TY  - JOUR
AU  - Smiljković, 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  - https://smile.stomf.bg.ac.rs/handle/123456789/2357
AB  - Four heteroaromatic compounds bearing nitrate esters were selected using a virtual-screening procedure as putative sterol 14-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, insilico 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)-1-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.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Chemmedchem
T1  - Nitrate Esters of Heteroaromatic Compounds as Candida albicans CYP51 Enzyme Inhibitors
VL  - 13
IS  - 3
SP  - 251
EP  - 258
DO  - 10.1002/cmdc.201700602
ER  - 

@article{
author = "Smiljković, 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 14-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, insilico 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)-1-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.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Chemmedchem",
title = "Nitrate Esters of Heteroaromatic Compounds as Candida albicans CYP51 Enzyme Inhibitors",
volume = "13",
number = "3",
pages = "251-258",
doi = "10.1002/cmdc.201700602"
}

Smiljković, 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
Wiley-V C H Verlag Gmbh, Weinheim., 13(3), 251-258.
https://doi.org/10.1002/cmdc.201700602

Smiljković 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;13(3):251-258.
doi:10.1002/cmdc.201700602 .

Smiljković, 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, 13, no. 3 (2018):251-258,
https://doi.org/10.1002/cmdc.201700602 . .

TY  - JOUR
AU  - Smiljković, Marija
AU  - Stanisavljević, Danijela
AU  - Stojković, Dejan
AU  - Petrović, Isidora
AU  - Marjanović-Vicentić, Jelena
AU  - Popović, Jelena
AU  - Golic-Grdadolnik, Simona
AU  - Marković, Dejan
AU  - Sanković-Babić, Snežana
AU  - Glamočlija, Jasmina
AU  - Stevanović, Milena
AU  - Soković, Marina
PY  - 2017
UR  - https://smile.stomf.bg.ac.rs/handle/123456789/2225
AB  - Bioactive potential of apigenin derivative apigenin-7-O-glucoside related to its antifungal activity on Candida spp. and cytotoxic effect on colon cancer cells was studied and compared with bioactive potential of apigenin. Antifungal activity was tested on 14 different isolates of Candida spp. using membrane permeability assay, measuring inhibition of reactive oxidative species and inhibition of CYP51 C. albicans enzyme. Cytotoxic potential of apigenin- 7-O-glucoside was tested on colon cancer HCT116 cells by measuring cell viability, apoptosis rate and apoptosis- and colon cancer-related gene expression. Obtained results indicated considerable antifungal activity of apigenin-7-O-glucoside towards all Candida isolates. Breakdown of C. albicans plasma membrane was achieved upon treatment with apigenin-7-O-glucoside for shorter period of time then with apigenin. Reduction of intra-and extracellular reactive oxidative species was achieved with minimum inhibitory concentrations of both compounds, suggesting that reactive oxidative species inhibition could be a mechanism of antifungal action. None of the compounds exhibited binding affinity to C. albicans CYP51 protein. Besides, apigenin-7-O-glucoside was more effective compared to apigenin in reduction of cell's viability and induction of cell death of HCT116 cells. Treatment with both compounds resulted in chromatin condensation, apoptotic bodies formation and apoptotic genes expression in HCT116 cells, but the apigenin-7-O-glucoside required a lower concentration to achieve the same effect. Compounds apigenin-7-O-glucoside and apigenin displayed prominent antifungal potential and cytotoxic effect on HCT116 cells. However, our results showed that apigenin-7-O-glucoside has more potent activity compared to apigenin in all assays that we used.
PB  - Excli Journal Managing Office, Dortmund
T2  - EXCLI Journal
T1  - Apigenin-7-o-glucoside versus apigenin: insight into the modes of anticandidal and cytotoxic actions
VL  - 16
SP  - 795
EP  - 807
DO  - 10.17179/excli2017-300
ER  - 

