Novel tetradentate diamine dioxime ligands: synthesis, characterization and in vivo behavior of their 99mTc-complexes
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Аутори
Mirković, Marija D.Janković, Drina
Vranješ-Đurić, Sanja
Radović, Magdalena
Stanković, Dragana
Mijin, Dušan Ž.
Nikolić, Nadežda S.
Чланак у часопису
Метаподаци
Приказ свих података о документуАпстракт
Two novel diamine dioxime ligands, 4,7-diaza-3,8-diethyldecane-2,9-dione bis oxime (3) and 4,9-diaza-3,10-diethyldodecane-2,11-dione bis oxime (5), were synthesized in order to develop new brain perfusion imaging agents, based on 99mTc(V)-complexes. The synthesis involved condensation of 2-hydroxyimino-3-pentanone with appropriate diamine in protic solvent which afforded the bis imine adducts. Subsequent reduction of imine functional groups yielded a diastereoisomeric mixture of 3 and 5. UVvisible, IR, 1H NMR, 13C NMR and elemental analysis were used to characterize the structures of the synthesized compounds. 99mTc-complexes of both diamine dioximes were prepared and radiolabeling conditions optimized to give the maximum yield. Physicochemical parameters of the labeled complexes as well as and their biodistribution in rats were investigated. Both compounds (3 and 5) formed 99mTc-complexes with a net charge of zero, determined by electrophoresis. The resultant lipophilic 99mTc-complexe...s of 3 and 5 were readily formed at pH similar to 9.0 within 10?min at room temperature with yields of 90% and 95%, respectively. The 99mTc-3 complex was found to be stable within 1 similar to h, while 99mTc-5 was stable for a few hours. A significant brain uptake of 99mTc-3 (2.1% injected dose) and 99mTc-5 (1.8% injected dose) complexes, 2?min after injection, is in accordance with their lipophilicity. The present study suggests that both ligands are promising candidates as new 99mTc-based brain-imaging agents. Copyright (c) 2012 John Wiley and Sons, Ltd.
Кључне речи:
diamine dioximes / 99mTc(V)-complexes / tetradentate ligands / brain imaging / in vivo behaviorИзвор:
Applied Organometallic Chemistry, 2012, 26, 7, 347-355Финансирање / пројекти:
- Магнетни и радионуклидима обележени наноструктурни материјали за примене у медицини (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-45015)
- Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (RS-MESTD-Basic Research (BR or ON)-172013)
DOI: 10.1002/aoc.2870
ISSN: 0268-2605
WoS: 000305555100005
Scopus: 2-s2.0-84862902017
Колекције
Институција/група
VinčaTY - JOUR AU - Mirković, Marija D. AU - Janković, Drina AU - Vranješ-Đurić, Sanja AU - Radović, Magdalena AU - Stanković, Dragana AU - Mijin, Dušan Ž. AU - Nikolić, Nadežda S. PY - 2012 UR - https://vinar.vin.bg.ac.rs/handle/123456789/4899 AB - Two novel diamine dioxime ligands, 4,7-diaza-3,8-diethyldecane-2,9-dione bis oxime (3) and 4,9-diaza-3,10-diethyldodecane-2,11-dione bis oxime (5), were synthesized in order to develop new brain perfusion imaging agents, based on 99mTc(V)-complexes. The synthesis involved condensation of 2-hydroxyimino-3-pentanone with appropriate diamine in protic solvent which afforded the bis imine adducts. Subsequent reduction of imine functional groups yielded a diastereoisomeric mixture of 3 and 5. UVvisible, IR, 1H NMR, 13C NMR and elemental analysis were used to characterize the structures of the synthesized compounds. 