Šegan, Sandra B.

Link to this page

Authority KeyName Variants
orcid::0000-0003-1204-5487
  • Šegan, Sandra B. (43)
Projects
The synthesis of aminoquinoline-based antimalarials and botulinum neurotoxin A inhibitors Structure-properties relationships of natural and synthetic molecules and their metal complexes
Microbial diversity study and characterization of beneficial environmental microorganisms Serbian Academy of Sciences and Arts
European Society of Clinical Microbiology and Infectious Diseases (ESCMID) Structure-activity relationship of newly synthesized biological active compound
OTKA (Hungary) [K112547] Center of Excellence for Molecular Food Sciences, University of Belgrade Faculty of Chemistry
Department of Defense Chemical Biological Defense Program through Defense Threat Reduction Agency (DTRA) info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172017/RS
The application of new genotypes and technological innovations for the purpose of improvement of fruit-growing and viticultural production National Cancer Institute, National Institutes of Health (USA) [HHSN261200800001E]
NATOs Public Diplomacy Division [SfP983638] city of Zagreb
Interactions of natural products, their derivatives and coordination compounds with proteins and nucleic acids Biological response modifiers in physiological and pathological conditions
Peroksidni antimalarici i njihove himere sa hinolinima: sinteza i biološka aktivnost Sinteza, analiza i aktivnost novih organskih polidentatnih liganada i njihovih kompleksa sa d-metalima
Mali Losinj Tourist Board Ministry of Science of the Republic of Serbia
National Cancer Institute, National Institutes of Health (U.S.) [HHSN261200800001E] National Institute of Allergy and Infectious Diseases (U.S.) [5-U01AI082051-02]

Author's Bibliography

N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa

Aleksic, Ivana; Jeremic, Jelena; Milivojević, Dušan; Ilić-Tomić, Tatjana; Šegan, Sandra B.; Zlatović, Mario; Opsenica, Dejan M.; Senerovic, Lidija

(American Chemical Society, 2019)

TY  - JOUR
AU  - Aleksic, Ivana
AU  - Jeremic, Jelena
AU  - Milivojević, Dušan
AU  - Ilić-Tomić, Tatjana
AU  - Šegan, Sandra B.
AU  - Zlatović, Mario
AU  - Opsenica, Dejan M.
AU  - Senerovic, Lidija
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3771
AB  - Pseudomonas aeruginosa is a leading cause of nosocomial infections that are becoming increasingly difficult to treat due to the occurrence of antibiotic resistant strains. Since P. aeruginosa virulence is controlled through quorum sensing, small molecule treatments inhibiting quorum sensing signaling pathways provide a promising therapeutic option. Consequently, we synthesized a series of N-octaneamino-4-aminoquinoline derivatives to optimize this chemotype’s antivirulence activity against P. aeruginosa via inhibition of pyocyanin production. The most potent derivative, which possesses a benzofuran substituent, provided effective inhibition of pyocyanin production (IC50 = 12 μM), biofilm formation (BFIC50 = 50 μM), and motility. Experimentally, the compound’s activity is achieved through competitive inhibition of PqsR, and structure–activity data were rationalized using molecular docking studies.
PB  - American Chemical Society
T2  - ACS Chemical Biology
T1  - N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa
DO  - 10.1021/acschembio.9b00682
ER  - 
@article{
author = "Aleksic, Ivana and Jeremic, Jelena and Milivojević, Dušan and Ilić-Tomić, Tatjana and Šegan, Sandra B. and Zlatović, Mario and Opsenica, Dejan M. and Senerovic, Lidija",
year = "2019",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3771",
abstract = "Pseudomonas aeruginosa is a leading cause of nosocomial infections that are becoming increasingly difficult to treat due to the occurrence of antibiotic resistant strains. Since P. aeruginosa virulence is controlled through quorum sensing, small molecule treatments inhibiting quorum sensing signaling pathways provide a promising therapeutic option. Consequently, we synthesized a series of N-octaneamino-4-aminoquinoline derivatives to optimize this chemotype’s antivirulence activity against P. aeruginosa via inhibition of pyocyanin production. The most potent derivative, which possesses a benzofuran substituent, provided effective inhibition of pyocyanin production (IC50 = 12 μM), biofilm formation (BFIC50 = 50 μM), and motility. Experimentally, the compound’s activity is achieved through competitive inhibition of PqsR, and structure–activity data were rationalized using molecular docking studies.",
publisher = "American Chemical Society",
journal = "ACS Chemical Biology",
title = "N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa",
doi = "10.1021/acschembio.9b00682"
}
Aleksic, I., Jeremic, J., Milivojević, D., Ilić-Tomić, T., Šegan, S. B., Zlatović, M., Opsenica, D. M.,& Senerovic, L. (2019). N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa.
ACS Chemical Biology
American Chemical Society..
https://doi.org/10.1021/acschembio.9b00682
Aleksic I, Jeremic J, Milivojević D, Ilić-Tomić T, Šegan SB, Zlatović M, Opsenica DM, Senerovic L. N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. ACS Chemical Biology. 2019;
Aleksic Ivana, Jeremic Jelena, Milivojević Dušan, Ilić-Tomić Tatjana, Šegan Sandra B., Zlatović Mario, Opsenica Dejan M., Senerovic Lidija, "N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa" ACS Chemical Biology (2019),
https://doi.org/10.1021/acschembio.9b00682 .
1
5
2
5

N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa

Aleksic, Ivana; Jeremic, Jelena; Milivojević, Dušan; Ilić-Tomić, Tatjana; Šegan, Sandra B.; Zlatović, Mario; Opsenica, Dejan M.; Senerovic, Lidija

(American Chemical Society, 2019)

TY  - JOUR
AU  - Aleksic, Ivana
AU  - Jeremic, Jelena
AU  - Milivojević, Dušan
AU  - Ilić-Tomić, Tatjana
AU  - Šegan, Sandra B.
AU  - Zlatović, Mario
AU  - Opsenica, Dejan M.
AU  - Senerovic, Lidija
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3772
AB  - Pseudomonas aeruginosa is a leading cause of nosocomial infections that are becoming increasingly difficult to treat due to the occurrence of antibiotic resistant strains. Since P. aeruginosa virulence is controlled through quorum sensing, small molecule treatments inhibiting quorum sensing signaling pathways provide a promising therapeutic option. Consequently, we synthesized a series of N-octaneamino-4-aminoquinoline derivatives to optimize this chemotype’s antivirulence activity against P. aeruginosa via inhibition of pyocyanin production. The most potent derivative, which possesses a benzofuran substituent, provided effective inhibition of pyocyanin production (IC50 = 12 μM), biofilm formation (BFIC50 = 50 μM), and motility. Experimentally, the compound’s activity is achieved through competitive inhibition of PqsR, and structure–activity data were rationalized using molecular docking studies.
PB  - American Chemical Society
T2  - ACS Chemical Biology
T1  - N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa
DO  - 10.1021/acschembio.9b00682
ER  - 
@article{
author = "Aleksic, Ivana and Jeremic, Jelena and Milivojević, Dušan and Ilić-Tomić, Tatjana and Šegan, Sandra B. and Zlatović, Mario and Opsenica, Dejan M. and Senerovic, Lidija",
year = "2019",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3772",
abstract = "Pseudomonas aeruginosa is a leading cause of nosocomial infections that are becoming increasingly difficult to treat due to the occurrence of antibiotic resistant strains. Since P. aeruginosa virulence is controlled through quorum sensing, small molecule treatments inhibiting quorum sensing signaling pathways provide a promising therapeutic option. Consequently, we synthesized a series of N-octaneamino-4-aminoquinoline derivatives to optimize this chemotype’s antivirulence activity against P. aeruginosa via inhibition of pyocyanin production. The most potent derivative, which possesses a benzofuran substituent, provided effective inhibition of pyocyanin production (IC50 = 12 μM), biofilm formation (BFIC50 = 50 μM), and motility. Experimentally, the compound’s activity is achieved through competitive inhibition of PqsR, and structure–activity data were rationalized using molecular docking studies.",
publisher = "American Chemical Society",
journal = "ACS Chemical Biology",
title = "N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa",
doi = "10.1021/acschembio.9b00682"
}
Aleksic, I., Jeremic, J., Milivojević, D., Ilić-Tomić, T., Šegan, S. B., Zlatović, M., Opsenica, D. M.,& Senerovic, L. (2019). N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa.
ACS Chemical Biology
American Chemical Society..
https://doi.org/10.1021/acschembio.9b00682
Aleksic I, Jeremic J, Milivojević D, Ilić-Tomić T, Šegan SB, Zlatović M, Opsenica DM, Senerovic L. N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. ACS Chemical Biology. 2019;
Aleksic Ivana, Jeremic Jelena, Milivojević Dušan, Ilić-Tomić Tatjana, Šegan Sandra B., Zlatović Mario, Opsenica Dejan M., Senerovic Lidija, "N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa" ACS Chemical Biology (2019),
https://doi.org/10.1021/acschembio.9b00682 .
1
5
2
5

Supplementary data for article: N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa

Aleksic, Ivana; Jeremic, Jelena; Milivojević, Dušan; Ilić-Tomić, Tatjana; Šegan, Sandra B.; Zlatović, Mario; Opsenica, Dejan M.; Senerovic, Lidija

(American Chemical Society, 2019)

TY  - BOOK
AU  - Aleksic, Ivana
AU  - Jeremic, Jelena
AU  - Milivojević, Dušan
AU  - Ilić-Tomić, Tatjana
AU  - Šegan, Sandra B.
AU  - Zlatović, Mario
AU  - Opsenica, Dejan M.
AU  - Senerovic, Lidija
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3773
PB  - American Chemical Society
T2  - ACS Chemical Biology
T1  - Supplementary data for article: N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa
ER  - 
@book{
author = "Aleksic, Ivana and Jeremic, Jelena and Milivojević, Dušan and Ilić-Tomić, Tatjana and Šegan, Sandra B. and Zlatović, Mario and Opsenica, Dejan M. and Senerovic, Lidija",
year = "2019",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3773",
publisher = "American Chemical Society",
journal = "ACS Chemical Biology",
title = "Supplementary data for article: N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa"
}
Aleksic, I., Jeremic, J., Milivojević, D., Ilić-Tomić, T., Šegan, S. B., Zlatović, M., Opsenica, D. M.,& Senerovic, L. (2019). Supplementary data for article: N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa.
ACS Chemical Biology
American Chemical Society..
Aleksic I, Jeremic J, Milivojević D, Ilić-Tomić T, Šegan SB, Zlatović M, Opsenica DM, Senerovic L. Supplementary data for article: N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. ACS Chemical Biology. 2019;
Aleksic Ivana, Jeremic Jelena, Milivojević Dušan, Ilić-Tomić Tatjana, Šegan Sandra B., Zlatović Mario, Opsenica Dejan M., Senerovic Lidija, "Supplementary data for article: N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa" ACS Chemical Biology (2019)

