Kinetin (N6-furfuryladenine) belongs to a group of plant growth hormones involved in cell division, differentiation and other physiological processes. One of the possible ways to obtain biologically active compounds is to complex biologically relevant natural compounds to suitable metal atoms. In this work, two structural groups of Zn(II) complexes [Zn(L(n))2Cl2]·Solv (1-5) and [Zn(HL(n))Cl3] · xL(n) (6-7); n=1-5, Solv=CH3OH for 1 and 2H2O for 2; x =1 for 6 and 2 for 7; involving a phytohormone kinetin and its derivatives (L(n)) were evaluated for their ability to modulate secretion of tumour necrosis factor (TNF)-α, interleukin (IL)-1β and matrix metalloproteinase (MMP)-2 in a lipopolysaccharide (LPS)-activated macrophage-like THP-1 cell model. The penetration of the complexes to cells was also detected. The mechanism of interactions of the zinc(II) complexes with a fluorescent sensor N-(6-methoxy-8-quinolyl)-p-toluene sulphonamide (TSQ) and sulfur-containing biomolecules (l-cysteine and reduced glutathione) was studied by electrospray-ionization mass spectrometry and flow-injection analysis with fluorescence detection. The present study showed that the tested complexes exhibited a low cytotoxic effect on the THP-1 cell line (IC50>40 µM), apart from complex 4, with an IC50=10.9 ± 1.1 µM. Regarding the inflammation-related processes, the Zn(II) complexes significantly decreased IL-1β production by a factor of 1.47-2.22 compared with the control (DMSO), but did not affect TNF-α and MMP-2 secretions. However, application of the Zn(II) complexes noticeably changed the pro-MMP-2/MMP-2 ratio towards a higher amount of maturated MMP-2, when they induced a 4-times higher production of maturated MMP-2 in comparison with the vehicle-treated cells under LPS stimulation. These results indicated that the complexes are able to modulate an inflammatory response by influencing secretion and activity of several inflammation-related cytokines and enzymes.

• MeSH
• Macrophage Activation drug effects   MeSH
• Aminoquinolines MeSH
• Anti-Inflammatory Agents chemical synthesis   pharmacology   MeSH
• Biological Transport MeSH
• Chlorides chemistry   MeSH
• Cysteine chemistry   MeSH
• Gene Expression drug effects   MeSH
• Fluorescent Dyes MeSH
• Glutathione chemistry   MeSH
• Interleukin-1beta antagonists & inhibitors   genetics   secretion   MeSH
• Cations, Divalent MeSH
• Kinetin chemistry   MeSH
• Coordination Complexes chemical synthesis   pharmacology   MeSH
• Humans MeSH
• Lipopolysaccharides pharmacology   MeSH
• Macrophages cytology   drug effects   secretion   MeSH
• Matrix Metalloproteinase 2 genetics   secretion   MeSH
• Cell Line, Tumor MeSH
• Tumor Necrosis Factor-alpha genetics   secretion   MeSH
• Tosyl Compounds MeSH
• Cell Survival drug effects   MeSH
• Zinc chemistry   MeSH
• Check Tag
• Humans MeSH
• Publication type
• Journal Article MeSH
• Research Support, Non-U.S. Gov't MeSH

Nukleární magnetická rezonanční spektroskopie je klíčovou fyzikálně-chemickou metodou studia chemických látek, která poskytuje unikátní informace o složení, struktuře a prostorovém uspořádání. Využívá se ke studiu jak organických, tak anorganických, koordinačních i přírodních sloučenin. Skriptum je určeno jako základní literatura k přednášce z nukleární magnetické rezonance pro studenty navazujících oborů přírodovědeckého chemického a farmaceutického směru. Výběr učiva byl proveden tak, aby čtenář získal základní informace o oboru a provádění měření na NMR spektrometru v roztoku.

• MeSH
• Chemical Phenomena MeSH
• Magnetic Resonance Spectroscopy classification   methods   instrumentation   MeSH

• Conspectus
• Fyzikální chemie
• NML Fields
• chemie, klinická chemie
• fyzika, biofyzika
• NML Publication type
• učebnice vysokých škol

