TY  - JOUR
AU  - Kaluđerović, Goran N.
AU  - Bulatović, Mirna
AU  - Krajnović, Tamara T.
AU  - Paschke, Reinhard
AU  - Zmejkovski, Bojana
AU  - Maksimović-Ivanić, Danijela D.
AU  - Mijatović, Sanja
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2222
AB  - Synthesis of platinum(II) conjugate with acetylated betulinic acid tris(hydroxymethyl) aminomethane ester (BATRIS) is presented (BATRISPt). HR-ESI-MS and multinuclear NMR spectroscopy, as well as elemental analysis were used for characterization of BATRISPt. Cytotoxicity (3-(4,5-dimethythiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), crystal violet (CV), and sulforhodamine B (SRB) assays) of BA, BATRIS, BATRISPt, and cisplatin were assessed on seven different tumor cell lines: melanoma B16, colon HCT116 and DLD-1, adenocarcinoma HeLa, breast MCF-7, and anaplastic thyroid tumor 8505C and SW1736; as well as normal MRC-5 fibroblasts. Furthermore, the effect of the mentioned compounds on the apoptosis (Annexin V/PI assay) and autophagy induction (acridine orange (AO) assay) as well as caspase 3, 8, and 9 activation were investigated on the selected B16 melanoma cell line. BATRISPt showed lower activity than BA, BATRIS, or cisplatin. All tested compounds triggered apoptosis in B16 cells. Induction of autophagy was observed in B16 cells exposed only to BATRIS. On the other hand, new conjugate activates caspases 8 and 9 in B16 cells with higher impact than BATRIS or cisplatin alone.
PB  - MDPI
T2  - Inorganics
T1  - (18-Crown-6)potassium(I) trichlorido[28-acetyl-3- (tris-(hydroxylmethyl)amino-ethane)betulinic ester-κN]platinum(II): Synthesis and in vitro antitumor activity
VL  - 5
IS  - 3
DO  - 10.3390/inorganics5030056
ER  - 

@article{
author = "Kaluđerović, Goran N. and Bulatović, Mirna and Krajnović, Tamara T. and Paschke, Reinhard and Zmejkovski, Bojana and Maksimović-Ivanić, Danijela D. and Mijatović, Sanja",
year = "2017",
abstract = "Synthesis of platinum(II) conjugate with acetylated betulinic acid tris(hydroxymethyl) aminomethane ester (BATRIS) is presented (BATRISPt). HR-ESI-MS and multinuclear NMR spectroscopy, as well as elemental analysis were used for characterization of BATRISPt. Cytotoxicity (3-(4,5-dimethythiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), crystal violet (CV), and sulforhodamine B (SRB) assays) of BA, BATRIS, BATRISPt, and cisplatin were assessed on seven different tumor cell lines: melanoma B16, colon HCT116 and DLD-1, adenocarcinoma HeLa, breast MCF-7, and anaplastic thyroid tumor 8505C and SW1736; as well as normal MRC-5 fibroblasts. Furthermore, the effect of the mentioned compounds on the apoptosis (Annexin V/PI assay) and autophagy induction (acridine orange (AO) assay) as well as caspase 3, 8, and 9 activation were investigated on the selected B16 melanoma cell line. BATRISPt showed lower activity than BA, BATRIS, or cisplatin. All tested compounds triggered apoptosis in B16 cells. Induction of autophagy was observed in B16 cells exposed only to BATRIS. On the other hand, new conjugate activates caspases 8 and 9 in B16 cells with higher impact than BATRIS or cisplatin alone.",
publisher = "MDPI",
journal = "Inorganics",
title = "(18-Crown-6)potassium(I) trichlorido[28-acetyl-3- (tris-(hydroxylmethyl)amino-ethane)betulinic ester-κN]platinum(II): Synthesis and in vitro antitumor activity",
volume = "5",
number = "3",
doi = "10.3390/inorganics5030056"
}

Kaluđerović, G. N., Bulatović, M., Krajnović, T. T., Paschke, R., Zmejkovski, B., Maksimović-Ivanić, D. D.,& Mijatović, S.. (2017). (18-Crown-6)potassium(I) trichlorido[28-acetyl-3- (tris-(hydroxylmethyl)amino-ethane)betulinic ester-κN]platinum(II): Synthesis and in vitro antitumor activity. in Inorganics
MDPI., 5(3).
https://doi.org/10.3390/inorganics5030056

Kaluđerović GN, Bulatović M, Krajnović TT, Paschke R, Zmejkovski B, Maksimović-Ivanić DD, Mijatović S. (18-Crown-6)potassium(I) trichlorido[28-acetyl-3- (tris-(hydroxylmethyl)amino-ethane)betulinic ester-κN]platinum(II): Synthesis and in vitro antitumor activity. in Inorganics. 2017;5(3).
doi:10.3390/inorganics5030056 .

