TY  - JOUR
AU  - Šegan, Sandra
AU  - Trifković, Jelena
AU  - Verbić, Tatjana
AU  - Opsenica, Dejan
AU  - Zlatović, Mario
AU  - Burnett, James
AU  - Šolaja, Bogdan
AU  - Milojković-Opsenica, Dušanka
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1305
AB  - The physicochemical properties, retention parameters (R-M(0)), partition coefficients (log P-OW), and pK(a) values for a series of thirteen 1,7-bis(aminoalkyl) diazachrysene (1,7-DAAC) derivatives were determined in order to reveal the characteristics responsible for their biological behavior. The investigated compounds inhibit three unrelated pathogens (the Botulinum neurotoxin serotype A light chain (BoNT/A LC), Plasmodium falciparum malaria, and Ebola filovirus) via three different mechanisms of action. To determine the most influential factors governing the retention and activities of the investigated diazachrysenes, R-M(0), log P-OW, and biological activity values were correlated with 2D and 3D molecular descriptors, using a partial least squares regression. The resulting quantitative structure-retention (property) relationships indicate the importance of descriptors related to the hydrophobicity of the molecules (e.g., predicted partition coefficients and hydrophobic surface area). Quantitative structure-activity relationship models for describing biological activity against the BoNT/A LC and malarial strains also include overall compound polarity, electron density distribution, and proton donor/acceptor potential. Furthermore, models for Ebola filovirus inhibition are presented qualitatively to provide insights into parameters that may contribute to the compounds' antiviral activities. Overall, the models form the basis for selecting structural features that significantly affect the compound's absorption, distribution, metabolism, excretion, and toxicity profiles.
PB  - Elsevier
T2  - Journal of Pharmaceutical and Biomedical Analysis
T1  - Correlation between structure, retention, property, and activity of biologically relevant 1,7-bis(aminoalkyl)diazachrysene derivatives
VL  - 72
SP  - 231
EP  - 239
DO  - 10.1016/j.jpba.2012.08.025
ER  - 

@article{
author = "Šegan, Sandra and Trifković, Jelena and Verbić, Tatjana and Opsenica, Dejan and Zlatović, Mario and Burnett, James and Šolaja, Bogdan and Milojković-Opsenica, Dušanka",
year = "2013",
abstract = "The physicochemical properties, retention parameters (R-M(0)), partition coefficients (log P-OW), and pK(a) values for a series of thirteen 1,7-bis(aminoalkyl) diazachrysene (1,7-DAAC) derivatives were determined in order to reveal the characteristics responsible for their biological behavior. The investigated compounds inhibit three unrelated pathogens (the Botulinum neurotoxin serotype A light chain (BoNT/A LC), Plasmodium falciparum malaria, and Ebola filovirus) via three different mechanisms of action. To determine the most influential factors governing the retention and activities of the investigated diazachrysenes, R-M(0), log P-OW, and biological activity values were correlated with 2D and 3D molecular descriptors, using a partial least squares regression. The resulting quantitative structure-retention (property) relationships indicate the importance of descriptors related to the hydrophobicity of the molecules (e.g., predicted partition coefficients and hydrophobic surface area). Quantitative structure-activity relationship models for describing biological activity against the BoNT/A LC and malarial strains also include overall compound polarity, electron density distribution, and proton donor/acceptor potential. Furthermore, models for Ebola filovirus inhibition are presented qualitatively to provide insights into parameters that may contribute to the compounds' antiviral activities. Overall, the models form the basis for selecting structural features that significantly affect the compound's absorption, distribution, metabolism, excretion, and toxicity profiles.",
publisher = "Elsevier",
journal = "Journal of Pharmaceutical and Biomedical Analysis",
title = "Correlation between structure, retention, property, and activity of biologically relevant 1,7-bis(aminoalkyl)diazachrysene derivatives",
volume = "72",
pages = "231-239",
doi = "10.1016/j.jpba.2012.08.025"
}

Šegan, S., Trifković, J., Verbić, T., Opsenica, D., Zlatović, M., Burnett, J., Šolaja, B.,& Milojković-Opsenica, D.. (2013). Correlation between structure, retention, property, and activity of biologically relevant 1,7-bis(aminoalkyl)diazachrysene derivatives. in Journal of Pharmaceutical and Biomedical Analysis
Elsevier., 72, 231-239.
https://doi.org/10.1016/j.jpba.2012.08.025

Šegan S, Trifković J, Verbić T, Opsenica D, Zlatović M, Burnett J, Šolaja B, Milojković-Opsenica D. Correlation between structure, retention, property, and activity of biologically relevant 1,7-bis(aminoalkyl)diazachrysene derivatives. in Journal of Pharmaceutical and Biomedical Analysis. 2013;72:231-239.
doi:10.1016/j.jpba.2012.08.025 .

Šegan, Sandra, Trifković, Jelena, Verbić, Tatjana, Opsenica, Dejan, Zlatović, Mario, Burnett, James, Šolaja, Bogdan, Milojković-Opsenica, Dušanka, "Correlation between structure, retention, property, and activity of biologically relevant 1,7-bis(aminoalkyl)diazachrysene derivatives" in Journal of Pharmaceutical and Biomedical Analysis, 72 (2013):231-239,
https://doi.org/10.1016/j.jpba.2012.08.025 . .