Thin-layer chromatography in medicinal chemistry

Šegan, Sandra B.; Opsenica, Dejan M.; Milojković-Opsenica, Dušanka

(Taylor and Francis Inc., 2019)

TY  - JOUR
AU  - Šegan, Sandra B.
AU  - Opsenica, Dejan M.
AU  - Milojković-Opsenica, Dušanka
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3686
AB  - Among widely used chromatographic methods modern thin-layer chromatography is not only the simplest to perform but is also considered as respectable analytical method in various phases of drug discovery and development processes such as monitoring of synthesis, identification of bioactive substances from various natural sources and their isolation and purification, determination of lipophilicity and other physico-chemical parameters, quantitative structure-activity relationship studies, bioautography, as well as qualitative and quantitative analysis of drugs and their metabolites. An overview of recently published papers dealing with application of thin-layer chromatography in medicinal chemistry is presented.
PB  - Taylor and Francis Inc.
T2  - Journal of Liquid Chromatography and Related Technologies
T1  - Thin-layer chromatography in medicinal chemistry
VL  - 42
IS  - 9-10
SP  - 238
EP  - 248
DO  - 10.1080/10826076.2019.1585615
ER  - 
@article{
author = "Šegan, Sandra B. and Opsenica, Dejan M. and Milojković-Opsenica, Dušanka",
year = "2019",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3686",
abstract = "Among widely used chromatographic methods modern thin-layer chromatography is not only the simplest to perform but is also considered as respectable analytical method in various phases of drug discovery and development processes such as monitoring of synthesis, identification of bioactive substances from various natural sources and their isolation and purification, determination of lipophilicity and other physico-chemical parameters, quantitative structure-activity relationship studies, bioautography, as well as qualitative and quantitative analysis of drugs and their metabolites. An overview of recently published papers dealing with application of thin-layer chromatography in medicinal chemistry is presented.",
publisher = "Taylor and Francis Inc.",
journal = "Journal of Liquid Chromatography and Related Technologies",
title = "Thin-layer chromatography in medicinal chemistry",
volume = "42",
number = "9-10",
pages = "238-248",
doi = "10.1080/10826076.2019.1585615"
}
Šegan, S. B., Opsenica, D. M.,& Milojković-Opsenica, D. (2019). Thin-layer chromatography in medicinal chemistry.
Journal of Liquid Chromatography and Related Technologies
Taylor and Francis Inc.., 42(9-10), 238-248.
https://doi.org/10.1080/10826076.2019.1585615
Šegan SB, Opsenica DM, Milojković-Opsenica D. Thin-layer chromatography in medicinal chemistry. Journal of Liquid Chromatography and Related Technologies. 2019;42(9-10):238-248
Šegan Sandra B., Opsenica Dejan M., Milojković-Opsenica Dušanka, "Thin-layer chromatography in medicinal chemistry" Journal of Liquid Chromatography and Related Technologies, 42, no. 9-10 (2019):238-248,
https://doi.org/10.1080/10826076.2019.1585615 .
1
5
5
5

Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy)phenylpiperazine dopamine D2 ligands

Šegan, Sandra B.; Penjišević, Jelena; Šukalović, Vladimir; Andrić, Deana; Milojković-Opsenica, Dušanka; Kostić-Rajačić, Slađana

(Elsevier, 2019)


                                            

                                            
Šegan, S. B., Penjišević, J., Šukalović, V., Andrić, D., Milojković-Opsenica, D.,& Kostić-Rajačić, S. (2019). Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy)phenylpiperazine dopamine D2 ligands.
Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences
Elsevier., 1124, 146-153.
https://doi.org/10.1016/j.jchromb.2019.06.006
Šegan SB, Penjišević J, Šukalović V, Andrić D, Milojković-Opsenica D, Kostić-Rajačić S. Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy)phenylpiperazine dopamine D2 ligands. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences. 2019;1124:146-153
Šegan Sandra B., Penjišević Jelena, Šukalović Vladimir, Andrić Deana, Milojković-Opsenica Dušanka, Kostić-Rajačić Slađana, "Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy)phenylpiperazine dopamine D2 ligands" Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, 1124 (2019):146-153,
https://doi.org/10.1016/j.jchromb.2019.06.006 .
2
1
2

Supplementary data for the article: Šegan, S.; Penjišević, J.; Šukalović, V.; Andrić, D.; Milojković-Opsenica, D.; Kostić-Rajačić, S. Investigation of Lipophilicity and Pharmacokinetic Properties of 2-(Methoxy)Phenylpiperazine Dopamine D2 Ligands. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 2019, 1124, 146–153. https://doi.org/10.1016/j.jchromb.2019.06.006

Šegan, Sandra B.; Penjišević, Jelena; Šukalović, Vladimir; Andrić, Deana; Milojković-Opsenica, Dušanka; Kostić-Rajačić, Slađana

(Elsevier, 2019)


                                            

                                            
Šegan, S. B., Penjišević, J., Šukalović, V., Andrić, D., Milojković-Opsenica, D.,& Kostić-Rajačić, S. (2019). Supplementary data for the article: Šegan, S.; Penjišević, J.; Šukalović, V.; Andrić, D.; Milojković-Opsenica, D.; Kostić-Rajačić, S. Investigation of Lipophilicity and Pharmacokinetic Properties of 2-(Methoxy)Phenylpiperazine Dopamine D2 Ligands. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 2019, 1124, 146–153. https://doi.org/10.1016/j.jchromb.2019.06.006.
Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences
Elsevier..
Šegan SB, Penjišević J, Šukalović V, Andrić D, Milojković-Opsenica D, Kostić-Rajačić S. Supplementary data for the article: Šegan, S.; Penjišević, J.; Šukalović, V.; Andrić, D.; Milojković-Opsenica, D.; Kostić-Rajačić, S. Investigation of Lipophilicity and Pharmacokinetic Properties of 2-(Methoxy)Phenylpiperazine Dopamine D2 Ligands. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 2019, 1124, 146–153. https://doi.org/10.1016/j.jchromb.2019.06.006. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences. 2019;
Šegan Sandra B., Penjišević Jelena, Šukalović Vladimir, Andrić Deana, Milojković-Opsenica Dušanka, Kostić-Rajačić Slađana, "Supplementary data for the article: Šegan, S.; Penjišević, J.; Šukalović, V.; Andrić, D.; Milojković-Opsenica, D.; Kostić-Rajačić, S. Investigation of Lipophilicity and Pharmacokinetic Properties of 2-(Methoxy)Phenylpiperazine Dopamine D2 Ligands. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 2019, 1124, 146–153. https://doi.org/10.1016/j.jchromb.2019.06.006" Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences (2019)

Thin-layer chromatography in quantitative structure-activity relationship studies

Milojković-Opsenica, Dušanka; Andrić, Filip; Šegan, Sandra B.; Trifković, Jelena; Tešić, Živoslav Lj.

(Taylor & Francis Inc, Philadelphia, 2018)

TY  - JOUR
AU  - Milojković-Opsenica, Dušanka
AU  - Andrić, Filip
AU  - Šegan, Sandra B.
AU  - Trifković, Jelena
AU  - Tešić, Živoslav Lj.
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2145
AB  - The methods of correlating molecular structure of substances expressed as descriptors, to their biological activity are commonly denoted as Quantitative Structure-Activity Relationships (QSARs). This concept, typically applied in drug discovery processes, is also widely used for correlation of molecular structure and physicochemical properties of solutes in so-called quantitative structure-property relationship (QSPR) studies, as well as for explanation of chromatographic behavior, i.e., separation mechanisms of analytes, where is termed as quantitative structure-retention relationship (QSRR). Mathematical expressions of structural characteristics of substances, named as molecular descriptors, can be calculated by various computational techniques or experimentally determined by different analytical methods. Thin-layer chromatography as a rapid, sensitive, and economical liquid chromatographic method has been widely used for determination of various chromatographic descriptors applicable in QSAR/QSPR studies. An overview of recently published papers dealing with this concept is presented. [GRAPHICS] .
PB  - Taylor & Francis Inc, Philadelphia
T2  - Journal of Liquid Chromatography and Related Technologies
T1  - Thin-layer chromatography in quantitative structure-activity relationship studies
VL  - 41
IS  - 6
SP  - 272
EP  - 281
DO  - 10.1080/10826076.2018.1447892
ER  - 
@article{
author = "Milojković-Opsenica, Dušanka and Andrić, Filip and Šegan, Sandra B. and Trifković, Jelena and Tešić, Živoslav Lj.",
year = "2018",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2145",
abstract = "The methods of correlating molecular structure of substances expressed as descriptors, to their biological activity are commonly denoted as Quantitative Structure-Activity Relationships (QSARs). This concept, typically applied in drug discovery processes, is also widely used for correlation of molecular structure and physicochemical properties of solutes in so-called quantitative structure-property relationship (QSPR) studies, as well as for explanation of chromatographic behavior, i.e., separation mechanisms of analytes, where is termed as quantitative structure-retention relationship (QSRR). Mathematical expressions of structural characteristics of substances, named as molecular descriptors, can be calculated by various computational techniques or experimentally determined by different analytical methods. Thin-layer chromatography as a rapid, sensitive, and economical liquid chromatographic method has been widely used for determination of various chromatographic descriptors applicable in QSAR/QSPR studies. An overview of recently published papers dealing with this concept is presented. [GRAPHICS] .",
publisher = "Taylor & Francis Inc, Philadelphia",
journal = "Journal of Liquid Chromatography and Related Technologies",
title = "Thin-layer chromatography in quantitative structure-activity relationship studies",
volume = "41",
number = "6",
pages = "272-281",
doi = "10.1080/10826076.2018.1447892"
}
Milojković-Opsenica, D., Andrić, F., Šegan, S. B., Trifković, J.,& Tešić, Ž. Lj. (2018). Thin-layer chromatography in quantitative structure-activity relationship studies.
Journal of Liquid Chromatography and Related Technologies
Taylor & Francis Inc, Philadelphia., 41(6), 272-281.
https://doi.org/10.1080/10826076.2018.1447892
Milojković-Opsenica D, Andrić F, Šegan SB, Trifković J, Tešić ŽL. Thin-layer chromatography in quantitative structure-activity relationship studies. Journal of Liquid Chromatography and Related Technologies. 2018;41(6):272-281
Milojković-Opsenica Dušanka, Andrić Filip, Šegan Sandra B., Trifković Jelena, Tešić Živoslav Lj., "Thin-layer chromatography in quantitative structure-activity relationship studies" Journal of Liquid Chromatography and Related Technologies, 41, no. 6 (2018):272-281,
https://doi.org/10.1080/10826076.2018.1447892 .
5
5
5

Antibacterial and antifungal properties of guanylhydrazones

Ajdačić, Vladimir; Lazić, Jelena O.; Mojicevic, Marija; Šegan, Sandra B.; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Serbian Chemical Soc, Belgrade, 2017)

