Docking studies, cytotoxicity evaluation and interactions of binuclear copper(ii) complexes with s-isoalkyl derivatives of thiosalicylic acid with some relevant biomolecules

The numerous side effects of platinum based chemotherapy has led to the design of new therapeutics with platinum replaced by another transition metal. Here, we investigated the interactions of previously reported copper(II) complexes containing S-isoalkyl derivatives, the salicylic acid with guanosine-5′-monophosphate and calf thymus DNA (CT-DNA) and their antitumor effects, in a colon carcinoma model. All three copper(II) complexes exhibited an affinity for binding to CT-DNA, but there was no indication of intercalation or the displacement of ethidium bromide. Molecular docking studies revealed a significant affinity of the complexes for binding to the minor groove of B-form DNA, which coincided with DNA elongation, and a higher affinity for binding to Z-form DNA, supporting the hypothesis that the complex binding to CT-DNA induces a local transition from B-form to Z-form DNA. These complexes show a moderate, but selective cytotoxic effect toward colon cancer cells in vitro. Binuclear complex of copper(II) with S-isoamyl derivative of thiosalicylic acid showed the highest cytotoxic effect, arrested tumor cells in the G2/M phase of the cell cycle, and significantly reduced the expression of inflammatory molecules pro-IL-1β, TNF-α, ICAM-1, and VCAM-1 in the tissue of primary heterotopic murine colon cancer, which was accompanied by a significantly reduced tumor growth and metastases in the lung and liver

Synthesis and characterization of novel triphenyltin(IV) compound with 3-(4-methyl-2-oxoquinolinyl)propanoic acid

U poslednjoj deceniji jedinjenja organokalaja(IV) privukla su veliku pažnju istraživača zbog svoje izvanredne citotoksične aktivnosti protiv raznih oblika tumora. Ovde je prikazana sinteza 3-(4-metil-2-oksohinolinil)propanske kiseline i njenog kompleksa trifenilkalaja(IV). Ligand je dobijen u dva koraka. U prvom koraku, u reakciji između 4-metil-hinolin-2-ona i metil-3-bromopropionata sintetisan je odgovarajući metil-estar, čijom hidrolizom, u drugom koraku, je dobijen ligand. U reakciji liganda, koji je deprotonovan LiOH, i ekvimolarne količine Ph3SnCl dobijen je kompleks u obliku belog taloga. Sintetisana jedinjenja su okarakterisana standardnim analitičkim metodama. Naredna istraživanja sintetisanih jedinjenja biće usmerena ka in vitro ispitivanju citotoksične aktivnosti prema raznim ćelijskim linijama karcinoma, kao i na ispitivanje mehanizma njihovog delovanja.Organotin(IV) compounds have greatly attracted researchers' attention in the last decade for their outstanding cytotoxic activity against different tumor cells. Herein, the synthesis of 3-(4-methyl-2-oxoquinolinyl)propanoic acid and its triphenyltin(IV) complex has been performed. The ligand precursor has been synthesized in two steps. In the first step, reaction between 4-methylquinoline-2-on and methyl 3-bromopropionate afforded corresponding methyl ester, whose hydrolysis, in the second step, produced targeted ligand. In the reaction of ligand precursor, which was deprotonated with LiOH, with equimolar amount of Ph3SnCl, the expected complex was obtained as white solid. The synthesized compounds have been characterized using standard analytical methods. The following research of synthesized compounds will be focused on in vitro cytotoxic activity against various cancer cell lines, as well as investigation of mechanism of their action

Synthesis, characterization and crystal structure of butyl N-(3-chloropropyl)-(2S)-alaninate hydrochloride

The synthesis of butyl N-(3-chloropropyl)-(2S)-alaninate hydrochloride is reported here. The compound was characterized by elemental analysis, infrared, and 1H- and 13C-NMR spectroscopy. The structure of butyl N-(3- chloropropyl)-(2S)-alaninate hydrochloride was confirmed by single-crystal X-ray analysis.The authors are grateful for the financial support to the Ministry of Education, Science and Technological Development of the Republic of Serbia (Projects No. 172016 and 172035).Peer Reviewe

Synthesis and characterization of novel tributyltin(IV) complex with 2-(4-hydroxy-2-oxoquinolinyl)propanoic acid

U datom radu opisana je sinteza 2-(4-hidroksi-2-oksohinolinil)propanske kiseline i njenog kompleksa tributilkalaja(IV). Ligand prekursor je dobijen hidrolizom metil-estra sintetisanog u reakciji između 4-hidroksi-2-hinolona i metil-2-bromopropanoata. U reakciji deprotonovanog liganda i ekvimolarne količine Bu3SnCl dobijen je kompleks u obliku belog taloga. Sintetisana jedinjenja su okarakterisana standardnim analitičkim metodama. Ligand prekursor i odgovarajući kompleks tributilkalaja(IV) biće testirani na antitumorsku aktivnost prema raznim tumorskim ćelijskim linijama.Synthesis of 2-(4-methyl-2-oxoquinolinyl)propanoic acid and its tributyltin(IV) complex has been performed. The ligand precursor has been obtained by the hydrolysis of methyl ester synthesized in the reaction between 4-hydroxy-2-quinolone and methyl 2- bromopropanoate. In the reaction of deprotonated ligand with equimolar amount of Bu3SnCl, the desired complex was precipitated as a white solid. The synthesized compounds have been characterized using standard analytical methods. The following research of ligand precursor and corresponding tributyltin(IV) complex will be focused on examining their antitumor activity against various cancer cell lines

Synthesis and characterization of novel triphenyltin(IV) complex with 2-(4-hydroxy-2-oxoquinolinyl)ethanoic acid

