, N. Terzic-Jovanovic, D. Milojkovic-Opsenica, J. Trifkovic, B. Solaja, D. Opsenica, Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters, Journal of Pharmaceutical and Biomedical Analysis (2014), http://dx.doi.org/10.1016/j.jpba.2014.04.029
- http://cer.ihtm.bg.ac.rs/handle/123456789/1599
DOI: 10.1016/j.jpba.2014.04.029
ISSN: 0731-7085
PubMed: 24876068
WoS: 000337780900023
Scopus: 2-s2.0-84901413732
Institucija/grupa
IHTMTY - JOUR AU - Šegan, Sandra AU - Terzić-Jovanović, Nataša AU - Milojković-Opsenica, Dušanka AU - Trifković, Jelena AU - Šolaja, Bogdan AU - Opsenica, Dejan PY - 2014 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/3166 AB - The chromatographic behavior of mixed 1,2,4,5-tetraoxanes, cholic and deoxycholic acid derivatives with distinct biological activity, was examined by high-performance thin-layer chromatography in order to correlate their structure and retention. Chromatographic systems were consisted of RP-18 or CN-silica as stationary phase, and binary mixtures of water with methanol, dioxane or acetone as mobile phase. Based on the respective retentions, the lipophilicity of the investigated compounds was determined. Multiple linear regression and partial least squares have been used to select variables that best describe the behavior of the investigated compounds in chromatographic systems and to quantify influences of most important parameters. The validation and cross-validation of the QSRR model suggest its applicability for prediction and understanding of retention of congeners. The models indicate the importance of nonpolar properties of the solutes and their ability for hydrophobic interactions, as well as the importance of proton donating abilities, hydrophilic and,pi interactions pointing out on that way the possible separation mechanism in the studied chromatographic systems. Observed correlations between structure and biological activity of mixed 1,2,4,5-tetraoxanes, indicate that the antimalarial activity against W2 and D6 Plasmodium falciparum strains, is governed by hydrophobic feature (measured with lipophilicity parameter), hydrophilic feature (measured with HLB, %HS, HB and HBA descriptors), and electronic feature (HOMO). PB - Elsevier T2 - Journal of Pharmaceutical and Biomedical Analysis T1 - Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters VL - 97 SP - 178 EP - 183 DO - 10.1016/j.jpba.2014.04.029 ER -
@article{ author = "Šegan, Sandra and Terzić-Jovanović, Nataša and Milojković-Opsenica, Dušanka and Trifković, Jelena and Šolaja, Bogdan and Opsenica, Dejan", year = "2014", abstract = "The chromatographic behavior of mixed 1,2,4,5-tetraoxanes, cholic and deoxycholic acid derivatives with distinct biological activity, was examined by high-performance thin-layer chromatography in order to correlate their structure and retention. Chromatographic systems were consisted of RP-18 or CN-silica as stationary phase, and binary mixtures of water with methanol, dioxane or acetone as mobile phase. Based on the respective retentions, the lipophilicity of the investigated compounds was determined. Multiple linear regression and partial least squares have been used to select variables that best describe the behavior of the investigated compounds in chromatographic systems and to quantify influences of most important parameters. The validation and cross-validation of the QSRR model suggest its applicability for prediction and understanding of retention of congeners. The models indicate the importance of nonpolar properties of the solutes and their ability for hydrophobic interactions, as well as the importance of proton donating abilities, hydrophilic and,pi interactions pointing out on that way the possible separation mechanism in the studied chromatographic systems. Observed correlations between structure and biological activity of mixed 1,2,4,5-tetraoxanes, indicate that the antimalarial activity against W2 and D6 Plasmodium falciparum strains, is governed by hydrophobic feature (measured with lipophilicity parameter), hydrophilic feature (measured with HLB, %HS, HB and HBA descriptors), and electronic feature (HOMO).", publisher = "Elsevier", journal = "Journal of Pharmaceutical and Biomedical Analysis", title = "Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters", volume = "97", pages = "178-183", doi = "10.1016/j.jpba.2014.04.029" }
Šegan, S., Terzić-Jovanović, N., Milojković-Opsenica, D., Trifković, J., Šolaja, B.,& Opsenica, D.. (2014). Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters. in Journal of Pharmaceutical and Biomedical Analysis Elsevier., 97, 178-183. https://doi.org/10.1016/j.jpba.2014.04.029
Šegan S, Terzić-Jovanović N, Milojković-Opsenica D, Trifković J, Šolaja B, Opsenica D. Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters. in Journal of Pharmaceutical and Biomedical Analysis. 2014;97:178-183. doi:10.1016/j.jpba.2014.04.029 .
Šegan, Sandra, Terzić-Jovanović, Nataša, Milojković-Opsenica, Dušanka, Trifković, Jelena, Šolaja, Bogdan, Opsenica, Dejan, "Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters" in Journal of Pharmaceutical and Biomedical Analysis, 97 (2014):178-183, https://doi.org/10.1016/j.jpba.2014.04.029 . .