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Publikation

Hübner, D.; Kaluđerović, M. R.; Gómez-Ruiz, S.; Kaluđerović, G. N.; Anionic chlorido(triphenyl)tin(IV) bearing N-phthaloylglycinato or 1,2,4-benzenetricarboxylato 1,2-anhydride ligands: potential cytotoxic and apoptosis-inducing agents against several types of cancer Chem. Biol. Drug Des. 89, 628-633, (2017) DOI: 10.1111/cbdd.12885

Two ionic triphenyltin(IV) chloride carboxylate compounds of the formula [NHEt3][Ph3SnCl(L)] [LH = N‐phthaloylglycine (P‐GlyH), 1; 1,2,4‐benzenetricarboxylic 1,2‐anhydride (BTCH), 2] were tested for the in vitro activity against 518A2 (melanoma), FaDu (head and neck carcinoma), HT‐29 (colon cancer), MCF‐7 (breast carcinoma), and SW1736 (thyroid cancer) cell lines. The ammonium salts of the carboxylic acids are found to be not active, while anionic [Ph3SnCl(L)]− exhibited high cytotoxicity in nM range, both higher activity and selectivity than cisplatin. Compounds 1 and 2 are inducing apoptosis, which was proved with the morphological and biochemical features such as membrane blebbing, translocation of phosphatidylserine, and DNA fragmentation. Thus, accumulation of cells in sub‐G1 phase is observed. Both anionic organotin(IV) compounds showed potent cytotoxic and apoptotic properties against five cancer cell lines of various histogenetic origin.
Publikation

Bensing, C.; Mojić, M.; Gómez-Ruiz, S.; Carralero, S.; Dojčinović, B.; Maksimović-Ivanić, D.; Mijatović, S.; Kaluđerović, G. N.; Evaluation of functionalized mesoporous silica SBA-15 as a carrier system for Ph3Sn(CH2)3OH against the A2780 ovarian carcinoma cell line Dalton Trans. 45, 18984-18993, (2016) DOI: 10.1039/C6DT03519A

SBA-15|Sn3, a mesoporous silica-based material (derivative of SBA-15) loaded with an organotin compound Ph3Sn(CH2)3OH (Sn3), possesses improved antitumor potential against the A2780 high-grade serous ovarian carcinoma cell line in comparison to Sn3. It is demonstrated that both the compound and the nanostructured material are internalized by the A2780 cells. A similar mode of action of Sn3 and SBA-15|Sn3 against the A2780 cell line was found. Explicitly, induction of apoptosis, caspase 2, 3, 8 and 9 activation, accumulation of cells in the hypodiploid phase as well as accumulation of ROS were observed. Interestingly, Sn3 loaded in the mesoporous silica-based material needed to reach a concentration 3.5 times lower than the IC50 value of the Sn3 compound, pointing out a higher effect of the SBA-15|Sn3 than Sn3 alone. Clonogenic potential, growth in 3D culture as well as mobility of cells were disturbed in the presence of SBA-15|Sn3. Such behavior could be associated with the suppression of p-38 MAPK. Less profound effect of Sn3 compared to SBA-15|Sn3 could be attributed to a different regulation of p-38 and STAT-3, which are mainly responsible for an appropriate cellular response to diverse stimuli or metastatic properties.
Publikation

Barroso, S.; Coelho, A. M.; Gómez-Ruiz, S.; Calhorda, M. J.; Žižak, ?.; Kaluđerović, G. N.; Martins, A. M.; Correction: Synthesis, cytotoxic and hydrolytic studies of titanium complexes anchored by a tripodal diamine bis(phenolate) ligand Dalton Trans. 44, 2497-2497, (2015) DOI: 10.1039/C4DT90194K

Correction for ‘Synthesis, cytotoxic and hydrolytic studies of titanium complexes anchored by a tripodal diamine bis(phenolate) ligand’ by Sónia Barroso et al., Dalton Trans., 2014, 43, 17422–17433.
Publikation

Bulatović, M. Z.; Maksimović-Ivanić, D.; Bensing, C.; Gómez-Ruiz, S.; Steinborn, D.; Schmidt, H.; Mojić, M.; Korać, A.; Golić, I.; Pérez-Quintanilla, D.; Momčilović, M.; Mijatović, S.; Kaluđerović, G. N.; Organozinn(IV)-beladenes mesoporöses SiO2 als biokompatible Strategie bei der Krebstherapie Angew. Chem. 126, 6092-6097, (2014) DOI: 10.1002/ange.201400763

Das große therapeutische Potenzial eines Organozinn(IV)‐beladenen nanostrukturierten SiO2 (SBA‐15pSn) wird am Beispiel der Rückbildung eines durch B16‐Zellen induzierten Melanoms bei syngenen C57BL/6‐Mäusen demonstriert. Neben Apoptose als grundlegendem Mechanismus der Antitumorwirkung einer Vielzahl von Chemotherapeutika ist der entscheidende Vorteil dieses mesoporösen zinnhaltigen Materials das Auslösen der Zelldifferenzierung – ein Effekt, der weder für metallbasierte Zytostatika noch für mesoporöse Materialien alleine bisher beobachtet wurde. Dieser nichtaggressive Wirkungsmechanismus ist hochwirksam gegen Tumorzellen aber im gewählten Konzentrationsbereich nichttoxisch für normales Gewebe. JNK‐unabhängige Apoptose (JNK: Jun amino‐terminal kinase), begleitet von der Bildung des melanozytenartigen nichtproliferativen Phänotyps der überlebenden Zellen demonstriert das außergewöhnliche Potenzial von SBA‐15pSn zur Unterdrückung von Tumorwachstum ohne eine unerwünschte kompensatorische Proliferation der erkrankten Zellen als Antwort auf den Zelltod in ihrer Nachbarschaft.
Publikation