N6-Isopentenyladenine (L1) was subjected to variously acidic media in 0.1 M, 1 M and 2 M HCl. In dependence on the acidity of the medium, the formation of three main acid hydrolysis products, involving the N6-isopentenyladeninium (HL1) (1), 7,8,9,10-tetrahydro-7,7-dimethyl-3H-pyrimido[2,1-i]purin-6-ium (HL2) (2) or 5-amino-4-(4,4-dimethyl-3,4,5,6-tetrahydropyrimidin-2-yl)-imidazolium (H(2)L3) (3-5) cations, were determined and characterized by multinuclear solution-state NMR spectroscopy and in the solid state by single crystal X-ray analysis. The coordination abilities of these transformation products have been also investigated. The compounds of the compositions [Zn(HL1)Cl(3)]·H(2)O (1), [Zn(3)(HL2)(2)Cl(8)] (2), (H(2)L3)[CuCl(4)] (4) and (H(2)L3)[ZnCl(4)] (5) have been prepared in dependence on the acidity of the medium used by the reactions of L1 with ZnCl(2)·1.5H(2)O or CuCl(2)·2H(2)O. Based on the NMR spectroscopic and X-ray crystallographic results, the mechanism of transformation of L1 in the acidic medium, involving the protonation, cyclization and ring fission, has been suggested.

• MeSH
• Cytokinins chemistry   MeSH
• Hydrolysis MeSH
• Isopentenyladenosine chemistry   MeSH
• Crystallography, X-Ray MeSH
• Acids chemistry   MeSH
• Magnetic Resonance Spectroscopy MeSH
• Models, Molecular MeSH
• Water chemistry   MeSH
• Publication type
• Journal Article MeSH
• Research Support, Non-U.S. Gov't MeSH

A series of novel octahedral ruthenium(III) complexes involving 6-benzylaminopurine (L) derivatives as N-donor ligands has been prepared by the reaction of [(DMSO)(2)H][trans-RuCl(4)(DMSO)(2)] with the corresponding L derivative. The complexes 1-12 have the general compositions trans-[RuCl(4)(DMSO)(n-Cl-LH)]⋅xSol (1-3), trans-[RuCl(4)(DMSO)(n-Br-LH)]·xSol (4-6), trans-[RuCl(4)(DMSO)(n-OMe-LH)]·xSol (7-9) and trans-[RuCl(4)(DMSO)(n-OH-LH)]·xSol (10-12); n=2, 3, and 4, x=0-1.5; and Sol = H(2)O, DMSO, EtOH and/or (Me)(2)CO. The complexes have been thoroughly characterized by elemental analysis, UV-visible, FTIR, Raman, and EPR spectroscopy, ES+(positive ionization electrospray) mass spectrometry, thermal analysis, cyclic voltammetry, magnetic and conductivity measurements. The X-ray molecular structure of trans-[RuCl(4)(DMSO)(3-Br-LH)]⋅(Me)(2)CO (5) revealed the distorted octahedral coordination in the vicinity of the central atom, and also confirmed that the 3-Br-L ligand is present as the N3-protonated N7-H tautomer and is coordinated to Ru(III) through the N9 atom of the purine moiety. The tested complexes have been found to be in vitro non-cytotoxic against K562, G361, HOS and MCF7 human cancer cell lines with IC(50)>100μM in contrast to the moderate results regarding the antiradical activity with IC(50)≈10(-3)M. On the contrary, in vivo antitumor activity screening showed that the prepared Ru(III) complexes possess higher pro-apoptotic activity than NAMI-A. The reduction of Ru(III) to Ru(II) and Ru(II)-species formation in tumor tissues was confirmed by means of a simple method of detection and visualization of intracellular Ru(II) by fluorescence microscopy. The originality of this method is based on the preparation of a Ru(II)-bipyridine complex in situ.

• MeSH
• Apoptosis drug effects   MeSH
• Dimethyl Sulfoxide analogs & derivatives   pharmacology   MeSH
• Kinetin chemical synthesis   chemistry   pharmacology   MeSH
• Coordination Complexes chemical synthesis   chemistry   pharmacology   MeSH
• Crystallography, X-Ray MeSH
• Leukemia L1210 drug therapy   pathology   MeSH
• Humans MeSH
• Mitosis drug effects   MeSH
• Molecular Conformation MeSH
• Mice, Inbred DBA MeSH
• Mice MeSH
• Cell Line, Tumor MeSH
• Necrosis MeSH
• Organometallic Compounds pharmacology   MeSH
• Antineoplastic Agents chemical synthesis   chemistry   pharmacology   MeSH
• Ruthenium MeSH
• Drug Screening Assays, Antitumor MeSH
• Neoplasm Transplantation MeSH
• Animals MeSH
• Check Tag
• Humans MeSH
• Mice MeSH
• Female MeSH
• Animals MeSH
• Publication type
• Journal Article MeSH
• Research Support, Non-U.S. Gov't MeSH

• Publication type
• Abstracts MeSH