TY  - DATA
AU  - Cakić, Nevenka
AU  - Verbić, Tatjana
AU  - Jelić, Ratomir
AU  - Platas-Iglesias, Carlos
AU  - Angelovski, Goran
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3623
PB  - Royal Soc Chemistry, Cambridge
T2  - Dalton Transactions
T1  - Supplementary data for the article: Cakić, N.; Verbić, T. Ž.; Jelić, R. M.; Platas-Iglesias, C.; Angelovski, G. Synthesis and Characterisation of Bismacrocyclic DO3A-Amide Derivatives - An Approach towards Metal-Responsive PARACEST Agents. Dalton Transactions 2016, 45 (15), 6555–6565. https://doi.org/10.1039/c5dt04625d
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3623
ER  - 

@misc{
author = "Cakić, Nevenka and Verbić, Tatjana and Jelić, Ratomir and Platas-Iglesias, Carlos and Angelovski, Goran",
year = "2016",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Dalton Transactions",
title = "Supplementary data for the article: Cakić, N.; Verbić, T. Ž.; Jelić, R. M.; Platas-Iglesias, C.; Angelovski, G. Synthesis and Characterisation of Bismacrocyclic DO3A-Amide Derivatives - An Approach towards Metal-Responsive PARACEST Agents. Dalton Transactions 2016, 45 (15), 6555–6565. https://doi.org/10.1039/c5dt04625d",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3623"
}

Cakić, N., Verbić, T., Jelić, R., Platas-Iglesias, C.,& Angelovski, G.. (2016). Supplementary data for the article: Cakić, N.; Verbić, T. Ž.; Jelić, R. M.; Platas-Iglesias, C.; Angelovski, G. Synthesis and Characterisation of Bismacrocyclic DO3A-Amide Derivatives - An Approach towards Metal-Responsive PARACEST Agents. Dalton Transactions 2016, 45 (15), 6555–6565. https://doi.org/10.1039/c5dt04625d. in Dalton Transactions
Royal Soc Chemistry, Cambridge..
https://hdl.handle.net/21.15107/rcub_cherry_3623

Cakić N, Verbić T, Jelić R, Platas-Iglesias C, Angelovski G. Supplementary data for the article: Cakić, N.; Verbić, T. Ž.; Jelić, R. M.; Platas-Iglesias, C.; Angelovski, G. Synthesis and Characterisation of Bismacrocyclic DO3A-Amide Derivatives - An Approach towards Metal-Responsive PARACEST Agents. Dalton Transactions 2016, 45 (15), 6555–6565. https://doi.org/10.1039/c5dt04625d. in Dalton Transactions. 2016;.
https://hdl.handle.net/21.15107/rcub_cherry_3623 .

Cakić, Nevenka, Verbić, Tatjana, Jelić, Ratomir, Platas-Iglesias, Carlos, Angelovski, Goran, "Supplementary data for the article: Cakić, N.; Verbić, T. Ž.; Jelić, R. M.; Platas-Iglesias, C.; Angelovski, G. Synthesis and Characterisation of Bismacrocyclic DO3A-Amide Derivatives - An Approach towards Metal-Responsive PARACEST Agents. Dalton Transactions 2016, 45 (15), 6555–6565. https://doi.org/10.1039/c5dt04625d" in Dalton Transactions (2016),
https://hdl.handle.net/21.15107/rcub_cherry_3623 .

TY  - JOUR
AU  - Cakić, Nevenka
AU  - Verbić, Tatjana
AU  - Jelić, Ratomir
AU  - Platas-Iglesias, Carlos
AU  - Angelovski, Goran
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1911
AB  - Three new bismacrocyclic Ln(3+) chelates consisting of triamide derivatives of cyclen with glycine, methyl and tert-butyl substituents (L1-3, respectively) linked to an acyclic EGTA-derived calcium chelator were synthesised as potential MRI contrast agents (EGTA -ethylene glycol-bis(2-aminoethylether)-N, N, N', N'-tetraacetic acid). Eu3+ and Yb3+ complexes of L1-3 were investigated as chemical exchange saturation transfer (CEST) agents. Moderate to minor CEST effects were observed for Eu2L1, Eu2L2 and Yb2L2 complexes in the absence of Ca2+, with negligible changes upon addition of this metal ion. Luminescence steady-state emission and lifetime experiments did not reveal any changes in the coordination environment of the complexes, while the number of inner-sphere water molecules remained constant in the absence and presence of Ca2+. The protonation constants of Eu2L1 and Eu2L2 and stability constants of their complexes with Ca2+, Mg2+ and Zn2+ were determined by means of potentiometric titrations. The results show that the charge of the complex dramatically affects the protonation constants of the EGTA-binding unit. The stability constants of the complexes formed with Ca2+, Mg2+ and Zn2+ are several orders of magnitude lower than those of EGTA. These findings indicate that the nature of Ln(3+) chelates and their charge are the main reasons for the observed results and weaker response of these EGTA-derived triamide derivatives compared to their tricarboxylate analogues.
PB  - Royal Soc Chemistry, Cambridge
T2  - Dalton Transactions
T1  - Synthesis and characterisation of bismacrocyclic DO3A-amide derivatives - an approach towards metal-responsive PARACEST agents
VL  - 45
IS  - 15
SP  - 6555
EP  - 6565
DO  - 10.1039/c5dt04625d
ER  - 