Kaluđerović, Goran N., Bulatović, Mirna, Krajnović, Tamara T., Paschke, Reinhard, Zmejkovski, Bojana, Maksimović-Ivanić, Danijela D., Mijatović, Sanja, "(18-Crown-6)potassium(I) trichlorido[28-acetyl-3- (tris-(hydroxylmethyl)amino-ethane)betulinic ester-κN]platinum(II): Synthesis and in vitro antitumor activity" in Inorganics, 5, no. 3 (2017),
https://doi.org/10.3390/inorganics5030056 . .

TY  - JOUR
AU  - Kommera, Harish
AU  - Kaluđerović, Goran N.
AU  - Kalbitz, Jutta
AU  - Paschke, Reinhard
PY  - 2011
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3411
AB  - In the present investigation the antiproliferative
activity of thirteen derivatives of betulinic acid and
betulin was tested against five different tumor cell lines.
The toxicity against normal human fibroblasts
(WWO70327) and the mode of cell death on HT-29
(colon cancer) as well as caspase activity induced by the
most active compounds, 9 (3-O-chloroacetylbetulinic
acid) and 15 (28-O-chloroacetylbetulin) were determined.
Investigated derivatives exerted a dose dependent antiproliferative
action at micromolar concentrations toward
target tumor cell lines. Treatment of HT-29 cells for 24 h
with 9 and 15 induced apoptosis, as observed by dye
exclusion test (trypan blue) and confirmed by the
appearance of a typical ladder pattern in the DNA
fragmentation assay.
PB  - Netherlands : Springer
T2  - Investigational  New Drugs
T1  - Lupane Triterpenoids—Betulin and Betulinic acid derivatives induce apoptosis in tumor cells
VL  - 29
IS  - 2
SP  - 266
EP  - 272
DO  - 10.1007/s10637-009-9358-x
ER  - 

@article{
author = "Kommera, Harish and Kaluđerović, Goran N. and Kalbitz, Jutta and Paschke, Reinhard",
year = "2011",
abstract = "In the present investigation the antiproliferative
activity of thirteen derivatives of betulinic acid and
betulin was tested against five different tumor cell lines.
The toxicity against normal human fibroblasts
(WWO70327) and the mode of cell death on HT-29
(colon cancer) as well as caspase activity induced by the
most active compounds, 9 (3-O-chloroacetylbetulinic
acid) and 15 (28-O-chloroacetylbetulin) were determined.
Investigated derivatives exerted a dose dependent antiproliferative
action at micromolar concentrations toward
target tumor cell lines. Treatment of HT-29 cells for 24 h
with 9 and 15 induced apoptosis, as observed by dye
exclusion test (trypan blue) and confirmed by the
appearance of a typical ladder pattern in the DNA
fragmentation assay.",
publisher = "Netherlands : Springer",
journal = "Investigational  New Drugs",
title = "Lupane Triterpenoids—Betulin and Betulinic acid derivatives induce apoptosis in tumor cells",
volume = "29",
number = "2",
pages = "266-272",
doi = "10.1007/s10637-009-9358-x"
}

Kommera, H., Kaluđerović, G. N., Kalbitz, J.,& Paschke, R.. (2011). Lupane Triterpenoids—Betulin and Betulinic acid derivatives induce apoptosis in tumor cells. in Investigational  New Drugs
Netherlands : Springer., 29(2), 266-272.
https://doi.org/10.1007/s10637-009-9358-x

Kommera H, Kaluđerović GN, Kalbitz J, Paschke R. Lupane Triterpenoids—Betulin and Betulinic acid derivatives induce apoptosis in tumor cells. in Investigational  New Drugs. 2011;29(2):266-272.
doi:10.1007/s10637-009-9358-x .

Kommera, Harish, Kaluđerović, Goran N., Kalbitz, Jutta, Paschke, Reinhard, "Lupane Triterpenoids—Betulin and Betulinic acid derivatives induce apoptosis in tumor cells" in Investigational  New Drugs, 29, no. 2 (2011):266-272,
https://doi.org/10.1007/s10637-009-9358-x . .