TY  - JOUR
AU  - Ajdačić, Vladimir
AU  - Lazić, Jelena O.
AU  - Mojicevic, Marija
AU  - Šegan, Sandra B.
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2508
AB  - A series of novel guanylhydrazones were designed, synthesized and characterized. All the compounds were screened for their antibacterial and antifungal activity. Compounds 26 and 27 showed excellent antibacterial activities against Staphylococcus aureus ATCC 25923 and Micrococcus luteus ATCC 379 with minimal inhibitory concentrations of 4 ae g mL(-1), and good antifungal activity against Candida parapsilosis ATCC 22019. These results suggested that the selected guanylhydrazones could serve as promising leads for improved antimicrobial development.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Antibacterial and antifungal properties of guanylhydrazones
VL  - 82
IS  - 6
SP  - 641
EP  - 649
DO  - 10.2298/JSC170213033A
ER  - 
@article{
author = "Ajdačić, Vladimir and Lazić, Jelena O. and Mojicevic, Marija and Šegan, Sandra B. and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2017",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2508",
abstract = "A series of novel guanylhydrazones were designed, synthesized and characterized. All the compounds were screened for their antibacterial and antifungal activity. Compounds 26 and 27 showed excellent antibacterial activities against Staphylococcus aureus ATCC 25923 and Micrococcus luteus ATCC 379 with minimal inhibitory concentrations of 4 ae g mL(-1), and good antifungal activity against Candida parapsilosis ATCC 22019. These results suggested that the selected guanylhydrazones could serve as promising leads for improved antimicrobial development.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Antibacterial and antifungal properties of guanylhydrazones",
volume = "82",
number = "6",
pages = "641-649",
doi = "10.2298/JSC170213033A"
}
Ajdačić, V., Lazić, J. O., Mojicevic, M., Šegan, S. B., Nikodinović-Runić, J.,& Opsenica, I. (2017). Antibacterial and antifungal properties of guanylhydrazones.
Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 82(6), 641-649.
https://doi.org/10.2298/JSC170213033A
Ajdačić V, Lazić JO, Mojicevic M, Šegan SB, Nikodinović-Runić J, Opsenica I. Antibacterial and antifungal properties of guanylhydrazones. Journal of the Serbian Chemical Society. 2017;82(6):641-649
Ajdačić Vladimir, Lazić Jelena O., Mojicevic Marija, Šegan Sandra B., Nikodinović-Runić Jasmina, Opsenica Igor, "Antibacterial and antifungal properties of guanylhydrazones" Journal of the Serbian Chemical Society, 82, no. 6 (2017):641-649,
https://doi.org/10.2298/JSC170213033A .
3
3
3

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

Šegan, Sandra B.; Božinović, Nina S.; Opsenica, Igor; Andrić, Filip

(Wiley-V C H Verlag Gmbh, Weinheim, 2017)

TY  - JOUR
AU  - Šegan, Sandra B.
AU  - Božinović, Nina S.
AU  - Opsenica, Igor
AU  - Andrić, Filip
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3076
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 B. and Božinović, Nina S. and Opsenica, Igor and Andrić, Filip",
year = "2017",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3076",
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. B., Božinović, N. S., 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.
Journal of Separation Science
Wiley-V C H Verlag Gmbh, Weinheim., 40(10), 2089-2096.
https://doi.org/10.1002/jssc.201601442
Šegan SB, Božinović NS, Opsenica I, Andrić F. Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs. Journal of Separation Science. 2017;40(10):2089-2096
Šegan Sandra B., Božinović Nina S., Opsenica Igor, Andrić Filip, "Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs" Journal of Separation Science, 40, no. 10 (2017):2089-2096,
https://doi.org/10.1002/jssc.201601442 .
13
12
12

Supplementary data for article: Šegan, S.; Božinović, 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. Journal of Separation Science 2017, 40 (10), 2089–2096. https://doi.org/10.1002/jssc.201601442

Šegan, Sandra B.; Božinović, Nina S.; Opsenica, Igor; Andrić, Filip

(Wiley-V C H Verlag Gmbh, Weinheim, 2017)

TY  - BOOK
AU  - Šegan, Sandra B.
AU  - Božinović, Nina S.
AU  - Opsenica, Igor
AU  - Andrić, Filip
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3077
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Journal of Separation Science
T1  - Supplementary data for article:           Šegan, S.; Božinović, 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. Journal of Separation Science 2017, 40 (10), 2089–2096. https://doi.org/10.1002/jssc.201601442
ER  - 
@book{
author = "Šegan, Sandra B. and Božinović, Nina S. and Opsenica, Igor and Andrić, Filip",
year = "2017",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3077",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Journal of Separation Science",
title = "Supplementary data for article:           Šegan, S.; Božinović, 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. Journal of Separation Science 2017, 40 (10), 2089–2096. https://doi.org/10.1002/jssc.201601442"
}
Šegan, S. B., Božinović, N. S., Opsenica, I.,& Andrić, F. (2017). Supplementary data for article:           Šegan, S.; Božinović, 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. Journal of Separation Science 2017, 40 (10), 2089–2096. https://doi.org/10.1002/jssc.201601442.
Journal of Separation Science
Wiley-V C H Verlag Gmbh, Weinheim..
Šegan SB, Božinović NS, Opsenica I, Andrić F. Supplementary data for article:           Šegan, S.; Božinović, 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. Journal of Separation Science 2017, 40 (10), 2089–2096. https://doi.org/10.1002/jssc.201601442. Journal of Separation Science. 2017;
Šegan Sandra B., Božinović Nina S., Opsenica Igor, Andrić Filip, "Supplementary data for article:           Šegan, S.; Božinović, 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. Journal of Separation Science 2017, 40 (10), 2089–2096. https://doi.org/10.1002/jssc.201601442" Journal of Separation Science (2017)

Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa

Aleksić, Ivana; Šegan, Sandra B.; Andrić, Filip; Zlatović, Mario; Morić, Ivana; Opsenica, Dejan M.; Šenerović, Lidija

(Amer Chemical Soc, Washington, 2017)

TY  - JOUR
AU  - Aleksić, Ivana
AU  - Šegan, Sandra B.
AU  - Andrić, Filip
AU  - Zlatović, Mario
AU  - Morić, Ivana
AU  - Opsenica, Dejan M.
AU  - Šenerović, Lidija
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3089
AB  - Antibiotic resistance has become a serious global threat to public health; therefore, improved strategies and structurally novel antimicrobials are urgently needed to combat infectious diseases. Here we report a new type of highly potent 4-aminoquinoline derivatives as quorum sensing inhibitors in Serratia marcescens and Pseudomonas aeruginosa, exhibiting weak bactericidal activities (minimum inhibitory concentration (MIC)  gt  400 mu M). Through detailed structure-activity study, we have identified 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines (5 and 10) as biofilm formation inhibitors with 50% biofilm inhibition at 69 mu M and 63 mu M in S. marcescens and P. aeruginosa, respectively. These two compounds, 5 and 10, are the first quinoline derivatives with anti-biofilm formation activity reported in S. marcescens. Quantitative structure-activity relationship (QSAR) analysis identified structural descriptors such as Wiener indices, hyper-distance-path index (HDPI), mean topological charge (MTC), topological charge index (TCI), and log D(o/w)exp as the most influential in biofilm inhibition in this bacterial species. Derivative 10 is one of the most potent quinoline type inhibitors of pyocyanin production described so far (IC50 = 2.5 mu M). While we have demonstrated that 5 and 10 act as Pseudomonas quinolone system (PQS) antagonists, the mechanism of inhibition of S. marcescens biofilm formation with these compounds remains open since signaling similar to P. aeruginosa PQS system has not yet been described in Serratia and activity of these compounds on acylhomoserine lactone (AHL) signaling has not been detected. Our data show that 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines present the promising scaffolds for developing antivirulence and anti-biofilm formation agents against multidrug-resistant bacterial species.
PB  - Amer Chemical Soc, Washington
T2  - ACS Chemical Biology
T1  - Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa
VL  - 12
IS  - 5
SP  - 1425
EP  - 1434
DO  - 10.1021/acschembio.6b01149
ER  - 
@article{
author = "Aleksić, Ivana and Šegan, Sandra B. and Andrić, Filip and Zlatović, Mario and Morić, Ivana and Opsenica, Dejan M. and Šenerović, Lidija",
year = "2017",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3089",
abstract = "Antibiotic resistance has become a serious global threat to public health; therefore, improved strategies and structurally novel antimicrobials are urgently needed to combat infectious diseases. Here we report a new type of highly potent 4-aminoquinoline derivatives as quorum sensing inhibitors in Serratia marcescens and Pseudomonas aeruginosa, exhibiting weak bactericidal activities (minimum inhibitory concentration (MIC)  gt  400 mu M). Through detailed structure-activity study, we have identified 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines (5 and 10) as biofilm formation inhibitors with 50% biofilm inhibition at 69 mu M and 63 mu M in S. marcescens and P. aeruginosa, respectively. These two compounds, 5 and 10, are the first quinoline derivatives with anti-biofilm formation activity reported in S. marcescens. Quantitative structure-activity relationship (QSAR) analysis identified structural descriptors such as Wiener indices, hyper-distance-path index (HDPI), mean topological charge (MTC), topological charge index (TCI), and log D(o/w)exp as the most influential in biofilm inhibition in this bacterial species. Derivative 10 is one of the most potent quinoline type inhibitors of pyocyanin production described so far (IC50 = 2.5 mu M). While we have demonstrated that 5 and 10 act as Pseudomonas quinolone system (PQS) antagonists, the mechanism of inhibition of S. marcescens biofilm formation with these compounds remains open since signaling similar to P. aeruginosa PQS system has not yet been described in Serratia and activity of these compounds on acylhomoserine lactone (AHL) signaling has not been detected. Our data show that 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines present the promising scaffolds for developing antivirulence and anti-biofilm formation agents against multidrug-resistant bacterial species.",
publisher = "Amer Chemical Soc, Washington",
journal = "ACS Chemical Biology",
title = "Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa",
volume = "12",
number = "5",
pages = "1425-1434",
doi = "10.1021/acschembio.6b01149"
}
Aleksić, I., Šegan, S. B., Andrić, F., Zlatović, M., Morić, I., Opsenica, D. M.,& Šenerović, L. (2017). Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa.
ACS Chemical Biology
Amer Chemical Soc, Washington., 12(5), 1425-1434.
https://doi.org/10.1021/acschembio.6b01149
Aleksić I, Šegan SB, Andrić F, Zlatović M, Morić I, Opsenica DM, Šenerović L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa. ACS Chemical Biology. 2017;12(5):1425-1434
Aleksić Ivana, Šegan Sandra B., Andrić Filip, Zlatović Mario, Morić Ivana, Opsenica Dejan M., Šenerović Lidija, "Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa" ACS Chemical Biology, 12, no. 5 (2017):1425-1434,
https://doi.org/10.1021/acschembio.6b01149 .
2
22
21
22

