Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters
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2014
Authors
Šegan, Sandra B.Terzić-Jovanović, Nataša
Milojković-Opsenica, Dušanka
Trifković, Jelena
Šolaja, Bogdan A.
Opsenica, Dejan M.
Article (Published version)
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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). (c) 2014 Elsevier B.V. All rights reserved.
Keywords:
Mixed 1,2,4,5-tetraoxanes / Lipophilicity / Quantitative structure-retention relationship (QSRR) / Quantitative structure activity relationship (QSAR) / Reversed-phase thin layer chromatography (RPTLC)Source:
Journal of Pharmaceutical and Biomedical Analysis, 2014, 97, 178-183Publisher:
- Elsevier Science Bv, Amsterdam
Funding / projects:
- The synthesis of aminoquinoline-based antimalarials and botulinum neurotoxin A inhibitors (RS-MESTD-Basic Research (BR or ON)-172008)
DOI: 10.1016/j.jpba.2014.04.029
ISSN: 0731-7085
PubMed: 24876068
WoS: 000337780900023
Scopus: 2-s2.0-84901413732
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Šegan, Sandra B. AU - Terzić-Jovanović, Nataša AU - Milojković-Opsenica, Dušanka AU - Trifković, Jelena AU - Šolaja, Bogdan A. AU - Opsenica, Dejan M. PY - 2014 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1795 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). (c) 2014 Elsevier B.V. All rights reserved. PB - Elsevier Science Bv, Amsterdam 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 B. and Terzić-Jovanović, Nataša and Milojković-Opsenica, Dušanka and Trifković, Jelena and Šolaja, Bogdan A. and Opsenica, Dejan M.", 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). (c) 2014 Elsevier B.V. All rights reserved.", publisher = "Elsevier Science Bv, Amsterdam", 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. B., Terzić-Jovanović, N., Milojković-Opsenica, D., Trifković, J., Šolaja, B. A.,& Opsenica, D. M.. (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 Science Bv, Amsterdam., 97, 178-183. https://doi.org/10.1016/j.jpba.2014.04.029
Šegan SB, Terzić-Jovanović N, Milojković-Opsenica D, Trifković J, Šolaja BA, Opsenica DM. 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 B., Terzić-Jovanović, Nataša, Milojković-Opsenica, Dušanka, Trifković, Jelena, Šolaja, Bogdan A., Opsenica, Dejan M., "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 . .