TY  - CONF
AU  - Korać, Jelena
AU  - Todorović, Nina
AU  - Zakrzewska, Joanna
AU  - Žižić, Milan
AU  - Spasojević, Ivan
PY  - 2018
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/2206
AB  - Adrenalin (Adr) je fiziološki važan kateholamin koji kao hormon, neurotransmiter i lek ima širok spektar dejstava. Konformacija je definisana inter i intramolekulskim interakcijama Adr sa rastvaračem, kao i vodoničnim vezama.1-3 Postoje brojne teorijske studije koje se bave proučavanjem vodoničnih veza i konformacije Adr u različitim rastvaračima, ali nedostaju eksperimentalni podaci. U ovom istraživanju koristili smo 1H NMR, 1H-1H COSY, 1H-15N HSQC i NOESY da se ispita i uporedi struktura Adr u polarnim rastvaračima - dimetil sulfoksidu (DMSO) i vodi. Glavne razlike su dobijene za NH2 i CH2 grupu. Obe grupe pokazuju hemijske neekvivalentne protone u DMSO, koji nisu prisutni u vodi. Efekat povećane temperature i izmene rastvarača u NMR spektru pokazuje da u dimetil sulfoksidu jedan od protona Adr iz NH2 grupe formira jaku intramolekulsku vezu sa alifatičnom OH grupom, koja je donor protona drugoj vodoničnoj vezi koju Adr formira sa samim rastvaračem. U skladu sa tim rezultatima zaključeno je da Adr u dimetil sulfoksidu zauzima "škorpion" konformaciju u kojoj kateholni prsten predstavlja telo, a bočni niz zakrivljeni rep škorpije. U vodi Adr ne gradi intramolekulsku vodoničnu vezu, što govori da njegova struktura u velikoj meri zavisi od same okoline. Ovo je veoma važno za razumevanje transporta i vezivanja za receptore, kao i za razumevanje interakcija kateholamina sa biološkim molekulima, što direktno utiče na biološke efekte.
PB  - Srpsko biološko društvo, Beograd
C3  - DRUGI KONGRES BIOLOGA SRBIJE
T1  - Struktura adrenalina u DMSO: NMR studija
EP  - 32
SP  - 32
UR  - https://hdl.handle.net/21.15107/rcub_rimsi_2206
ER  - 

@conference{
author = "Korać, Jelena and Todorović, Nina and Zakrzewska, Joanna and Žižić, Milan and Spasojević, Ivan",
year = "2018",
abstract = "Adrenalin (Adr) je fiziološki važan kateholamin koji kao hormon, neurotransmiter i lek ima širok spektar dejstava. Konformacija je definisana inter i intramolekulskim interakcijama Adr sa rastvaračem, kao i vodoničnim vezama.1-3 Postoje brojne teorijske studije koje se bave proučavanjem vodoničnih veza i konformacije Adr u različitim rastvaračima, ali nedostaju eksperimentalni podaci. U ovom istraživanju koristili smo 1H NMR, 1H-1H COSY, 1H-15N HSQC i NOESY da se ispita i uporedi struktura Adr u polarnim rastvaračima - dimetil sulfoksidu (DMSO) i vodi. Glavne razlike su dobijene za NH2 i CH2 grupu. Obe grupe pokazuju hemijske neekvivalentne protone u DMSO, koji nisu prisutni u vodi. Efekat povećane temperature i izmene rastvarača u NMR spektru pokazuje da u dimetil sulfoksidu jedan od protona Adr iz NH2 grupe formira jaku intramolekulsku vezu sa alifatičnom OH grupom, koja je donor protona drugoj vodoničnoj vezi koju Adr formira sa samim rastvaračem. U skladu sa tim rezultatima zaključeno je da Adr u dimetil sulfoksidu zauzima "škorpion" konformaciju u kojoj kateholni prsten predstavlja telo, a bočni niz zakrivljeni rep škorpije. U vodi Adr ne gradi intramolekulsku vodoničnu vezu, što govori da njegova struktura u velikoj meri zavisi od same okoline. Ovo je veoma važno za razumevanje transporta i vezivanja za receptore, kao i za razumevanje interakcija kateholamina sa biološkim molekulima, što direktno utiče na biološke efekte.",
publisher = "Srpsko biološko društvo, Beograd",
journal = "DRUGI KONGRES BIOLOGA SRBIJE",
title = "Struktura adrenalina u DMSO: NMR studija",
pages = "32-32",
url = "https://hdl.handle.net/21.15107/rcub_rimsi_2206"
}

Korać, J., Todorović, N., Zakrzewska, J., Žižić, M.,& Spasojević, I.. (2018). Struktura adrenalina u DMSO: NMR studija. in DRUGI KONGRES BIOLOGA SRBIJE
Srpsko biološko društvo, Beograd., 32-32.
https://hdl.handle.net/21.15107/rcub_rimsi_2206

Korać J, Todorović N, Zakrzewska J, Žižić M, Spasojević I. Struktura adrenalina u DMSO: NMR studija. in DRUGI KONGRES BIOLOGA SRBIJE. 2018;:32-32.
https://hdl.handle.net/21.15107/rcub_rimsi_2206 .

Korać, Jelena, Todorović, Nina, Zakrzewska, Joanna, Žižić, Milan, Spasojević, Ivan, "Struktura adrenalina u DMSO: NMR studija" in DRUGI KONGRES BIOLOGA SRBIJE (2018):32-32,
https://hdl.handle.net/21.15107/rcub_rimsi_2206 .

TY  - JOUR
AU  - Korać Jačić, Jelena
AU  - Todorović, Nina
AU  - Zakrzewska, Joanna
AU  - Žižić, Milan
AU  - Spasojević, Ivan
PY  - 2018
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/1161
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
EP  - 1541
IS  - 5
SP  - 1533
VL  - 29
DO  - 10.1007/s11224-018-1144-y
ER  - 

@article{
author = "Korać Jačić, Jelena and Todorović, Nina and Zakrzewska, Joanna and Žižić, 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",
pages = "1541-1533",
number = "5",
volume = "29",
doi = "10.1007/s11224-018-1144-y"
}

Korać Jačić, J., Todorović, N., Zakrzewska, J., Žižić, 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

Korać Jačić J, Todorović N, Zakrzewska J, Žižić 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 .

Korać Jačić, Jelena, Todorović, Nina, Zakrzewska, Joanna, Žižić, 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 . .