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Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs

Thumbnail
2017
9_jssc.201601442.pdf (1.100Mb)
Autori
Šegan, Sandra
Bozinovic, Nina
Opsenica, Igor
Andrić, Filip
Članak u časopisu (Recenzirana verzija)
Metapodaci
Prikaz svih podataka o dokumentu
Apstrakt
Lipophilicity 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 ran...ked 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.

Ključne reči:
benzothiepino[3,2-c]pyridines / lipophilicity / multicriteria ranking / multivariate data analysis / sum of ranking differences
Izvor:
Journal of Separation Science, 2017, 40, 10, 2089-2096
Izdavač:
  • Wiley-V C H Verlag Gmbh, Weinheim
Finansiranje / projekti:
  • Sinteza aminohinolina i njihovih derivata kao antimalarika i inhibitora botulinum neurotoksina A (RS-172008)
  • Korelacija strukture i osobina prirodnih i sintetičkih molekula i njihovih kompleksa sa metalima (RS-172017)
Napomena:
  • This 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
  • http://cer.ihtm.bg.ac.rs/handle/123456789/2243

DOI: 10.1002/jssc.201601442

ISSN: 1615-9306

PubMed: 28322031

WoS: 000402140300001

Scopus: 2-s2.0-85018854422
[ Google Scholar ]
15
12
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/2982
Kolekcije
  • Radovi istraživača / Researchers' publications
Institucija/grupa
IHTM
TY  - JOUR
AU  - Šegan, Sandra
AU  - Bozinovic, Nina
AU  - Opsenica, Igor
AU  - Andrić, Filip
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2982
AB  - Lipophilicity 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.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Journal of Separation Science
T1  - Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs
VL  - 40
IS  - 10
SP  - 2089
EP  - 2096
DO  - 10.1002/jssc.201601442
ER  - 
@article{
author = "Šegan, Sandra and Bozinovic, Nina and Opsenica, Igor and Andrić, Filip",
year = "2017",
abstract = "Lipophilicity 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.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Journal of Separation Science",
title = "Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs",
volume = "40",
number = "10",
pages = "2089-2096",
doi = "10.1002/jssc.201601442"
}
Šegan, S., Bozinovic, N., Opsenica, I.,& Andrić, F.. (2017). Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs. in Journal of Separation Science
Wiley-V C H Verlag Gmbh, Weinheim., 40(10), 2089-2096.
https://doi.org/10.1002/jssc.201601442
Šegan S, Bozinovic N, Opsenica I, Andrić F. Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs. in Journal of Separation Science. 2017;40(10):2089-2096.
doi:10.1002/jssc.201601442 .
Šegan, Sandra, Bozinovic, Nina, Opsenica, Igor, Andrić, Filip, "Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs" in Journal of Separation Science, 40, no. 10 (2017):2089-2096,
https://doi.org/10.1002/jssc.201601442 . .

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