Supplementary data for article: Aleksić, I.; Šegan, S.; Andrić, F.; Zlatović, M.; Moric, I.; Opsenica, D. M.; Senerovic, L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia Marcescens and Pseudomonas Aeruginosa. ACS Chemical Biology 2017, 12 (5), 1425–1434. https://doi.org/10.1021/acschembio.6b01149

Aleksić, Ivana; Šegan, Sandra B.; Andrić, Filip; Zlatović, Mario; Morić, Ivana; Opsenica, Dejan M.; Šenerović, Lidija

(Amer Chemical Soc, Washington, 2017)

TY  - BOOK
AU  - Aleksić, Ivana
AU  - Šegan, Sandra B.
AU  - Andrić, Filip
AU  - Zlatović, Mario
AU  - Morić, Ivana
AU  - Opsenica, Dejan M.
AU  - Šenerović, Lidija
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3090
PB  - Amer Chemical Soc, Washington
T2  - ACS Chemical Biology
T1  - Supplementary data for article: Aleksić, I.; Šegan, S.; Andrić, F.; Zlatović, M.; Moric, I.; Opsenica, D. M.; Senerovic, L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia Marcescens and Pseudomonas Aeruginosa. ACS Chemical Biology 2017, 12 (5), 1425–1434. https://doi.org/10.1021/acschembio.6b01149
ER  - 
@book{
author = "Aleksić, Ivana and Šegan, Sandra B. and Andrić, Filip and Zlatović, Mario and Morić, Ivana and Opsenica, Dejan M. and Šenerović, Lidija",
year = "2017",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3090",
publisher = "Amer Chemical Soc, Washington",
journal = "ACS Chemical Biology",
title = "Supplementary data for article: Aleksić, I.; Šegan, S.; Andrić, F.; Zlatović, M.; Moric, I.; Opsenica, D. M.; Senerovic, L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia Marcescens and Pseudomonas Aeruginosa. ACS Chemical Biology 2017, 12 (5), 1425–1434. https://doi.org/10.1021/acschembio.6b01149"
}
Aleksić, I., Šegan, S. B., Andrić, F., Zlatović, M., Morić, I., Opsenica, D. M.,& Šenerović, L. (2017). Supplementary data for article: Aleksić, I.; Šegan, S.; Andrić, F.; Zlatović, M.; Moric, I.; Opsenica, D. M.; Senerovic, L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia Marcescens and Pseudomonas Aeruginosa. ACS Chemical Biology 2017, 12 (5), 1425–1434. https://doi.org/10.1021/acschembio.6b01149.
ACS Chemical Biology
Amer Chemical Soc, Washington..
Aleksić I, Šegan SB, Andrić F, Zlatović M, Morić I, Opsenica DM, Šenerović L. Supplementary data for article: Aleksić, I.; Šegan, S.; Andrić, F.; Zlatović, M.; Moric, I.; Opsenica, D. M.; Senerovic, L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia Marcescens and Pseudomonas Aeruginosa. ACS Chemical Biology 2017, 12 (5), 1425–1434. https://doi.org/10.1021/acschembio.6b01149. ACS Chemical Biology. 2017;
Aleksić Ivana, Šegan Sandra B., Andrić Filip, Zlatović Mario, Morić Ivana, Opsenica Dejan M., Šenerović Lidija, "Supplementary data for article: Aleksić, I.; Šegan, S.; Andrić, F.; Zlatović, M.; Moric, I.; Opsenica, D. M.; Senerovic, L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia Marcescens and Pseudomonas Aeruginosa. ACS Chemical Biology 2017, 12 (5), 1425–1434. https://doi.org/10.1021/acschembio.6b01149" ACS Chemical Biology (2017)

alpha-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives

Popović-Đorđevic, Jelena; Jevtić, Ivana I.; Grozdanic, Nadja Dj; Šegan, Sandra B.; Zlatović, Mario; Ivanović, Milovan; Stanojković, Tatjana

(Taylor & Francis Ltd, Abingdon, 2017)

TY  - JOUR
AU  - Popović-Đorđevic, Jelena
AU  - Jevtić, Ivana I.
AU  - Grozdanic, Nadja Dj
AU  - Šegan, Sandra B.
AU  - Zlatović, Mario
AU  - Ivanović, Milovan
AU  - Stanojković, Tatjana
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2383
AB  - The inhibitory activities of selected cyclic urea and carbamate derivatives (1-13) toward alpha-glucosidase (alpha-Gls) in in vitro assay were examined in this study. All examined compounds showed higher inhibitory activity (IC50) against alpha-Gls compared to standard antidiabetic drug acarbose. The most potent was benzyl (3,4,5-trimethoxyphenyl) carbamate (12) with IC50 = 49.85 +/- 0.10 mu M. In vitro cytotoxicity of the investigated compounds was tested on three human cancer cell lines HeLa, A549 and MDA-MB-453 using MTT assay. The best antitumour activity was achieved with compound 2 (trans-5-phenethyl-1-phenylhexahydro-1H-imidazo[4,5-c] pyridin-2(3H)-one) against MDA-MB-453 human breast cancer cell line (IC50 = 83.41 +/- 1.60 mu M). Cyclic ureas and carbamates showed promising anti-alpha-glucosidase activity and should be further tested as potential antidiabetic drugs. The PLS model of preliminary QSAR study indicated that, in planing the future synthesis of more potent compounds, the newly designed should have the substituents capable of polar interactions with receptor sites in various positions, while avoiding the increase of their lipophilicity.
PB  - Taylor & Francis Ltd, Abingdon
T2  - Journal of Enzyme Inhibition and Medicinal Chemistry
T1  - alpha-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives
VL  - 32
IS  - 1
SP  - 298
EP  - 303
DO  - 10.1080/14756366.2016.1250754
ER  - 
@article{
author = "Popović-Đorđevic, Jelena and Jevtić, Ivana I. and Grozdanic, Nadja Dj and Šegan, Sandra B. and Zlatović, Mario and Ivanović, Milovan and Stanojković, Tatjana",
year = "2017",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2383",
abstract = "The inhibitory activities of selected cyclic urea and carbamate derivatives (1-13) toward alpha-glucosidase (alpha-Gls) in in vitro assay were examined in this study. All examined compounds showed higher inhibitory activity (IC50) against alpha-Gls compared to standard antidiabetic drug acarbose. The most potent was benzyl (3,4,5-trimethoxyphenyl) carbamate (12) with IC50 = 49.85 +/- 0.10 mu M. In vitro cytotoxicity of the investigated compounds was tested on three human cancer cell lines HeLa, A549 and MDA-MB-453 using MTT assay. The best antitumour activity was achieved with compound 2 (trans-5-phenethyl-1-phenylhexahydro-1H-imidazo[4,5-c] pyridin-2(3H)-one) against MDA-MB-453 human breast cancer cell line (IC50 = 83.41 +/- 1.60 mu M). Cyclic ureas and carbamates showed promising anti-alpha-glucosidase activity and should be further tested as potential antidiabetic drugs. The PLS model of preliminary QSAR study indicated that, in planing the future synthesis of more potent compounds, the newly designed should have the substituents capable of polar interactions with receptor sites in various positions, while avoiding the increase of their lipophilicity.",
publisher = "Taylor & Francis Ltd, Abingdon",
journal = "Journal of Enzyme Inhibition and Medicinal Chemistry",
title = "alpha-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives",
volume = "32",
number = "1",
pages = "298-303",
doi = "10.1080/14756366.2016.1250754"
}
Popović-Đorđevic, J., Jevtić, I. I., Grozdanic, N. D., Šegan, S. B., Zlatović, M., Ivanović, M.,& Stanojković, T. (2017). alpha-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives.
Journal of Enzyme Inhibition and Medicinal Chemistry
Taylor & Francis Ltd, Abingdon., 32(1), 298-303.
https://doi.org/10.1080/14756366.2016.1250754
Popović-Đorđevic J, Jevtić II, Grozdanic ND, Šegan SB, Zlatović M, Ivanović M, Stanojković T. alpha-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives. Journal of Enzyme Inhibition and Medicinal Chemistry. 2017;32(1):298-303
Popović-Đorđevic Jelena, Jevtić Ivana I., Grozdanic Nadja Dj, Šegan Sandra B., Zlatović Mario, Ivanović Milovan, Stanojković Tatjana, "alpha-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives" Journal of Enzyme Inhibition and Medicinal Chemistry, 32, no. 1 (2017):298-303,
https://doi.org/10.1080/14756366.2016.1250754 .
7
9
10

Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa

Aleksić, Ivana; Šegan, Sandra B.; Andrić, Filip; Zlatović, Mario; Morić, Ivana; Opsenica, Dejan M.; Šenerović, Lidija

(Amer Chemical Soc, Washington, 2017)