@article{
author = "Cakić, Nevenka and Verbić, Tatjana and Jelić, Ratomir and Platas-Iglesias, Carlos and Angelovski, Goran",
year = "2016",
abstract = "Three new bismacrocyclic Ln(3+) chelates consisting of triamide derivatives of cyclen with glycine, methyl and tert-butyl substituents (L1-3, respectively) linked to an acyclic EGTA-derived calcium chelator were synthesised as potential MRI contrast agents (EGTA -ethylene glycol-bis(2-aminoethylether)-N, N, N', N'-tetraacetic acid). Eu3+ and Yb3+ complexes of L1-3 were investigated as chemical exchange saturation transfer (CEST) agents. Moderate to minor CEST effects were observed for Eu2L1, Eu2L2 and Yb2L2 complexes in the absence of Ca2+, with negligible changes upon addition of this metal ion. Luminescence steady-state emission and lifetime experiments did not reveal any changes in the coordination environment of the complexes, while the number of inner-sphere water molecules remained constant in the absence and presence of Ca2+. The protonation constants of Eu2L1 and Eu2L2 and stability constants of their complexes with Ca2+, Mg2+ and Zn2+ were determined by means of potentiometric titrations. The results show that the charge of the complex dramatically affects the protonation constants of the EGTA-binding unit. The stability constants of the complexes formed with Ca2+, Mg2+ and Zn2+ are several orders of magnitude lower than those of EGTA. These findings indicate that the nature of Ln(3+) chelates and their charge are the main reasons for the observed results and weaker response of these EGTA-derived triamide derivatives compared to their tricarboxylate analogues.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Dalton Transactions",
title = "Synthesis and characterisation of bismacrocyclic DO3A-amide derivatives - an approach towards metal-responsive PARACEST agents",
volume = "45",
number = "15",
pages = "6555-6565",
doi = "10.1039/c5dt04625d"
}

Cakić, N., Verbić, T., Jelić, R., Platas-Iglesias, C.,& Angelovski, G.. (2016). Synthesis and characterisation of bismacrocyclic DO3A-amide derivatives - an approach towards metal-responsive PARACEST agents. in Dalton Transactions
Royal Soc Chemistry, Cambridge., 45(15), 6555-6565.
https://doi.org/10.1039/c5dt04625d

Cakić N, Verbić T, Jelić R, Platas-Iglesias C, Angelovski G. Synthesis and characterisation of bismacrocyclic DO3A-amide derivatives - an approach towards metal-responsive PARACEST agents. in Dalton Transactions. 2016;45(15):6555-6565.
doi:10.1039/c5dt04625d .

Cakić, Nevenka, Verbić, Tatjana, Jelić, Ratomir, Platas-Iglesias, Carlos, Angelovski, Goran, "Synthesis and characterisation of bismacrocyclic DO3A-amide derivatives - an approach towards metal-responsive PARACEST agents" in Dalton Transactions, 45, no. 15 (2016):6555-6565,
https://doi.org/10.1039/c5dt04625d . .

