TY  - JOUR
AU  - Korac, Jelena
AU  - Todorović, Nina
AU  - Zakrzewska, Joanna
AU  - Zizic, Milan
AU  - Spasojević, Ivan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2426
AB  - Epinephrine (Epi) is a physiologically important catecholamine. Molecular conformation of Epi controls the interactions with other molecules and its biological effects. There have been a number of theoretical studies addressing conformation and hydrogen bonding of Epi in different solvents, but experimental data are scarce. Herein, we applied H-1 NMR, H-1-H-1 COSY, H-1-N-15 HSQC, and NOESY to examine and compare the conformation of Epi in polar solvents-dimethyl sulfoxide (DMSO) and water. The main differences were observed for NH2 and CH2 groups. Both showed chemical nonequivalence of protons in DMSO that was not present in water. The analysis of the effects of increasing temperature and solvent substitution on NMR signals showed that one of the protons in amine group forms a strong intramolecular hydrogen bond with aliphatic OH group, which is H-donor in another hydrogen bond with DMSO. NOESY provided data on the spatial positions of protons in the side chain, allowing for 3D model of the structure of Epi in DMSO to be built. In close, Epi molecule forms an additional 5-membered ring that encompasses bifurcate intra-/intermolecular hydrogen bonds, and acquires conformation that resembles the shape of a "scorpion"-the catechol ring representing the body and the side chain being a forward-curved tail. The conformation of Epi in water lacks the intramolecular hydrogen bond and most likely largely depends on hydrogen bonds with water molecules.
PB  - Springer/Plenum Publishers, New York
T2  - Structural Chemistry
T1  - The conformation of epinephrine in polar solvents: an NMR study
VL  - 29
IS  - 5
SP  - 1533
EP  - 1541
DO  - 10.1007/s11224-018-1144-y
ER  - 

@article{
author = "Korac, Jelena and Todorović, Nina and Zakrzewska, Joanna and Zizic, Milan and Spasojević, Ivan",
year = "2018",
abstract = "Epinephrine (Epi) is a physiologically important catecholamine. Molecular conformation of Epi controls the interactions with other molecules and its biological effects. There have been a number of theoretical studies addressing conformation and hydrogen bonding of Epi in different solvents, but experimental data are scarce. Herein, we applied H-1 NMR, H-1-H-1 COSY, H-1-N-15 HSQC, and NOESY to examine and compare the conformation of Epi in polar solvents-dimethyl sulfoxide (DMSO) and water. The main differences were observed for NH2 and CH2 groups. Both showed chemical nonequivalence of protons in DMSO that was not present in water. The analysis of the effects of increasing temperature and solvent substitution on NMR signals showed that one of the protons in amine group forms a strong intramolecular hydrogen bond with aliphatic OH group, which is H-donor in another hydrogen bond with DMSO. NOESY provided data on the spatial positions of protons in the side chain, allowing for 3D model of the structure of Epi in DMSO to be built. In close, Epi molecule forms an additional 5-membered ring that encompasses bifurcate intra-/intermolecular hydrogen bonds, and acquires conformation that resembles the shape of a "scorpion"-the catechol ring representing the body and the side chain being a forward-curved tail. The conformation of Epi in water lacks the intramolecular hydrogen bond and most likely largely depends on hydrogen bonds with water molecules.",
publisher = "Springer/Plenum Publishers, New York",
journal = "Structural Chemistry",
title = "The conformation of epinephrine in polar solvents: an NMR study",
volume = "29",
number = "5",
pages = "1533-1541",
doi = "10.1007/s11224-018-1144-y"
}

Korac, J., Todorović, N., Zakrzewska, J., Zizic, M.,& Spasojević, I.. (2018). The conformation of epinephrine in polar solvents: an NMR study. in Structural Chemistry
Springer/Plenum Publishers, New York., 29(5), 1533-1541.
https://doi.org/10.1007/s11224-018-1144-y

Korac J, Todorović N, Zakrzewska J, Zizic M, Spasojević I. The conformation of epinephrine in polar solvents: an NMR study. in Structural Chemistry. 2018;29(5):1533-1541.
doi:10.1007/s11224-018-1144-y .

Korac, Jelena, Todorović, Nina, Zakrzewska, Joanna, Zizic, Milan, Spasojević, Ivan, "The conformation of epinephrine in polar solvents: an NMR study" in Structural Chemistry, 29, no. 5 (2018):1533-1541,
https://doi.org/10.1007/s11224-018-1144-y . .