TY  - JOUR
AU  - Aleksić, Ivana
AU  - Šegan, Sandra B.
AU  - Andrić, Filip
AU  - Zlatović, Mario
AU  - Morić, Ivana
AU  - Opsenica, Dejan M.
AU  - Šenerović, Lidija
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2461
AB  - Antibiotic resistance has become a serious global threat to public health; therefore, improved strategies and structurally novel antimicrobials are urgently needed to combat infectious diseases. Here we report a new type of highly potent 4-aminoquinoline derivatives as quorum sensing inhibitors in Serratia marcescens and Pseudomonas aeruginosa, exhibiting weak bactericidal activities (minimum inhibitory concentration (MIC)  gt  400 mu M). Through detailed structure-activity study, we have identified 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines (5 and 10) as biofilm formation inhibitors with 50% biofilm inhibition at 69 mu M and 63 mu M in S. marcescens and P. aeruginosa, respectively. These two compounds, 5 and 10, are the first quinoline derivatives with anti-biofilm formation activity reported in S. marcescens. Quantitative structure-activity relationship (QSAR) analysis identified structural descriptors such as Wiener indices, hyper-distance-path index (HDPI), mean topological charge (MTC), topological charge index (TCI), and log D(o/w)exp as the most influential in biofilm inhibition in this bacterial species. Derivative 10 is one of the most potent quinoline type inhibitors of pyocyanin production described so far (IC50 = 2.5 mu M). While we have demonstrated that 5 and 10 act as Pseudomonas quinolone system (PQS) antagonists, the mechanism of inhibition of S. marcescens biofilm formation with these compounds remains open since signaling similar to P. aeruginosa PQS system has not yet been described in Serratia and activity of these compounds on acylhomoserine lactone (AHL) signaling has not been detected. Our data show that 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines present the promising scaffolds for developing antivirulence and anti-biofilm formation agents against multidrug-resistant bacterial species.
PB  - Amer Chemical Soc, Washington
T2  - ACS Chemical Biology
T1  - Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa
VL  - 12
IS  - 5
SP  - 1425
EP  - 1434
DO  - 10.1021/acschembio.6b01149
ER  - 
@article{
author = "Aleksić, Ivana and Šegan, Sandra B. and Andrić, Filip and Zlatović, Mario and Morić, Ivana and Opsenica, Dejan M. and Šenerović, Lidija",
year = "2017",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2461",
abstract = "Antibiotic resistance has become a serious global threat to public health; therefore, improved strategies and structurally novel antimicrobials are urgently needed to combat infectious diseases. Here we report a new type of highly potent 4-aminoquinoline derivatives as quorum sensing inhibitors in Serratia marcescens and Pseudomonas aeruginosa, exhibiting weak bactericidal activities (minimum inhibitory concentration (MIC)  gt  400 mu M). Through detailed structure-activity study, we have identified 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines (5 and 10) as biofilm formation inhibitors with 50% biofilm inhibition at 69 mu M and 63 mu M in S. marcescens and P. aeruginosa, respectively. These two compounds, 5 and 10, are the first quinoline derivatives with anti-biofilm formation activity reported in S. marcescens. Quantitative structure-activity relationship (QSAR) analysis identified structural descriptors such as Wiener indices, hyper-distance-path index (HDPI), mean topological charge (MTC), topological charge index (TCI), and log D(o/w)exp as the most influential in biofilm inhibition in this bacterial species. Derivative 10 is one of the most potent quinoline type inhibitors of pyocyanin production described so far (IC50 = 2.5 mu M). While we have demonstrated that 5 and 10 act as Pseudomonas quinolone system (PQS) antagonists, the mechanism of inhibition of S. marcescens biofilm formation with these compounds remains open since signaling similar to P. aeruginosa PQS system has not yet been described in Serratia and activity of these compounds on acylhomoserine lactone (AHL) signaling has not been detected. Our data show that 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines present the promising scaffolds for developing antivirulence and anti-biofilm formation agents against multidrug-resistant bacterial species.",
publisher = "Amer Chemical Soc, Washington",
journal = "ACS Chemical Biology",
title = "Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa",
volume = "12",
number = "5",
pages = "1425-1434",
doi = "10.1021/acschembio.6b01149"
}
Aleksić, I., Šegan, S. B., Andrić, F., Zlatović, M., Morić, I., Opsenica, D. M.,& Šenerović, L. (2017). Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa.
ACS Chemical Biology
Amer Chemical Soc, Washington., 12(5), 1425-1434.
https://doi.org/10.1021/acschembio.6b01149
Aleksić I, Šegan SB, Andrić F, Zlatović M, Morić I, Opsenica DM, Šenerović L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa. ACS Chemical Biology. 2017;12(5):1425-1434
Aleksić Ivana, Šegan Sandra B., Andrić Filip, Zlatović Mario, Morić Ivana, Opsenica Dejan M., Šenerović Lidija, "Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa" ACS Chemical Biology, 12, no. 5 (2017):1425-1434,
https://doi.org/10.1021/acschembio.6b01149 .
2
22
21
22

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

Šegan, Sandra B.; Božinović, Nina S.; Opsenica, Igor; Andrić, Filip

(Wiley-V C H Verlag Gmbh, Weinheim, 2017)

TY  - JOUR
AU  - Šegan, Sandra B.
AU  - Božinović, Nina S.
AU  - Opsenica, Igor
AU  - Andrić, Filip
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2462
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 B. and Božinović, Nina S. and Opsenica, Igor and Andrić, Filip",
year = "2017",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2462",
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. B., Božinović, N. S., 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.
Journal of Separation Science
Wiley-V C H Verlag Gmbh, Weinheim., 40(10), 2089-2096.
https://doi.org/10.1002/jssc.201601442
Šegan SB, Božinović NS, Opsenica I, Andrić F. Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs. Journal of Separation Science. 2017;40(10):2089-2096
Šegan Sandra B., Božinović Nina S., Opsenica Igor, Andrić Filip, "Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs" Journal of Separation Science, 40, no. 10 (2017):2089-2096,
https://doi.org/10.1002/jssc.201601442 .
13
12
12

Supplementary data for the article: Šegan, S.; Opsenica, I.; Zlatović, M.; Milojković-Opsenica, D.; Šolaja, B. Quantitative Structure Retention/Activity Relationships of Biologically Relevant 4-Amino-7-Chloroquinoline Based Compounds. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 2016, 1012–1013, 144–152. https://doi.org/10.1016/j.jchromb.2016.01.033

Šegan, Sandra B.; Opsenica, Igor; Zlatović, Mario; Milojković-Opsenica, Dušanka; Šolaja, Bogdan A.

(Elsevier Science Bv, Amsterdam, 2016)

TY  - BOOK
AU  - Šegan, Sandra B.
AU  - Opsenica, Igor
AU  - Zlatović, Mario
AU  - Milojković-Opsenica, Dušanka
AU  - Šolaja, Bogdan A.
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3603
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Chromatography B: Analytical Technologies in the Biomedical and L
T1  - Supplementary data for the article: Šegan, S.; Opsenica, I.; Zlatović, M.; Milojković-Opsenica, D.; Šolaja, B. Quantitative Structure Retention/Activity Relationships of Biologically Relevant 4-Amino-7-Chloroquinoline Based Compounds. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 2016, 1012–1013, 144–152. https://doi.org/10.1016/j.jchromb.2016.01.033
ER  - 
@book{
author = "Šegan, Sandra B. and Opsenica, Igor and Zlatović, Mario and Milojković-Opsenica, Dušanka and Šolaja, Bogdan A.",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3603",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Chromatography B: Analytical Technologies in the Biomedical and L",
title = "Supplementary data for the article: Šegan, S.; Opsenica, I.; Zlatović, M.; Milojković-Opsenica, D.; Šolaja, B. Quantitative Structure Retention/Activity Relationships of Biologically Relevant 4-Amino-7-Chloroquinoline Based Compounds. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 2016, 1012–1013, 144–152. https://doi.org/10.1016/j.jchromb.2016.01.033"
}
Šegan, S. B., Opsenica, I., Zlatović, M., Milojković-Opsenica, D.,& Šolaja, B. A. (2016). Supplementary data for the article: Šegan, S.; Opsenica, I.; Zlatović, M.; Milojković-Opsenica, D.; Šolaja, B. Quantitative Structure Retention/Activity Relationships of Biologically Relevant 4-Amino-7-Chloroquinoline Based Compounds. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 2016, 1012–1013, 144–152. https://doi.org/10.1016/j.jchromb.2016.01.033.
Journal of Chromatography B: Analytical Technologies in the Biomedical and L
Elsevier Science Bv, Amsterdam..
Šegan SB, Opsenica I, Zlatović M, Milojković-Opsenica D, Šolaja BA. Supplementary data for the article: Šegan, S.; Opsenica, I.; Zlatović, M.; Milojković-Opsenica, D.; Šolaja, B. Quantitative Structure Retention/Activity Relationships of Biologically Relevant 4-Amino-7-Chloroquinoline Based Compounds. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 2016, 1012–1013, 144–152. https://doi.org/10.1016/j.jchromb.2016.01.033. Journal of Chromatography B: Analytical Technologies in the Biomedical and L. 2016;
Šegan Sandra B., Opsenica Igor, Zlatović Mario, Milojković-Opsenica Dušanka, Šolaja Bogdan A., "Supplementary data for the article: Šegan, S.; Opsenica, I.; Zlatović, M.; Milojković-Opsenica, D.; Šolaja, B. Quantitative Structure Retention/Activity Relationships of Biologically Relevant 4-Amino-7-Chloroquinoline Based Compounds. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 2016, 1012–1013, 144–152. https://doi.org/10.1016/j.jchromb.2016.01.033" Journal of Chromatography B: Analytical Technologies in the Biomedical and L (2016)

Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives

Božinović, Nina S.; Šegan, Sandra B.; Vojnović, Sandra; Pavić, Aleksandar; Šolaja, Bogdan A.; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Wiley, Hoboken, 2016)

TY  - JOUR
AU  - Božinović, Nina S.
AU  - Šegan, Sandra B.
AU  - Vojnović, Sandra
AU  - Pavić, Aleksandar
AU  - Šolaja, Bogdan A.
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3620
AB  - A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.
PB  - Wiley, Hoboken
T2  - Chemical Biology and Drug Design
T1  - Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives
VL  - 88
IS  - 6
SP  - 795
EP  - 806
DO  - 10.1111/cbdd.12809
ER  - 
@article{
author = "Božinović, Nina S. and Šegan, Sandra B. and Vojnović, Sandra and Pavić, Aleksandar and Šolaja, Bogdan A. and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3620",
abstract = "A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology and Drug Design",
title = "Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives",
volume = "88",
number = "6",
pages = "795-806",
doi = "10.1111/cbdd.12809"
}
Božinović, N. S., Šegan, S. B., Vojnović, S., Pavić, A., Šolaja, B. A., Nikodinović-Runić, J.,& Opsenica, I. (2016). Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives.
Chemical Biology and Drug Design
Wiley, Hoboken., 88(6), 795-806.
https://doi.org/10.1111/cbdd.12809
Božinović NS, Šegan SB, Vojnović S, Pavić A, Šolaja BA, Nikodinović-Runić J, Opsenica I. Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives. Chemical Biology and Drug Design. 2016;88(6):795-806
Božinović Nina S., Šegan Sandra B., Vojnović Sandra, Pavić Aleksandar, Šolaja Bogdan A., Nikodinović-Runić Jasmina, Opsenica Igor, "Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives" Chemical Biology and Drug Design, 88, no. 6 (2016):795-806,
https://doi.org/10.1111/cbdd.12809 .
1
6
7
6

Supplementary material for the article: Božinović, N.; Šegan, S.; Vojnovic, S.; Pavic, A.; Šolaja, B. A.; Nikodinovic-Runic, J.; Opsenica, I. M. Synthesis and Anti-Candida Activity of Novel Benzothiepino[3,2-c]Pyridine Derivatives. Chemical Biology and Drug Design 2016, 88 (6), 795–806. https://doi.org/10.1111/cbdd.12809

Božinović, Nina S.; Šegan, Sandra B.; Vojnović, Sandra; Pavić, Aleksandar; Šolaja, Bogdan A.; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Wiley, Hoboken, 2016)