Bulatović, M. Z.; Maksimović-Ivanić, D.; Bensing, C.; Gómez-Ruiz, S.; Steinborn, D.; Schmidt, H.; Mojić, M.; Korać, A.; Golić, I.; Pérez-Quintanilla, D.; Momčilović, M.; Mijatović, S.; Kaluđerović, G. N.; Organotin(IV)-Loaded Mesoporous Silica as a Biocompatible Strategy in Cancer Treatment Angew. Chem. Int. Ed. 53, 5982-5987, (2014) DOI: 10.1002/anie.201400763

The strong therapeutic potential of an organotin(IV) compound loaded in nanostructured silica (SBA‐15pSn) is demonstrated: B16 melanoma tumor growth in syngeneic C57BL/6 mice is almost completely abolished. In contrast to apoptosis as the basic mechanism of the anticancer action of numerous chemotherapeutics, the important advantage of this SBA‐15pSn mesoporous material is the induction of cell differentiation, an effect unknown for metal‐based drugs and nanomaterials alone. This non‐aggressive mode of drug action is highly efficient against cancer cells but is in the concentration range used nontoxic for normal tissue. JNK (Jun‐amino‐terminal kinase)‐independent apoptosis accompanied by the development of the melanocyte‐like nonproliferative phenotype of survived cells indicates the extraordinary potential of SBA‐15pSn to suppress tumor growth without undesirable compensatory proliferation of malignant cells in response to neighboring cell death.
Publikation

Barroso, S.; Coelho, A. M.; Gómez-Ruiz, S.; Calhorda, M. J.; Žižak, ?.; Kaluđerović, G. N.; Martins, A. M.; Synthesis, cytotoxic and hydrolytic studies of titanium complexes anchored by a tripodal diamine bis(phenolate) ligand Dalton Trans. 43, 17422-17433, (2014) DOI: 10.1039/C4DT00975D

The reactivity, cytotoxic studies and hydrolytic behaviour of diamine bis(phenolate) titanium complexes are reported. The reactions of [Ti(tBu2O2NN′)Cl]2(μ-O) (1) with LiOiPr or HOiPr in the presence of NEt3, aiming at the synthesis of the alkoxido derivative of 1 led to no reaction or to the synthesis of the monomeric complex [Ti(tBu2O2NN′)(OiPr)2] (3), respectively. A small amount of the alkoxidotitanium dimer [Ti(tBu2O2NN′)(OiPr)]2(μ-O) (2) crystallized out of a solution of 3 and DFT calculations showed that the transformation of 1 into 3 is a thermodynamically favorable process in the presence of a base (NEt3) (ΔG = −14.7 kcal mol−1). 2 was quantitatively obtained through the direct reaction of the ligand precursor H2(tBu2O2NN′) with titanium tetra(isopropoxido). Further reaction of 2 with an excess of TMSCl was revealed to be the most suitable method for the preparation of [Ti(tBu2O2NN′)Cl2] (4). 1 and 3 disclosed cytotoxic activity towards HeLa, Fem-x, MDA-MB-361 and K562 cells and 1 exhibited moderate binding affinity to FS-DNA. 1H NMR hydrolysis studies attested the fast decomposition of 4 in the presence of D2O. The hydrolysis of 3 is slower and proceeds through the formation of [Ti(tBu2O2NN′)(OH)]2(μ-O) (5) that was crystallographically characterized. Upon D2O addition 1 immediately forms complex new species, stable in solution for long periods (weeks).
Publikation

Gómez-Ruiz, S.; Žižak, ?.; Kaluđerović, G. N.; Structural studies and cytotoxic activity against human cancer cell lines of mono and dinuclear tin(IV) complexes with the α,α′-dimercapto-o-xylene ligand Inorg. Chim. Acta 423, 117-122, (2014) DOI: 10.1016/j.ica.2014.04.023

The reaction of α,α′-dimercapto-o-xylene (H2dmox) with SnPh2Cl2 (1:1) and SnPh3Cl (1:2) in the presence of two equivalents of NEt3 led to the formation of the complexes [SnPh2(dmox)] (1) and [SnPh3(μ-dmox)]2 (2), respectively. Both complexes have been characterized by multinuclear NMR and IR spectroscopy, mass spectrometry and elemental analysis. In addition, the molecular structure of complex 2 has been determined by single crystal X-ray diffraction studies. The cytotoxic activity of 1 and 2 was tested against the tumor cell lines human cervix adenocarcinoma HeLa, breast carcinoma MDA-MB-453, colon carcinoma LS174 and human myelogenous leukemia K562. In addition, the toxicity of both complexes to non-stimulated and stimulated peripheral blood mononuclear cells (PBMC) has been tested. The in vitro cytotoxicity tests show very high antiproliferative activity of both complexes, being much higher that of 2. In addition, this compound shows a higher cytotoxic activity towards cancer cell lines than to non-stimulated and stimulated PBMC, indicating a slight selectivity to cancer cell lines.

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