TY  - JOUR
AU  - Isaković, Anđelka M.
AU  - Petričević, Saša
AU  - Ristić, Slavica M.
AU  - Popadić, Dušan
AU  - Kravić-Stevović, Tamara
AU  - Zogović, Nevena
AU  - Poljarević, Jelena
AU  - Živanović-Radnić, Tatjana
AU  - Sabo, Tibor
AU  - Isaković, Aleksandra J.
AU  - Marković, Ivanka
AU  - Trajković, Vladimir S.
AU  - Misirlić-Denčić, Sonja
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2086
AB  - Melanoma, an aggressive skin tumor with high metastatic potential, is associated with high mortality and increasing morbidity. Multiple available chemotherapeutic and immunotherapeutic modalities failed to improve survival in advanced disease, and the search for new agents is ongoing. The aim of this study was to investigate antimelanoma effects of O, O-diethyl-(S, S)-ethylenediamineN, N'di-2-(3-cyclohexyl) propanoate dihydrochloride (EE), a previously synthesized and characterized organic compound. Mouse melanoma B16 cell viability was assessed using acid phosphatase, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide, sulforhodamine B, and lactate dehydrogenase assays. Apoptosis and autophagy were investigated using flow cytometry, fluorescence and electron microscopy, and western blotting. In vivo antitumor potential was assessed in subcutaneous mouse melanoma model after 14 days of treatment with EE. Tumor mass and volume were measured, and RT-PCR was used for investigating the expression of autophagy-related, proapoptotic, and antiapoptotic molecules in tumor tissue. Investigated organic compound exerts significant cytotoxic effect against B16 cells. EE induced apoptosis, as confirmed by phosphatidyl serine externalisation, caspase activation, and ultrastructural features typical for apoptosis seen on fluorescence and electron microscopes. The apoptotic mechanism included prompt disruption of mitochondrial membrane potential and oxidative stress. No autophagy was observed. Antimelanoma action and apoptosis induction were confirmed in vivo, as EE decreased mass and volume of tumors, and increased expression of several proapoptotic genes. EE possesses significant antimelanoma action and causes caspasedependent apoptosis mediated by mitochondrial damage and reactive oxygen species production. Decrease in tumor growth and increase in expression of proapoptotic genes in tumor tissue suggest that EE warrants further investigation as a candidate agent in treating melanoma. Copyright (C) 2018 Wolters Kluwer Health, Inc. All rights reserved.
PB  - Lippincott Williams & Wilkins, Philadelphia
T2  - Melanoma Research
T1  - In vitro and in vivo antimelanoma effect of ethyl ester cyclohexyl analog of ethylenediamine dipropanoic acid
VL  - 28
IS  - 1
SP  - 8
EP  - 20
DO  - 10.1097/CMR.0000000000000409
ER  - 

@article{
author = "Isaković, Anđelka M. and Petričević, Saša and Ristić, Slavica M. and Popadić, Dušan and Kravić-Stevović, Tamara and Zogović, Nevena and Poljarević, Jelena and Živanović-Radnić, Tatjana and Sabo, Tibor and Isaković, Aleksandra J. and Marković, Ivanka and Trajković, Vladimir S. and Misirlić-Denčić, Sonja",
year = "2018",
abstract = "Melanoma, an aggressive skin tumor with high metastatic potential, is associated with high mortality and increasing morbidity. Multiple available chemotherapeutic and immunotherapeutic modalities failed to improve survival in advanced disease, and the search for new agents is ongoing. The aim of this study was to investigate antimelanoma effects of O, O-diethyl-(S, S)-ethylenediamineN, N'di-2-(3-cyclohexyl) propanoate dihydrochloride (EE), a previously synthesized and characterized organic compound. Mouse melanoma B16 cell viability was assessed using acid phosphatase, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide, sulforhodamine B, and lactate dehydrogenase assays. Apoptosis and autophagy were investigated using flow cytometry, fluorescence and electron microscopy, and western blotting. In vivo antitumor potential was assessed in subcutaneous mouse melanoma model after 14 days of treatment with EE. Tumor mass and volume were measured, and RT-PCR was used for investigating the expression of autophagy-related, proapoptotic, and antiapoptotic molecules in tumor tissue. Investigated organic compound exerts significant cytotoxic effect against B16 cells. EE induced apoptosis, as confirmed by phosphatidyl serine externalisation, caspase activation, and ultrastructural features typical for apoptosis seen on fluorescence and electron microscopes. The apoptotic mechanism included prompt disruption of mitochondrial membrane potential and oxidative stress. No autophagy was observed. Antimelanoma action and apoptosis induction were confirmed in vivo, as EE decreased mass and volume of tumors, and increased expression of several proapoptotic genes. EE possesses significant antimelanoma action and causes caspasedependent apoptosis mediated by mitochondrial damage and reactive oxygen species production. Decrease in tumor growth and increase in expression of proapoptotic genes in tumor tissue suggest that EE warrants further investigation as a candidate agent in treating melanoma. Copyright (C) 2018 Wolters Kluwer Health, Inc. All rights reserved.",
publisher = "Lippincott Williams & Wilkins, Philadelphia",
journal = "Melanoma Research",
title = "In vitro and in vivo antimelanoma effect of ethyl ester cyclohexyl analog of ethylenediamine dipropanoic acid",
volume = "28",
number = "1",
pages = "8-20",
doi = "10.1097/CMR.0000000000000409"
}