TY  - BOOK
AU  - Božinović, Nina S.
AU  - Šegan, Sandra B.
AU  - Vojnović, Sandra
AU  - Pavić, Aleksandar
AU  - Šolaja, Bogdan A.
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3621
PB  - Wiley, Hoboken
T2  - Chemical Biology and Drug Design
T1  - Supplementary material for the article: Božinović, N.; Šegan, S.; Vojnovic, S.; Pavic, A.; Šolaja, B. A.; Nikodinovic-Runic, J.; Opsenica, I. M. Synthesis and Anti-Candida Activity of Novel Benzothiepino[3,2-c]Pyridine Derivatives. Chemical Biology and Drug Design 2016, 88 (6), 795–806. https://doi.org/10.1111/cbdd.12809
ER  - 
@book{
author = "Božinović, Nina S. and Šegan, Sandra B. and Vojnović, Sandra and Pavić, Aleksandar and Šolaja, Bogdan A. and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3621",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology and Drug Design",
title = "Supplementary material for the article: Božinović, N.; Šegan, S.; Vojnovic, S.; Pavic, A.; Šolaja, B. A.; Nikodinovic-Runic, J.; Opsenica, I. M. Synthesis and Anti-Candida Activity of Novel Benzothiepino[3,2-c]Pyridine Derivatives. Chemical Biology and Drug Design 2016, 88 (6), 795–806. https://doi.org/10.1111/cbdd.12809"
}
Božinović, N. S., Šegan, S. B., Vojnović, S., Pavić, A., Šolaja, B. A., Nikodinović-Runić, J.,& Opsenica, I. (2016). Supplementary material for the article: Božinović, N.; Šegan, S.; Vojnovic, S.; Pavic, A.; Šolaja, B. A.; Nikodinovic-Runic, J.; Opsenica, I. M. Synthesis and Anti-Candida Activity of Novel Benzothiepino[3,2-c]Pyridine Derivatives. Chemical Biology and Drug Design 2016, 88 (6), 795–806. https://doi.org/10.1111/cbdd.12809.
Chemical Biology and Drug Design
Wiley, Hoboken..
Božinović NS, Šegan SB, Vojnović S, Pavić A, Šolaja BA, Nikodinović-Runić J, Opsenica I. Supplementary material for the article: Božinović, N.; Šegan, S.; Vojnovic, S.; Pavic, A.; Šolaja, B. A.; Nikodinovic-Runic, J.; Opsenica, I. M. Synthesis and Anti-Candida Activity of Novel Benzothiepino[3,2-c]Pyridine Derivatives. Chemical Biology and Drug Design 2016, 88 (6), 795–806. https://doi.org/10.1111/cbdd.12809. Chemical Biology and Drug Design. 2016;
Božinović Nina S., Šegan Sandra B., Vojnović Sandra, Pavić Aleksandar, Šolaja Bogdan A., Nikodinović-Runić Jasmina, Opsenica Igor, "Supplementary material for the article: Božinović, N.; Šegan, S.; Vojnovic, S.; Pavic, A.; Šolaja, B. A.; Nikodinovic-Runic, J.; Opsenica, I. M. Synthesis and Anti-Candida Activity of Novel Benzothiepino[3,2-c]Pyridine Derivatives. Chemical Biology and Drug Design 2016, 88 (6), 795–806. https://doi.org/10.1111/cbdd.12809" Chemical Biology and Drug Design (2016)

Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives

Božinović, Nina S.; Šegan, Sandra B.; Vojnović, Sandra; Pavić, Aleksandar; Šolaja, Bogdan A.; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Wiley, Hoboken, 2016)

TY  - JOUR
AU  - Božinović, Nina S.
AU  - Šegan, Sandra B.
AU  - Vojnović, Sandra
AU  - Pavić, Aleksandar
AU  - Šolaja, Bogdan A.
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2346
AB  - A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.
PB  - Wiley, Hoboken
T2  - Chemical Biology and Drug Design
T1  - Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives
VL  - 88
IS  - 6
SP  - 795
EP  - 806
DO  - 10.1111/cbdd.12809
ER  - 
@article{
author = "Božinović, Nina S. and Šegan, Sandra B. and Vojnović, Sandra and Pavić, Aleksandar and Šolaja, Bogdan A. and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2346",
abstract = "A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology and Drug Design",
title = "Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives",
volume = "88",
number = "6",
pages = "795-806",
doi = "10.1111/cbdd.12809"
}
Božinović, N. S., Šegan, S. B., Vojnović, S., Pavić, A., Šolaja, B. A., Nikodinović-Runić, J.,& Opsenica, I. (2016). Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives.
Chemical Biology and Drug Design
Wiley, Hoboken., 88(6), 795-806.
https://doi.org/10.1111/cbdd.12809
Božinović NS, Šegan SB, Vojnović S, Pavić A, Šolaja BA, Nikodinović-Runić J, Opsenica I. Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives. Chemical Biology and Drug Design. 2016;88(6):795-806
Božinović Nina S., Šegan Sandra B., Vojnović Sandra, Pavić Aleksandar, Šolaja Bogdan A., Nikodinović-Runić Jasmina, Opsenica Igor, "Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives" Chemical Biology and Drug Design, 88, no. 6 (2016):795-806,
https://doi.org/10.1111/cbdd.12809 .
1
6
7
6

Linear modeling of the soil-water partition coefficient normalized to organic carbon content by reversed-phase thin-layer chromatography

Andrić, Filip; Šegan, Sandra B.; Dramićanin, Aleksandra M.; Majstorović, Helena; Milojković-Opsenica, Dušanka

(Elsevier Science Bv, Amsterdam, 2016)

TY  - JOUR
AU  - Andrić, Filip
AU  - Šegan, Sandra B.
AU  - Dramićanin, Aleksandra M.
AU  - Majstorović, Helena
AU  - Milojković-Opsenica, Dušanka
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3561
AB  - Soil-water partition coefficient normalized to the organic carbon.content (K-OC) is one of the crucial properties influencing the fate of organic compounds in the environment. Chromatographic methods are well established alternative for direct sorption techniques used for K-OC determination. The present work proposes reversed-phase thin-layer chromatography (RP-TLC) as a simpler, yet equally accurate method as officially recommended HPLC technique. Several TLC systems were studied including octadecyl-(RP18) and cyano-(CN) modified silica layers in combination with methanol-water and acetonitrile-water mixtures as mobile phases. In total 50 compounds of different molecular shape, size, and various ability to establish specific interactions were selected (phenols, beznodiazepines, triazine herbicides, and polyaromatic hydrocarbons). Calibration set of 29 compounds with known logK(OC) values determined by sorption experiments was used to build simple univariate calibrations, Principal Component Regression (PCR) and Partial Least Squares (PLS) models between logK(OC) and TLC retention parameters. Models exhibit good statistical performance, indicating that CN-layers contribute better to logK(OC) modeling than RP18-silica. The most promising TLC methods, officially recommended HPLC method, and four in silico estimation approaches have been compared by non-parametric Sum of Ranking Differences approach (SRD). The best estimations of logK(OC) values were achieved by simple univariate calibration of TLC retention data involving CN-silica layers and moderate content of methanol (40-50% v/v). They were ranked far well compared to the officially recommended HPLC method which was ranked in the middle. The worst estimates have been obtained from in silico computations based on octanol-water partition coefficient. Linear Solvation Energy Relationship study revealed that increased polarity of CN-layers over RP18 in combination with methanol-water mixtures is the key to better modeling of logK(OC) through significant diminishing of dipolar and proton accepting influence of the mobile phase as well as enhancing molar refractivity in excess of the chromatographic systems. (C) 2016 Elsevier B.V. All rights reserved.
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Chromatography A
T1  - Linear modeling of the soil-water partition coefficient normalized to organic carbon content by reversed-phase thin-layer chromatography
VL  - 1458
SP  - 136
EP  - 144
DO  - 10.1016/j.chroma.2016.06.063
ER  - 
@article{
author = "Andrić, Filip and Šegan, Sandra B. and Dramićanin, Aleksandra M. and Majstorović, Helena and Milojković-Opsenica, Dušanka",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3561",
abstract = "Soil-water partition coefficient normalized to the organic carbon.content (K-OC) is one of the crucial properties influencing the fate of organic compounds in the environment. Chromatographic methods are well established alternative for direct sorption techniques used for K-OC determination. The present work proposes reversed-phase thin-layer chromatography (RP-TLC) as a simpler, yet equally accurate method as officially recommended HPLC technique. Several TLC systems were studied including octadecyl-(RP18) and cyano-(CN) modified silica layers in combination with methanol-water and acetonitrile-water mixtures as mobile phases. In total 50 compounds of different molecular shape, size, and various ability to establish specific interactions were selected (phenols, beznodiazepines, triazine herbicides, and polyaromatic hydrocarbons). Calibration set of 29 compounds with known logK(OC) values determined by sorption experiments was used to build simple univariate calibrations, Principal Component Regression (PCR) and Partial Least Squares (PLS) models between logK(OC) and TLC retention parameters. Models exhibit good statistical performance, indicating that CN-layers contribute better to logK(OC) modeling than RP18-silica. The most promising TLC methods, officially recommended HPLC method, and four in silico estimation approaches have been compared by non-parametric Sum of Ranking Differences approach (SRD). The best estimations of logK(OC) values were achieved by simple univariate calibration of TLC retention data involving CN-silica layers and moderate content of methanol (40-50% v/v). They were ranked far well compared to the officially recommended HPLC method which was ranked in the middle. The worst estimates have been obtained from in silico computations based on octanol-water partition coefficient. Linear Solvation Energy Relationship study revealed that increased polarity of CN-layers over RP18 in combination with methanol-water mixtures is the key to better modeling of logK(OC) through significant diminishing of dipolar and proton accepting influence of the mobile phase as well as enhancing molar refractivity in excess of the chromatographic systems. (C) 2016 Elsevier B.V. All rights reserved.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Chromatography A",
title = "Linear modeling of the soil-water partition coefficient normalized to organic carbon content by reversed-phase thin-layer chromatography",
volume = "1458",
pages = "136-144",
doi = "10.1016/j.chroma.2016.06.063"
}
Andrić, F., Šegan, S. B., Dramićanin, A. M., Majstorović, H.,& Milojković-Opsenica, D. (2016). Linear modeling of the soil-water partition coefficient normalized to organic carbon content by reversed-phase thin-layer chromatography.
Journal of Chromatography A
Elsevier Science Bv, Amsterdam., 1458, 136-144.
https://doi.org/10.1016/j.chroma.2016.06.063
Andrić F, Šegan SB, Dramićanin AM, Majstorović H, Milojković-Opsenica D. Linear modeling of the soil-water partition coefficient normalized to organic carbon content by reversed-phase thin-layer chromatography. Journal of Chromatography A. 2016;1458:136-144
Andrić Filip, Šegan Sandra B., Dramićanin Aleksandra M., Majstorović Helena, Milojković-Opsenica Dušanka, "Linear modeling of the soil-water partition coefficient normalized to organic carbon content by reversed-phase thin-layer chromatography" Journal of Chromatography A, 1458 (2016):136-144,
https://doi.org/10.1016/j.chroma.2016.06.063 .
3
8
5
8

Supplementary data for the article: Andrić, F.; Šegan, S.; Dramićanin, A.; Majstorović, H.; Milojković-Opsenica, D. Linear Modeling of the Soil-Water Partition Coefficient Normalized to Organic Carbon Content by Reversed-Phase Thin-Layer Chromatography. Journal of Chromatography A 2016, 1458, 136–144. https://doi.org/10.1016/j.chroma.2016.06.063

Andrić, Filip; Šegan, Sandra B.; Dramićanin, Aleksandra M.; Majstorović, Helena; Milojković-Opsenica, Dušanka

(Elsevier Science Bv, Amsterdam, 2016)