U datom radu opisana je sinteza 2-(4-hidroksi-2-oksohinolinil)etanske kiseline i njenog kompleksa trifenilkalaja(IV). Ligand je dobijen hidrolizom metil-estra sintetisanog u reakciji između4-hidroksi-2-hinolona i metil-2-bromoetanoata. U reakciji deprotonovanog liganda i ekvimolarne količine Ph3SnCl dobijen je kompleks u obliku belog taloga. Sintetisana jedinjenja su okarakterisana standardnim analitičkim metodama. Naredna istraživanja sintetisanih jedinjenja biće usmerena ka ispitivanju antitumorske aktivnosti prema raznim ćelijskim linijama karcinoma.Synthesis of 2-(4-methyl-2-oxoquinolinyl)ethanoic acid and its triphenyltin(IV) complex has been performed. The ligand has been obtained by the hydrolysis of methyl ester synthesized in the reaction between 4-hydroxy-2-quinolone and methyl 2-bromoethanoate. In the reaction of deprotonated ligand with equimolar amount of Ph3SnCl, the desired complex was precipitated as a white solid. The synthesized compounds have been characterized using standard analytical methods. The following research of synthesized compounds will be focused on examining their antitumor activity against various cancer cell lines

CCDC 932753: Experimental Crystal Structure Determination

Related Article: Srećko R. Trifunović, Vesna D. Miletić, Verica V. Jevtić, Auke Meetsma, Zoran D. Matović|2013|Dalton Trans.|42|13357|doi:10.1039/C3DT51099A,An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Evaluation of DNA/BSA interactions and DFT calculations of gold(III), zinc(II) and palladium(II) complexes with triammonium N-dithiocarboxyiminodiacetate

Dithiocarbamates, with their high lipophilic character and good chelating properties, could provide stabile transition metal complexes and enable these metal-based drugs to reach their biological targets. Palladium(II) and gold(III) complexes, due to its structural similarity with platinum(II)compounds, could be competitive candidates for implementing and developing new pharmacological agents. Herein, novel gold(III) complex with triammonium N-carboxyiminodiacetate as ligand has been synthesized and characterized by elemental analysis, molar conductivity measurements, FT-IR and 1H and 13C NMR spectroscopy. The proposed structure was examined and compared with analogue palladium(II) and zinc(II) complexes by density functional theory (B3LYP/def2tzvp). Additionally, DNA-binding studies by UV/Vis-spectrometer as well as ethidium-bromide (EB) and bovine serum albumin (BSA) quenching studies by spectrofluorometer were performed for gold(III), palladium(II) and zinc(II) dithiocarbamate complexes. The investigated complexes showed a good affinity to calf thymus DNA (CT-DNA) and BSA, with a higher affinity to BSA. Palladium(II) complex exhibited 5-fold a stronger affinity to DNA binding in comparison to zinc(II), but no significantly higher than gold(III) complex. Furthermore, palladium(II) and gold(III) complexes demonstrated a similar affinity toward BSA and these interactions are stronger than showed by zinc(II) complex.Supplementary material: [https://cherry.chem.bg.ac.rs/handle/123456789/4438

Synthesis and characterization of palladium(II) complexes with glycine coumarin derivatives

A Pd(II) complex with methyl 2-((1-(2,4-dioxochroman-3-ylidene)ethyl)amino)acetate was synthesized. The structures of both the ligand and Pd(II) complex were determined by elemental analysis, IR and NMR spectroscopy. Recrystallization of Pd(II) complex from DMF/water solution resulted in its hydrolysis and formation of dimethylamine-(2-((1-(2,4-dioxochroman-3-ylidene)ethyl)amino)acetato)palladium(II) complex, the structure of which was determined by elemental analysis, IR, 1H and 13C NMR spectroscopy, as well as X-ray analysis. [Projekat Ministarstva nauke Republike Srbije, br. OI 172055 i br. OI 172016

Synthesis, characterization and cytotoxicity of a new palladium(II) complex with a coumarin-derived ligand 3-(1-(3-hydroxypropylamino)ethylidene)chroman-2,4-dione. Crystal structure of the 3-(1-(3-hydroxypropylamino)ethylidene)-chroman-2,4-dione

The new coumarine derivative, 3-(1-(3-hydroxypropylamino)ethylidene)chroman-2,4-dione, and corresponding palladium(II) complex have been synthesized and characterized by microanalysis, infrared, 1H and 13C NMR spectroscopy. The structure of the ligand, solved using a monocrystal X-ray structural analysis, consists of two crystallographic different pseudocentrosymmetrically related molecules of 3-(1-(3-hydroxypropylamino)ethylidene)chroman-2,4-dione, while the structure of the square-planar palladium(II) complex was proposed on the basis of DFT calculations. The palladium(II) complex decreased viability of U251 human glioma and B16 mouse melanoma cells in a dose and time dependent manner, while its ligand exhibited only moderate cytotoxicity.Inorganica Chimica Acta (2017), 466: 188-19

Synthesis, characterization and cytotoxicity of a new palladium(II) complex with a coumarin-derived ligand. Crystal structure of 4-hydroxy-3-(1-(p-tolylimino)ethyl)-2H-chromen-2-one-palladium(II) complex

The new coumarine derivative, 4-hydroxy-3-(1-(p-tolylimino)ethyl)-2H-chromen-2-one, and corresponding palladium(II) complex have been synthesized and characterized by microanalysis, infrared, H-1 and C-13 NMR spectroscopy. The proposed structure of the complex was confirmed on the basis of an X-ray structural study. In vitro antitumor activity for the ligand and complex was investigated. (C) 2013 Elsevier B.V. All rights reserved.Ministry of Education, Science and Technological Development of the Republic of Serbia [OI172016, OI172021, III41010, III41031]; Research Center of Serbian Academy of Arts and Sciences and the University of Kragujeva