TY  - JOUR
AU  - Kommera, Harish
AU  - Kaluđerović, Goran N.
AU  - Kalbitz, Jutta
AU  - Dräger, Birgit
AU  - Paschke, Reinhard
PY  - 2010
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3179
AB  - In the present investigations five new derivatives of betulinic and betulonic acid were synthesized and the effect of this structural variations on anticancer activity was studied and discussed. The antiproliferative activity of betulinic and betulonic acid derivatives was studied against eight tumor cell lines of different histogenic origin. The derivatives exerted a dose dependent antiproliferative action at micromolar concentrations toward target tumor cell lines. The apoptotic mode of cell death on colon cancer cell line HT-29 was induced by the most active compounds 5, 2-amino-3-hydroxy-2-(hydroxymethyl)propyl (3-O-acetyl)betulinate, and 9, 2-amino-3-hydroxy-2-(hydroxymethyl)propyl betulonate. Treatment of HT-29 cells with 5 and 9 induced apoptosis, as observed by dye exclusion test (trypan blue) and by the appearance of a typical ladder pattern in the DNA fragmentation assay and FITC annexin V assay. Cell cycle perturbations caused by compound 5 are also presented.
PB  - Elsevier
T2  - European Journal of Medicinal Chemistry
T1  - Small structural changes of pentacyclic lupane type triterpenoid derivatives lead to significant differences in their anticancer properties
VL  - 45
IS  - 8
SP  - 3346
EP  - 3353
DO  - 10.1016/j.ejmech.2010.04.018
ER  - 

@article{
author = "Kommera, Harish and Kaluđerović, Goran N. and Kalbitz, Jutta and Dräger, Birgit and Paschke, Reinhard",
year = "2010",
abstract = "In the present investigations five new derivatives of betulinic and betulonic acid were synthesized and the effect of this structural variations on anticancer activity was studied and discussed. The antiproliferative activity of betulinic and betulonic acid derivatives was studied against eight tumor cell lines of different histogenic origin. The derivatives exerted a dose dependent antiproliferative action at micromolar concentrations toward target tumor cell lines. The apoptotic mode of cell death on colon cancer cell line HT-29 was induced by the most active compounds 5, 2-amino-3-hydroxy-2-(hydroxymethyl)propyl (3-O-acetyl)betulinate, and 9, 2-amino-3-hydroxy-2-(hydroxymethyl)propyl betulonate. Treatment of HT-29 cells with 5 and 9 induced apoptosis, as observed by dye exclusion test (trypan blue) and by the appearance of a typical ladder pattern in the DNA fragmentation assay and FITC annexin V assay. Cell cycle perturbations caused by compound 5 are also presented.",
publisher = "Elsevier",
journal = "European Journal of Medicinal Chemistry",
title = "Small structural changes of pentacyclic lupane type triterpenoid derivatives lead to significant differences in their anticancer properties",
volume = "45",
number = "8",
pages = "3346-3353",
doi = "10.1016/j.ejmech.2010.04.018"
}

Kommera, H., Kaluđerović, G. N., Kalbitz, J., Dräger, B.,& Paschke, R.. (2010). Small structural changes of pentacyclic lupane type triterpenoid derivatives lead to significant differences in their anticancer properties. in European Journal of Medicinal Chemistry
Elsevier., 45(8), 3346-3353.
https://doi.org/10.1016/j.ejmech.2010.04.018

Kommera H, Kaluđerović GN, Kalbitz J, Dräger B, Paschke R. Small structural changes of pentacyclic lupane type triterpenoid derivatives lead to significant differences in their anticancer properties. in European Journal of Medicinal Chemistry. 2010;45(8):3346-3353.
doi:10.1016/j.ejmech.2010.04.018 .

Kommera, Harish, Kaluđerović, Goran N., Kalbitz, Jutta, Dräger, Birgit, Paschke, Reinhard, "Small structural changes of pentacyclic lupane type triterpenoid derivatives lead to significant differences in their anticancer properties" in European Journal of Medicinal Chemistry, 45, no. 8 (2010):3346-3353,
https://doi.org/10.1016/j.ejmech.2010.04.018 . .

