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Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters

Authorized Users Only
2014
Authors
Šegan, Sandra
Terzić Jovanović, Nataša
Milojković-Opsenica, Dušanka
Trifković, Jelena
Šolaja, Bogdan
Opsenica, Dejan
Article (Published version)
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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 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).

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, 178-183
Publisher:
  • Elsevier Science Bv, Amsterdam
Projects:
  • The synthesis of aminoquinoline-based antimalarials and botulinum neurotoxin A inhibitors (RS-172008)
Note:
  • The peer-reviewed version: http://cer.ihtm.bg.ac.rs/handle/123456789/3166

DOI: 10.1016/j.jpba.2014.04.029

ISSN: 0731-7085

PubMed: 24876068

WoS: 000337780900023

Scopus: 2-s2.0-84901413732
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/1599
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