Antiproliferative and proapoptotic activity of molecular copper(II) complex of N-1-tosylcytosine

Glavaš‐Obrovac, Ljubica; Jukić, Marijana; Mišković, Katarina; Marković, Ivana; Saftić, Dijana; Ban, Ž.; Matić, Josipa; Žinić, Mladen

doi:10.1016/j.jtemb.2017.10.009

Cited by 8 publications

(17 citation statements)

References 37 publications

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“…The C5-[1,2,3]triazolyl-flex-nucleoside analogs (7)(8)(9)(10)(11)(12)(13)(14)(16)(17)(18)(19)(20), ribofuranoside conjugates (23)(24)(25)(26)(27)(28), and 5-azido-ribosylsulfonamides (31)(32)(33) were tested for their effects on the growth of the non-tumor MDCK1 (Madine-Darby canine kidney) cell line, leukemia and lymphoma cell lines: Hut78 (T-cell lymphoma), K562 (acute monocytic leukemia), Burkitt lymphoma (Raji), and carcinoma cell lines: HeLa (human cervical adenocarcinoma), CaCo-2 (human colorectal adenocarcinoma), and NCI-H358 (human non-small cell lung cancer). The obtained results, presented as the concentration achieving 50% of cell growth inhibition (IC 50 value), show that the investigated compounds influenced tumor cell growth differently depending on the cell line and the dose applied.…”

Section: Evaluation Of Antiproliferative Activitymentioning

confidence: 99%

“…IR spectra were obtained as KBr pellets on a PerkinElmer 297 spectrophotometer. NMR spectra were recorded on AV600 and AV300 MHz spectrometers (Bruker BioSpin GmbH, Rheinstetten, Germany), operated at 600.13 or 300.13 MHz for 1 H nuclei and at 150.92 MHz or 75.46 MHz for 13 C, using DMSO-d 6 as the internal standard (labels in the spectra: Ph = phenyl group; TP = thiophene ring; brd = broad doublets, brs = broad singlets). Mass spectrometry was performed on an Agilent 6410 Triple Quad mass spectrometer (Agilent Technologies, Santa Clara, CA, USA).…”

Section: General Informationmentioning

confidence: 99%

“…[1][2][3][4][5][6][7][8] In the search for new biologically active nucleobase/nucleoside mimics, structural modifications usually involving changes in the sugar and/or nucleobase domain have been widely exploited. For example, recently reported modified nucleosides in which the furanose ring has been replaced by an alternative alkyl-or aryl-SO 2 -moiety to give N1-sulfonylpyrimidines [9][10][11][12][13][14] or N9-sulfonylpurines 15,16 have revealed potent in vitro [10][11][12][13][14]17 and in vivo 18,19 antitumor activity. Additionally, introducing aromatic functionalities to the natural nucleobase can result in nucleoside mimics with new mechanisms of action.…”

Section: Introductionmentioning

confidence: 99%

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1,2,3-Triazole-containing flex-nucleoside analogs and sulfonamido-ribofuranoside conjugates: design, synthesis, and antiproliferative potential

Saftić,

Ban,

Špoljarić

et al. 2023

New J. Chem.

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Section: Evaluation Of Antiproliferative Activitymentioning

confidence: 99%

Section: General Informationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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1,2,3-Triazole-containing flex-nucleoside analogs and sulfonamido-ribofuranoside conjugates: design, synthesis, and antiproliferative potential

Saftić,

Ban,

Špoljarić

et al. 2023

New J. Chem.

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“…[30][31][32][33] Previously, we have synthesized N-sulfonylpyrimidine derivatives I (Figure 2) as a new type of sulfonylcycloureas. [34][35][36][37] These compounds showed strong antiproliferative activity on human tumor cell lines, in in vitro [38][39][40][41] and in vivo [42][43][44][45] conditions. T Figure 1.…”

Section: Introductionmentioning

confidence: 99%

An Efficient Synthesis and In vitro Cytostatic Activity of 5-Aminosulfonyl Uracil Derivatives

Ismaili

Ban

Matić

et al. 2019

Croat. chem. acta (Online)

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Efficient synthesis of 5-aminosulfonyl uracil derivatives 2-9 and results of their antiproliferative activity are provided. Sulfonylation of the amino group in 5-aminouracil 1 with selected arylsulfonyl chlorides occurs regioselectively when the reaction is carried out in pyridine at room temperature. Simple isolation of the products by recrystallization of the crude product mixture from aqueous methanol provides good to excellent yields. The prepared 5-aminosulfonyl uracil derivatives 2-9 were tested for the antiproliferative activity on a panel of seven tumor cell lines of different histological origin (HeLa, Caco-2, NCI-H358, Raji, HuT78, Jurkat, K562) and normal MDCK I cells. Derivatives 2-9 were found more efficient to lymphoma and leukemia cells compared to solid tumor and normal cells.

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“…We have described the synthesis of novel N ‐1‐sulfonylpyrimidine derivatives which showed strong antitumor activity in in vitro and in vivo conditions. Inspired by the numerous reports on the antitumor activity of metal complexes, we prepared N ‐1‐sulfonylpyrimidine metal complexes . N ‐1‐sulfonylcytosine is capable to form palladium (II) and other transition metal complexes including Cu(II) .…”

Section: Introductionmentioning

confidence: 99%

The transformation from 2°‐amine to 3°‐amine of cyclam ring alters the fragmentation patterns of 1‐tosylcytosine‐cyclam conjugates

et al. 2018

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The novel N-1-sulfonylcytosine-cyclam conjugates 1 and 2 conjugates are ionized by electrospray ionization mass spectrometry (ESI MS) in positive and negative modes (ES and ES ) as singly protonated/deprotonated species or as singly or doubly charged metal complexes. Their structure and fragmentation behavior is examined by collision induced experiments. It was observed that the structure of the conjugate dictated the mode of the ionization: 1 was analyzed in ES mode while 2 in positive mode. Complexation with metal ions did not have the influence on the ionization mode. Zn and Cu complexes with ligand 1 followed the similar fragmentation pattern in negative ionization mode. The transformation from 2°-amine in 1 to 3°-amine of cyclam ring in 2 leads to the different fragmentation patterns due to the modification of the protonation priority which changed the fragmentation channels within the conjugate itself. Cu ions formed complexes practically immediately, and the priority had the cyclam portion of the ligand 2. The structure of the formed Zn complexes with ligand 2 depended on the number of 3° amines within the cyclam portion of the conjugate and the ratio of the metal:ligand used. The cleavage of the cyclam ring of metal complexes is driven by the formation of the fragment that suited the coordinating demand of the metal ions and the collision energy applied. Finally, it was shown that the structure of the cyclam conjugate dictates the fragmentation reactions and not the metal ions.

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Antiproliferative and proapoptotic activity of molecular copper(II) complex of N-1-tosylcytosine

Cited by 8 publications

References 37 publications

1,2,3-Triazole-containing flex-nucleoside analogs and sulfonamido-ribofuranoside conjugates: design, synthesis, and antiproliferative potential

1,2,3-Triazole-containing flex-nucleoside analogs and sulfonamido-ribofuranoside conjugates: design, synthesis, and antiproliferative potential

An Efficient Synthesis and In vitro Cytostatic Activity of 5-Aminosulfonyl Uracil Derivatives

The transformation from 2°‐amine to 3°‐amine of cyclam ring alters the fragmentation patterns of 1‐tosylcytosine‐cyclam conjugates

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