TY  - DATA
AU  - Vibhute, Sandip M.
AU  - Engelmann, Joern
AU  - Verbić, Tatjana
AU  - Maier, Martin E.
AU  - Logothetis, Nikos K.
AU  - Angelovski, Goran
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3532
PB  - Royal Soc Chemistry, Cambridge
T2  - Organic and Biomolecular Chemistry
T1  - Supplementary data for article: Vibhute, S. M.; Engelmann, J.; Verbić, T.; Maier, M. E.; Logothetis, N. K.; Angelovski, G. Synthesis and Characterization of PH-Sensitive, Biotinylated MRI Contrast Agents and Their Conjugates with Avidin. Organic and Biomolecular Chemistry 2013, 11 (8), 1294–1305. https://doi.org/10.1039/c2ob26555a
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3532
ER  - 

@misc{
author = "Vibhute, Sandip M. and Engelmann, Joern and Verbić, Tatjana and Maier, Martin E. and Logothetis, Nikos K. and Angelovski, Goran",
year = "2013",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Organic and Biomolecular Chemistry",
title = "Supplementary data for article: Vibhute, S. M.; Engelmann, J.; Verbić, T.; Maier, M. E.; Logothetis, N. K.; Angelovski, G. Synthesis and Characterization of PH-Sensitive, Biotinylated MRI Contrast Agents and Their Conjugates with Avidin. Organic and Biomolecular Chemistry 2013, 11 (8), 1294–1305. https://doi.org/10.1039/c2ob26555a",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3532"
}

Vibhute, S. M., Engelmann, J., Verbić, T., Maier, M. E., Logothetis, N. K.,& Angelovski, G.. (2013). Supplementary data for article: Vibhute, S. M.; Engelmann, J.; Verbić, T.; Maier, M. E.; Logothetis, N. K.; Angelovski, G. Synthesis and Characterization of PH-Sensitive, Biotinylated MRI Contrast Agents and Their Conjugates with Avidin. Organic and Biomolecular Chemistry 2013, 11 (8), 1294–1305. https://doi.org/10.1039/c2ob26555a. in Organic and Biomolecular Chemistry
Royal Soc Chemistry, Cambridge..
https://hdl.handle.net/21.15107/rcub_cherry_3532

Vibhute SM, Engelmann J, Verbić T, Maier ME, Logothetis NK, Angelovski G. Supplementary data for article: Vibhute, S. M.; Engelmann, J.; Verbić, T.; Maier, M. E.; Logothetis, N. K.; Angelovski, G. Synthesis and Characterization of PH-Sensitive, Biotinylated MRI Contrast Agents and Their Conjugates with Avidin. Organic and Biomolecular Chemistry 2013, 11 (8), 1294–1305. https://doi.org/10.1039/c2ob26555a. in Organic and Biomolecular Chemistry. 2013;.
https://hdl.handle.net/21.15107/rcub_cherry_3532 .

Vibhute, Sandip M., Engelmann, Joern, Verbić, Tatjana, Maier, Martin E., Logothetis, Nikos K., Angelovski, Goran, "Supplementary data for article: Vibhute, S. M.; Engelmann, J.; Verbić, T.; Maier, M. E.; Logothetis, N. K.; Angelovski, G. Synthesis and Characterization of PH-Sensitive, Biotinylated MRI Contrast Agents and Their Conjugates with Avidin. Organic and Biomolecular Chemistry 2013, 11 (8), 1294–1305. https://doi.org/10.1039/c2ob26555a" in Organic and Biomolecular Chemistry (2013),
https://hdl.handle.net/21.15107/rcub_cherry_3532 .

TY  - JOUR
AU  - Vibhute, Sandip M.
AU  - Engelmann, Joern
AU  - Verbić, Tatjana
AU  - Maier, Martin E.
AU  - Logothetis, Nikos K.
AU  - Angelovski, Goran
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1595
AB  - Responsive or smart contrast agents (SCAs) provide new opportunities in magnetic resonance imaging (MRI) to examine a number of physiological and pathological events. However, their application in vivo remains challenging. Therefore, much research is focused on the optimization of their properties, to enable their use in additional imaging modalities, pre-targeted delivery, or to increase the local concentration of the agent. The key feature in the SCA synthetic modification is the retention of their physicochemical properties related to the specific MR response. Here, we report the preparation and characterization of pH sensitive SCAs appended with a phosphonate pendant arm and either an aliphatic (GdL1) or aromatic linker (GdL2). The longitudinal relaxivity of GdL1 and GdL2 increases by 146% and 31%, respectively, while the pH decreases from 9 to 5. These two SCAs were converted to the biotinylated systems GdL3 and GdL4 and their interaction with avidin was investigated. The binding affinity with avidin was assessed with a fluorescence displacement assay and with MRI phantom experiments in a 3T MRI scanner. The fluorometric assay and MRI E-titrations revealed a 3:1 binding mode of GdL3-4 to avidin with the binding affinity as high as that of the parent avidin-biotin complex. The high binding affinity was confirmed with MRI by a competitive assay. The avidin-GdL3-4 complexes thus obtained exhibit changes in both r(1) and r(2) that are pH dependent. The results reveal a new pathway for the modification and improvement of SCAs to make them more suitable for in vivo application.
PB  - Royal Soc Chemistry, Cambridge
T2  - Organic and Biomolecular Chemistry
T1  - Synthesis and characterization of pH-sensitive, biotinylated MRI contrast agents and their conjugates with avidin
VL  - 11
IS  - 8
SP  - 1294
EP  - 1305
DO  - 10.1039/c2ob26555a
ER  - 

