TY  - JOUR
AU  - Ivanov, Marija
AU  - Matsoukas, Minos-Timotheos
AU  - Kritsi, Eftichia
AU  - Zelenko, Urska
AU  - Golic Grdadolnik, Simona
AU  - Calhelha, Ricardo C.
AU  - Ferreira, Isabel C. F. R.
AU  - Sanković-Babić, Snežana
AU  - Glamočlija, Jasmina
AU  - Fotopoulou, Theano
AU  - Koufaki, Maria
AU  - Zoumpoulakis, Panagiotis
AU  - Soković, Marina
PY  - 2018
UR  - http://doi.wiley.com/10.1002/cmdc.201700602
UR  - http://www.ncbi.nlm.nih.gov/pubmed/29235267
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/2968
AB  - Four heteroaromatic compounds bearing nitrate esters were selected using a virtual-screening procedure as putative sterol 14α-demethylase (CYP51) Candida albicans inhibitors. Compounds were examined for their inhibition on C. albicans growth and biofilm formation as well as for their toxicity. NMR spectroscopy studies, in silico docking, and molecular dynamics simulations were used to investigate further the selectivity of these compounds to fungal CYP51. All compounds exhibited good antimicrobial properties, indicated with low minimal inhibitory concentrations and ability to inhibit formation of fungal biofilm. Moreover, all of the compounds had the ability to inhibit growth of C. albicans cells. N-(2-Nitrooxyethyl)-1Η-indole-2-carboxamide was the only compound with selectivity on C. albicans CYP51 that did not exhibit cytotoxic effect on cells isolated from liver and should be further investigated for selective application in new leads for the treatment of candidiasis.
T2  - ChemMedChem
T1  - Nitrate Esters of Heteroaromatic Compounds as Candida albicans CYP51 Enzyme Inhibitors.
IS  - 4
VL  - 32
DO  - 10.1002/cmdc.201700602
SP  - 342
EP  - 349
ER  - 

@article{
author = "Ivanov, Marija and Matsoukas, Minos-Timotheos and Kritsi, Eftichia and Zelenko, Urska and Golic Grdadolnik, Simona and Calhelha, Ricardo C. and Ferreira, Isabel C. F. R. and Sanković-Babić, Snežana and Glamočlija, Jasmina and Fotopoulou, Theano and Koufaki, Maria and Zoumpoulakis, Panagiotis and Soković, Marina",
year = "2018",
abstract = "Four heteroaromatic compounds bearing nitrate esters were selected using a virtual-screening procedure as putative sterol 14α-demethylase (CYP51) Candida albicans inhibitors. Compounds were examined for their inhibition on C. albicans growth and biofilm formation as well as for their toxicity. NMR spectroscopy studies, in silico docking, and molecular dynamics simulations were used to investigate further the selectivity of these compounds to fungal CYP51. All compounds exhibited good antimicrobial properties, indicated with low minimal inhibitory concentrations and ability to inhibit formation of fungal biofilm. Moreover, all of the compounds had the ability to inhibit growth of C. albicans cells. N-(2-Nitrooxyethyl)-1Η-indole-2-carboxamide was the only compound with selectivity on C. albicans CYP51 that did not exhibit cytotoxic effect on cells isolated from liver and should be further investigated for selective application in new leads for the treatment of candidiasis.",
journal = "ChemMedChem",
title = "Nitrate Esters of Heteroaromatic Compounds as Candida albicans CYP51 Enzyme Inhibitors.",
number = "4",
volume = "32",
doi = "10.1002/cmdc.201700602",
pages = "342-349"
}

Ivanov, M., Matsoukas, M., Kritsi, E., Zelenko, U., Golic Grdadolnik, S., Calhelha, R. C., Ferreira, I. C. F. R., Sanković-Babić, S., Glamočlija, J., Fotopoulou, T., Koufaki, M., Zoumpoulakis, P.,& Soković, M.. (2018). Nitrate Esters of Heteroaromatic Compounds as Candida albicans CYP51 Enzyme Inhibitors.. in ChemMedChem, 32(4), 342-349.
https://doi.org/10.1002/cmdc.201700602

Ivanov M, Matsoukas M, Kritsi E, Zelenko U, Golic Grdadolnik S, Calhelha RC, Ferreira ICFR, Sanković-Babić S, Glamočlija J, Fotopoulou T, Koufaki M, Zoumpoulakis P, Soković M. Nitrate Esters of Heteroaromatic Compounds as Candida albicans CYP51 Enzyme Inhibitors.. in ChemMedChem. 2018;32(4):342-349.
doi:10.1002/cmdc.201700602 .

Ivanov, Marija, Matsoukas, Minos-Timotheos, Kritsi, Eftichia, Zelenko, Urska, Golic Grdadolnik, Simona, Calhelha, Ricardo C., Ferreira, Isabel C. F. R., Sanković-Babić, Snežana, Glamočlija, Jasmina, Fotopoulou, Theano, Koufaki, Maria, Zoumpoulakis, Panagiotis, Soković, Marina, "Nitrate Esters of Heteroaromatic Compounds as Candida albicans CYP51 Enzyme Inhibitors." in ChemMedChem, 32, no. 4 (2018):342-349,
https://doi.org/10.1002/cmdc.201700602 . .