TY  - JOUR
AU  - Vetter, Cornelia
AU  - Kaluđerović, Goran N.
AU  - Paschke, Reinhard
AU  - Kluge, Ralph
AU  - Schmidt, Jürgen
AU  - Steinborn, Dirk
PY  - 2010
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3175
AB  - Reactions of [PtMe3(bpy)(Me2CO)][BF4] (2) with the thionucleobases 2-thiouracil (s2Ura), 4-thiouracil (s 4Ura) and 2,4-dithiouracil (s2s4Ura) resulted in the formation of complexes of the type [PtMe3 (bPy)(L-κS)] [BF4] (L= s2Ura, 3; s4Ura, 4; s 2s4Ura, 5). The complexes were characterized by NMR spectroscopy (1H, 13C, 195Pt), IR spectroscopy as well as microanalyses. The coordination through the C4=S groups (4, 5) was additionally confirmed by DFT calculations, where it was shown that these complexes [PtMe3(bpy)(L-κS4)]+ (L=s 4Ura, s2s4Ura) are about 5.8 (4b) and 3.3 kcal/mol (5b), respectively, more stable than the respective complexes, having thiouracil ligands bound through the C2=X groups (X=O, 4a; S, 5a). For [PtMe3(bpy)(s2Ura-κS2)][BF4] (3) no preferred coordination mode could be assigned solely based on DFT calculations. Analysis of NMR spectra showed the κS2 coordination. In vitro cytotoxic studies of complexes 3-5 on nine different cell lines (8505C, A253, FaDu, A431, A549, A2780, DLD-1, HCT-8, HT-29) revealed in most cases moderate activities. However, 3 and 5 showed significant activity towards A549 and A2780, respectively, possessing IC50 values comparable to those of cisplatin. Cell cycle perturbations and trypan blue exclusion test on cancer cell line A431 using [PtMe3(bpy)(s 2s4Ura-κS4)][BF4] (5) showed induction of apoptotic cell death. Furthermore, the reaction of [PtMe 3(OAc-κ2O,O′)(Me2CO)] (6) with 4-thiouracil yielded the dinuclear complex [(PtMe3)2(μ-s 4Ura-H)2] (7), which has been characterized by microanalysis, NMR (1H, 13C, 195Pt) and IR spectroscopy as well as ESI mass spectrometry. X-ray diffraction analysis of crystals yielded in an isolated case exhibited the presence of a hexanuclear thiouracilato platinum(IV) complex, possessing each three different kinds of methyl platinum(IV) moieties and 4-thiouracilato ligands. This exhibited the ability of 4-thiouracil platinum(IV) complexes to form multinuclear complexes.
PB  - Elsevier
T2  - Inorganica Chimica Acta
T1  - Synthesis, characterization and in vitro cytotoxicity studies of platinum(IV) complexes with thiouracil ligands
VL  - 363
IS  - 11
SP  - 2452
EP  - 2460
DO  - 10.1016/j.ica.2010.03.079
ER  - 

@article{
author = "Vetter, Cornelia and Kaluđerović, Goran N. and Paschke, Reinhard and Kluge, Ralph and Schmidt, Jürgen and Steinborn, Dirk",
year = "2010",
abstract = "Reactions of [PtMe3(bpy)(Me2CO)][BF4] (2) with the thionucleobases 2-thiouracil (s2Ura), 4-thiouracil (s 4Ura) and 2,4-dithiouracil (s2s4Ura) resulted in the formation of complexes of the type [PtMe3 (bPy)(L-κS)] [BF4] (L= s2Ura, 3; s4Ura, 4; s 2s4Ura, 5). The complexes were characterized by NMR spectroscopy (1H, 13C, 195Pt), IR spectroscopy as well as microanalyses. The coordination through the C4=S groups (4, 5) was additionally confirmed by DFT calculations, where it was shown that these complexes [PtMe3(bpy)(L-κS4)]+ (L=s 4Ura, s2s4Ura) are about 5.8 (4b) and 3.3 kcal/mol (5b), respectively, more stable than the respective complexes, having thiouracil ligands bound through the C2=X groups (X=O, 4a; S, 5a). For [PtMe3(bpy)(s2Ura-κS2)][BF4] (3) no preferred coordination mode could be assigned solely based on DFT calculations. Analysis of NMR spectra showed the κS2 coordination. In vitro cytotoxic studies of complexes 3-5 on nine different cell lines (8505C, A253, FaDu, A431, A549, A2780, DLD-1, HCT-8, HT-29) revealed in most cases moderate activities. However, 3 and 5 showed significant activity towards A549 and A2780, respectively, possessing IC50 values comparable to those of cisplatin. Cell cycle perturbations and trypan blue exclusion test on cancer cell line A431 using [PtMe3(bpy)(s 2s4Ura-κS4)][BF4] (5) showed induction of apoptotic cell death. Furthermore, the reaction of [PtMe 3(OAc-κ2O,O′)(Me2CO)] (6) with 4-thiouracil yielded the dinuclear complex [(PtMe3)2(μ-s 4Ura-H)2] (7), which has been characterized by microanalysis, NMR (1H, 13C, 195Pt) and IR spectroscopy as well as ESI mass spectrometry. X-ray diffraction analysis of crystals yielded in an isolated case exhibited the presence of a hexanuclear thiouracilato platinum(IV) complex, possessing each three different kinds of methyl platinum(IV) moieties and 4-thiouracilato ligands. This exhibited the ability of 4-thiouracil platinum(IV) complexes to form multinuclear complexes.",
publisher = "Elsevier",
journal = "Inorganica Chimica Acta",
title = "Synthesis, characterization and in vitro cytotoxicity studies of platinum(IV) complexes with thiouracil ligands",
volume = "363",
number = "11",
pages = "2452-2460",
doi = "10.1016/j.ica.2010.03.079"
}

