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Correlation between structure, retention, property, and activity of biologically relevant 1,7-bis(aminoalkyl)diazachrysene derivatives
dc.creator | Šegan, Sandra | |
dc.creator | Trifković, Jelena | |
dc.creator | Verbić, Tatjana | |
dc.creator | Opsenica, Dejan | |
dc.creator | Zlatović, Mario | |
dc.creator | Burnett, James | |
dc.creator | Šolaja, Bogdan | |
dc.creator | Milojković-Opsenica, Dušanka | |
dc.date.accessioned | 2019-01-30T17:36:52Z | |
dc.date.available | 2019-01-30T17:36:52Z | |
dc.date.issued | 2013 | |
dc.identifier.issn | 0731-7085 | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/1305 | |
dc.description.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. | en |
dc.publisher | Elsevier | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172008/RS// | |
dc.relation | National Cancer Institute, National Institutes of Health (USA) [HHSN261200800001E] | |
dc.relation | NATOs Public Diplomacy Division [SfP983638] | |
dc.rights | restrictedAccess | |
dc.source | Journal of Pharmaceutical and Biomedical Analysis | |
dc.subject | 1,7-Bis(aminoalkyl)-diazachrysene derivatives (1,7-DAAC) | en |
dc.subject | Lipophilicity | en |
dc.subject | Acidity constants | en |
dc.subject | Quantitative structure-retention relationship (QSRR) | en |
dc.subject | Quantitative structure-activity relationship (QSAR) | en |
dc.title | Correlation between structure, retention, property, and activity of biologically relevant 1,7-bis(aminoalkyl)diazachrysene derivatives | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Златовиц, Марио; Солаја, Богдан; Шеган, Сандра; Опсеница, Дејан; Милојковиц-Опсеница, Дусанка; Трифковиц, Јелена; Вербиц, Татјана; Бурнетт, Јамес; | |
dc.citation.volume | 72 | |
dc.citation.spage | 231 | |
dc.citation.epage | 239 | |
dc.citation.other | 72: 231-239 | |
dc.citation.rank | M21 | |
dc.identifier.pmid | 22985530 | |
dc.identifier.doi | 10.1016/j.jpba.2012.08.025 | |
dc.identifier.scopus | 2-s2.0-84869079937 | |
dc.identifier.wos | 000311819100033 | |
dc.type.version | publishedVersion |