TY  - BOOK
AU  - Andrić, Filip
AU  - Šegan, Sandra B.
AU  - Dramićanin, Aleksandra M.
AU  - Majstorović, Helena
AU  - Milojković-Opsenica, Dušanka
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3562
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Chromatography A
T1  - Supplementary data for the article: Andrić, F.; Šegan, S.; Dramićanin, A.; Majstorović, H.; Milojković-Opsenica, D. Linear Modeling of the Soil-Water Partition Coefficient Normalized to Organic Carbon Content by Reversed-Phase Thin-Layer Chromatography. Journal of Chromatography A 2016, 1458, 136–144. https://doi.org/10.1016/j.chroma.2016.06.063
ER  - 
@book{
author = "Andrić, Filip and Šegan, Sandra B. and Dramićanin, Aleksandra M. and Majstorović, Helena and Milojković-Opsenica, Dušanka",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3562",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Chromatography A",
title = "Supplementary data for the article: Andrić, F.; Šegan, S.; Dramićanin, A.; Majstorović, H.; Milojković-Opsenica, D. Linear Modeling of the Soil-Water Partition Coefficient Normalized to Organic Carbon Content by Reversed-Phase Thin-Layer Chromatography. Journal of Chromatography A 2016, 1458, 136–144. https://doi.org/10.1016/j.chroma.2016.06.063"
}
Andrić, F., Šegan, S. B., Dramićanin, A. M., Majstorović, H.,& Milojković-Opsenica, D. (2016). Supplementary data for the article: Andrić, F.; Šegan, S.; Dramićanin, A.; Majstorović, H.; Milojković-Opsenica, D. Linear Modeling of the Soil-Water Partition Coefficient Normalized to Organic Carbon Content by Reversed-Phase Thin-Layer Chromatography. Journal of Chromatography A 2016, 1458, 136–144. https://doi.org/10.1016/j.chroma.2016.06.063.
Journal of Chromatography A
Elsevier Science Bv, Amsterdam..
Andrić F, Šegan SB, Dramićanin AM, Majstorović H, Milojković-Opsenica D. Supplementary data for the article: Andrić, F.; Šegan, S.; Dramićanin, A.; Majstorović, H.; Milojković-Opsenica, D. Linear Modeling of the Soil-Water Partition Coefficient Normalized to Organic Carbon Content by Reversed-Phase Thin-Layer Chromatography. Journal of Chromatography A 2016, 1458, 136–144. https://doi.org/10.1016/j.chroma.2016.06.063. Journal of Chromatography A. 2016;
Andrić Filip, Šegan Sandra B., Dramićanin Aleksandra M., Majstorović Helena, Milojković-Opsenica Dušanka, "Supplementary data for the article: Andrić, F.; Šegan, S.; Dramićanin, A.; Majstorović, H.; Milojković-Opsenica, D. Linear Modeling of the Soil-Water Partition Coefficient Normalized to Organic Carbon Content by Reversed-Phase Thin-Layer Chromatography. Journal of Chromatography A 2016, 1458, 136–144. https://doi.org/10.1016/j.chroma.2016.06.063" Journal of Chromatography A (2016)

Multivariate assessment of lipophilicity scales-computational and reversed phase thin-layer chromatographic indices

Andrić, Filip; Bajusz, David; Racz, Anita; Šegan, Sandra B.; Héberger, Karoly

(Elsevier Science Bv, Amsterdam, 2016)

TY  - JOUR
AU  - Andrić, Filip
AU  - Bajusz, David
AU  - Racz, Anita
AU  - Šegan, Sandra B.
AU  - Héberger, Karoly
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3576
AB  - Needs for fast, yet reliable means of assessing the lipophilicities of diverse compounds resulted in the development of various in silico and chromatographic approaches that are faster, cheaper, and greener compared to the traditional shake-flask method. However, at present no accepted "standard" approach exists for their comparison and selection of the most appropriate one(s). This is of utmost importance when it comes to the development of new lipophilicity indices, or the assessment of the lipophilicity of newly synthesized compounds. In this study, 50 well-known, diverse compounds of significant pharmaceutical and environmental importance have been selected and examined. Octanol-water partition coefficients have been measured with the shake-flask method for most of them. Their retentions have been studied in typical reversed thin-layer chromatographic systems, involving the most frequently employed stationary phases (octadecyl- and cyano-modified silica), and acetonitrile and methanol as mobile phase constituents. Twelve computationally estimated logP-s and twenty chromatographic indices together with the shake-flask octanol-water partition coefficient have been investigated with classical chemometric approaches such as principal component analysis (PCA), hierarchical cluster analysis (HCA), Pearson's and Spearman's correlation matrices, as well as novel non-parametric methods: sum of ranking differences (SRD) and generalized pairwise correlation method (GPCM). Novel SRD and GPCM methods have been introduced based on the Comparisons with One VAriable (lipophilicity metric) at a Time (COVAT). For the visualization of COVAT results, a heatmap format was introduced. Analysis of variance (ANOVA) was applied to reveal the dominant factors between computational logPs and various chromatographic measures. In consensus-based comparisons, the shake-flask method performed the best, closely followed by computational estimates, while the chromatographic estimates often overlap with in silico assessments, mostly with methods involving octadecyl-modified silica stationary phases. The ones that employ cyano-modified silica perform generally worse. The introduction of alternative coloring schemes for the covariance matrices and SRD/GPCM heatmaps enables the discovery of intrinsic relationships among lipophilicity scales and the selection of best/worst measures. Closest to the recommended logK(ow) values are ClogP and the first principal component scores obtained on octadecyl-silica stationary phase in combination with methanol-water mobile phase, while the usage of slopes derived from Soczewinski-Matyisik equation should be avoided. (C) 2016 Elsevier B.V. All rights reserved.
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Pharmaceutical and Biomedical Analysis
T1  - Multivariate assessment of lipophilicity scales-computational and reversed phase thin-layer chromatographic indices
VL  - 127
SP  - 81
EP  - 93
DO  - 10.1016/j.jpba.2016.04.001
ER  - 
@article{
author = "Andrić, Filip and Bajusz, David and Racz, Anita and Šegan, Sandra B. and Héberger, Karoly",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3576",
abstract = "Needs for fast, yet reliable means of assessing the lipophilicities of diverse compounds resulted in the development of various in silico and chromatographic approaches that are faster, cheaper, and greener compared to the traditional shake-flask method. However, at present no accepted "standard" approach exists for their comparison and selection of the most appropriate one(s). This is of utmost importance when it comes to the development of new lipophilicity indices, or the assessment of the lipophilicity of newly synthesized compounds. In this study, 50 well-known, diverse compounds of significant pharmaceutical and environmental importance have been selected and examined. Octanol-water partition coefficients have been measured with the shake-flask method for most of them. Their retentions have been studied in typical reversed thin-layer chromatographic systems, involving the most frequently employed stationary phases (octadecyl- and cyano-modified silica), and acetonitrile and methanol as mobile phase constituents. Twelve computationally estimated logP-s and twenty chromatographic indices together with the shake-flask octanol-water partition coefficient have been investigated with classical chemometric approaches such as principal component analysis (PCA), hierarchical cluster analysis (HCA), Pearson's and Spearman's correlation matrices, as well as novel non-parametric methods: sum of ranking differences (SRD) and generalized pairwise correlation method (GPCM). Novel SRD and GPCM methods have been introduced based on the Comparisons with One VAriable (lipophilicity metric) at a Time (COVAT). For the visualization of COVAT results, a heatmap format was introduced. Analysis of variance (ANOVA) was applied to reveal the dominant factors between computational logPs and various chromatographic measures. In consensus-based comparisons, the shake-flask method performed the best, closely followed by computational estimates, while the chromatographic estimates often overlap with in silico assessments, mostly with methods involving octadecyl-modified silica stationary phases. The ones that employ cyano-modified silica perform generally worse. The introduction of alternative coloring schemes for the covariance matrices and SRD/GPCM heatmaps enables the discovery of intrinsic relationships among lipophilicity scales and the selection of best/worst measures. Closest to the recommended logK(ow) values are ClogP and the first principal component scores obtained on octadecyl-silica stationary phase in combination with methanol-water mobile phase, while the usage of slopes derived from Soczewinski-Matyisik equation should be avoided. (C) 2016 Elsevier B.V. All rights reserved.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Pharmaceutical and Biomedical Analysis",
title = "Multivariate assessment of lipophilicity scales-computational and reversed phase thin-layer chromatographic indices",
volume = "127",
pages = "81-93",
doi = "10.1016/j.jpba.2016.04.001"
}
Andrić, F., Bajusz, D., Racz, A., Šegan, S. B.,& Héberger, K. (2016). Multivariate assessment of lipophilicity scales-computational and reversed phase thin-layer chromatographic indices.
Journal of Pharmaceutical and Biomedical Analysis
Elsevier Science Bv, Amsterdam., 127, 81-93.
https://doi.org/10.1016/j.jpba.2016.04.001
Andrić F, Bajusz D, Racz A, Šegan SB, Héberger K. Multivariate assessment of lipophilicity scales-computational and reversed phase thin-layer chromatographic indices. Journal of Pharmaceutical and Biomedical Analysis. 2016;127:81-93
Andrić Filip, Bajusz David, Racz Anita, Šegan Sandra B., Héberger Karoly, "Multivariate assessment of lipophilicity scales-computational and reversed phase thin-layer chromatographic indices" Journal of Pharmaceutical and Biomedical Analysis, 127 (2016):81-93,
https://doi.org/10.1016/j.jpba.2016.04.001 .
37
34
36

Supplementary data for the article: Andrić, F.; Bajusz, D.; Rácz, A.; Šegan, S.; Héberger, K. Multivariate Assessment of Lipophilicity Scales—Computational and Reversed Phase Thin-Layer Chromatographic Indices. J. Pharm. Biomed. Anal. 2016, 127, 81–93. https://doi.org/10.1016/j.jpba.2016.04.001

Andrić, Filip; Bajusz, David; Racz, Anita; Šegan, Sandra B.; Héberger, Karoly

(Elsevier Science Bv, Amsterdam, 2016)