Vetter, C., Kaluđerović, G. N., Paschke, R., Kluge, R., Schmidt, J.,& Steinborn, D.. (2010). Synthesis, characterization and in vitro cytotoxicity studies of platinum(IV) complexes with thiouracil ligands. in Inorganica Chimica Acta
Elsevier., 363(11), 2452-2460.
https://doi.org/10.1016/j.ica.2010.03.079

Vetter C, Kaluđerović GN, Paschke R, Kluge R, Schmidt J, Steinborn D. Synthesis, characterization and in vitro cytotoxicity studies of platinum(IV) complexes with thiouracil ligands. in Inorganica Chimica Acta. 2010;363(11):2452-2460.
doi:10.1016/j.ica.2010.03.079 .

Vetter, Cornelia, Kaluđerović, Goran N., Paschke, Reinhard, Kluge, Ralph, Schmidt, Jürgen, Steinborn, Dirk, "Synthesis, characterization and in vitro cytotoxicity studies of platinum(IV) complexes with thiouracil ligands" in Inorganica Chimica Acta, 363, no. 11 (2010):2452-2460,
https://doi.org/10.1016/j.ica.2010.03.079 . .

TY  - JOUR
AU  - Zmejkovski, Bojana
AU  - Kaluđerović, Goran N.
AU  - Gómez-Ruiz, S.
AU  - Žižak, Željko
AU  - Steinborn, D.
AU  - Schmidt, H.
AU  - Paschke, Reinhard
AU  - Juranić, Zorica
AU  - Sabo, Tibor
PY  - 2009
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/578
AB  - New R2eddip-type esters (R = cyclopentyl, L3·2HCl 1.5H2O; cyclohexyl, L4·2HCl·H2O) and corresponding palladium(II) complexes, [PdCl2L3] (3) and [PdCl2L4]·H2O (4), as well as [PdCl2L2] (2; L2 diisobutyl ester of eddip) were synthesized and characterized by IR, 1H and 13C NMR spectroscopies and elemental analysis. The crystal structure of L3·2HCl·2CHCl3 was resolved and is given herein. The NMR spectroscopy confirmed the presence of two isomers (from three possible) for each palladium(II) complex. DFT calculations support the formation of two diastereoisomers. In addition, antitumoral investigations were performed and these investigations also included the diisopropyl ester of eddip (L1) and corresponding palladium(II) complex, [PdCl2L1] (1). In vitro antiproliferative activity was determined against several tumor cell lines HeLa, Fem-x, K562 and rested and stimulated normal immunocompetent cells (human peripheral blood mononuclear cells -PBMCs) using MTT test.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux
T2  - European Journal of Medicinal Chemistry
T1  - Palladium(II) complexes with R2edda-derived ligands. Part II. Synthesis, characterization and in vitro antitumoral studies of R2eddip esters and palladium(II) complexes
VL  - 44
IS  - 9
SP  - 3452
EP  - 3458
DO  - 10.1016/j.ejmech.2009.02.002
ER  - 

@article{
author = "Zmejkovski, Bojana and Kaluđerović, Goran N. and Gómez-Ruiz, S. and Žižak, Željko and Steinborn, D. and Schmidt, H. and Paschke, Reinhard and Juranić, Zorica and Sabo, Tibor",
year = "2009",
abstract = "New R2eddip-type esters (R = cyclopentyl, L3·2HCl 1.5H2O; cyclohexyl, L4·2HCl·H2O) and corresponding palladium(II) complexes, [PdCl2L3] (3) and [PdCl2L4]·H2O (4), as well as [PdCl2L2] (2; L2 diisobutyl ester of eddip) were synthesized and characterized by IR, 1H and 13C NMR spectroscopies and elemental analysis. The crystal structure of L3·2HCl·2CHCl3 was resolved and is given herein. The NMR spectroscopy confirmed the presence of two isomers (from three possible) for each palladium(II) complex. DFT calculations support the formation of two diastereoisomers. In addition, antitumoral investigations were performed and these investigations also included the diisopropyl ester of eddip (L1) and corresponding palladium(II) complex, [PdCl2L1] (1). In vitro antiproliferative activity was determined against several tumor cell lines HeLa, Fem-x, K562 and rested and stimulated normal immunocompetent cells (human peripheral blood mononuclear cells -PBMCs) using MTT test.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux",
journal = "European Journal of Medicinal Chemistry",
title = "Palladium(II) complexes with R2edda-derived ligands. Part II. Synthesis, characterization and in vitro antitumoral studies of R2eddip esters and palladium(II) complexes",
volume = "44",
number = "9",
pages = "3452-3458",
doi = "10.1016/j.ejmech.2009.02.002"
}