@article{
author = "Smiljković, Marija and Stanisavljević, Danijela and Stojković, Dejan and Petrović, Isidora and Marjanović-Vicentić, Jelena and Popović, Jelena and Golic-Grdadolnik, Simona and Marković, Dejan and Sanković-Babić, Snežana and Glamočlija, Jasmina and Stevanović, Milena and Soković, Marina",
year = "2017",
abstract = "Bioactive potential of apigenin derivative apigenin-7-O-glucoside related to its antifungal activity on Candida spp. and cytotoxic effect on colon cancer cells was studied and compared with bioactive potential of apigenin. Antifungal activity was tested on 14 different isolates of Candida spp. using membrane permeability assay, measuring inhibition of reactive oxidative species and inhibition of CYP51 C. albicans enzyme. Cytotoxic potential of apigenin- 7-O-glucoside was tested on colon cancer HCT116 cells by measuring cell viability, apoptosis rate and apoptosis- and colon cancer-related gene expression. Obtained results indicated considerable antifungal activity of apigenin-7-O-glucoside towards all Candida isolates. Breakdown of C. albicans plasma membrane was achieved upon treatment with apigenin-7-O-glucoside for shorter period of time then with apigenin. Reduction of intra-and extracellular reactive oxidative species was achieved with minimum inhibitory concentrations of both compounds, suggesting that reactive oxidative species inhibition could be a mechanism of antifungal action. None of the compounds exhibited binding affinity to C. albicans CYP51 protein. Besides, apigenin-7-O-glucoside was more effective compared to apigenin in reduction of cell's viability and induction of cell death of HCT116 cells. Treatment with both compounds resulted in chromatin condensation, apoptotic bodies formation and apoptotic genes expression in HCT116 cells, but the apigenin-7-O-glucoside required a lower concentration to achieve the same effect. Compounds apigenin-7-O-glucoside and apigenin displayed prominent antifungal potential and cytotoxic effect on HCT116 cells. However, our results showed that apigenin-7-O-glucoside has more potent activity compared to apigenin in all assays that we used.",
publisher = "Excli Journal Managing Office, Dortmund",
journal = "EXCLI Journal",
title = "Apigenin-7-o-glucoside versus apigenin: insight into the modes of anticandidal and cytotoxic actions",
volume = "16",
pages = "795-807",
doi = "10.17179/excli2017-300"
}

Smiljković, M., Stanisavljević, D., Stojković, D., Petrović, I., Marjanović-Vicentić, J., Popović, J., Golic-Grdadolnik, S., Marković, D., Sanković-Babić, S., Glamočlija, J., Stevanović, M.,& Soković, M.. (2017). Apigenin-7-o-glucoside versus apigenin: insight into the modes of anticandidal and cytotoxic actions. in EXCLI Journal
Excli Journal Managing Office, Dortmund., 16, 795-807.
https://doi.org/10.17179/excli2017-300

Smiljković M, Stanisavljević D, Stojković D, Petrović I, Marjanović-Vicentić J, Popović J, Golic-Grdadolnik S, Marković D, Sanković-Babić S, Glamočlija J, Stevanović M, Soković M. Apigenin-7-o-glucoside versus apigenin: insight into the modes of anticandidal and cytotoxic actions. in EXCLI Journal. 2017;16:795-807.
doi:10.17179/excli2017-300 .

Smiljković, Marija, Stanisavljević, Danijela, Stojković, Dejan, Petrović, Isidora, Marjanović-Vicentić, Jelena, Popović, Jelena, Golic-Grdadolnik, Simona, Marković, Dejan, Sanković-Babić, Snežana, Glamočlija, Jasmina, Stevanović, Milena, Soković, Marina, "Apigenin-7-o-glucoside versus apigenin: insight into the modes of anticandidal and cytotoxic actions" in EXCLI Journal, 16 (2017):795-807,
https://doi.org/10.17179/excli2017-300 . .