TY  - BOOK
AU  - Andrić, Filip
AU  - Bajusz, David
AU  - Racz, Anita
AU  - Šegan, Sandra B.
AU  - Héberger, Karoly
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3577
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Pharmaceutical and Biomedical Analysis
T1  - Supplementary data for the article: Andrić, F.; Bajusz, D.; Rácz, A.; Šegan, S.; Héberger, K. Multivariate Assessment of Lipophilicity Scales—Computational and Reversed Phase Thin-Layer Chromatographic Indices. J. Pharm. Biomed. Anal. 2016, 127, 81–93. https://doi.org/10.1016/j.jpba.2016.04.001
ER  - 
@book{
author = "Andrić, Filip and Bajusz, David and Racz, Anita and Šegan, Sandra B. and Héberger, Karoly",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3577",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Pharmaceutical and Biomedical Analysis",
title = "Supplementary data for the article: Andrić, F.; Bajusz, D.; Rácz, A.; Šegan, S.; Héberger, K. Multivariate Assessment of Lipophilicity Scales—Computational and Reversed Phase Thin-Layer Chromatographic Indices. J. Pharm. Biomed. Anal. 2016, 127, 81–93. https://doi.org/10.1016/j.jpba.2016.04.001"
}
Andrić, F., Bajusz, D., Racz, A., Šegan, S. B.,& Héberger, K. (2016). Supplementary data for the article: Andrić, F.; Bajusz, D.; Rácz, A.; Šegan, S.; Héberger, K. Multivariate Assessment of Lipophilicity Scales—Computational and Reversed Phase Thin-Layer Chromatographic Indices. J. Pharm. Biomed. Anal. 2016, 127, 81–93. https://doi.org/10.1016/j.jpba.2016.04.001.
Journal of Pharmaceutical and Biomedical Analysis
Elsevier Science Bv, Amsterdam..
Andrić F, Bajusz D, Racz A, Šegan SB, Héberger K. Supplementary data for the article: Andrić, F.; Bajusz, D.; Rácz, A.; Šegan, S.; Héberger, K. Multivariate Assessment of Lipophilicity Scales—Computational and Reversed Phase Thin-Layer Chromatographic Indices. J. Pharm. Biomed. Anal. 2016, 127, 81–93. https://doi.org/10.1016/j.jpba.2016.04.001. Journal of Pharmaceutical and Biomedical Analysis. 2016;
Andrić Filip, Bajusz David, Racz Anita, Šegan Sandra B., Héberger Karoly, "Supplementary data for the article: Andrić, F.; Bajusz, D.; Rácz, A.; Šegan, S.; Héberger, K. Multivariate Assessment of Lipophilicity Scales—Computational and Reversed Phase Thin-Layer Chromatographic Indices. J. Pharm. Biomed. Anal. 2016, 127, 81–93. https://doi.org/10.1016/j.jpba.2016.04.001" Journal of Pharmaceutical and Biomedical Analysis (2016)

Quantitative structure retention/activity relationships of biologically relevant 4-amino-7-chloroquinoline based compounds

Šegan, Sandra B.; Opsenica, Igor; Zlatović, Mario; Milojković-Opsenica, Dušanka; Šolaja, Bogdan A.

(Elsevier Science Bv, Amsterdam, 2016)

TY  - JOUR
AU  - Šegan, Sandra B.
AU  - Opsenica, Igor
AU  - Zlatović, Mario
AU  - Milojković-Opsenica, Dušanka
AU  - Šolaja, Bogdan A.
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2059
AB  - The chromatographic behaviour of series of 4-amino-7-chloroquinoline (4,7-ACQ) based compounds was studied by reversed-phase thin-layer chromatography (RPTLC) with binary mobile phases containing water and the organic modifiers, DMSO or acetone. The lipophilicity of the studied compounds was determined by extrapolation of retention parameters R-M to pure water content in mobile phase. In order to obtain some basic insight into the chromatographic behaviour and structural features of investigated compounds, PCA was performed on both chromatographic data (R-M values) and calculated 2D and 3D structural descriptors. Both QSRR and QSAR models were built by means of the partial least squares (PLS) statistical method. It was found that descriptors which encode hydrophobic (dispersive) interactions have positive influence on retention, while influence of descriptors encoding polar interactions was negative. According to the obtained PLS model for inhibition of botulinum neurotoxin serotype A light chain, hydrophobic interactions influence positively on the mechanism of action of the investigated 4,7-ACQ while polar interactions are less favoured. Contrary, the results of PLS modelling of activity against Plasmodium falciparum strains (W2, D6 and TM91C235) indicate that higher polarity of 4,7-ACQ contribute to their higher antimalarial activity. (C) 2016 Elsevier B.V. All rights reserved.
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Chromatography B: Analytical Technologies in the Biomedical and L
T1  - Quantitative structure retention/activity relationships of biologically relevant 4-amino-7-chloroquinoline based compounds
VL  - 1012
SP  - 144
EP  - 152
DO  - 10.1016/j.jchromb.2016.01.033
ER  - 
@article{
author = "Šegan, Sandra B. and Opsenica, Igor and Zlatović, Mario and Milojković-Opsenica, Dušanka and Šolaja, Bogdan A.",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2059",
abstract = "The chromatographic behaviour of series of 4-amino-7-chloroquinoline (4,7-ACQ) based compounds was studied by reversed-phase thin-layer chromatography (RPTLC) with binary mobile phases containing water and the organic modifiers, DMSO or acetone. The lipophilicity of the studied compounds was determined by extrapolation of retention parameters R-M to pure water content in mobile phase. In order to obtain some basic insight into the chromatographic behaviour and structural features of investigated compounds, PCA was performed on both chromatographic data (R-M values) and calculated 2D and 3D structural descriptors. Both QSRR and QSAR models were built by means of the partial least squares (PLS) statistical method. It was found that descriptors which encode hydrophobic (dispersive) interactions have positive influence on retention, while influence of descriptors encoding polar interactions was negative. According to the obtained PLS model for inhibition of botulinum neurotoxin serotype A light chain, hydrophobic interactions influence positively on the mechanism of action of the investigated 4,7-ACQ while polar interactions are less favoured. Contrary, the results of PLS modelling of activity against Plasmodium falciparum strains (W2, D6 and TM91C235) indicate that higher polarity of 4,7-ACQ contribute to their higher antimalarial activity. (C) 2016 Elsevier B.V. All rights reserved.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Chromatography B: Analytical Technologies in the Biomedical and L",
title = "Quantitative structure retention/activity relationships of biologically relevant 4-amino-7-chloroquinoline based compounds",
volume = "1012",
pages = "144-152",
doi = "10.1016/j.jchromb.2016.01.033"
}
Šegan, S. B., Opsenica, I., Zlatović, M., Milojković-Opsenica, D.,& Šolaja, B. A. (2016). Quantitative structure retention/activity relationships of biologically relevant 4-amino-7-chloroquinoline based compounds.
Journal of Chromatography B: Analytical Technologies in the Biomedical and L
Elsevier Science Bv, Amsterdam., 1012, 144-152.
https://doi.org/10.1016/j.jchromb.2016.01.033
Šegan SB, Opsenica I, Zlatović M, Milojković-Opsenica D, Šolaja BA. Quantitative structure retention/activity relationships of biologically relevant 4-amino-7-chloroquinoline based compounds. Journal of Chromatography B: Analytical Technologies in the Biomedical and L. 2016;1012:144-152
Šegan Sandra B., Opsenica Igor, Zlatović Mario, Milojković-Opsenica Dušanka, Šolaja Bogdan A., "Quantitative structure retention/activity relationships of biologically relevant 4-amino-7-chloroquinoline based compounds" Journal of Chromatography B: Analytical Technologies in the Biomedical and L, 1012 (2016):144-152,
https://doi.org/10.1016/j.jchromb.2016.01.033 .
1
12
12
13

Chromatographic methods in determination of the soil-water partition coefficient

Andrić, Filip; Šegan, Sandra B.; Tešić, Živoslav Lj.; Milojković-Opsenica, Dušanka

(Taylor & Francis Inc, Philadelphia, 2016)

TY  - JOUR
AU  - Andrić, Filip
AU  - Šegan, Sandra B.
AU  - Tešić, Živoslav Lj.
AU  - Milojković-Opsenica, Dušanka
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2265
AB  - The soil-water partition coefficient normalized to the soil organic carbon content (K-OC) is one of essential properties governing the fate of organic chemicals in the soil-water compartment. It is a parameter of utmost importance when it comes to the removal of toxic organics in the waste water management facilities or placing a new chemical on the market. Since direct determination of K-OC based on tests involving soil-sorption measurements are expensive, time-consuming, tedious, and subject to different experimental difficulties and artifacts, different alternative methods have been developed for rapid indirect experimental determination and estimation of K-OC values. In the scope of the present work, we provide critical and historical overview of development and application of the main chromatographic methods, both high-performance liquid chromatography and thin-layer chromatographic techniques for indirect experimental determination of the soil-water partition coefficient as well as mobility assessment of environmentally important compounds in the soil. Chromatographic methods proved to be promising in this field, which is clearly demonstrated by their implementation in official guidelines for testing the chemicals.
PB  - Taylor & Francis Inc, Philadelphia
T2  - Journal of Liquid Chromatography and Related Technologies
T1  - Chromatographic methods in determination of the soil-water partition coefficient
VL  - 39
IS  - 5-6
SP  - 249
EP  - 256
DO  - 10.1080/10826076.2016.1163173
ER  - 
@article{
author = "Andrić, Filip and Šegan, Sandra B. and Tešić, Živoslav Lj. and Milojković-Opsenica, Dušanka",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2265",
abstract = "The soil-water partition coefficient normalized to the soil organic carbon content (K-OC) is one of essential properties governing the fate of organic chemicals in the soil-water compartment. It is a parameter of utmost importance when it comes to the removal of toxic organics in the waste water management facilities or placing a new chemical on the market. Since direct determination of K-OC based on tests involving soil-sorption measurements are expensive, time-consuming, tedious, and subject to different experimental difficulties and artifacts, different alternative methods have been developed for rapid indirect experimental determination and estimation of K-OC values. In the scope of the present work, we provide critical and historical overview of development and application of the main chromatographic methods, both high-performance liquid chromatography and thin-layer chromatographic techniques for indirect experimental determination of the soil-water partition coefficient as well as mobility assessment of environmentally important compounds in the soil. Chromatographic methods proved to be promising in this field, which is clearly demonstrated by their implementation in official guidelines for testing the chemicals.",
publisher = "Taylor & Francis Inc, Philadelphia",
journal = "Journal of Liquid Chromatography and Related Technologies",
title = "Chromatographic methods in determination of the soil-water partition coefficient",
volume = "39",
number = "5-6",
pages = "249-256",
doi = "10.1080/10826076.2016.1163173"
}
Andrić, F., Šegan, S. B., Tešić, Ž. Lj.,& Milojković-Opsenica, D. (2016). Chromatographic methods in determination of the soil-water partition coefficient.
Journal of Liquid Chromatography and Related Technologies
Taylor & Francis Inc, Philadelphia., 39(5-6), 249-256.
https://doi.org/10.1080/10826076.2016.1163173
Andrić F, Šegan SB, Tešić ŽL, Milojković-Opsenica D. Chromatographic methods in determination of the soil-water partition coefficient. Journal of Liquid Chromatography and Related Technologies. 2016;39(5-6):249-256
Andrić Filip, Šegan Sandra B., Tešić Živoslav Lj., Milojković-Opsenica Dušanka, "Chromatographic methods in determination of the soil-water partition coefficient" Journal of Liquid Chromatography and Related Technologies, 39, no. 5-6 (2016):249-256,
https://doi.org/10.1080/10826076.2016.1163173 .
3
2
3