@article{
author = "Vibhute, Sandip M. and Engelmann, Joern and Verbić, Tatjana and Maier, Martin E. and Logothetis, Nikos K. and Angelovski, Goran",
year = "2013",
abstract = "Responsive or smart contrast agents (SCAs) provide new opportunities in magnetic resonance imaging (MRI) to examine a number of physiological and pathological events. However, their application in vivo remains challenging. Therefore, much research is focused on the optimization of their properties, to enable their use in additional imaging modalities, pre-targeted delivery, or to increase the local concentration of the agent. The key feature in the SCA synthetic modification is the retention of their physicochemical properties related to the specific MR response. Here, we report the preparation and characterization of pH sensitive SCAs appended with a phosphonate pendant arm and either an aliphatic (GdL1) or aromatic linker (GdL2). The longitudinal relaxivity of GdL1 and GdL2 increases by 146% and 31%, respectively, while the pH decreases from 9 to 5. These two SCAs were converted to the biotinylated systems GdL3 and GdL4 and their interaction with avidin was investigated. The binding affinity with avidin was assessed with a fluorescence displacement assay and with MRI phantom experiments in a 3T MRI scanner. The fluorometric assay and MRI E-titrations revealed a 3:1 binding mode of GdL3-4 to avidin with the binding affinity as high as that of the parent avidin-biotin complex. The high binding affinity was confirmed with MRI by a competitive assay. The avidin-GdL3-4 complexes thus obtained exhibit changes in both r(1) and r(2) that are pH dependent. The results reveal a new pathway for the modification and improvement of SCAs to make them more suitable for in vivo application.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Organic and Biomolecular Chemistry",
title = "Synthesis and characterization of pH-sensitive, biotinylated MRI contrast agents and their conjugates with avidin",
volume = "11",
number = "8",
pages = "1294-1305",
doi = "10.1039/c2ob26555a"
}

Vibhute, S. M., Engelmann, J., Verbić, T., Maier, M. E., Logothetis, N. K.,& Angelovski, G.. (2013). Synthesis and characterization of pH-sensitive, biotinylated MRI contrast agents and their conjugates with avidin. in Organic and Biomolecular Chemistry
Royal Soc Chemistry, Cambridge., 11(8), 1294-1305.
https://doi.org/10.1039/c2ob26555a

Vibhute SM, Engelmann J, Verbić T, Maier ME, Logothetis NK, Angelovski G. Synthesis and characterization of pH-sensitive, biotinylated MRI contrast agents and their conjugates with avidin. in Organic and Biomolecular Chemistry. 2013;11(8):1294-1305.
doi:10.1039/c2ob26555a .

Vibhute, Sandip M., Engelmann, Joern, Verbić, Tatjana, Maier, Martin E., Logothetis, Nikos K., Angelovski, Goran, "Synthesis and characterization of pH-sensitive, biotinylated MRI contrast agents and their conjugates with avidin" in Organic and Biomolecular Chemistry, 11, no. 8 (2013):1294-1305,
https://doi.org/10.1039/c2ob26555a . .