99mTc-complexes of both diamine dioximes were prepared and radiolabeling conditions optimized to give the maximum yield. Physicochemical parameters of the labeled complexes as well as and their biodistribution in rats were investigated. Both compounds (3 and 5) formed 99mTc-complexes with a net charge of zero, determined by electrophoresis. The resultant lipophilic 99mTc-complexes of 3 and 5 were readily formed at pH similar to 9.0 within 10?min at room temperature with yields of 90% and 95%, respectively. The 99mTc-3 complex was found to be stable within 1 similar to h, while 99mTc-5 was stable for a few hours. A significant brain uptake of 99mTc-3 (2.1% injected dose) and 99mTc-5 (1.8% injected dose) complexes, 2?min after injection, is in accordance with their lipophilicity. The present study suggests that both ligands are promising candidates as new 99mTc-based brain-imaging agents. Copyright (c) 2012 John Wiley and Sons, Ltd. T2 - Applied Organometallic Chemistry T1 - Novel tetradentate diamine dioxime ligands: synthesis, characterization and in vivo behavior of their 99mTc-complexes VL - 26 IS - 7 SP - 347 EP - 355 DO - 10.1002/aoc.2870 ER -
@article{ author = "Mirković, Marija D. and Janković, Drina and Vranješ-Đurić, Sanja and Radović, Magdalena and Stanković, Dragana and Mijin, Dušan Ž. and Nikolić, Nadežda S.", year = "2012", abstract = "Two novel diamine dioxime ligands, 4,7-diaza-3,8-diethyldecane-2,9-dione bis oxime (3) and 4,9-diaza-3,10-diethyldodecane-2,11-dione bis oxime (5), were synthesized in order to develop new brain perfusion imaging agents, based on 99mTc(V)-complexes. The synthesis involved condensation of 2-hydroxyimino-3-pentanone with appropriate diamine in protic solvent which afforded the bis imine adducts. Subsequent reduction of imine functional groups yielded a diastereoisomeric mixture of 3 and 5. UVvisible, IR, 1H NMR, 13C NMR and elemental analysis were used to characterize the structures of the synthesized compounds. 99mTc-complexes of both diamine dioximes were prepared and radiolabeling conditions optimized to give the maximum yield. Physicochemical parameters of the labeled complexes as well as and their biodistribution in rats were investigated. Both compounds (3 and 5) formed 99mTc-complexes with a net charge of zero, determined by electrophoresis. The resultant lipophilic 99mTc-complexes of 3 and 5 were readily formed at pH similar to 9.0 within 10?min at room temperature with yields of 90% and 95%, respectively. The 99mTc-3 complex was found to be stable within 1 similar to h, while 99mTc-5 was stable for a few hours. A significant brain uptake of 99mTc-3 (2.1% injected dose) and 99mTc-5 (1.8% injected dose) complexes, 2?min after injection, is in accordance with their lipophilicity. The present study suggests that both ligands are promising candidates as new 99mTc-based brain-imaging agents. Copyright (c) 2012 John Wiley and Sons, Ltd.", journal = "Applied Organometallic Chemistry", title = "Novel tetradentate diamine dioxime ligands: synthesis, characterization and in vivo behavior of their 99mTc-complexes", volume = "26", number = "7", pages = "347-355", doi = "10.1002/aoc.2870" }
Mirković, M. D., Janković, D., Vranješ-Đurić, S., Radović, M., Stanković, D., Mijin, D. Ž.,& Nikolić, N. S.. (2012). Novel tetradentate diamine dioxime ligands: synthesis, characterization and in vivo behavior of their 99mTc-complexes. in Applied Organometallic Chemistry, 26(7), 347-355. https://doi.org/10.1002/aoc.2870
Mirković MD, Janković D, Vranješ-Đurić S, Radović M, Stanković D, Mijin DŽ, Nikolić NS. Novel tetradentate diamine dioxime ligands: synthesis, characterization and in vivo behavior of their 99mTc-complexes. in Applied Organometallic Chemistry. 2012;26(7):347-355. doi:10.1002/aoc.2870 .
Mirković, Marija D., Janković, Drina, Vranješ-Đurić, Sanja, Radović, Magdalena, Stanković, Dragana, Mijin, Dušan Ž., Nikolić, Nadežda S., "Novel tetradentate diamine dioxime ligands: synthesis, characterization and in vivo behavior of their 99mTc-complexes" in Applied Organometallic Chemistry, 26, no. 7 (2012):347-355, https://doi.org/10.1002/aoc.2870 . .