Isaković, A. M., Petričević, S., Ristić, S. M., Popadić, D., Kravić-Stevović, T., Zogović, N., Poljarević, J., Živanović-Radnić, T., Sabo, T., Isaković, A. J., Marković, I., Trajković, V. S.,& Misirlić-Denčić, S.. (2018). In vitro and in vivo antimelanoma effect of ethyl ester cyclohexyl analog of ethylenediamine dipropanoic acid. in Melanoma Research
Lippincott Williams & Wilkins, Philadelphia., 28(1), 8-20.
https://doi.org/10.1097/CMR.0000000000000409

Isaković AM, Petričević S, Ristić SM, Popadić D, Kravić-Stevović T, Zogović N, Poljarević J, Živanović-Radnić T, Sabo T, Isaković AJ, Marković I, Trajković VS, Misirlić-Denčić S. In vitro and in vivo antimelanoma effect of ethyl ester cyclohexyl analog of ethylenediamine dipropanoic acid. in Melanoma Research. 2018;28(1):8-20.
doi:10.1097/CMR.0000000000000409 .

Isaković, Anđelka M., Petričević, Saša, Ristić, Slavica M., Popadić, Dušan, Kravić-Stevović, Tamara, Zogović, Nevena, Poljarević, Jelena, Živanović-Radnić, Tatjana, Sabo, Tibor, Isaković, Aleksandra J., Marković, Ivanka, Trajković, Vladimir S., Misirlić-Denčić, Sonja, "In vitro and in vivo antimelanoma effect of ethyl ester cyclohexyl analog of ethylenediamine dipropanoic acid" in Melanoma Research, 28, no. 1 (2018):8-20,
https://doi.org/10.1097/CMR.0000000000000409 . .

TY  - JOUR
AU  - Vuković, Nikola S.
AU  - Životić, Dragana R.
AU  - Mendonca Filho, Joao Graciano
AU  - Kravić-Stevović, Tamara
AU  - Hamor-Vido, Maria
AU  - Mendonca, Joalice de Oliveira
AU  - Stojanović, Ksenija A.
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2062
AB  - The artificial maturation changes of the humic coal organic matter (OM) from late diagenesis to the semianthracite stage of coalification were investigated using the closed-system pyrolysis. Two extracted coal samples, a subbituminous coal 26C (with a random vitrinite reflectance Rr = 0.42%) and a high volatile bituminous coal 30C (Rr = 0.56%), were pyrolysed during 4 hat two different temperatures, 250 degrees C and 400 degrees C. The applied petrographic and organic geochemical analyses showed that the humic coal OM is sensitive to the artificial thermal stress. A good correlation between the changes in petrographic characteristics and the derived liquid products was observed. The contents of all vitrinite macerals, as well as total vitrinite, increased during the thermal maturation. The abundance of liptinite macerals decreased during the maturation and they practically disappeared after 4 h of the pyrolysis at 400 degrees C. The total inertinite contents increased after the pyrolysis at 250 degrees C, yet to be decreased after the pyrolysis at 400 degrees C. The content of organic carbon increased from coals to the solid residues at 400 degrees C, whereas the contents of total hydrogen and sulphur decreased. The yields of gases, liquid products and solid residues at respective temperatures were very similar for both coals, regardless of the rank. As expected, the pyrolysis at 400 degrees C gave higher gas and liquid yields than at 250 degrees C. Regarding the liquid pyrolysates, more pronounced changes were observed in the distribution of aromatic compounds than in saturated biomarkers. The distributions of the aromatics indicate that apart from cracking and isomerisation (the formation of thermodynamically more stable isomers), the reactions of dehydrocyclization, condensation (the formation of more stable conjugated systems) and aromatization, as well as reactions involving H2S, elemental sulphur and reactive phenyl radicals released during the pyrolysis, also play an important role. It was shown that bentonitic clay plays a more important role in the subsequent aromatization of the OM than the initial maturity of the coal OM. n-Alkane parameters were useful at lower maturities (up to similar to 0.75% Rr), whereas sterane, naphthalene and phenanthrene maturity ratios are applicable at higher maturities ( gt 0.75% Rr). Hopane parameters showed variable sensitivities over the investigated maturity range (0.5-1.8% Rr). The most sensitive maturity parameters in the wide range of the humic OM maturity (0.5-1.8% Rr) are vitrinite reflectance, phenylnaphthalene ratio, methylchrysene index 2 and a parameter proposed in this study, based on the distribution of methylfluorenes (MF): (2- + 3-MF) / (1- + 4-MF). Generally, maturity parameters based solely on the isomerisation reactions of alkylaromatics, which do not include alkylation/dealkylation processes, are more appropriate for the humic OM, particularly at higher maturities. (C) 2016 Elsevier B.V. All rights reserved.
PB  - Elsevier Science Bv, Amsterdam
T2  - International Journal of Coal Geology
T1  - The assessment of maturation changes of humic coal organic matter - Insights from closed-system pyrolysis experiments
VL  - 154
SP  - 213
EP  - 239
DO  - 10.1016/j.coal.2016.01.007
ER  - 