TY  - JOUR
AU  - Bajic, Aleksandar
AU  - Zakrzewska, Joanna
AU  - Gođevac, Dejan
AU  - Anđus, Pavle
AU  - Jones, David R.
AU  - Spasić, Mihajlo
AU  - Spasojević, Ivan
PY  - 2011
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/781
AB  - The cytoprotective activity of F16BP has been documented in severe conditions such as convulsions, reperfusion injury, septic shock, diabetic complications, hypothermia-induced injury, UV-provoked skin damage and in other processes including apoptosis and excitotoxicity. F16BP shows very efficient cytoprotective activity in astroglial cells exposed to H2O2-provoked oxidative stress and during neuronal injury caused by hypoxic conditions. As most of the aforementioned processes involve iron activity-related conditions, we investigated the ferric and ferrous iron binding properties of F16BP under physiological conditions using P-31 NMR and EPR spectroscopy. Our results indicate that cytoprotective F16BP activity is predominantly based on ferrous iron sequestration. P-31 NMR spectroscopy of F16BP employing paramagnetic properties of iron clearly showed that F16BP forms stabile complexes with Fe2+ which was verified by EPR of another divalent cation-Mn2+. On the other hand, F16BP does not sequester ferric iron nor does it increase its redox activity as shown by P-31 NMR and EPR spin-trapping. Therefore, F16BP may be beneficial in neurodegenerative and other conditions that are characterised by ferric iron stores and deposits.
PB  - Elsevier Sci Ltd, Oxford
T2  - Carbohydrate Research
T1  - Relevance of the ability of fructose 1,6-bis(phosphate) to sequester ferrous but not ferric ions
VL  - 346
IS  - 3
SP  - 416
EP  - 420
DO  - 10.1016/j.carres.2010.12.008
ER  - 

@article{
author = "Bajic, Aleksandar and Zakrzewska, Joanna and Gođevac, Dejan and Anđus, Pavle and Jones, David R. and Spasić, Mihajlo and Spasojević, Ivan",
year = "2011",
abstract = "The cytoprotective activity of F16BP has been documented in severe conditions such as convulsions, reperfusion injury, septic shock, diabetic complications, hypothermia-induced injury, UV-provoked skin damage and in other processes including apoptosis and excitotoxicity. F16BP shows very efficient cytoprotective activity in astroglial cells exposed to H2O2-provoked oxidative stress and during neuronal injury caused by hypoxic conditions. As most of the aforementioned processes involve iron activity-related conditions, we investigated the ferric and ferrous iron binding properties of F16BP under physiological conditions using P-31 NMR and EPR spectroscopy. Our results indicate that cytoprotective F16BP activity is predominantly based on ferrous iron sequestration. P-31 NMR spectroscopy of F16BP employing paramagnetic properties of iron clearly showed that F16BP forms stabile complexes with Fe2+ which was verified by EPR of another divalent cation-Mn2+. On the other hand, F16BP does not sequester ferric iron nor does it increase its redox activity as shown by P-31 NMR and EPR spin-trapping. Therefore, F16BP may be beneficial in neurodegenerative and other conditions that are characterised by ferric iron stores and deposits.",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "Carbohydrate Research",
title = "Relevance of the ability of fructose 1,6-bis(phosphate) to sequester ferrous but not ferric ions",
volume = "346",
number = "3",
pages = "416-420",
doi = "10.1016/j.carres.2010.12.008"
}

Bajic, A., Zakrzewska, J., Gođevac, D., Anđus, P., Jones, D. R., Spasić, M.,& Spasojević, I.. (2011). Relevance of the ability of fructose 1,6-bis(phosphate) to sequester ferrous but not ferric ions. in Carbohydrate Research
Elsevier Sci Ltd, Oxford., 346(3), 416-420.
https://doi.org/10.1016/j.carres.2010.12.008

Bajic A, Zakrzewska J, Gođevac D, Anđus P, Jones DR, Spasić M, Spasojević I. Relevance of the ability of fructose 1,6-bis(phosphate) to sequester ferrous but not ferric ions. in Carbohydrate Research. 2011;346(3):416-420.
doi:10.1016/j.carres.2010.12.008 .

Bajic, Aleksandar, Zakrzewska, Joanna, Gođevac, Dejan, Anđus, Pavle, Jones, David R., Spasić, Mihajlo, Spasojević, Ivan, "Relevance of the ability of fructose 1,6-bis(phosphate) to sequester ferrous but not ferric ions" in Carbohydrate Research, 346, no. 3 (2011):416-420,
https://doi.org/10.1016/j.carres.2010.12.008 . .