TY  - JOUR
AU  - Opsenica, Igor
AU  - Terzić-Jovanović, Nataša
AU  - Opsenica, Dejan M.
AU  - Angelovski, Goran
AU  - Lehnig, Manfred
AU  - Eilbracht, Peter
AU  - Tinant, Bernard
AU  - Juranić, Zorica D.
AU  - Smith, Kirsten S.
AU  - Yang, Young S.
AU  - Diaz, Damaris S.
AU  - Smith, Philip L.
AU  - Milhous, Wilbur K.
AU  - Dokovic, Dejan
AU  - Šolaja, Bogdan A.
PY  - 2006
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/783
AB  - Mixed tetraoxanes 5a and 13 synthesized from cholic acid and 4-oxocyclohexanecarboxylic acid were as active as artemisinin against chloroquine-susceptible, chloroquine-resistant, and multidrug-resistant Plasmodium falciparum strains (IC50, IC90). Most active 13 is metabolically stable in in vitro metabolism studies. In vivo studies on tetraoxanes with a C(4'') methyl group afforded compound 15, which cured 4/5 mice at 600 and 200 mg, kg(-1), day(-1), and 2/5 mice at 50 mg, kg(-1), day(-1), showing no toxic effects. Tetraoxane 19 was an extremely active antiproliferative with LC50 of 17 nM and maximum tolerated dose of 400 mg/kg. In Fe(II)-induced scission of tetraoxane antimalarials only RO center dot radicals were detected by EPR experiments. This finding and the indication of Fe(IV)=O species led us to propose that RO center dot radicals are probably capable of inducing the parasite's death. Our results suggest that C radicals are possibly not the only lethal species derived from peroxide prodrug antimalarials, as currently believed.
PB  - Amer Chemical Soc, Washington
T2  - Journal of Medicinal Chemistry
T1  - Tetraoxane antimalarials and their reaction with Fe(II)
VL  - 49
IS  - 13
SP  - 3790
EP  - 3799
DO  - 10.1021/jm050966r
ER  - 

@article{
author = "Opsenica, Igor and Terzić-Jovanović, Nataša and Opsenica, Dejan M. and Angelovski, Goran and Lehnig, Manfred and Eilbracht, Peter and Tinant, Bernard and Juranić, Zorica D. and Smith, Kirsten S. and Yang, Young S. and Diaz, Damaris S. and Smith, Philip L. and Milhous, Wilbur K. and Dokovic, Dejan and Šolaja, Bogdan A.",
year = "2006",
abstract = "Mixed tetraoxanes 5a and 13 synthesized from cholic acid and 4-oxocyclohexanecarboxylic acid were as active as artemisinin against chloroquine-susceptible, chloroquine-resistant, and multidrug-resistant Plasmodium falciparum strains (IC50, IC90). Most active 13 is metabolically stable in in vitro metabolism studies. In vivo studies on tetraoxanes with a C(4'') methyl group afforded compound 15, which cured 4/5 mice at 600 and 200 mg, kg(-1), day(-1), and 2/5 mice at 50 mg, kg(-1), day(-1), showing no toxic effects. Tetraoxane 19 was an extremely active antiproliferative with LC50 of 17 nM and maximum tolerated dose of 400 mg/kg. In Fe(II)-induced scission of tetraoxane antimalarials only RO center dot radicals were detected by EPR experiments. This finding and the indication of Fe(IV)=O species led us to propose that RO center dot radicals are probably capable of inducing the parasite's death. Our results suggest that C radicals are possibly not the only lethal species derived from peroxide prodrug antimalarials, as currently believed.",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Medicinal Chemistry",
title = "Tetraoxane antimalarials and their reaction with Fe(II)",
volume = "49",
number = "13",
pages = "3790-3799",
doi = "10.1021/jm050966r"
}

Opsenica, I., Terzić-Jovanović, N., Opsenica, D. M., Angelovski, G., Lehnig, M., Eilbracht, P., Tinant, B., Juranić, Z. D., Smith, K. S., Yang, Y. S., Diaz, D. S., Smith, P. L., Milhous, W. K., Dokovic, D.,& Šolaja, B. A.. (2006). Tetraoxane antimalarials and their reaction with Fe(II). in Journal of Medicinal Chemistry
Amer Chemical Soc, Washington., 49(13), 3790-3799.
https://doi.org/10.1021/jm050966r

Opsenica I, Terzić-Jovanović N, Opsenica DM, Angelovski G, Lehnig M, Eilbracht P, Tinant B, Juranić ZD, Smith KS, Yang YS, Diaz DS, Smith PL, Milhous WK, Dokovic D, Šolaja BA. Tetraoxane antimalarials and their reaction with Fe(II). in Journal of Medicinal Chemistry. 2006;49(13):3790-3799.
doi:10.1021/jm050966r .

Opsenica, Igor, Terzić-Jovanović, Nataša, Opsenica, Dejan M., Angelovski, Goran, Lehnig, Manfred, Eilbracht, Peter, Tinant, Bernard, Juranić, Zorica D., Smith, Kirsten S., Yang, Young S., Diaz, Damaris S., Smith, Philip L., Milhous, Wilbur K., Dokovic, Dejan, Šolaja, Bogdan A., "Tetraoxane antimalarials and their reaction with Fe(II)" in Journal of Medicinal Chemistry, 49, no. 13 (2006):3790-3799,
https://doi.org/10.1021/jm050966r . .