Zmejkovski, B., Kaluđerović, G. N., Gómez-Ruiz, S., Žižak, Ž., Steinborn, D., Schmidt, H., Paschke, R., Juranić, Z.,& Sabo, T.. (2009). Palladium(II) complexes with R2edda-derived ligands. Part II. Synthesis, characterization and in vitro antitumoral studies of R2eddip esters and palladium(II) complexes. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux., 44(9), 3452-3458.
https://doi.org/10.1016/j.ejmech.2009.02.002

Zmejkovski B, Kaluđerović GN, Gómez-Ruiz S, Žižak Ž, Steinborn D, Schmidt H, Paschke R, Juranić Z, Sabo T. Palladium(II) complexes with R2edda-derived ligands. Part II. Synthesis, characterization and in vitro antitumoral studies of R2eddip esters and palladium(II) complexes. in European Journal of Medicinal Chemistry. 2009;44(9):3452-3458.
doi:10.1016/j.ejmech.2009.02.002 .

Zmejkovski, Bojana, Kaluđerović, Goran N., Gómez-Ruiz, S., Žižak, Željko, Steinborn, D., Schmidt, H., Paschke, Reinhard, Juranić, Zorica, Sabo, Tibor, "Palladium(II) complexes with R2edda-derived ligands. Part II. Synthesis, characterization and in vitro antitumoral studies of R2eddip esters and palladium(II) complexes" in European Journal of Medicinal Chemistry, 44, no. 9 (2009):3452-3458,
https://doi.org/10.1016/j.ejmech.2009.02.002 . .

TY  - JOUR
AU  - Kaluđerović, Goran N.
AU  - Schmidt, Harry
AU  - Schwieger, Sebastian
AU  - Wagner, Christoph
AU  - Paschke, Reinhard
AU  - Dietrich, Andrea
AU  - Mueller, Thomas
AU  - Steinborn, Dirk
PY  - 2008
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4329
AB  - The novel N,N-type bidentate ligand precursors, diethyl, dipropyl esters of ethylenediamine-N,N′-diacetic acid dihydrochloride (HOOCCH2NHCH2CH2NHCH2COOH • 2HCl, H2edda • 2HCl), and the corresponding tetrachloroplatinum(IV) complexes, [PtCl4(R2edda)] • H2O (ROOCCH2NHCH2CH2NHCH2COOR, R = Me, Et, n-Pr), were synthesized. The esters coordinated as bidentate ligands via both N donor atoms. The esters, as well as the complexes, have been characterized by infrared, 1H and 13C NMR spectroscopy and elemental analysis. Solid state structures of both dimethyl and diethyl ester platinum(IV) complexes have been determined by X-ray crystallography. Quantum chemical calculations were performed in order to investigate diastereoselectivity in the formation of the platinum(IV) complexes. The in vitro cytotoxic evaluation of the investigated complexes in human tumor cell lines 1411HP, H12.1 (both testicular germ cell tumors), DLD-1 (colon carcinoma), 518A2 (melanoma), A549 (lung carcinoma) and liposarcoma showed a dose-dependent antiproliferative effect in all cell lines. Remarkably, the highest cytotoxic activity was observed in the cisplatin-resistant cell line 1411HP. In addition, at higher concentrations the treatment with these complexes led to the induction of apoptosis in all cell lines except for DLD-1.
PB  - Elsevier
T2  - Inorganica Chimica Acta
T1  - Platinum(IV) complexes with ethylenediamine-N,N0-diacetate diester (R2edda) ligands: Synthesis, characterization and in vitro antitumoral activity
VL  - 361
IS  - 5
SP  - 1395
EP  - 1404
DO  - 10.1016/j.ica.2007.09.010
ER  - 