@article{
author = "Vuković, Nikola S. and Životić, Dragana R. and Mendonca Filho, Joao Graciano and Kravić-Stevović, Tamara and Hamor-Vido, Maria and Mendonca, Joalice de Oliveira and Stojanović, Ksenija A.",
year = "2016",
abstract = "The artificial maturation changes of the humic coal organic matter (OM) from late diagenesis to the semianthracite stage of coalification were investigated using the closed-system pyrolysis. Two extracted coal samples, a subbituminous coal 26C (with a random vitrinite reflectance Rr = 0.42%) and a high volatile bituminous coal 30C (Rr = 0.56%), were pyrolysed during 4 hat two different temperatures, 250 degrees C and 400 degrees C. The applied petrographic and organic geochemical analyses showed that the humic coal OM is sensitive to the artificial thermal stress. A good correlation between the changes in petrographic characteristics and the derived liquid products was observed. The contents of all vitrinite macerals, as well as total vitrinite, increased during the thermal maturation. The abundance of liptinite macerals decreased during the maturation and they practically disappeared after 4 h of the pyrolysis at 400 degrees C. The total inertinite contents increased after the pyrolysis at 250 degrees C, yet to be decreased after the pyrolysis at 400 degrees C. The content of organic carbon increased from coals to the solid residues at 400 degrees C, whereas the contents of total hydrogen and sulphur decreased. The yields of gases, liquid products and solid residues at respective temperatures were very similar for both coals, regardless of the rank. As expected, the pyrolysis at 400 degrees C gave higher gas and liquid yields than at 250 degrees C. Regarding the liquid pyrolysates, more pronounced changes were observed in the distribution of aromatic compounds than in saturated biomarkers. The distributions of the aromatics indicate that apart from cracking and isomerisation (the formation of thermodynamically more stable isomers), the reactions of dehydrocyclization, condensation (the formation of more stable conjugated systems) and aromatization, as well as reactions involving H2S, elemental sulphur and reactive phenyl radicals released during the pyrolysis, also play an important role. It was shown that bentonitic clay plays a more important role in the subsequent aromatization of the OM than the initial maturity of the coal OM. n-Alkane parameters were useful at lower maturities (up to similar to 0.75% Rr), whereas sterane, naphthalene and phenanthrene maturity ratios are applicable at higher maturities ( gt 0.75% Rr). Hopane parameters showed variable sensitivities over the investigated maturity range (0.5-1.8% Rr). The most sensitive maturity parameters in the wide range of the humic OM maturity (0.5-1.8% Rr) are vitrinite reflectance, phenylnaphthalene ratio, methylchrysene index 2 and a parameter proposed in this study, based on the distribution of methylfluorenes (MF): (2- + 3-MF) / (1- + 4-MF). Generally, maturity parameters based solely on the isomerisation reactions of alkylaromatics, which do not include alkylation/dealkylation processes, are more appropriate for the humic OM, particularly at higher maturities. (C) 2016 Elsevier B.V. All rights reserved.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "International Journal of Coal Geology",
title = "The assessment of maturation changes of humic coal organic matter - Insights from closed-system pyrolysis experiments",
volume = "154",
pages = "213-239",
doi = "10.1016/j.coal.2016.01.007"
}

Vuković, N. S., Životić, D. R., Mendonca Filho, J. G., Kravić-Stevović, T., Hamor-Vido, M., Mendonca, J. d. O.,& Stojanović, K. A.. (2016). The assessment of maturation changes of humic coal organic matter - Insights from closed-system pyrolysis experiments. in International Journal of Coal Geology
Elsevier Science Bv, Amsterdam., 154, 213-239.
https://doi.org/10.1016/j.coal.2016.01.007

Vuković NS, Životić DR, Mendonca Filho JG, Kravić-Stevović T, Hamor-Vido M, Mendonca JDO, Stojanović KA. The assessment of maturation changes of humic coal organic matter - Insights from closed-system pyrolysis experiments. in International Journal of Coal Geology. 2016;154:213-239.
doi:10.1016/j.coal.2016.01.007 .

Vuković, Nikola S., Životić, Dragana R., Mendonca Filho, Joao Graciano, Kravić-Stevović, Tamara, Hamor-Vido, Maria, Mendonca, Joalice de Oliveira, Stojanović, Ksenija A., "The assessment of maturation changes of humic coal organic matter - Insights from closed-system pyrolysis experiments" in International Journal of Coal Geology, 154 (2016):213-239,
https://doi.org/10.1016/j.coal.2016.01.007 . .