Show simple item record

dc.creatorŠegan, Sandra
dc.creatorBozinovic, Nina
dc.creatorOpsenica, Igor
dc.creatorAndrić, Filip
dc.date.accessioned2019-06-30T11:51:56Z
dc.date.available2018-05-21
dc.date.issued2017
dc.identifier.issn1615-9306
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/2982
dc.description.abstractLipophilicity is one of the essential properties influencing drug absorption, excretion and metabolism. It is used for screening viable drug candidates. Chromatographic behavior of thiepino[3,2-c: 6,7-c'] dipyridine and 16 benzothiepino[3,2-c] pyridine derivatives as potential antifungal drugs was studied using thin-layer chromatography under typical reversed-phase conditions and two microemulsion chromatographic systems. Seventeen chromatographic and nine in silico lipophilicity measures were estimated. They were compared by classical multivariate approaches: principal component analysis, hierarchical cluster analysis, and ranked and grouped by the non-parametricmethod-Sum of ranking differences. Two computational and two chromatographic descriptors from the typical reversed-phase conditions using acetone/ water mixtures emerged as the best candidates for lipophilicity estimation. The principal component scores related to typical reversed-phase conditions using dioxane/ water were ranked as statistically insignificant ( the worst). Microemulsion systems were positioned in between, performing worse than in silico estimates. Thiepine derivatives were ranked and grouped by sum of ranking differences, fusing multiple lipophilicity measures. In multicriteria maximization ranking, the compound substituted by phenyl group at position 8 was selected as the most lipophilic one. It is also the most active against Candida albicans. The ranking confirmed that introduction of phenyl core is essential for increasing the lipophilicity of the studied compounds.en
dc.publisherWiley-V C H Verlag Gmbh, Weinheim
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172008/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172017/RS//
dc.rightsembargoedAccess
dc.sourceJournal of Separation Science
dc.subjectbenzothiepino[3,2-c]pyridinesen
dc.subjectlipophilicityen
dc.subjectmulticriteria rankingen
dc.subjectmultivariate data analysisen
dc.subjectsum of ranking differencesen
dc.titleConsensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugsen
dc.typearticle
dc.rights.licenseBY-NC-ND
dcterms.abstractОпсеница, Игор; Aндриц, Филип; Бозиновиц, Нина; Шеган, Сандра;
dc.citation.volume40
dc.citation.issue10
dc.citation.spage2089
dc.citation.epage2096
dc.citation.other40(10): 2089-2096
dc.citation.rankM21
dc.description.otherThis is the peer-reviewed version of the following article: Šegan, S.; Božinović, N.; Opsenica, I.; Andrić, F. Consensus-Based Comparison of Chromatographic and Computationally Estimated Lipophilicity of Benzothiepino3,2-cPyridine Derivatives as Potential Antifungal Drugs. Journal of Separation Science 2017, 40 (10), 2089–2096, [https://dx.doi.org/10.1002/jssc.201601442]
dc.description.other[http://cer.ihtm.bg.ac.rs/handle/123456789/2243]
dc.identifier.pmid28322031
dc.identifier.doi10.1002/jssc.201601442
dc.identifier.rcubConv_3728
dc.identifier.fulltexthttp://cer.ihtm.bg.ac.rs/bitstream/id/7298/9_jssc.201601442.pdf
dc.identifier.scopus2-s2.0-85018854422
dc.identifier.wos000402140300001
dc.type.versionacceptedVersion


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record