@article{
author = "Kaluđerović, Goran N. and Schmidt, Harry and Schwieger, Sebastian and Wagner, Christoph and Paschke, Reinhard and Dietrich, Andrea and Mueller, Thomas and Steinborn, Dirk",
year = "2008",
abstract = "The novel N,N-type bidentate ligand precursors, diethyl, dipropyl esters of ethylenediamine-N,N′-diacetic acid dihydrochloride (HOOCCH2NHCH2CH2NHCH2COOH • 2HCl, H2edda • 2HCl), and the corresponding tetrachloroplatinum(IV) complexes, [PtCl4(R2edda)] • H2O (ROOCCH2NHCH2CH2NHCH2COOR, R = Me, Et, n-Pr), were synthesized. The esters coordinated as bidentate ligands via both N donor atoms. The esters, as well as the complexes, have been characterized by infrared, 1H and 13C NMR spectroscopy and elemental analysis. Solid state structures of both dimethyl and diethyl ester platinum(IV) complexes have been determined by X-ray crystallography. Quantum chemical calculations were performed in order to investigate diastereoselectivity in the formation of the platinum(IV) complexes. The in vitro cytotoxic evaluation of the investigated complexes in human tumor cell lines 1411HP, H12.1 (both testicular germ cell tumors), DLD-1 (colon carcinoma), 518A2 (melanoma), A549 (lung carcinoma) and liposarcoma showed a dose-dependent antiproliferative effect in all cell lines. Remarkably, the highest cytotoxic activity was observed in the cisplatin-resistant cell line 1411HP. In addition, at higher concentrations the treatment with these complexes led to the induction of apoptosis in all cell lines except for DLD-1.",
publisher = "Elsevier",
journal = "Inorganica Chimica Acta",
title = "Platinum(IV) complexes with ethylenediamine-N,N0-diacetate diester (R2edda) ligands: Synthesis, characterization and in vitro antitumoral activity",
volume = "361",
number = "5",
pages = "1395-1404",
doi = "10.1016/j.ica.2007.09.010"
}

Kaluđerović, G. N., Schmidt, H., Schwieger, S., Wagner, C., Paschke, R., Dietrich, A., Mueller, T.,& Steinborn, D.. (2008). Platinum(IV) complexes with ethylenediamine-N,N0-diacetate diester (R2edda) ligands: Synthesis, characterization and in vitro antitumoral activity. in Inorganica Chimica Acta
Elsevier., 361(5), 1395-1404.
https://doi.org/10.1016/j.ica.2007.09.010

Kaluđerović GN, Schmidt H, Schwieger S, Wagner C, Paschke R, Dietrich A, Mueller T, Steinborn D. Platinum(IV) complexes with ethylenediamine-N,N0-diacetate diester (R2edda) ligands: Synthesis, characterization and in vitro antitumoral activity. in Inorganica Chimica Acta. 2008;361(5):1395-1404.
doi:10.1016/j.ica.2007.09.010 .

Kaluđerović, Goran N., Schmidt, Harry, Schwieger, Sebastian, Wagner, Christoph, Paschke, Reinhard, Dietrich, Andrea, Mueller, Thomas, Steinborn, Dirk, "Platinum(IV) complexes with ethylenediamine-N,N0-diacetate diester (R2edda) ligands: Synthesis, characterization and in vitro antitumoral activity" in Inorganica Chimica Acta, 361, no. 5 (2008):1395-1404,
https://doi.org/10.1016/j.ica.2007.09.010 . .

TY  - JOUR
AU  - Kaluđerović, Goran N.
AU  - Schmidt, Harry
AU  - Paschke, Reinhard
AU  - Kalinowski, Bernd
AU  - Dietrich, Andrea
AU  - Mueller, Thomas
AU  - Steinborn, Dirk
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4252
AB  - Four dipeptide complexes of the type [PtX2(dipeptide)] · H2O (X = Cl, I, dipeptide = l-methionylglycine, l-methionyl-l-leucine) were prepared. The complexes were characterized by 1H, 13C, 195Pt NMR and infrared spectroscopy, DTG and elemental analysis. From the infrared, 1H and 13C NMR spectroscopy it was concluded that dipeptides coordinate bidentately via sulfur and amine nitrogen donor atoms. Confirmed with 13C and 195Pt NMR spectroscopy, each of the complexes exists in two diastereoisomeric forms, which are related by inversion of configuration at the sulfur atom. The 1H NMR spectrum for the platinum(II) complex with l-methionylglycine and chloro ligands exhibited reversible, intramolecular inversion of configuration at the S atom; ΔG≠ = 72 kJ mol−1 at coalescence temperature 349 K was calculated. In vitro cytotoxicity studies using the human tumor cell lines liposarcoma, lung carcinoma A549 and melanoma 518A2 revealed considerable activity of the platinum(II) complex with l-methionylglycine and chloro ligands. Further in vitro cytotoxic evaluation using human testicular germ cell tumor cell lines 1411HP and H12.1 and colon carcinoma cell line DLD-1 showed moderate cytotoxic activity for all platinum(II) complexes only in the cisplatin-sensitive cell line H12.1. Platinum uptake studies using atomic absorption spectroscopy indicated no relationship between uptake and activity. Potential antitumoral activity of this class of platinum(II) complexes is dependent on the kind of ligands as well as on tumor cell type.
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - Platinum(II) complexes with l-methionylglycine and l-methionyl-l-leucine ligands: Synthesis, characterization and in vitro antitumoral activity
VL  - 101
IS  - 3
SP  - 543
EP  - 549
DO  - 10.1016/j.jinorgbio.2006.11.016
ER  - 