TY  - JOUR
AU  - Fotopoulou, Theano
AU  - Ćirić, Ana
AU  - Kritsi, Eftichia
AU  - Calhelha, Ricardo C.
AU  - Ferreira, Isabel C.F.R.
AU  - Soković, Marina
AU  - Zoumpoulakis, Panagiotis
AU  - Koufaki, Maria
PY  - 2016
UR  - http://radar.ibiss.bg.ac.rs/handle/123456789/6747
AB  - Natural b-thujaplicin displays a remarkable array of biological activities for the prevention or
treatment of various disorders while its tropolone scaffold inspired the synthesis of new analogs. The
main goal of the current study was to evaluate the influence of 4-substituted piperazine moieties at
position 7 of the b-thujaplicin scaffold, on the antimicrobial activity. In order to determine the
biological activity of the b-thujaplicin derivatives, a microdilution method was used against a wide
variety of bacteria and fungi. Pseudomonas aeruginosa PAO 1 was used for testing antiquorum and
antibiofilm effects. Four human tumor cell lines (MCF-7, NCI-H460, HeLa, and HepG2) and a porcine
liver derived cell line (PLP2) were used for testing antitumor and cytotoxic activity. The compounds
present better antibacterial and antifungal activity in comparison with approved antimicrobials used
as control agents. b-Thujaplicin showed strong antibacterial and antifungal activities against all
tested species. Further studies of their antibacterial activity revealed that all compounds presented
good antibiofilm and antiquorum effects. Fungi were more susceptible than bacteria to the tested
compounds, with the exception of MK150, which possessed the best antibacterial effect. None of the
tested compounds, at the GI50 values obtained for the tumor cell lines, have shown toxicity for non tumor liver cells (PLP2). The prediction of physicochemical properties of the compounds was
performed to further explain the structure–activity relationship. Finally, in order to explore a possible
mechanism of action of the synthesized compounds, molecular docking studies were performed on
CYP51 (14-a lanosterol demethylase), an important component of the fungal cell membrane.
PB  - Weinheim, Germany: WILEY-VCH Verlag GmbH & Co. KGaA,
T2  - Archiv der Pharmazie
T1  - Antimicrobial/Antibiofilm Activity and Cytotoxic Studies of b-Thujaplicin Derivatives
IS  - 9
VL  - 349
DO  - 10.1002/ardp.201600095
SP  - 698
EP  - 709
ER  - 

@article{
author = "Fotopoulou, Theano and Ćirić, Ana and Kritsi, Eftichia and Calhelha, Ricardo C. and Ferreira, Isabel C.F.R. and Soković, Marina and Zoumpoulakis, Panagiotis and Koufaki, Maria",
year = "2016",
abstract = "Natural b-thujaplicin displays a remarkable array of biological activities for the prevention or
treatment of various disorders while its tropolone scaffold inspired the synthesis of new analogs. The
main goal of the current study was to evaluate the influence of 4-substituted piperazine moieties at
position 7 of the b-thujaplicin scaffold, on the antimicrobial activity. In order to determine the
biological activity of the b-thujaplicin derivatives, a microdilution method was used against a wide
variety of bacteria and fungi. Pseudomonas aeruginosa PAO 1 was used for testing antiquorum and
antibiofilm effects. Four human tumor cell lines (MCF-7, NCI-H460, HeLa, and HepG2) and a porcine
liver derived cell line (PLP2) were used for testing antitumor and cytotoxic activity. The compounds
present better antibacterial and antifungal activity in comparison with approved antimicrobials used
as control agents. b-Thujaplicin showed strong antibacterial and antifungal activities against all
tested species. Further studies of their antibacterial activity revealed that all compounds presented
good antibiofilm and antiquorum effects. Fungi were more susceptible than bacteria to the tested
compounds, with the exception of MK150, which possessed the best antibacterial effect. None of the
tested compounds, at the GI50 values obtained for the tumor cell lines, have shown toxicity for non tumor liver cells (PLP2). The prediction of physicochemical properties of the compounds was
performed to further explain the structure–activity relationship. Finally, in order to explore a possible
mechanism of action of the synthesized compounds, molecular docking studies were performed on
CYP51 (14-a lanosterol demethylase), an important component of the fungal cell membrane.",
publisher = "Weinheim, Germany: WILEY-VCH Verlag GmbH & Co. KGaA,",
journal = "Archiv der Pharmazie",
title = "Antimicrobial/Antibiofilm Activity and Cytotoxic Studies of b-Thujaplicin Derivatives",
number = "9",
volume = "349",
doi = "10.1002/ardp.201600095",
pages = "698-709"
}

Fotopoulou, T., Ćirić, A., Kritsi, E., Calhelha, R. C., Ferreira, I. C.F.R., Soković, M., Zoumpoulakis, P.,& Koufaki, M.. (2016). Antimicrobial/Antibiofilm Activity and Cytotoxic Studies of b-Thujaplicin Derivatives. in Archiv der Pharmazie
Weinheim, Germany: WILEY-VCH Verlag GmbH & Co. KGaA,., 349(9), 698-709.
https://doi.org/10.1002/ardp.201600095

Fotopoulou T, Ćirić A, Kritsi E, Calhelha RC, Ferreira IC, Soković M, Zoumpoulakis P, Koufaki M. Antimicrobial/Antibiofilm Activity and Cytotoxic Studies of b-Thujaplicin Derivatives. in Archiv der Pharmazie. 2016;349(9):698-709.
doi:10.1002/ardp.201600095 .

Fotopoulou, Theano, Ćirić, Ana, Kritsi, Eftichia, Calhelha, Ricardo C., Ferreira, Isabel C.F.R., Soković, Marina, Zoumpoulakis, Panagiotis, Koufaki, Maria, "Antimicrobial/Antibiofilm Activity and Cytotoxic Studies of b-Thujaplicin Derivatives" in Archiv der Pharmazie, 349, no. 9 (2016):698-709,
https://doi.org/10.1002/ardp.201600095 . .