@article{
author = "Kaluđerović, Goran N. and Schmidt, Harry and Paschke, Reinhard and Kalinowski, Bernd and Dietrich, Andrea and Mueller, Thomas and Steinborn, Dirk",
year = "2007",
abstract = "Four dipeptide complexes of the type [PtX2(dipeptide)] · H2O (X = Cl, I, dipeptide = l-methionylglycine, l-methionyl-l-leucine) were prepared. The complexes were characterized by 1H, 13C, 195Pt NMR and infrared spectroscopy, DTG and elemental analysis. From the infrared, 1H and 13C NMR spectroscopy it was concluded that dipeptides coordinate bidentately via sulfur and amine nitrogen donor atoms. Confirmed with 13C and 195Pt NMR spectroscopy, each of the complexes exists in two diastereoisomeric forms, which are related by inversion of configuration at the sulfur atom. The 1H NMR spectrum for the platinum(II) complex with l-methionylglycine and chloro ligands exhibited reversible, intramolecular inversion of configuration at the S atom; ΔG≠ = 72 kJ mol−1 at coalescence temperature 349 K was calculated. In vitro cytotoxicity studies using the human tumor cell lines liposarcoma, lung carcinoma A549 and melanoma 518A2 revealed considerable activity of the platinum(II) complex with l-methionylglycine and chloro ligands. Further in vitro cytotoxic evaluation using human testicular germ cell tumor cell lines 1411HP and H12.1 and colon carcinoma cell line DLD-1 showed moderate cytotoxic activity for all platinum(II) complexes only in the cisplatin-sensitive cell line H12.1. Platinum uptake studies using atomic absorption spectroscopy indicated no relationship between uptake and activity. Potential antitumoral activity of this class of platinum(II) complexes is dependent on the kind of ligands as well as on tumor cell type.",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "Platinum(II) complexes with l-methionylglycine and l-methionyl-l-leucine ligands: Synthesis, characterization and in vitro antitumoral activity",
volume = "101",
number = "3",
pages = "543-549",
doi = "10.1016/j.jinorgbio.2006.11.016"
}

Kaluđerović, G. N., Schmidt, H., Paschke, R., Kalinowski, B., Dietrich, A., Mueller, T.,& Steinborn, D.. (2007). Platinum(II) complexes with l-methionylglycine and l-methionyl-l-leucine ligands: Synthesis, characterization and in vitro antitumoral activity. in Journal of Inorganic Biochemistry
Elsevier., 101(3), 543-549.
https://doi.org/10.1016/j.jinorgbio.2006.11.016

Kaluđerović GN, Schmidt H, Paschke R, Kalinowski B, Dietrich A, Mueller T, Steinborn D. Platinum(II) complexes with l-methionylglycine and l-methionyl-l-leucine ligands: Synthesis, characterization and in vitro antitumoral activity. in Journal of Inorganic Biochemistry. 2007;101(3):543-549.
doi:10.1016/j.jinorgbio.2006.11.016 .

Kaluđerović, Goran N., Schmidt, Harry, Paschke, Reinhard, Kalinowski, Bernd, Dietrich, Andrea, Mueller, Thomas, Steinborn, Dirk, "Platinum(II) complexes with l-methionylglycine and l-methionyl-l-leucine ligands: Synthesis, characterization and in vitro antitumoral activity" in Journal of Inorganic Biochemistry, 101, no. 3 (2007):543-549,
https://doi.org/10.1016/j.jinorgbio.2006.11.016 . .